Key West Condo 4.9 Star Review

The Jungle Breeze condo at LaBrisa Condominiums.
*Ocean View
*Free WiFi
* Free Covered Parking
* Final cleaning included in price
* KING size bed.
* Accommodates 2 adults
* Recently renovated this condo features all new flooring and a brand new kitchen
* Full size washer and dryer.

This is not a hotel; it is a privat.......read more

1 Bedrooms - Sleeps 2
Condo in Key West

Key West Vacation Rental 5.0 Star Review

PRESTIGIOUS TROPICAL RETREAT...
Indulge in this spectacular two-story home situated in the premier gated community of historic Truman Annex. Escape to a sun-kissed dream as soon you enter this picturesque community, surrounded by swaying palm trees inviting you to enter your island vacation home which is tucked away on a quiet lane. Totaling 4 b.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West.

This pristine Florida Bungalow is 2 bedrooms, 2 bathroom single family home and offers all the amenities you need to make this your perfect vacation. Including off-street parking, swimming pool, quaint gazebo equipped with wet bar and custom seating. Th.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

key west Condo 4.9 Star Review

Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms, the kitchen and the living room. Birds of various types, boating activities, lush oasis gardens are just a few reasons why people keep returning to our paradise property. "Click" on 'more information' also "click" o.......read more

3 Bedrooms - Sleeps 8
Condo in key west

Key West Condo 4.9 Star Review

Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and dining area. The living room features comfy furniture and a panel TV. One queen bedroom and one twin bedroom. Enjoy outdoor dining on the brick patio surrounded by a tropical landscape.
Villa Fleur is located in the Shipyard Co.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 4.9 Star Review

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. This two bedroom Villa Vista is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.

The number one reason .......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Apartment 4.9 Star Review

The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everthing you need to fix your own cocktails and prepare some shrimp on the shared propane grill in the Courtyard.

Located in a .......read more

Studio - Sleeps 2
Apartment in Key West

Key West Condo 4.9 Star Review

Please call or text if you’d like to book our home
702 232... 3750

When booking our home please include a brief description of who you’ll be traveling with and what brings you to the area with your reservation request. We like to know who will be staying in our home ?

Welcome to your front row seat of the New Truman Waterfron.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 4.8 Star Review

THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a private wonderland on the quieter end of Duval Street. Enjoy morning coffee or people watching on the elevated, partially covered front porch. The home’s backyard oasis includes a covered rear patio, a pool with waterfall feature an.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlantic Ocean. The spectacular view can be seen immediately upon entering the condo. The floor to ceiling glass walls provide a full sea panorama from the living room, dining room, kitchen and master bedroom. The 31 foot oceanfront ba.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 4.7 Star Review

Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath jacuzzi, have front row seats to the variegated lights of Mother Nature's Sunrises, have the convenience of a fully equipped kitchen, two sitting areas for extra comfort and flexibility and for countless hours to enjoy the views.......read more

2 Bedrooms - Sleeps 8
Condo in Key West

Key West Condo 5.0 Star Review

This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorated. Fresh paint throughout, all new hardwood flooring, new kitchen with granite counter tops, stainless steel appliances, and brand new designer furnishings make this a home away from home. A large rear courtyard with a wood sun d.......read more

2 Bedrooms - Sleeps 5
Condo in Key West

Key West Condo 4.8 Star Review

Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. If the dates you need are not available check my other Key West vacation rental (Henry's.......read more

2 Bedrooms - Sleeps 5
Condo in Key West

Key West Apartment 4.8 Star Review

Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets.

The building once housed the Chrysler/Deso.......read more

1 Bedrooms - Sleeps 6
Apartment in Key West

Naval Air Station Key West Vacation Rental 5.0 Star Review

Come escape to paradise in this newly updated and available home steps from Duval! Equipped with all the amenities for an extended stay in the heart of Key West. Has oversized pool shared w/ other rental units within complex.

PROPERTY: Newly renovated 2 bed 2 bath property in Historic Old Town. Secured behind a secluded white picket fence, t.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Naval Air Station Key West

Key West Vacation Rental

Tricksy's Place located in the heart of Old Town, Key West is a perfect retreat to relax, and the perfect starting point to explore all that our beautiful tropical island has to offer. Only one block from Duval St., a short walk to the Southernmost Point, Hemingway House, Key West Lighthouse, and more. Stay in and cook an elegant meal in our modern.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Condo 4.9 Star Review

Our condo is located is in the heart of Key West's Old Town. This neighborhood is filled with historic homes dating from the period when Key West was the wealthiest city in the United States. The condo is in a historic home with three other condo units. The location is ideal to explore Key West by foot or bike. Great restaurants are within a fi.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo

f bedrooms, full kitchen, screened in patio with a relaxing pool, and dock area perfect for sunset over the Gulf of Mexico. Free covered parking. A great place to rest from your frolicking fun times!.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Apartment

The Maria Luz a is located in a Historic Conch house from the early 1900’s updated and decorated by its owner.
Features original hardwood floors, updated bathroom. The galley-style kitchen is fully stocked with all the necessary essentials. Other features include also features WIFI, cold A/C, private washer and dryer in the unit.
You c.......read more

1 Bedrooms - Sleeps 2
Apartment in Key West

Key West Vacation Rental

The Cordelia is located in a Historic Conch house from the early 1900’s updated and decorated by its owner. Features original hardwood floors, new bathroom and chic decor items. The galley-style kitchen is equipped with white quartz countertops, a black retro tile backsplash, and stainless-steel appliances; fully stocked with all the necessary e.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Vacation Rental

The Gisela is located in the rear of an adorable Conch Cottage. Finished with a soft and neutral color scheme that will take your breath away. Enter through your private entrance into the living room with features high ceilings and a spectacular light filled living space. 45-inch flat-screen TV with cable and streaming services. Between the kitch.......read more

1 Bedrooms - Sleeps 1
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Enjoy a stylish experience at this centrally-located apartment. Just a short walk from some of Key West best restaurants and shopping. This 1 bedroom, 1 bath has been beautifully furnished, features stainless steel appliances, private washer and dryer in unit, private porch with a view of a lush courtyard........read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Apart-hotel

Tropical Key West welcomes you to a classic Florida condominium, offering a one bedroom unit with plush queen bed, fully equipped kitchen, dining area, living room with sleeper sofa, TV, stereo and DVD player, and private balcony with pool or harbor views. Walk to Duval St. and Mallory Square! You will be in the middle of it all while you enjoy the.......read more

1 Bedrooms - Sleeps 4
Apart-hotel in Key West

Key West Vacation Rental 4.6 Star Review

You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This property doubles as our second home when we are in town. Renovations include new wood flooring, fresh paint, new kitchen with stainless appliances and granite tops. All furnishings and accessories are new. Private courtyard with sundec.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental

Spacious home with open floor plan. Completely renovated in 2018. Large heated pool and hot tub in a quiet tropical oasis. Located 2 blocks from the famous Duval with restaurants, shopping & live music........read more

7 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throughout the house to open up and let in the Key West sun. Relax in the living with a large screen TV or sit on the front porch to read a book and relax with the breezes or if needed, the porch fan. The kitchen is perfect to cook your.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Apartment 4.8 Star Review

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. This pet friendly accommodation is the perfect location for exploring Key West. You can walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval St with it's many restaurants, shops, galleries and museums. .......read more

1 Bedrooms - Sleeps 2
Apartment in Key West

Key West Condo 4.9 Star Review

Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. The living room is furnished with comfy furniture and a 50"TV. The bedrooms have queen beds. Enjoy outdoor dining on the deck surrounded by a tropical landscape.
Villa Nomade is located in the Shipyard Condominiums at the Truman.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Apartment 4.3 Star Review

WELCOME TO LITTLE CASITA!

If looking for the perfect couple’s retreat, look no further!

This one bedroom, one bath historic apartment is located just blocks from Key West’s famous Duval Street & Historic Seaport where you’ll find restaurants, shops, and bars. The residential neighborhood will make you feel like a local!

.......read more

1 Bedrooms - Sleeps 2
Apartment in Key West

Key West Condo 4.8 Star Review

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa Porta is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. Please email us even if the av.......read more

1 Bedrooms - Sleeps 4
Condo in Key West

Key West Cabin 4.7 Star Review

Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high-end amenity that you could possibly desire. Two master bedrooms, two full .......read more

2 Bedrooms - Sleeps 6
Cabin in Key West

Key West Cottage 4.8 Star Review

50% OFF I JUST HAD A CANCELLATION FOR THE WEEK OF DECEMBER 2-9. Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private townhome (one of only .......read more

2 Bedrooms - Sleeps 6
Cottage in Key West

Key West Vacation Rental 5.0 Star Review

Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.

As soon as you step inside, you'll b.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Welcome to this Key West Tropical charmer located only 15 minutes away from Downtown Duval Street. This townhome is located in a gated community called the Key West Golf Club.
This pleasant, bright and spacious townhome comes with a large backyard space for entertaining or just lounging around and is located on a quiet cul de sac. This townhome .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Condo

This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings.

As you enter "Caroline on My Mind," you'll notice a stairway adorned with wainscoting, leading you to the entry. The ho.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 5.0 Star Review

Discover your private paradise in the Keys! This exquisite waterfront home offers a unique opportunity to experience the beauty of the area with your own private beach, resort-style tiki hut, pool, and a 50ft dock. Just 15 minutes away from Duval Street, this is your ultimate getaway.

Highlights of your stay:

*A 1/3-acre property wit.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo 4.9 Star Review

This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into individual condominiums many years ago, located just one block from Duval Street in the Heart of Old Town Key West. Our casual atmosphere allows you to chill out and enjoy having the best of Key West within easy walking distance of al.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Cottage 5.0 Star Review

Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to restaurants, docks, and Duvall St. Easy to get to everything yet quiet and secluded........read more

1 Bedrooms - Sleeps 4
Cottage in Key West

Key West Apartment 4.7 Star Review

Located in the heart of historic Old Town Key West, just steps away from world-renowned Duval Street, La Casa de Luna is a  ground level one bedroom, one bathroom condo that is part of a large house with a relaxing veranda. Easy walking distance to all your favorite restaurants and bistros.

Open the door to the full kitchen with refrigerato.......read more

1 Bedrooms - Sleeps 4
Apartment in Key West

Key West Hotel resort

Welcome to your own private sanctuary among the lush landscape of Key West - envision old-fashioned screen-enclosed porches, gardens bursting with tropical flowers and crystal clear water views. Hyatt Beach House Resort’s breathtaking gulf coast setting is matched only by the top-tier amenities and meticulous attention to detail that Hyatt is ren.......read more

2 Bedrooms - Sleeps 6
Hotel resort in Key West

Key West Apartment 5.0 Star Review

WELCOME TO CASITA IN THE CLOUD!


Your search for the perfect island getaway has ended!

This large 3 story, two bedrooms, two bath apartment boasts all the amenities you’d expect from your island home. Upon entry, you’ll be greeted by a loving foyer with a set of stairs leading you to the surprisingly spacious living room, ki.......read more

2 Bedrooms - Sleeps 4
Apartment in Key West

Key West Vacation Rental 5.0 Star Review

OLD TOWN CLASSIC...
This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding location of Southard and Ashe Streets, this upscale abode is just minutes from Duval's many restaurants and bars. You are within walking and biking distance to museums, shopping, and Fort Zachary Taylor beach. Come inside this bri.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

MODERN TROPICAL JEWEL WITH STUNNING OCEAN VIEWS…
This contemporary and spacious custom-built gated home will beguile your senses, luring you inside with the finest of amenities and stunning design. Just a stone's throw away from the infamous Whitehead Southernmost Buoy, you are truly seated in the heart of paradise in this small gated communit.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 3.8 Star Review

BAHAMA VILLAGE TREASURE...
This charming Old Town home is just 3 blocks from the world-famous Duval Street, award-winning restaurants and delightful boutiques of Petronia Street in colorful and historic Bahama Village. Let your island soul unwind in this small but mighty abode that exudes Key West charm!
***PRIMARY GUEST MUST BE AT LEAST 25 Y.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

****This property requires a minimum stay of 28 nights in the same calendar month****

***Brand New Pool with waterfall, saltwater, heater, and a chiller to maximize comfort!


Tropical Properties Vacation Rentals invites you to our beautiful historic home located in Historic Old Town Key West. This home is located just two blocks f.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.5 Star Review

"Welcome to Duval Square" a secluded and gated community located on
upper Duval St; these properties are some of the most prestigious
on the island, which offer lush tropical landscaping, swimming pool
and private jacuzzi. This location is perfect for either complete
seclusion or if you prefer to view the many sights from above. Y.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.3 Star Review

LOCAL LIVING....
Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated,  4 bedroom home, with 3 baths in an amazing location.  Enjoy sunny Key West weather by spending time relaxing outdoors or soaking in the private pool.
***GUESTS MUST BE 25 YEARS OF AGE OR OLDER

FURNISHINGS..
Newly designer de.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 2 1/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Apartment

★Excellent Key West Location - Oceanside Property - 2-Bedroom - 2-Bathroom - Sleeps 6. 
★Very Clean - Very Nice Property.

Guests can enjoy the beautiful ocean breeze right next to the property. Guests may also enjoy the relaxing pool and the fully-equipped health and fitness center. 

LOCATION:
Enjoy the white sands of the .......read more

2 Bedrooms - Sleeps 6
Apartment in Key West

Key West Apartment

★Excellent Key West Location - Oceanside Property - 2-Bedroom - 2-Bathroom - Sleeps 6. 
★Very Clean - Very Nice Property.

Guests can enjoy the beautiful ocean breeze right next to the property. Guests may also enjoy the relaxing pool and the fully-equipped health and fitness center. 

LOCATION:
Enjoy the white sands of the .......read more

2 Bedrooms - Sleeps 6
Apartment in Key West

Key West Vacation Rental 5.0 Star Review

~~7 day minimum~~​Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private President's Lane area of the prestigious Truman Annex.  Offering exquisite amenities, pool access, and an unbeatable location close to Duval Street, Truman Waterfront Park, and Ft. Zachary Taylor Beach provides a fantastic Sunsh.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

A gorgeous 3 bedroom / 2 bathroom vacation rental home with high vaulted ceilings and French doors. Three private bedrooms with all "smart" flat screen tv's and high speed internet. The backyard features a large covered patio and an in-ground heated swimming pool for the winter months and a chiller for the summer months perfect for relaxing anytim.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Recently renovated home located on a quiet lane just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heaven, Hemingway House and Willie T’s are all just a few hundred feet from the front door, and you’d never know it because the house is on a private and quiet one-block lane.

The house itself ha.......read more

2 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Condo 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

There’s no doubt you’ve heard of Duval Street; phenomenal restaurants, eclectic shops and legendary nightlife. This immaculate condo is just a half block away, giving you access to everything Duval Street has to offer while still all.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 4.9 Star Review

Relax at Villa Mer in luxurious surroundings. Renovated in 2019 it has a fully equipped kitchen with bar seating. The living room features comfy furniture and a 50"TV. The bedrooms have queen beds. Enjoy outdoor dining on the brick patio surrounded by a tropical landscape.
Villa Mer is located in the Shipyard Condominiums at the Truman Annex. T.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Apartment 3.5 Star Review

Mermaid's Retreat

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captivating histo.......read more

1 Bedrooms - Sleeps 2
Apartment in Key West

Key West Condo

Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located near the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, bo.......read more

1 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 4.7 Star Review

The Bonaire Suite is a bi-level suite decorated in a rich contemporary palm tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door.

Downstairs is a living room with sofa that converts to a queen bed and a love seat decorated with rich pa.......read more

1 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Apartment 4.8 Star Review

Eyebrow Suite is a spacious two bedroom suite with one of the best locations on the island. Its large front porch and palm tree filled fenced-in yard invite you to a private oasis on Olivia street, just one half block from Duval street. You'll feel like a local as you sip a drink, read the newspaper, or just people watch from the front porch.
read more

2 Bedrooms - Sleeps 4
Apartment in Key West

Key West Cottage

Down a hidden lane in the heart of Old Town Key West you will find Loco Court. The compound is located one block off Duval St but is completely private and serene.
The compound consists of THREE STAND ALONE COTTAGES alongside a tranquil PRIVATE POOL and connected to each other by a spacious deck.

The first cottage (unit 1) and second .......read more

4 Bedrooms - Sleeps 12
Cottage in Key West

Key West Condo 4.9 Star Review

We stick to a Saturday check in during the in season months (Jan-April)

Greetings from Paradise, where the temperature is 82 degrees, water temperature 80, and the wind SE at 10, just enough breeze to blow sand in my margarita.

'Margarita Villas' are located in historic Old Town in a beautiful, very private gated compound that has wo.......read more

2 Bedrooms - Sleeps 5
Condo in Key West

Key West Condo

Louisa's Garden

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Book this wonderful, ground-level, Old Town getaway with all the comforts of home including central air conditioning and complimentary internet access! This vacation rental features a.......read more

1 Bedrooms - Sleeps 2
Condo in Key West

Key West Vacation Rental 5.0 Star Review

Flagler Station

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Recline next to a shimmering pool, with a banana tree and avocado tree completing your view! This pleasant home is designed for guest comfort from top to bottom, with everything from .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a tw.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

Resort-style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amid lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure. One of our most popular properties, it was renovated by two fabulously funky sisters who share an affinity for Key West style. It features all the .......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 4.7 Star Review

This condo has a unique location in the Gated Truman Annex. It is very quiet, but yet very close to all Key West has to offer.
The entrance road to the Ft Zachary Taylor St. Beach Park is right at the end of our block, for Lazy Days of snorkeling, swimming and sightseeing. The best sunset spot.
Duval St. is 2 blocks up, with shopping, res.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Villa 4.4 Star Review

"In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval, and because it is way at the end of an unknown lane i.......read more

4 Bedrooms - Sleeps 10
Villa in Key West

Key West Vacation Rental 5.0 Star Review

Julia Whitehead Guest Suites

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captiv.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa Rosa is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.

The number one reason why.......read more

1 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 4.6 Star Review

This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping.
Due to local zoning laws we can only.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

NEWLY REMODELED in the Summer of 2022 this 2 bedrooms, 2-bathroom condo checks all the boxes for your vacation needs!

Located in the 1800 Atlantic condo complex with two large communal swimming pools, spa, tennis courts, fitness facilities, private beach, walking paths, BBQ area and recreation room/ library. The opportunities for entertainme.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 5.0 Star Review

Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen with stainless appliances and granite tops. New hardwood downstairs and tile floors upstairs, all new furnishings and accessories, and private courtyard with sundeck overlooking a private park. The 2 Bedrooms are upstairs and each .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental

Enjoy a carefree vacation in a 2 bedroom 1.5 bath, 2-story townhome, located on Southard Court in the Truman Annex, downtown Key West. This home is situated right in front of the community pool.

The first floor has an open floor plan with a full kitchen, dining area, and living area which opens to a beautiful backyard patio. There is also a .......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 4.9 Star Review

Welcome to Mai Tai Terrace located in The Shipyard subdivision of Truman Annex in beautiful Key West.

This 2-bedroom, 2-bathroom end unit condo is spacious and comfortable for guests of all types.

An open concept living, dining and kitchen allows this second story condo to flow freely. With vaulted ceilings and large windows this tr.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Villa

An absolute dream home in the most highly sought after location of Key West - the Casa Marina. You will feel at home and never want to leave this thoughtfully designed home. The entire house has been meticulously, professionally redesigned. Located in the most exclusive area of Key West, steps away from the Atlantic beaches, great dining and entert.......read more

3 Bedrooms - Sleeps 6
Villa in Key West

Key West Condo 5.0 Star Review

A beautiful 2 bedroom, 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old Town Key West. A wonderful mix of a private community yet easy walking distance to the Duval Street attractions, Mallory Square, and Fort Zachary Taylor State .......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 5.0 Star Review

HALF PRICE! A GREAT WEEK THIS NOVEMBER 25-DEC 2 Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two bedroom, one bathroom condominium or casita .......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo

WHERE LIFE IS PURE…
This dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West charm within its tranquil setting. Peacefully located with convenience to everything, this home truly has it all making your Key West love story one never to forget! 
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
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3 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo

Welcome to the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, restaurant, bar and much more onsite.
Relax in the jacuzzi or sauna during your stay or work out in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental

HISTORIC ISLAND CHARM...
Located in the Casa Marina Area of Old Town which is known for lovely and sophisticated homes, this unmatched retreat is no exception. Modern architectural elegance emanates from every corner, inviting you to bask in serenity and escape everyday reality. Winner of the Ceramic Star from the Historic Florida Keys Foundatio.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.3 Star Review

Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, you will not find a better or quieter location to enjoy all that Key West has to offer.
This storied and historic 1883 Conch home has been lovingly and thoughtfully renovated to perfection. Gleaming Dade Coun.......read more

2 Bedrooms - Sleeps 7
Vacation Rental Home in Key West

Key West Condo

Welcome to the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, restaurant, bar and much more onsite.
Relax in the jacuzzi or sauna during your stay or work out in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Apartment 4.7 Star Review

Seagrass Suite

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Welcome to Julia Whitehead Lighthouse Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captivating his.......read more

1 Bedrooms - Sleeps 2
Apartment in Key West

Key West Apartment 5.0 Star Review

Summary:
This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West getaway. Tastefully decorated with trendy decor and modern furnishings, this property has a welcoming and clean feel. Comprised of two lofts on Duval, this recently renovated compound is perfect for up to 12 guests.

With a p.......read more

4 Bedrooms - Sleeps 12
Apartment in Key West

Key West Vacation Rental 5.0 Star Review

VINTAGE ISLAND PARADISE...
Tucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the midst of Old Town Key West. Elegant architectural design with an unmatched collection of artwork, this mature retreat creates a blissful ambiance. A well known ficus tree among the infinite landscape makes this the legendary "Fic.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with new quartz counter tops and stainless-steel appliances with a gas cook top. The large living and dining are.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

- 28 Night Minimum Rental
- Private Heated Pool
- Private 65 Foot Deepwater Dock in Protected Harbor
- 10 Minutes by Car to Downtown Key West
- Open Floor Plan

Dock your boat in the backyard and enjoy lagoon views from this family and pet friendly one story private home. Take advantage of the deep water access to both Atlan.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Condo

This cute and quite space is perfect for a visiting professional or as a vacation rental for 1 or 2 people.

Central air conditioning and ceiling fans ensure comfort even when the breeze isn't blowing. All rooms in residence are beautifully furnished and include recessed lighting and dimmers to enjoy a sense of peace and tranquility throughou.......read more

2 Bedrooms - Sleeps 2
Condo in Key West

Key West Vacation Rental 5.0 Star Review

Tropical 2-story conch architecture townhome located in the Key West Golf Club Resort with incredible amenities, on the 17th fairway, sleeps 4 comfortably, and is located at the end of a quiet street with easy access to street parking. The 2-BR floorpan is one of the largest in the community offering wider spaces with more square footage. 2 porches.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

Featuring direct marina access and located just 2 miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just 3 miles from vibrant Duval Street, and 4 miles from historic and majestic Mallory Square.

This two bedroom condo features a.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental

Imagine the ultimate Key West dream home that feels like a faraway oasis - a short ferry ride to Sunset Key will have you feeling like you're living on your own island. Here you’re softly serenaded with the sounds of the surrounding sea and rustling fronds of the palm trees, while you chill-out on your own private rooftop deck to enjoy the changi.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

THE PROPERTY: Awarded the Florida Keys Preservation Star, this stunning home and outdoor space will entice you to live like a local. From its covered front porch to its rear entertaining area, you won’t want to leave. As you enter via the sunny yellow doors you will be captivated by the gingerbread balustrade, staircase book nook and beautiful Da.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West House boat 4.7 Star Review

2 BDRM 2.5 BATH. SLEEPS 6. OPEN OCEAN VIEW.
POOL, PRIVATE BEACH, RESTAURANT, BAR, GYM, TIKI, LAUNDRY ON BOARD.
15 MIN FROM DOWNTOWN.

Two queen bedrooms on first level. Open ocean view second level salon & galley, floor to ceiling windows, sliding glass doors leading to spacious fore and aft decks and spiral stairs to expansive, furnis.......read more

2 Bedrooms - Sleeps 6
House boat in Key West

Key West Condo 4.8 Star Review

Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath with approximately 1350 square feet of living space. Guests will enjoy absolutely breathtaking ocean views and the colors of the sunset from the 35-foot balcony, as well as from both bedrooms and the living room.

The Living s.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.4 Star Review

Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just three miles from vibrant Duval Street, and four miles from historic and majestic Mallory Square.

The property features two pools, a hot tub, park-style grills.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

If you’re looking for a Florida Keys home that rivals the seaside homes found in ‘Coastal Living’ magazine, look no further! COASTAL LOVING is an inviting two-story private home that offers a relaxing vacation setting and comfortab.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo 4.6 Star Review

This luxurious recently renovated condo features a wonderful contempory interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking.......read more

2 Bedrooms - Sleeps 5
Condo in Key West

Key West Vacation Rental

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.6 Star Review

Welcome to Key West. Located on this beautiful island 13 miles from downtown is this quaint 2-level beach home. With sleeping for up to 10 people, you can bring the entire family or your best friends to experience the beauty of the Lower Keys. While you are at it, don’t forget your Fur Babies and your boat!


Then as you step out on the .......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

The moment you walk thru the door you are greeted by soothing tropical colors and high vaulted ceilings.
The large master en suite is located on the first floor. It has a large closet and bathroom. The bathroom has a clawed tub and stand up shower with access to an outdoor shower if wishing to live like a local.
The Living Room is most invit.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Cottage 4.9 Star Review

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town Distri.......read more

3 Bedrooms - Sleeps 6
Cottage in Key West

Key West Vacation Rental 4.9 Star Review

ALLOW THE PERFECT VACATION TO UNFOLD...
The epitome of laid-back, island living is found within this classic, Conch style home bringing endless charm to your tropical vacation. Steps from high end galleries, bars and restaurants, yet tucked away on a quaint and colorful lane, this home entails all the desired amenities that will truly immerse y.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

** 20% Discounts Available for October, November, and December 2022 ** A great opportunity to stay in one of the best homes in the Key West Golf Club!!!

Monthly rentals available. Key West has strict rules for rental properties and, as such, most newer homes must be rented for 28 days or more. (I would consider longer stays as well, conta.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West House boat 4.8 Star Review

*Our business is growing with new natural setting stay at our moorings in quiet secluded area in Key West Harbor!” We have our own water taxi to take you to the boat then back to shore upon departures. We also can share with you the other options for going back and forth more often to explore downtown Key West.

Have you ever wanted to ge.......read more

2 Bedrooms - Sleeps 6
House boat in Key West

Key West Condo 4.8 Star Review

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The Villa Grande is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. The number one reason why people choose th.......read more

3 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.6 Star Review

$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You will not be disappointed!

Location..Location...Location...this one has it all! Resort is located on the Ocean and is within steps of famous Duval Street. The Galleon Resort offers many amenities to enhance your vacation need.......read more

1 Bedrooms - Sleeps 2
Condo in Key West

Key West Vacation Rental 5.0 Star Review

Rockland Key Rental House is a cute Key West home that is located only 9 miles from Key West. So enjoy the quaint and quiet beauty of the Keys with fast access to party central downtown. There is a peanut pool that is sunny all day – which makes in very warm and inviting. There's back covered deck with a ceiling fan to enjoy dinner outside (and t.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

Imagine enjoying morning coffee, an afternoon cocktail, or an evening meal of stone crabs on a spacious and comfy third-floor balcony with refreshing sea breezes and a gorgeous view of the Atlantic Ocean. If this sounds perfect, Salacia is the tropical island getaway for you.

Named after the Roman female divinity of the sea, Salacia is a two.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only 1/2 block from the fabulous shops, restaurants and bars that made Duval Street famous.

Beautifully furnished and luxuriously appointed, Bahama House has three bedrooms, all with private.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.0 Star Review

The Tipsy Mermaid

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Nestled in a peaceful gated community, this two-level townhome is located right on a golf course in the gated grounds of the Key West Golf Club, only a few miles from those pristine.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

This one bedroom apartment on the ground floor is completely restored with a full kitchen and laundry. This unit has everything you need for an extended stay.Walk out to the private garden from your living room. Located on one of the best streets in Old Town. You are just 3 blocks from the Harbor, home to the freshest seafood restaurant and the bes.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

Pilar’s Secret is tucked away in the heart of Key West just half a block off famous Duval Street. This hidden oasis is the perfect spot for you to truly discover the ultimate Key West experience. Located down a quiet nondescript lane this gorgeous property is positively Key West with well appointed luxury throughout.

Pilar’s Secret offer.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sofa. Jacuzzi Tub in Master. Property features Pool, Sauna, Private Beach, Tiki Bar, Rooftop viewing deck, Grills and daily activities. Premium location for easy walks to Duval Street, Mallory Square, Key West Aquarium, Shipwreckers.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental

This is a two-story Victorian Town Home with 1st and 2nd floor private verandas overlooking historic Fleming Street. It features a full living room with queen sofa bed, complete kitchen, and an open spiral staircase leading to the second floor master bedroom with a king bed and private bath. Also features original artwork, flat panel TVs, air condi.......read more

Studio - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 4.9 Star Review

This newly redecorated town home is the perfect place to enjoy the tranquility of an island paradise vacation while still located in the heart of Old Town Key West.

The living area is decorated in the greens and blues of the Caribbean with an open floor plan, comfortable seating, hardwood floors, and ceiling fans. The kitchen features all t.......read more

3 Bedrooms - Sleeps 8
Condo in Key West

Key West Vacation Rental 4.9 Star Review

Dolphin Watch is located in prestigious Truman Annex and is one of the few private waterfront homes. We are less than two blocks from Duval Street and beautiful Mallory Square sunsets. You can also see the sunset from your own private balcony! Walking distance to famous Fort Zachary State Park and Beach. The living area, master bedroom, bath, and.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

"Flip Flop Inn" is a beautiful 3 Bedroom 3 Bath home, (each bedroom has its own private full bath), plus a pull-out Queen sofa, and a Queen size Futon. We're located in the luxurious gated safe community of Coral Hammock. The grounds are beautifully landscaped and include a large community pool and a fitness room. Two parking spots are also incl.......read more

3 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

Casa Margarita is the perfect luxury retreat if you are looking for a peaceful place that also is in the heart of Old Town Key West. This three-bedroom, three-bath home features a large backyard with lush tropical landscaping, a heated pool, and a large hot tub with a capacity of up to six people. With a spacious covered patio, ample seating, and .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo 4.6 Star Review

All the amenities of a fantastic resort suite and free assigned parking in the middle of everything in Key West...2/1 that is 1 min away from the beach and 2 blocks off Duval surrounded by amazing entertainment Green Parrot is across the street) and some of the best and most famous Key West Restaurants and Landmarks...you will love it!!!
Souther.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 4.8 Star Review

Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean views from a 38-foot private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year.

Click on the calendar icon to check dated that are available........read more

2 Bedrooms - Sleeps 5
Condo in Key West

Key West House boat 4.0 Star Review

Come aboard for your dream yacht vacation. Docked at one of the most exclusive marinas in the Key West area,. This 66' foot yacht allows you to experience the lifestyle of the rich and famous. Boasting large living room, 3 staterooms, 3 bathrooms, a full kitchen & outdoor grill, it has all of the comforts of home, plus exclusive access to top notc.......read more

3 Bedrooms - Sleeps 1
House boat in Key West

Key West Vacation Rental 4.5 Star Review

Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, coffee shops and bars with live music are all within walking distance. A pleasant 10 minute walk (0.5 miles) will take you to the bustling entertainment part of town located primarily along Duval St.

If you want to unwin.......read more

3 Bedrooms - Sleeps 5
Vacation Rental Home in Key West

Key West Condo 4.6 Star Review

City of Key West Business License # 28224

We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'.
This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plas.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.6 Star Review

This 2,000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a third bedroom w/bath. A pull out sofa bed allows for total accommodations for 8 people. With the master suites on opposite ends of the condo, it is a great set-up for 2 or 3 couples as well as for friends or families who .......read more

3 Bedrooms - Sleeps 8
Condo in Key West

Key West Vacation Rental 4.9 Star Review

We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee or celebrate another amazing sunset with an evening cocktail on one of four open air decks surrounding this beautifully appointed townhouse in the prestigious Key West Golf Club. Located directly off a gorgeous, heated pool compl.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Location! Style! Elegance! This restored "beach" home is fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, this location can not be beat. The home's history is rich...neighboring the historic Gato Cigar factory which is now restored and used as county offices. Duval Squ.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Condo 5.0 Star Review

Harbor Place is one of the most prestigious properties in Key West!

This unit offers breath taking water views overlooking Marina and Cruise Ship Docks. The amenities are rounded out with a large lap pool overlooking the Key West Harbor. The large 40 foot deck area is one of the best feature for this Condo. The Harbor Place Condo is located.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.6 Star Review

Welcome to our lovely condo which is located in the famed Truman Annex Complex right in the heart of fabulous Key West. Our condo has 2 bedrooms and 1 bath.. Enjoy everything that Key West has to offer and more. Lounge on the newly refinished deck. Enjoy the beautiful landscaping and the picturesque scenery. Take a short walk to the heated pool, g.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 4.9 Star Review

Welcome to our new fully renovated townhouse hosted by HomeAway Premier Partner Roy Svenningsen. This home is located in a lush, family oriented gated community across from the Key West Golf course.
The home features all new stainless steel appliances, new furniture, all new flooring, marble counters, and top quality mattresses.
In the center.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

KEY WEST Hotel resort 5.0 Star Review

ONLY AVAILABLE 2/20-2/27: PRIME REAL ESTATE IN THE HEART OF KEY WEST. HYATT RESIDENCE CLUB COVETED RESORT SUNSET HARBOR !! You’re just minutes from the free-spirited art, music and entertainment scene of Old Town and the countless recreational activities of this beloved Gulf coast destination. From museums to galleries to food, Key West is in a .......read more

2 Bedrooms - Sleeps 4
Hotel resort in KEY WEST

Key West Apartment 4.9 Star Review

At Mango Hideaway you can savor the peace and quiet of your private deck with Jacuzzi.
Located 1/2 block off Duval street this king junior suite features tropical bamboo furniture, Kitchenette and a spacious shower.
The kitchenette is stocked with essentials including a full size fridge with ice maker and microwave for light cooking and in-.......read more

1 Bedrooms - Sleeps 3
Apartment in Key West

Key West Vacation Rental 4.6 Star Review

Beautiful 2-story townhouse; master bedroom with King Bed and double doors to deck; full bath; second bedroom with two twins; washer and dryer; ceiling fans; TV's; hardwood floors in bedrooms, hall and stairs to second floor.

First floor has a welcoming front porch; kitchen; dining area; living room with two double french doors to lovely de.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition TV and surround stereo throughout the home. High Speed internet and faxing available as well.

High security inside: guarded and gated Truman Annex. Only three blocks to Jimmy Buffets, Slop.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo 5.0 Star Review

TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! Amazing LOCATION! Large front yard and porch to watch Key West pass by. Beautiful, sunny and spacious living areas with private, large landscaped backyard with two dining areas. First Floor. See what's so special about the Shabby Chicken...it's not too shabby after all........read more

2 Bedrooms - Sleeps 5
Condo in Key West

Key West Condo 4.7 Star Review

Enjoy the comforts of home in the midst of paradise.

Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet service. The unit is on the 3rd floor, accessible by elevator. Has completely equipped kitche.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 5.0 Star Review

Stay at Key West and have the time of your life, and do so at a significant discount.

Atlantic ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium offering a master suite with king bed and adjoining bath with walk-in shower and jetted tub, and guest bedroom with queen bed and full b.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo

Tropical Key West welcomes you to a classic Florida condominium, offering a one bedroom unit with plush queen bed, fully equipped kitchen, dining area, seating area with TV, stereo and DVD player, and private balcony with pool or harbor views. Amenities include: onsite washer and dryer, coffeemaker, ceiling fans and wireless Internet access for a n.......read more

1 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 2.5 Star Review

Welcome to Hyatt Residence Club Key West, Beach House. We believe great destinations in Key West should offer more than a good night's sleep, and we take pride in offering you the best of everything -- a great location, luxurious rooms and unparalleled service. Whether your stay in Key West is for business or pleasure, it should be a worry-free exp.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West House boat 4.6 Star Review

*Our business model has changed. We are excited to share our moorings at North Fleming Key for the Adventurous vacationers.”

Plan for your fall and winter adventure reservations starting now!

Have you ever wanted to get away from it all and be in a very basic and simple natural environment? This is it- just like CAMPING or Glampi.......read more

2 Bedrooms - Sleeps 4
House boat in Key West

Key West Vacation Rental 4.6 Star Review

Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool.
The home has is well stocked with towels, bedding and house hold appliances and blow dryer.
This .......read more

3 Bedrooms - Sleeps 5
Vacation Rental Home in Key West

Key West Condo 4.9 Star Review

Give me a call if you have any questions!
702-232-3750

Welcome to your home away from home and enter through the canopy of trees to the secure, patrolled Shipyard Condominium's in the desirable Truman Annex Complex. Professionally designed to maximize relaxation and encourage adventure. Beautiful
Relax on the balcony with your gl.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 4.7 Star Review

OVERVIEW
The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as having “an open, crisp, private space”. The house has two (2) gabled ceilings, which creates a contemporary, spacious living environment. The downstairs floor is Golden Oak Pergo. All window, door, and floor trim is.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Key West

Key West Condo

These are 7-night rentals, with check-in on Saturdays only.

Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort's observation deck gu.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 5.0 Star Review

Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's throw away from the pulsating rhythm of Duval Street and the island's most mesmerizing beaches; Petite Pearl is your sanctuary for the perfect blend of thrill and tranquility.

As you cross the threshold, you're welcomed by a c.......read more

1 Bedrooms - Sleeps 2
Condo in Key West

Key West Vacation Rental

The k2 escape is the very best in indoor/ outdoor living. The full size heated pool is surrounded by lush mature tropical landscaping with your very own backyard poolside sandy beach. Tiki hut bar, outside cabana living room, zen outdoor shower and sun deck enhance this Centrally located Key West retreat. Including a Weber grill, Bose outdoor speak.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo

Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down and forget the rush and stress of your day-to-day life. Bask beside the lushly landscaped pool that gives you the illusion that you’re softly floating on the open sea, gra.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Apartment 4.9 Star Review

Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and shower, complete kitchen with refrigerator, stove, and s.......read more

1 Bedrooms - Sleeps 4
Apartment in Key West

Key West Vacation Rental

A 3/2 home in the historic district of Old Town Key West. Walk to Duval, but nestled in a quiet neighborhood next to St. Mary Star of the Sea. Each bedroom features a private balcony. We believe the house was built in the late 1800’s. It was moved in the 30’s when the land it sat on was taken for use by the Navy. The land it originally sat on .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental

Perfect for the whole family, enjoy your stay on Von Phister St! Enjoy sunny Key West from our bright and spacious home from the rocking chairs on the front porch or the heated pool in the backyard. Close to the beach and White Street Pier, you can easily have the perfect beach day followed by ice-cream at the towns staple, Dairy Queen. Experience .......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time. But when you rent this Heavenly Hideout at Key West Mile Marker Zero - Rainbow’s End, you’re spot on, and you can do exactly that.

This penthouse hideout is liter.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo 4.5 Star Review

Sunrise Suite 203 is a quiet alternative to the bustling noise of downtown Key West. Located just a 10-minute drive from all of the nightlife, shopping, restaurants, and activities of world-famous Duval Street, Sunrise Suite is your own private condo in our island paradise. You will enjoy the conveniences of a hotel with the comforts and space of h.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental

Located on the corner point of Olivia & Packer streets in Old Town, this recently renovated home has been transformed into a sharply modern, custom designed 2 Bedroom, 2 Full Bath showpiece. Enjoy a rare covered carport for off-street parking. Dramatic woodwork marries linear lighting to create a stunning open living room & kitchen entertainment sp.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 5.0 Star Review

Monthly rental, makes island living easy. It's a spacious, warm, and inviting one bedroom unit in a four unit building, much larger than many other one bedroom homes in Key West. The home is located at the edge of Old Town near the Casa Marina District, close to Higgs Beach on the Atlantic, Southernmost Point, and Duval Street. It's a great locatio.......read more

1 Bedrooms - Sleeps 2
Condo in Key West

Key West Vacation Rental 5.0 Star Review

Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom Balinese style home . The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classi.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

REMARKABLE GEM JUST OFF DUVAL ST!
Get lost in this impressive retreat, uniquely designed to capture the true essence of island life within an elegant and upscale setting. A sweet surprise just off Duval St, this lavish and newly renovated creation is perfectly located making this an unmatched Key West escape. Unlike any other home, enjoy your o.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon. Enjoy alfresco dining in the tropical gardens while you enjoy the wonderful weather that Key West offers!!

The Carriage House building at the Hollinsed House 1st Floor - "Poolside Sui.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Cabin 4.7 Star Review

Welcome to sweet paradise! Located pn Petronia Street, the Orange Blossom Suite is in close proximity to all the fun-filled action of Duval St; however, it is private enough to not hear any of it! Orange Blossom Suite shares a huge back patio with one other suite (Deckside Suite; managed by us), and BBQ grill. Walk to fine dining or cook your ow.......read more

1 Bedrooms - Sleeps 4
Cabin in Key West

Key West Condo 4.7 Star Review

Discover paradise of Key West in a distinctive setting. Luxury, two-bedroom, two-bath, (sleeps 6) condominium set in a tropical garden with sweeping balconies. Located on Smather's Beach. Your vacation hideaway is decorated in authentic island tradition with fully-equipped kitchen, living room and dining area. Two large bedrooms with king beds a.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 5.0 Star Review

We are Craig & Cindy and we thank you for inquiring about our Truman Annex Key West vacation homes. Truman Annex is ideally located in 'Old Town' Key West and is an easy walk to all the fun in Key West, from the Mallory Square Sunset Festival to Ft. Zach Beach to the Truman Waterfront Park to Duval Street (restaurants, nightclubs and shopping) to .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Cottage 4.9 Star Review

This historic Conch house is an excellent vacation home which has been thoughtfully remodeled to provide the best in modern comfort, while carefully preserving the home's historic Key West architecture. There are antique Dade County pine walls and floors throughout the cottage. The open-concept kitchen, living room, and dining area have fantastic 1.......read more

2 Bedrooms - Sleeps 6
Cottage in Key West

Key West Vacation Rental 5.0 Star Review

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: Step inside the white picket fence and enjoy your private escape. Surrounded by lush greenery and palm trees, this home with modern amenities is tucked into a charming, historic neighborhood. From here you c.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Cottage 5.0 Star Review

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: This home’s white picket fence and rocking chair front porch beckon you to come inside. Explore the uniqueness of this updated property including its location in Bahama Village, private pool, and pool hous.......read more

2 Bedrooms - Sleeps 4
Cottage in Key West

Key West Vacation Rental 4.9 Star Review

THE PROPERTY: This comfortably furnished duplex home comes with Key West charm and contemporary touches. Walkable to many shops and attractions, you will feel like a local in no time. Only two blocks to Duval Street, you can relax and enjoy your time here, whether you select the upper or lower floor of this home.

The entire house includes a.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

THE PROPERTY: Enjoy fresh air and sunshine from your front porch, private pool or hot tub at Casablanca Grande. You are not far from the excitement of Duval Street in this home but far enough away to enjoy peace and quiet. This home consists of BOTH sides of a duplex.

This duplex is unpretentious and comfortably furnished. There is sleeping .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: This family-friendly, canal-front cottage is perfect for a relaxing old world getaway. Located in an upscale area of New Town and just a 10-minute Uber ride to Old Town, you can enjoy the hustle and bustle o.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.6 Star Review

Beautiful townhome in the gated community of Coral Hammock. Located across the street from the Key West Golf Club, and only a few minutes from deep sea fishing, boat rentals, sandy beaches, shopping, restaurants, and exciting Duval Street. Great place to relax after seeing the sights of Key West.

This unit has three bedrooms, master bedroom .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Condo 5.0 Star Review

3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in shower. The other 2 bedrooms have queen size beds .......read more

3 Bedrooms - Sleeps 8
Condo in Key West

Key West Cottage 4.9 Star Review

THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip in your pool. Whether you lounge in the cabana or enjoy dinner under the stars, this home has it all! Close to the sights and sounds of Duval Street yet quietly surrounded by Bougainvillea and palm trees, you will love this locati.......read more

4 Bedrooms - Sleeps 8
Cottage in Key West

Key West Condo 5.0 Star Review

This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the length of the unit. The unit is tiled throughout with a full size fully equipped eat in Kitchen. There is also a full size washer dryer for your convenience. Both bedrooms and the living room have TV's. There is an extensive dining are.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.7 Star Review

Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious walk in shower. King size bed with a flat screen TV .......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 5.0 Star Review

THE PROPERTY: Walkable to Duval Street, the Truman Suites collection is comprised of two homes. One home includes four, 1 or 2- bedroom suites: Bess, Harry, Margaret, and Martha. The Harry and the Margaret suites are on the first floor and the Bess, and the Martha suites are on the second floor of the home. The second home, John Truman’s Hideaway.......read more

7 Bedrooms - Sleeps 18
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

THE PROPERTY: Enjoy the walkable location of this charming property. As you enter the home from its covered rocking chair front porch, you are in the open concept living room and kitchen. The compact kitchen with peninsula seating is equipped with everything you need to prepare meals or snacks. The living room is comfortably furnished, including a .......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an extra large floor plan with a nice ocean view.
This property features 2 queen beds in the master bedroom and a king in the guest bedroom. Full size washer/ dryer and 1 assigned private parking space. High speed wireless intern.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 4.6 Star Review

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: As you enter the carport and begin to unwind, you will be greeted by beautiful porches and tropical greenery. Drop your luggage at the door and go for a swim. Around back, a private pool with waterfall featu.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

THE PROPERTY: This one bedroom, one bath, first-floor duplex is conveniently located in Old Town. Walkable to so many Key West activities, you won’t need a car, just a pair of sandals or a bicycle. Tucked down a quiet lane, this casual home is comfortably furnished. It sits just a block and a half from Duval Street yet it’s oh so tranquil. As y.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Condo 4.5 Star Review

2 Bedroom Garden-View Condo at 1800 Atlantic Key West
with king in the Master bedroom, queen in the guest bedroom and a queen sleeper sofa in the living room. Beautifully renovated custom kitchen in the fall of 2017. Granite counters, Enjoy the many upgrades in this fine unit. Commercial grade sleeper sofa for your added comfort.

Flat sc.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 5.0 Star Review

THE PROPERTY: If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. As you enter your portal to paradise via the custom iron gecko gate, you will immediately feel as if you have left all your cares behind. You will be greeted by the home's stunning French doors, pool, lounge area and second story.......read more

3 Bedrooms - Sleeps 7
Vacation Rental Home in Key West

Key West Condo 4.7 Star Review

The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very beautiful. The decor is everything you would desire in a Key West accommodation: tropical, clean lines and filled with every need possible.

This Unit was built for the Developer and is unique with many extra features which i.......read more

3 Bedrooms - Sleeps 10
Condo in Key West

Key West Condo 4.8 Star Review

Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the comforts of home with a fab
Key West is a playgro.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.6 Star Review

Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open onto the 40 ft private balcony that has views of the nature preserve and Atlantic ocean. Fully equipped with all the modern conveniences you would need for an enjoyable vacation. This unit is set up with a King bed in each bedroom .......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 5.0 Star Review

This is a beautifully renovated high end luxurious monthly rental at 1800 Atlantic. The moment you walk in you will appreciate the attention to detail. Enjoy the lovely views of the complex and Atlantic ocean from the private balcony. The master bedroom suite has a king size bed. The renovated bathroom features a large walk in shower and double v.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 4.8 Star Review

THE PROPERTY: This comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches. To explore the first-floor home, search for “Poinciana Garden” or book “Poinciana Paradise” to reserve the entire home for family or friends.

Walkable to many shops and attractions, you will feel like a local in no t.......read more

1 Bedrooms - Sleeps 3
Vacation Rental Home in Key West

Key West Condo 4.9 Star Review

WEEKLY RENTAL: This property has a 7 night minimum stay.

THE PROPERTY: This 2-bedroom 1 bathroom condo with an oversized shared pool is a wonderful place to kick back and relax after exploring the island. Located near the excitement of Duval Street yet tucked back near the water, this tree-lined community is in a perfect location. For histo.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 5.0 Star Review

THE PROPERTIES: With plenty of space in an ideal location, Maisons de Luxe combines a large two-story home with a stylish two-story cottage. Family, friends, or wedding guests will appreciate being together yet apart in this smart setting. If you need less space than Maisons de Luxe offers, each property may be rented separately.

GRAND MAIS.......read more

6 Bedrooms - Sleeps 12
Vacation Rental Home in Key West

Key West Condo 4.3 Star Review

The Grand Vista - 2 bedroom suite - Totally renovated in 2022 - pictures coming soon.

2 Bedroom 2 bath suite, some renovations with flat screen plasma TV's in both bedrooms and the living room. , King bed in the Master bedroom, king in the guest bedroom and a queen sleeper sofa in the living room. Full size fully equipped eat in kitchen, .......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.0 Star Review

This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through breeze and expansive views of the tropical courtyard.
As assigned private parking space will convey with your rental. You can feel secure in our fortress or a property.
Key West is an Island with so much to offer, perfect for .......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.8 Star Review

This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you would need. Both bedrooms and the living room have sliding glass doors that open onto an extensive private balcony with the best view in Key West. You can lie in bed and watch the sunrise from your unit.
Both batrhooms and the ki.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 4.8 Star Review

Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the master bedroom, 2 twins in the guest bedroom (which can also be converted to a King bed upon request) and a queen sleeper sofa in the living room.

Anchor Drop is beautifully renovated and decorated by an interior designer. Cu.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Apartment 4.0 Star Review

You will love this quiet tree-top studio in the heart of Old Town Key West. Located just a block away from the Historic Light house and Hemingway house and very close to Duval Street. This is a cosy studio ideal for one person or a couple looking for a reasonable Key West get-away. There is internet access and satellite TV. Parking is on street. Th.......read more

Studio - Sleeps 2
Apartment in Key West

Key West Vacation Rental 4.9 Star Review

THE PROPERTY: This home’s Key West charm and modern amenities make for a wonderful stay. From the Adirondack chair front porch to the private backyard pool, you will quickly fall into the island vibe in this home. A mix of historic Dade County pine and gentle white walls adds to the allure of this home.

As you enter the first floor and lo.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

THE PROPERTY: Walkable to Duval Street, the Martha Truman is on the second floor, in the back of the building, away from the street. The suites that comprise the Truman Suites collection can be booked individually or together for larger groups. The property is ideally located only half a block to Duval Street, where it all happens. It is close to m.......read more

1 Bedrooms - Sleeps 3
Vacation Rental Home in Key West

Key West Condo 4.7 Star Review

Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated bathrooms. Master bathroom has a tub and walk in shower.
There is a king in the master bedroom, a queen and twin in the guest bedroom and a queen sleeper sofa in the living room. Both bedrooms and the living room open on to th.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 4.7 Star Review

THE PROPERTY: Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too. This unpretentious home has been beautifully updated and is ready to welcome you. The living room looks out to the covered front porch and has lots of natural light, large screen, TV, cool wall AC and a comfy slip-covered sofa. The room is adorne.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

THE PROPERTY: By bringing the outdoors in, this home allows you to live like a true Floridian. The fenced yard provides you with privacy to enjoy your pool. Sun yourself on the lounge chairs or dine under the stars. And if that isn’t enough, you can enjoy life on the lanai. Read a book, take a nap, or keep an eye on the kiddos while they splash i.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Condo 4.7 Star Review

Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors. "Moonlight" is located in an upscale private community within walking or bikin.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 4.8 Star Review

THE PROPERTY: This comfortably furnished first-floor duplex home comes with Key West charm and contemporary touches. To explore the second-floor home, search for “Poinciana Treetop,” or book “Poinciana Paradise” to reserve the entire home for family or friends.

Walkable to many shops and attractions, you will feel like a local in no .......read more

1 Bedrooms - Sleeps 3
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offers a full size fully equipped Kitchen, Washer/dryer, 2 bedrooms and 2 bathrooms. Both bedrooms and the living room open onto a 40 ft private balcony with views of the Tropical Gardens.
The master bedroom has a queen bedroom, th.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 4.1 Star Review

Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to your private balcony with great views of the property and Atlantic Ocean. The Owners are fishing enthusiasts as you will see when you relax in the comforts of home away from home.
King in master, 2 twins in guest and a sleeper .......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.8 Star Review

WEEKLY RENTAL: This property has a 7 night minimum stay.

THE PROPERTY: As you open the white picket gate to this three-story townhouse, your tropical courtyard and outdoor dining area will delight you. Through the oversized French doors with transoms, you will find your living room, dining area, updated kitchen and half bath. This home ha.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 4.9 Star Review

THE PROPERTY: An open staircase leading to the second floor is where your vacation begins! The reverse floor plan, tres chic décor, and open living room with vaulted ceiling are dazzling. Relax and mingle with guests in this beautiful, functional space. The petite yet mighty eat-in kitchen is equipped with stainless steel appliances and everything.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 4.4 Star Review

Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has a new King in the master suite, brand new king in the guest bedroom and a queen sleeper sofa in the living room. The property has a Mexican tile floor in the living area's adding to the Island feel. Newly renovated kitchen in 20.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.7 Star Review

Lovely, quiet two bedrom two bath garden-view unit, located very close to the pool. The unit is tiled throughout. Both bedrooms and the living room open on to a beautiful private balcony overlooking the tropical courtyard and gardens. King in the master bedroom,queen in the guest bedroom and two inner spring roll-away for extra guests. There is a f.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.8 Star Review

Casa Coastal East – C231
After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its new owners. From new interior design work and furnishings, courtesy of Royal Furniture of Key West, to new closets, drapes and local art, includes works from the gallery of Alan Maltz, the tranquility of the Keys begins the mi.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 4.7 Star Review

THE PROPERTY: The Margaret Truman Suite is on the first floor, in the back of the building, away from the street. The suites that comprise the Truman Suites collection can be booked individually or together for larger groups. This property is located a half block from Duval Street and is close to many attractions, including the Lighthouse, Southern.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: Enjoy beverages on the balconies or a splash in the pool, as you being to unwind and enjoy your vacation. Filled with sunshine and happiness, this two-story pink gem provides space and privacy for families o.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

THE PROPERTY: Between the welcoming front porch and the private pool, you will be sure to enjoy fresh air and sunshine during your stay. This unpretentious home is comfortably furnished and ready to welcome you and your fur baby. The living room looks out to the covered front porch and has lots of natural light. Wall AC, TV, a queen sleeper sofa, a.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 4.6 Star Review

Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the master bedroom, 2 twins in the guest bedroom and a queen size sleeper sofa in the living room.. Totally renovated fall of 2017, Custom Kitchen and bathrooms. Tiled throughout.

All new beds. Master bedroom has a king, the g.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Apartment 4.9 Star Review

THE PROPERTY: The Harry Truman Suite is on the first floor, in the front of the building. The suites that comprise the Truman Suites collection can be booked individually or together for larger groups. The property is ideally located only a half block to Duval Street. It is also close to many attractions and walkable to the Lighthouse, Southernmost.......read more

2 Bedrooms - Sleeps 5
Apartment in Key West

Key West Vacation Rental 4.7 Star Review

THE PROPERTY: Walkable to Duval Street, the Bess Truman Suite is on the second floor, in the front of the building. The suites that comprise the Truman Suites collection can be booked individually or together for larger groups. The property is ideally located only a half block to Duval Street. It is also close to many attractions and walkable to th.......read more

1 Bedrooms - Sleeps 3
Vacation Rental Home in Key West

Key West Apartment 3.8 Star Review

This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer.

Quaint and charming, with a view of the famous Key West Lighthouse from the front of the.......read more

2 Bedrooms - Sleeps 4
Apartment in Key West

Key West Vacation Rental 4.8 Star Review

THE PROPERTY: Bohemian bits indoors and lush landscaping outdoors will give you that tropical island feeling you are looking for. Warm wood tones and exposed beams can be found in the main living area. The family room with sofa, chair, and TV is open to the kitchen and dining areas. A wooden island with seating is the perfect place to enjoy a snack.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

THE PROPERTY: Nancy & Carl invite you to share their love of the island in their enchanted 3-bedroom home. Live like a local in this unique Key West property. Designed for relaxation and indoor-outdoor living, this home exudes local architecture, art, and joie de vivre. From its welcoming front porch to its private back yard, you will know from the.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: Dreaming of putting your toes in the sand or sipping coffee on your dock? Then this is the vacation home for you! The lush backyard is gated and leads out to the warm Gulf of Mexico. Just steps from the wate.......read more

3 Bedrooms - Sleeps 7
Vacation Rental Home in Key West

Key West Vacation Rental 4.6 Star Review

PERFECT GETAWAY JUST STEPS FROM DUVAL...
Private family home with poolside cottage totals three bedrooms and three full bathrooms. Enjoy this spacious home and great outdoor pool and dining area where you can take advantage of the unbeatable Key West tropical surroundings.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS AND A.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Condo 4.7 Star Review

Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from your fabulous private balcony.

There is wireless internet. Full kitchen and Washer/Dryer. This unit is good value.

The property is available for rent from May until January each year, owned by one of the complex's or.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 4.6 Star Review

Casa Papa Del Mar
Two Bedroom Premiere Ocean View
With a complete 2023 renovation, the décor is inspired by the life and travels of “Papa” Earnest Hemingway.
This is a beautiful top floor two-bedroom ocean-view unit at 1800 Atlantic condos. It has pristine ocean-views from all rooms where sliding glass doors open on to your own 50 .......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.9 Star Review

This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic heated pool and gigantic hot tub right on the Ocean........read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 4.8 Star Review

PERFECTLY located, 100 y-o "Conch" House, w AAA+ front-porch, and 3 full baths to go w 3 BRs... brand-new kitchen, completely renovated since 2015... outstanding back yard w gas grill.... house and yard are enclosed by barrier of FL palms, for privacy... 4 blocks from the historic and delicious "Blue Heaven", where Hemingway boxed, and 4 blocks fro.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Newer home, 4 bedroom, 3 full baths. Oceanfront property with sea wall, with swim ladder so you can enjoy a swim in the canal. Sunbath on this beautifully landscaped home, with palm trees and a key lime tree to pick some fresh key limes. Close to beaches , restaurants and the key west golf course. Well behaved pets always welcomed! This home slee.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.6 Star Review

STUNNING KEY WEST RETREAT…
Just renovated, this island gem exudes the utmost island spirit with authentic historic character. Meticulously preserved with the finest of luxuries, the blissful functionality of this home exceeds a standard of excellence that cannot be missed.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS & .......read more

3 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

Spacious 1 bedroom. 1st floor in Old Town. Only 2 other condos in compound. On desirable Frances Street, just 3 blocks from seaport, 5 blocks to Duval. Granite kitchen, Washer/Dryer, outdoor propane grill, travertine floors, tiled shower, central AC, large screenT.V., bedroom T.V, WiFi. Fully furnished. Walk out of multiple french doors to la.......read more

1 Bedrooms - Sleeps 2
Condo in Key West

Key West Condo 4.8 Star Review

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom villa is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.

The number one reason why peo.......read more

1 Bedrooms - Sleeps 4
Condo in Key West

Key West Condo 3.5 Star Review

2 bedroom 2 bathroom luxurious waterfront condominium located at Sunset Marina Waterfront Residences. Sunset Marina is an exclusive gated community with a state of the art concrete floating dock system and has a 6' controlled depth. The Gulf is located right outside the property with immediate access to the Atlantic. Take in Key West World Famous S.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 4.6 Star Review

If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace right across the street from the beach. Make yo.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, it soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites. The Cuban Club Suite stands as an award-.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo

*BRAND NEW LISTING* 'Summer Breeze' will make you and your family feel fine! This is a gorgeous, clean, upgraded, top floor, 2/2 condo, with a spectacular view! Common pool, grill area, tennis court and a nice friendly atmosphere will make you and your family happy to have chosen this great property. Smathers Beach is across the street, Higgs Be.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental

Searching for the perfect vacation home away from it all? Your hunt ends in here! A Wave from it All is a recently remodeled and tastefully decorated 2-story townhome with its own private pool that epitomizes island living at its finest while offering all the comforts of home. Best of all, this home is nestled in the Truman Annex, a palm tree lined.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.3 Star Review

CLASSIC OLD KEY WEST HOME...
This home is boasting a rare combination of location and character. A mix of historic details and modern charm are evident throughout. Perfect for couples traveling together or those who have visitors during their stay in Paradise.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS AND AMENITIES...........read more

2 Bedrooms - Sleeps 7
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

When you think of Key West, you think of spending relaxing days with your toes in the sand under the palm trees, and fun-filled nights walking through the Streets of Old Town on your way to catch the sunset at Mallory Square. Experience .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

FRESH! FRESH! FRESH! Everything in this house is brand NEW and clean from linens, bed spreads, furniture, and the paint to name a few!

Looking for a vacation get away? A home away from home? This 1400 square foot, gorgeous water front stilt house gives you plenty of room to relax, have fun and most importantly right now social distance. N.......read more

3 Bedrooms - Sleeps 9
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful gated Truman Annex community. It’s close to all the major attractions yet just far enough away to be quiet and relaxing. Duval Street, the center of it all, is just two blocks way. The nightly Sunset Celebration at Mallory Sq.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 4.0 Star Review

So Close to Everything in Old Town but far enough away to be able to relax on quiet on one of the best Streets in Key West. Private Pool Separate kitchen and guest house. A special home for a special vacation........read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.5 Star Review

Located at the artsy 1200 block of world famous Duval Street, Mermaid Cove is the ideal affordable getaway for your Key West vacation. You are in the heart of historic Old Town Key West, where an eclectic mix of restaurants, art galleries, beaches, bars, museums, and night life are within walking or biking distance. Out the front door is Banana Caf.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Condo 5.0 Star Review

NEW LISTING APRIL 2022!

Welcome to Latitude Adjustment located in the Truman Annex Shipyard just steps from beaches, restaurants & bars, Key West Ampitheater, Southernmost Point, Hemingway House and so much more!

Recently renovated and many upgrades throughout this condo is designed for a turnkey home away from home! Luxe finishing su.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental

A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at the Bight Harbor Marina! Perfect getaway for up to 4 people in a comfortable townhouse, including all amenities. This 2 bedroom, 1.5 bathroom newly refurbished unit, is full of "Conch" charm and authentic Key West feel........read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

A colorful three bedroom, two full bath, private, and historic home is a wonderful spot to vacation, live like a local, honeymoon, or work from home. Tucked quietly on a lazy lane 2 blocks from world famous Duval Street! You will be just around the corner to The Hemingway House , famous Blue Heaven Restaurant and the Key West Lighthouse.
Our .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Summary:
Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps from the beach as well as the Southernmost Point of the continental USA. Turquoise blue waters await you on the rooftop sundeck - perfect for tanning, reading and sipping your morning coffee. Relax under the southernmost stars or .......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

A FEAST FOR THE EYES…
This exquisite 3 bedroom, 3 bath abode will delight your artistic senses with its gorgeous interior and lush outside spaces. Owned by a renowned London-based designer, this worldly and sophisticated showpiece home displays amazing attention to detail and has been fully renovated and restored for your pleasure. This is a f.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Condo 5.0 Star Review

Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common area with queen size pullout couch. Hotel style accommodations with cleaning services mid week.

Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perfectly situated on the western side.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo

Time to chill at the perfect a beer or glass of wine at the bar directly on the water with canal views. Just a mile from Key West International Airport, 3 miles from vibrant Duval Street, and 4 miles from historic and majestic Mallory Square, Coconut Mallory has the perfect location for that incredible south Florida experience. This two bedroom, t.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.8 Star Review

Please choose a Saturday check-in, all rentals will be in seven night increments.

Thank you for your interest in booking with Dash Realty Group, Windermere Florida.
Dash Realty Group is registered in Florida as a licensed Fla. Seller of Travel Ref. No. ST42435.

Overlooking the Gulf of Mexico in historic Old Town, The Galleon Reso.......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo 4.8 Star Review

Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 baths and private patio with tropical views. Amenities include: Central AC, Dishwasher, Washer/Dryer, Color Cable TV, VCR, CD Player, Ceiling Fans, Sleeper Sofa, Community Pool, Sleeper Sofa, Full Kitchen,

This and.......read more

2 Bedrooms - Sleeps 5
Condo in Key West

Key West Vacation Rental 4.3 Star Review

On the entire island of Key West there are fewer than 50 private homes on open water and only a few with their own private dock. Enjoy kayaking the crystal clear waters or relax in the private heated pool during the day, watch the sunset from the new dock and then enjoy the fine restaurants and Key West nightlife. Our renovated Gulf front, Key West.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

Built in 1917 as a “club” for Cuban cigar makers and their families as their home away from home, it soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites.

Escape the stress and cares of yo.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

If Cleopatra and Anthony had dreamed of a Key West hideaway, this spacious three bedroom, three bath “Royal Escape” would have been it!  In keeping with its name and royal lineage, the Royal Escape is located in the prestigious Casa Marina district within walking distance to both beaches and Duval Street. It offers tropical seclusion and easy .......read more

3 Bedrooms - Sleeps 10
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Fleming-O (pronounced “Flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and only two blocks from world famous Duval Street and its restaurants, bars, art galleries, and shops. This completely upgraded Conch Cottage has all the modern amenities you would expect. The contemporary kitchen with a cathedral.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Cottage 4.7 Star Review

We have a wonderful MONTHLY rental to offer you: an historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV, this intimate house boasts many fun and thoughtful features which will help make your stay in Key West special. It is located in a wonderfully private yet centra.......read more

4 Bedrooms - Sleeps 6
Cottage in Key West

Key West Condo 5.0 Star Review

This is for A WEEK'S Stay Only in a 2 Bedroom 2 Bathroom Villa for 6 People.

Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and beautiful contemporary design creates an environment of relaxation and restoration.
Guests are encouraged to slow down and relax, to dip into .......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 4.3 Star Review

The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded and private. The raised vaulted ceiling creates an open living environment. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Cottage 4.6 Star Review

Key West cottage architecture has been thoroughly "time-tested" in "island life and culture" in this somewhat infamous little wooden "cigar maker's" cottage located on famous Duval Street, at the "classier upper-end." Since its original construction in the early 1900's this note-worthy Cockadoodle Cottage vacation rental has been recreated, redesig.......read more

2 Bedrooms - Sleeps 6
Cottage in Key West

Key West Apartment 4.8 Star Review

This property recently fully renovated. Original house was built in 1892. 1 bedroom 1 bathroom apartment with hardwood flooring, high ceilings, gourmet kitchen ,beautiful island decor and great porch located on the White Street.
Just few steps away from the best Cuban coffee shop in Key West and walking distance from beach.
Apartment is full.......read more

1 Bedrooms - Sleeps 3
Apartment in Key West

Key West Vacation Rental 4.2 Star Review

Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and all that Key West has to offer. .......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Apartment 4.5 Star Review

Summary:
Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Collins offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balcony overlooking Duval Street you can be as much connected to or above the action as your whim de.......read more

2 Bedrooms - Sleeps 10
Apartment in Key West

Key West Apartment 4.9 Star Review

Summary:
Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This unique property offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balcony overlooking Duval Street you can be as much apart or above the action as you desire.......read more

2 Bedrooms - Sleeps 8
Apartment in Key West

Key West Vacation Rental

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

THE GILDED PINEAPPLE is a classic Key West home located on one of the most desirable streets in Old Town. This completely renovated, historic home gets its’ name from the elegant, oversized golden door knocker shaped like a pineapple t.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental

Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excitement of tropical adventures. This enchanting 3 bedroom, 3.5 bathroom monthly vacation rental offers a serene retreat amidst the vibrant atmosphere of the island, ensuring an unforgettable experience for you and your loved ones.read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental

Summary:
- "Lil Bit" is a rare find in the historic Bahama Village neighborhood.
- This historic beach home is modern and renovated to have an elevated feel but the charm and character of old Key West.
- Perfect for a couple or visitors looking for a monthly stay, this home is equipped with everything you should need.
- While it is a.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 4.7 Star Review

Tucked among a colony of freestanding Conch style cottages, amid lush tropical landscaping, sits the newly renovated Hidden Oasis. Features of this property include a private bedroom with king bed, full kitchen, living room with queen sleeper sofa, cable TV, gas BBQ grill, shaded private deck with outdoor dining, and poolside location at a great n.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

OVERVIEW
The Cigar House is a 100+ year old“Cigar maker’s house”. The recently completely renovated house is charming, spacious, secluded and private. The cottage has a raised vaulted wood ceiling, creating a rustic, Caribbean ambiance. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of t.......read more

3 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Hotel resort

Beautiful resort property with waterfront tiki bar to enjoy wonderful drinks and food made fresh, swimming pool with sand beach and private cabanas, hot tub, private screened porch in each unit, grill area for grilling your fresh catch, private parking, pier for relaxing or parking your boat, quiet resort, fishing pier.......read more

2 Bedrooms - Sleeps 6
Hotel resort in Key West

Key West Villa 4.7 Star Review

READ ADDITIONAL REVIEWS & 20% discount for 2023 only -I will deduct it from vrbo quote-Old Town -Whitehead St- BEST LOCATION -On Whitehead St. -Steps to Duval -Sleeps 7 Walk a few blocks to new Truman Annex water park & Ft Zach Beach or FREE community pool 4 blocks..OUTSIDE SHOWER.. As seen in the March 2015 issue of Island Jane Magazine, this Hemi.......read more

3 Bedrooms - Sleeps 6
Villa in Key West

Key West Vacation Rental 4.9 Star Review

Beautiful 3 bedroom, 2 bath home with den. Canal-front with included boat dockage, private backyard and a large swim spa. Den can be closed off for 4th bedroom. Internet included along with central AC, Direct TV, linens and checkout cleaning. Only minutes from Key West. 50' Dock. Great for boating or exploring the wonderful area of Key West. read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild rooster. After a morning stroll, you are ready to enjoy an alfresco breakfast that was just created in your new kitchen. Sit back, relax, you are now on Key West time!
This 2 bedroom 2.5 bath townhouse is prepared to meet your v.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 5.0 Star Review

Book it before it's gone! 7 Day rental - available from Saturday 4/27/24 to Saturday 5/4/24 only.

Cozy and comfortable 1 BR efficiency condo at the spectacular Coconut Beach Resort! Enjoy the lap of luxury at this private Timeshare property in beautiful Key West, located along the southern coast of the island. With its private beach, large .......read more

1 Bedrooms - Sleeps 2
Condo in Key West

Key West Vacation Rental 5.0 Star Review

Welcome to Key West Oasis! This beautiful and sophisticated estate checks all the boxes and is located on one of the most exclusive lanes in Truman Annex.
Meticulously maintained, immaculate inside and out this 5-bedroom 5.5-bathroom estate welcomes guests who seek a Key West experience like no other.
Positioned on a 4,700 sq foot lot that .......read more

5 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental

Welcome to SOUTHERNMOST SUNSHINE!

Located in the heart of Old Town Key West just a few steps away from the Atlantic Ocean, Southernmost Point and 1 block to Duval Street.

It doesn’t get any better than this 4 bedroom / 3 bathroom 1938 fully restored historical home.

When you arrive the home you are greeted with picturesque.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a modern kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in closet, a private bath with a large s.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.6 Star Review

Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon. Enjoy alfresco dining in the tropical gardens while you enjoy the wonderful weather that Key West offers!!

The Hollinsed House's 1st Floor - "ShangriLa Suite" is a large deluxe studio.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Condo

Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close to all the action & far enough away to enjoy a quiet getaway. Get comfortable in this clean & comfy home, which offers two private balconies, updated kitchen & modern bath. Desirable Southard Square is surrounded by tranquil tropical gardens & a he.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 4.0 Star Review

CLOSE TO PERFECT, far from normal! This stunning 2 bedroom, 2.5 bathroom townhouse with private pool will check all the boxes for your favorite home away from home!

Located on the Key West Golf Club just 5 miles to downtown Close to Perfect offers a spacious open floor plan. It was recently remodeled and was beautifully furnished for guest.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo

Book it before it's gone! 7 day rental - available from Saturday 11/16/24 to Saturday 11/23/24 only.

Cozy and comfortable 1 BR efficiency condo at the spectacular Coconut Beach Resort! Enjoy the lap of luxury at this private Timeshare property in beautiful Key West, located along the southern coast of the island. With its private beach, lar.......read more

1 Bedrooms - Sleeps 2
Condo in Key West

Key West Vacation Rental 4.8 Star Review

Welcome to Fairway Villa a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course.

This one of a kind floor plan that is spacious and newly remodeled and furnished to perfection! A coveted corner unit with large fenced yard and private pool overlooking the Golf Course 2nd fairway.

Offering a turn key rental for .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Apartment

Location, Location!! Welcome to our Key West Condo! This beautiful Upper Duval condo is walkable to everything in Key West. Known as the "Uptown of Old Town Key West" and the "elegant end of Duval." What we love is that you can be in the excitement of Duval St, on South beach, at the Southernmost Point, or at the free MLK Pool, in just minutes .......read more

2 Bedrooms - Sleeps 6
Apartment in Key West

Key West Vacation Rental 5.0 Star Review

Our home is in Old Town Key West, within walking distance of Duval Street, White Street art galleries, restaurants, bars and Higgs Beach.
You’ll love our architect remodeled 100+ year old cottage with original details, open floor plan, high wood ceilings, rustic reclaimed white oak wood floors and large back yard oasis (rare for Old Town) w.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Key West

Key West Vacation Rental 5.0 Star Review

'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE Lane

This home is a perfect example of WHY people come to Key West to stay for a month or more! Live the island lifestyle outside enjoying the front porch, the second floor balcony, and the side lounge area with cocktail pool.

The weather in Key West is absolutely ama.......read more

4 Bedrooms - Sleeps 7
Vacation Rental Home in Key West

Key West Condo

Welcome to "Truman's Treasure," where you can fully embrace the vibrant and unique Key West lifestyle. This beautifully updated 2nd floor condo, though without an elevator, offers a cozy retreat nestled on the outskirts of Old Town. Truman's Treasure provides you with a central location that's close to Key West's finest beaches, renowned restaurant.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental 5.0 Star Review

This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on one of the best streets in Old Town you are just three blocks from the Harbor….home to the freshest seafood restaurants and best happy hours on the island…or walk to Duval street to experience the local music scene, bar hopping.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo 4.8 Star Review

Stunning, Modern 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completely renovated. Fully appointed, new kitchen with all new appliances, washer/dryer in unit, comfortable private back patio oasis with comfortable furniture for lounging and entertaining. and outdoor Shower. End unit, in a gated community. Conveni.......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Apartment 4.6 Star Review

This light and airy studio occupies the entire second floor of the Eyebrow House,featuring a sitting area with a queen sleeper sofa and a full kitchen with dishwasher. Enjoy a cocktail or gaze at the stars in the private hot tub on treetop deck. Completely equipped for your every need. Guest staying in this suite must be able to walk up a single fl.......read more

1 Bedrooms - Sleeps 4
Apartment in Key West

Key West House boat 4.3 Star Review

This is the prefect getaway to enjoy Key West .
You'll love this incredible and different experience.
Living on the water is ideal for adventurers who enjoy water activities, wildlife, & sunsets. The views of the water and mangroves are spectacular.
PLEASE READ THE ENTIRE DESCRIPTION. LIVING ON A BOAT MIGHT NOT BE RIGHT FOR YOUR GROUP.read more

1 Bedrooms - Sleeps 2
House boat in Key West

Key West Vacation Rental 5.0 Star Review

Welcome to 24 Beach Dr, a stunning waterfront property in the desirable community of Saddlebunch Key in Key West, Florida. This beautiful 2-bedroom, 2-bathroom home boasts breathtaking water views and is the perfect retreat for those seeking a peaceful, tropical getaway.

The interior of the home is a perfect blend of style and functionality,.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Key West

Key West Vacation Rental 4.9 Star Review

About this space
Atlantis House with just two exclusive rooms, the Master suite and the Garden suite, is the most private and romantic guesthouse in Key West. Rated a 2021 Travelers’ Choice Award by Trip Advisor. Perfect for Honeymoons and Anniversaries. A "little jewel" tucked away inside a lush tropical garden just steps away from the beache.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

Casa Loca is perfect for guests who want to enjoy the finest Key West has to offer! The perfect location, less than one block from Duval Street, this 3 bedroom, 2.5 bath house will amaze you with its extraordinary decor and attention to detail. Sit on the fabulous island style porch and enjoy the classic Key West scenery.

As you enter the ma.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Apartment 5.0 Star Review

Truman @ Duval - Unit E

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Enjoy central living in the heart of Key West at this studio walk-up. Ideally situated at the bustling intersection of Truman Ave. and Duval St., this cheery rental boasts wal.......read more

1 Bedrooms - Sleeps 2
Apartment in Key West

Key West Condo 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know yo.......read more

3 Bedrooms - Sleeps 6
Condo in Key West

Key West Vacation Rental 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

CARSTEN CONCH COTTAGE is a modern take on a Key West classic. This single story 2 bedroom cottage has all of the modern touches you’d hope to find in a vacation home while honoring the architectural history of the island. Whether you.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Key West

Key West Condo

PLEASE READ CAREFULLY BEFORE YOU EMAIL OWNER

This rental is for a 7 NIGHT HOLIDAY 1 week RENTAL ONLY!

This is for 7 nights Saturday to Saturday rental ONLY !! No alterations to the listed dates are available. MINIMUM RENTAL AGE is 25 years old. Maximum occupancy is for 6 people.

Coconut Beach Resort; a private quaint tropical .......read more

2 Bedrooms - Sleeps 6
Condo in Key West

Key West Condo

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

BACKCOUNTRY VIEWS is the ideal vacation setting for those looking to relax in a peaceful, tropically inspired condo that offers an incredible view of the water and breathtaking Key West sunsets. Located in the private gated community of .......read more

2 Bedrooms - Sleeps 4
Condo in Key West

Key West Vacation Rental

Experience Old Town Key West in a classic conch home! This home is only steps from shopping, restaurants, the historic seaport, beaches, and Duval! At the same time, it’s on one of the premier streets in Key West that allows for a private and a relaxing retreat.

This home is completely renovated, but maintains its classic Key West heritag.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Key West

Key West Vacation Rental 4.8 Star Review

Located in the Heart of Historic Old Town
Monthly Rental
Pet Friendly.  Up to 2 dogs, 40 lbs. max each.  
La Cala is a Newly Renovated Historic Home Situated on a Corner Lot within Walking Distance to Everything you want to See and Do in Key West!
1 Block off Caroline Street where you will Enjoy All of the Harbor Restaurants and ju.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Key West

Key West Condo 4.9 Star Review

ENTER YOUR GARDEN PARADISE...
Release your cares and bask in the beauty of this adults only, tropical inn of Travelers Palm with unique suites and studios, offering king beds, private baths and gorgeous garden views. You are only a relaxing three block stroll from all of the excitement of Duval Street, yet tucked away in a private setting that e.......read more

Studio - Sleeps 2
Condo in Key West

Key West Condo 4.7 Star Review

A GLORIOUS GARDEN AWAITS YOU...
A mere three blocks from all of the food, fun and shenanigans of Duval Street, yet tucked away in a serene and private setting that will soothe your traveler's soul, the adult only COCONUT PALM STUDIO within the Travelers Palm Inn welcomes you to unwind with everything two people need to be comfortable in paradise.......read more

Studio - Sleeps 2
Condo in Key West