Key West Vacation Rentals by Owner
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Vacation Rentals by Owner in Key West Florida -- We have partnered directly with a major provider for By Owner Rentals, and now have the selection and value to offer our visitors searching for places to rent in Florida.
Your Condo by the Beach with Ocean View
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 privately owned condo facing the ocean with a view of swaying palms and turquoise waters. The Jungle Breeze condo is the perfect getaway for a romantic cou.......
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
DETAILS AND AMENITIES...
Enter this inviting open floor plan with incredible natural lighting throughout. Three sets of French doors take you from the living/kitchen space out to the outdoor entertainment area, consisting of a private heated lap pool all to yourself, propane gas grill, swing set, outdoor dining for 4, additional outdoor seating and pool loungers. Wood flooring, high ceilings and breezy ceiling fans in each room will keep you cool and refreshed on a sultry summer's day. Whip .......
10.0 Star Review
4 Bedrooms
- Sleeps 8
Key West Vacation Rental
Pets Allowed 
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Welcome to Bottom’s Up Bungalow — Your Private Tropical Escape in Old Town Key West
Step into a world of comfort and island charm at Bottom’s Up Bungalow, perfectly situated in the serene Meadows subdivision, just minutes from the vibrant heart of Key West. This immaculate 2-bedroom, 2-bathroom single-family home combines classic Florida bungalow appeal with modern amenities to create an inviting retreat that has earned over 100 glowing five-star reviews from delighted guests.
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
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" on 'More info on Brad & Dee' to learn more about island.
1800 Atlantic is located in the middle of the Island on the Atlantic side. Two miles u.......
Villa Fleur at Shipyard Condominiums
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 Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Jus.......
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
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 why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West.
1/2 block to Hard Rock Cafe
Simonton Studio, an Old Town get-away for 2
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.
Located in a 6 unit compound this tiny Association is located in the heart of Old Town on Simonton St. Walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval street with it's shops, restaurants, galleries and museu.......
Key West Rooster
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 Waterfront Park with water views and beautiful sunsets right from our porch. There are only a few homes in the Shipyard with a view like this! Most of th.......
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
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 and lush landscaping. A gas grill and outdoor furniture allow you to dine under the stars. Alternatively, enjoy dining in the open chef’s kitchen with.......
Peaceful Setting Amongst The Active Island Life Style
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 balcony is accessed from both the living area and master bedroom. The master bedroom has a king size bed, walk-in closet, and en suite bath. the guest b.......
Rare Penthouse 2 bed/2bath additional King in loft
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 of the Gulf of Mexico and the tarpon swimming below. This can be your place in the sun, a world of quiet pleasures and glorious sunsets, you'll revel.......
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always received great reviews on cleanliness. There will always be disinfectant wipes, liquid hand soap, dish detergent, laundry detergent, dishwasher tablets and a multitude of other cleaning supplies available for your use during your stay. It’s not just a place on the map, it’s a frame of mind, an At.......
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
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 deck and outdoor grill is perfect for entertaining. Located in the heart of old town Key West, Truman Annex is a gated community of private homes and c.......
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
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 Piece Of Paradise) located in the same 1800 Atlantic complex.
Both these Key West vacation rental properties were decorated and are managed (a.......
Key West Suites Hotel - Adam Scott Rote Suite
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/Desoto car dealership, a furniture store, and later a clothing store when the Beatles came to make a purchase which caused the cashier to pass out on the .......
Location, location, location in the heart of Old Town!
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 kitchen, or walk one block to Duval to the many restaurants and bars that Key West is famous for or do some shopping at the numerous unique shops........
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
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 sundeck, and night lighting overlooking a private park. The 2 Bedrooms are upstairs and each have high vaulted ceilings. King bed in owner's suite and two t.......
Shady Palms - Stay In Comfort- May - Aug 10% OFF - 2BD/2.5Bath - Private Pool
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 fresh caught fish with enough room to seat four at the countertop.
The master has a queen bed with its own ensuite that has a shower with multiple.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Key West Vacation Rental
Pets Allowed
Superb Location, Affordably Priced
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 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. Come home to a king size bed, full kitchen and everything you need to make your own cocktails.
This newly redecorated Studio features a seating area , flat .......
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
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 availability calendar looks full.
The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all thin.......
A Touch of Bermuda in Key West
Note: Minimum stay is 29 days / 28 nights. Saturday-to-Saturday bookings required. Exceptions made for special events including boat races and Fantasy Fest. Pets by special permission.
About This Property
A Touch of Bermuda is a privately owned Bermuda-style conch cottage in the Shipyard section of Truman Annex — one of only seven private townhomes available for rent in this gated, 24-hour secured community in the heart of Old Town Key West. This is not a cookie-cutter condo. It .......
The Gumbo Limbo Cottage - Your Happy Place - 2BD/2.5 Bath
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 be greeted by hardwood floors and vaulted ceilings that flow throughout the home. The front reading room, complete with a small refrigerator and desk, .......
Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!
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 home boasts an open and comfortable living area, allowing ample natural light to fill the space. The living room features high-vaulted ceilings and cath.......
Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!
Welcome to your private slice of paradise in the Keys! This exquisite waterfront home offers an unparalleled opportunity to immerse yourself in coastal luxury. Nestled on a sprawling 1/3-acre property, our retreat boasts breathtaking grounds and a mesmerizing ambiance that promises an unforgettable stay.
Highlights of Your Stay:
🌅 Spectacular Indoor-Outdoor Living: Soak in stunning bay views from our spacious patio deck, perfect for al fresco dining or simply admiring the gorgeo.......
10.0 Star Review
4 Bedrooms
- Sleeps 8
Key West Vacation Rental
Pets Allowed
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
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 all the restaurants, bars, entertainment and museums that we are most famous for.
Mingle with other guests around the tropical gardens surroundin.......
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!
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 bright and sunny retreat that boasts fully renovated baths and kitchen, wood floors, high ceilings, and Dade County Pine walls.
***PRIMARY GUEST MUST.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pets Allowed
SEA FOREVER ~ Downtown Ocean View Home w/ 3 BR, 3.5 Ba w/ Pool!
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 Southernmost Buoy, you are truly seated in the heart of paradise in this small gated community. Designer finishes and top-of-the-line fixtures can be found throughout and will soothe and spoil your inner pleasure-seeker. This vibrant and bustling area i.......
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
****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 from Duval Street and in the center of all things Key West. This home was originally built in 1929 and has been painstakingly restored to include every.......
Duval Square Retreat w/ Private Hot Tub, Pool, Parking & Walkable Location!
Welcome to Your Tropical Escape at Duval Square
Discover the perfect Key West getaway in this beautiful 2-bedroom, 2.5-bathroom retreat located in the exclusive gated community of Duval Square. Nestled on upper Duval Street—just steps from restaurants, cafés, and island conveniences - this property offers the ideal blend of privacy, luxury, and unbeatable location.
Property Highlights:
~ Spacious & Stylish Living
Relax in the bright, comfortable living room featuring a so.......
Key West dream townhouse -Sleeps 6 Like new! Old Town - Perfect location
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 the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all!
We are proud to br.......
Hyatt Windward Pointe 2 Bedroom
Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coast. Overlooking the Atlantic Ocean, the resort features spacious two-bedroom suites with fully equipped kitchens, private balconies, and elegant living spaces, perfect for relaxing or entertaining.
Guests can unwind in the lush tropical gardens, enjoy the sparkling infinity-edge pool, or lounge in the whirlpool spa. The resort also offers a poolside restaurant, poolside.......
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Hyatt Windward Pointe 2 Bedroom
Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coast. Overlooking the Atlantic Ocean, the resort features spacious two-bedroom suites with fully equipped kitchens, private balconies, and elegant living spaces, perfect for relaxing or entertaining.
Guests can unwind in the lush tropical gardens, enjoy the sparkling infinity-edge pool, or lounge in the whirlpool spa. The resort also offers a poolside restaurant, poolside.......
Tranquil Beauty-Private Pool - Outside Lanai-Beaches Nearby
TRANQUIL BEAUTY: 3 BR’s, 2 Baths Private Haven paradise with huge private heated pool and landscaped back yard!
ENJOY KEY WEST at its peaceful best in your 3BR, 2 bath private hideaway in a quiet neighborhood near Higgs and Smathers beaches and only a 10 minute bike or Uber ride from Duval Street.
OUTDOORS: Refresh while listening to the waterfall and getting some sun floating in your large, very private, heated and chilled pool. Rinse in the outdoor shower. Enjoy the recently upgrade.......
Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
Welcome to our Key West retreat — a home we cherish and live in part of the year, now open for guests who appreciate comfort, character, and a lived-in sense of ease that you won’t find in a typical vacation rental.
Located just one block from the iconic Green Parrot Bar and two blocks from Duval Street, you’ll be surrounded by the best of Bahama Village — from Blue Heaven, Hemingway House, and Willie T’s to endless galleries, cafes, and music. Yet you’d never guess how close .......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pets Allowed
**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + LAST KEY SERVICES...
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 allowing you to get a restful night’s sleep. SOUL OF DUVAL truly captures the essence of what makes Key West so special, with its playful decor, luxuri.......
Sunset Harbor - Old Town Key West Location - Beautiful Property
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, boat tours, and more.
Property amenities include: onsite washer and dryers, wireless internet access, pool, hot tub, and excellent location. Take.......
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
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 cottage (unit 2) each consist of a one bedroom, one bathroom, open kitchen and living room with high ceilings. The third cottage (unit 3) consists of.......
Truman Annex Best Location in Town
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 won awards as the best development in Florida. (And yes it does have a blender).
It’s just off Duval Street, with its bustling shops and nightl.......
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 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 two-story private home that not only transcends island living at its finest but also offers an ideal location for enjoying all that Key West has to offe.......
Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.
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, restaurants and world class entertainment.
The 2 porches, for privacy and sun options, also separates this from other properties.
We also have a .......
Amelia`s Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool
`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 all the way at the end of an unknown lane it is well hidden from public view. Unless you`ve stayed in this villa before, there`s no-way you`d ever know it`s just steps off Upper Duval S.......
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
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 people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West.
1/2 block to Hard Rock Cafe
2.......
Freshly Renovated Cottage Old Town MONTHLY
This freshly renovated cottage 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 rent by the month. You do not have to stay the whole month, but we are not allowed to do nightly rentals.
Awesome galley kitchen sparkles with plen.......
ATLANTIC HIDEAWAY- Key West
Atlantic Hideaway at 1800 Atlantic – Luxury 2BR Condo with Resort Amenities
Welcome to Atlantic Hideaway, your private escape in paradise. Located in the highly desirable 1800 Atlantic condo complex, this beautifully updated 2-bedroom, 2-bathroom third-floor unit offers spacious accommodations, resort-style amenities, and a prime Key West location. Just 1 mile from the Key West International Airport and 2 miles from Duval Street, you're perfectly situated to explore all that the island .......
MAI TAI TERRACE - KEY WEST
Welcome to Mai Tai Terrace – Your Tropical Getaway in Key West
Located in The Shipyard subdivision of the sought-after Truman Annex, this bright and breezy 2-bedroom, 2-bath end-unit condo offers the perfect island escape just steps from the best of Key West.
SPACIOUS, SUNNY AND PERFECTLY POSITIONED
Situated on the second floor, this open-concept condo features vaulted ceilings, large windows, and a light-filled layout that flows seamlessly from kitchen to lanai—perfect .......
A Fish Bowl at The Truman Annex in Key West
A Fish Bowl has been completely remodeled with attention to detail. A beautiful 1 bedroom, 1 bath downstairs condo located in The Shipyard section of Truman Annex. The new kitchen sparkles with brand new top-of-the-line appliances, cabinetry and every amenity needed. The gourmet kitchen opens nicely to a sunny living room with glass doors leading to a private garden area with room for outside dining and lounging.
From the private patio, the back gate opens to the refreshing waters of the .......
A Touch Of Cuba In Key West
MINIMUM STAY 29 DAYS/28 NIGHTS
About This Property
A Touch of Cuba is a privately owned, two-bedroom, one-bathroom condominium in the Shipyard section of Truman Annex — one of Key West's most sought-after residential neighborhoods. Located on Southard Street, the main entrance to the Truman Annex, the property is within walking distance of Duval Street, the Ernest Hemingway Home, the Key West Butterfly Conservatory, and the island's best restaurants, galleries, and beaches.
This.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Key West Vacation Rental
Pets Allowed
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w/ Pool!
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
DETAILS AND AMENITIES…
Pull up to the first floor of this island beauty showcasing lush, vibrant foliage surrounding this quaint abode. Step on.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pets Allowed
Heart of Key West - 2BR Waterfront at the Galleon Resort
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the jacuzzi or sauna during your stay or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.
Key West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum.......
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Old Town Beauty built in 1883
Enjoy the lovely Key West ocean breeze from your private Tree House. This is the quietest area of Old Town but only4 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. Its less than 4 blocks to Blue Heaven, Santiago's, Moon Dog Cafe.
This storied and historic 1883 Conch home has been lovingly and thoughtfully renovated to perfection. Gleaming Dade County Pine floors and walls, period windows, period bath fixtures w.......
Heart of Key West - 2BR Waterfront at the Galleon Resort
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the jacuzzi or sauna during your stay or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.
Key West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum.......
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Sky Suites Retreat - Balcony Overlooking Duval
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 private, shaded balcony overlooking Duval Street, this modern duplex is walking distance to all of Key West's best restaurants, attractions.......
THE FICUS HOUSE ~ Adult Only, Lush 3 BR, 2.5 Ba Gem with Pool and Cottage!
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 "Ficus House."
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE. THIS HOME IS NOT SUITABLE FOR CHILDREN.
DETAILS AND AMENITIES...
An enchant.......
4 Bed House w/ Heated Pool and Dock - 4 Min. to Key West
- 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
- 600 Pound ice machine
- Chest freezer for bait
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 Atlantic and Gulf sides of the Keys. All of this just 10 minutes by car to downtown Key West........
10.0 Star Review
4 Bedrooms
- Sleeps 13
Key West Vacation Rental
Pets Allowed
Key West Tropical Townhome on Golf Course
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 on the front of the home and 2 large rear screened in porches to enjoy the outdoors. The living room faces the fairway, has a large flat screen TV, c.......
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
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 spacious primary bedroom with a king size bed and hardwood flooring, a connecting ensuite full bathroom with shower and bathtub. The guest bedroom fea.......
~LILLY'S PAD~ Upscale elegance with a private pool and parking!
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 Dade County pine walls.
Moving into the open concept kitchen and living room, high ceilings, designer finishes and natural light will greet you........
Key West Luxury Houseboat
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, furnished, 3rd level sun deck. Full Kitchen.
Read More:
FIRST LEVEL:
Enter the boat from the cushioned floor front deck through full s.......
Key West's Crown Jewel
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 spaces:
The wood beamed, soaring ceilings of the living room provide an extremely open feeling. Upgraded appointments include high speed (up to 100 .......
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
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, picnic tables, onsite bar, and much more.
This spacious two bedroom condo features a king primary suite with hardwood flooring, a connecting ensu.......
Things to Do while on Vacation In Key West Florida
Key West is just about the perfect vacation destination in Florida. As cliché as it sounds, there truly is something for everyone. Whether you are looking to party like a rock star or seeking a relaxing vacation in nature, Key West has what you are looking for. Whether you are interested in bar hopping, beach hopping, dolphin watching, bird and wildlife watching, or some of the best people watching around; Key West is a must-visit spot in Florida.
Duval Street
You truly can’t visit Key West without experiencing Duval Street. This 1.2-mile street is the main thoroughfare and has so much to offer. Click here to see the live feeds of Duval Street from the world-famous Sloppy Joes, coined a Key West tradition. There are more than 100 bars and dozens of shops and boutiques along this stretch. If you love live music be sure to visit the Green Parrot Bar and The Hogs Breath Saloon, both locations are well-known for hosting phenomenal national act.
The Ernest Hemmingway Home and Museum
If you enjoy literature and history, you will want to plan a visit to Hemingway Home & Museum. The estate was built in 1851 and is the most popular tourist attraction in Key West. Ernest Hemingway lived there from 1931 to 1939 and wrote some of his most popular literary works on the estate.
Mallory Square – Sunset Celebration
One of Key West’s most popular activities is the Sunset Celebration at Mallory Square Dock. People visit from all over the world to catch these exquisite sunsets and experience this nightly arts festival. There are street performers, food vendors, art installations, and extraordinary shopping options.
Key West Butterfly and Nature Conservatory
If you are a nature-lover, you will want to plan a visit to The Key West Butterfly & Nature Conservatory. Click here to check out the live webcams set up at the conservatory. You can walk among hundreds of butterflies and beautiful, colorful birds inside their habitat.
Dry Tortugas National Park
You can also take a ferry ride on the Yankee Freedom to visit Fort Jefferson Dry Tortugas National park. Take a guided tour and learn about life at the fort in the 1860s. The park is 100-square-miles and, aside from the fort, is known for is gorgeous blue waters, coral reefs, and wildlife watching.
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Key West, Florida is known for water sports, lively nightlife, beaches, historic sites and its pastel, conch-style architecture. Located at the southernmost point in the Florida Keys and the United States, visitors can enjoy the Ernest Hemingway Home and Museum, tour the Harry S. Truman Little White House, explore beautiful tropical gardens or visit Mallory Square, a waterfront plaza just west of Duval Street where its “Sunset Celebration” is one of the most popular things to see and do in Key West.