Key West Private Vacation Homes

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
Pet Friendly

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.

10.0 Star Review

2 Bedrooms - Sleeps 6
Key West Vacation Rental

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.......

10.0 Star Review

5 Bedrooms - Sleeps 10
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 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........

10.0 Star Review

3 Bedrooms - Sleeps 6
Key West Vacation Rental

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.......

9.4 Star Review

2 Bedrooms - Sleeps 8
Key West Vacation Rental

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
Pet Friendly

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, .......

10.0 Star Review

2 Bedrooms - Sleeps 4
Key West Vacation Rental

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
Pet Friendly

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
Pet Friendly

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.......

9.6 Star Review

3 Bedrooms - Sleeps 6
Key West Vacation Rental
Pet Friendly

****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.......

10.0 Star Review

4 Bedrooms - Sleeps 8
Key West Vacation Rental

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.......

9.4 Star Review

2 Bedrooms - Sleeps 6
Key West Vacation Rental

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.......

10.0 Star Review

2 Bedrooms - Sleeps 6
Key West Vacation Rental

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.......

10.0 Star Review

3 Bedrooms - Sleeps 8
Key West Vacation Rental

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
Pet Friendly

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.......

9.8 Star Review

2 Bedrooms - Sleeps 6
Key West Vacation Rental

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.......

9.0 Star Review

1 Bedrooms - Sleeps 4
Key West Vacation Rental

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.......

9.4 Star Review

2 Bedrooms - Sleeps 7
Key West Vacation Rental
Pet Friendly

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.......

10.0 Star Review

3 Bedrooms - Sleeps 6
Key West Vacation Rental

- 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
Pet Friendly

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.......

10.0 Star Review

2 Bedrooms - Sleeps 4
Key West Vacation Rental

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........

10.0 Star Review

3 Bedrooms - Sleeps 6
Key West Vacation Rental

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 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 comfortable accommodations. This easy living home combines a classic Key West design with the finest modern updates and conveniences. If you ever decide to pul.......

10.0 Star Review

4 Bedrooms - Sleeps 8
Key West Vacation Rental
Pet Friendly

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 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 dab in the middle of Old Town. SEAPORT SENSATION is one of the newly built breathtaking townhomes at Old Town Villas that allows you to enjoy the luxu.......

3 Bedrooms - Sleeps 8
Key West Vacation Rental
Pet Friendly

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 deck you are only steps away from the Gulf of Mexico. You can relax on your private patio or enjoy the private beach with kayaks and paddleboards. The.......

9.6 Star Review

5 Bedrooms - Sleeps 10
Key West Vacation Rental
Pet Friendly

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 you into the Key West spirit.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS & AMENITIES...
A friendly front porch awaits your.......

9.8 Star Review

2 Bedrooms - Sleeps 6
Key West Vacation Rental
Pet Friendly

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 baths, graciously spread out over three floors. The ground floor features a fabulous gourmet kitchen, dining area, half bath, and sitting room with a.......

9.8 Star Review

3 Bedrooms - Sleeps 8
Key West Vacation Rental

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 best happy hours on the island. Or Walk down to Duval street to experience the local music scene and bar hopping, restaurants and shopping. Located in a .......

10.0 Star Review

1 Bedrooms - Sleeps 4
Key West Vacation Rental
Pet Friendly

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 kitchen are located on the second floor where you can enjoy the fantastic view of the harbour and sunsets. Downstairs offers 3 bedrooms/2 baths and l.......

9.8 Star Review

4 Bedrooms - Sleeps 8
Key West Vacation Rental

"Flip Flop Inn" is a beautiful 3 Bedroom 3 Bath home, (each bedroom has its own private full bath), 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 included in your rental. We are ideally located at mile marker 5 which is only a 10 min hop to downtown Key West, Duval St, and all the action. The Key West golf course is directly a.......

9.6 Star Review

4 Bedrooms - Sleeps 8
Key West Vacation Rental
Pet Friendly

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 unwind and relax, lounge under the palm trees of the large pool located within this seven house gated community and soak in the Key West easy lifestyle you.......

9.6 Star Review

4 Bedrooms - Sleeps 5
Key West Vacation Rental
Pet Friendly

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 complete with a waterfall, this is your home away from home to spend your days relaxing, playing a round of golf, fishing, snorkeling and enjoying all that.......

10.0 Star Review

2 Bedrooms - Sleeps 4
Key West Vacation Rental
Pet Friendly

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 Square is directly across the street with three restaurants, shops, and even a salon and convenience store. The best homemade ice cream in Key West is j.......

10.0 Star Review

3 Bedrooms - Sleeps 6
Key West Vacation Rental

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 of the community is a beautiful pool and a clubhouse with a fitness area.
Included is parking for two cars, WiFi and high speed internet.
Close.......

10.0 Star Review

3 Bedrooms - Sleeps 8
Key West Vacation Rental

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, Sloppy Joes and Duval Street entertainment. One of the nicest homes in the best area of Key West. Watch sailboats and sunsets from the decks during the da.......

9.4 Star Review

3 Bedrooms - Sleeps 8
Key West Vacation Rental
Pet Friendly

MARITIME-INSPIRED LIVING…
Come unwind in this desirable retreat, tucked in a quiet and private lane just a stone's throw from all the excitement of Duval Street. Your location is ideal with swaying palm trees and gentle sea breezes all around. This upscale delight beckons you into your tropical haven beneath the twinkling stars of Key West. Allow your delightful island story to unfold.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS & AMENITIES…
The open concept fea.......

10.0 Star Review

3 Bedrooms - Sleeps 8
Key West Vacation Rental
Pet Friendly