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Townhome, 2 Bedrooms, 2.5 Baths, (Sleeps 4)
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,...
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Amenities & Details
About this property
Bright Key West Beauty
This perfectly positioned rental with access to a shared pool puts you close to everything in Key West, so bring the whole family for a memorable tropical retreat.
Situated in the premiere gated community of Truman Annex, this home is just steps from historic Old Town....
Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
Best Deal in Truman Annex - Céad Míle Fáilte (Irish)
2 Bedroom 1 bathroom Condo - sleeps up to 5
Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool
Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table and...
Private Home, DownTown, Villa description
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a...
Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset.
You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
It wasn't that long ago that President Truman took casual walks in this same location- now it's your turn! President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in front of one of the community pools in the...
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree.
Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer. Located in the exclusive gated community of the Truman Annex, this...
This spacious home with a large outside deck is tucked away on a quiet lane of Truman Annex, yet only a short walk to all attractions. Artist Garden makes an ideal vacation rental for those who like to enjoy a Duval crawl and a quiet peaceful vacation at the same time
A bright and breezy 2...
Just steps away from Harry Truman's 'Little White House' you’ll find your vacation dreams come true!
Located in the historic brick Foundry building, Key West Found is a spacious two bedroom, two and a half bath, three-story townhome. Enter through a wrought iron gate to your own tropical...
Spend your Key West vacation in style here at this high-end house! There's plenty of room for everybody in this house's eight bedrooms, and you're steps away from the ocean.
Key West's most popular attractions surround this home - walk down to Mallory Square a few blocks...
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!
Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in the heart...
Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation!
Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex.
Master bedroom with queen bed...
Banana's Foster Guesthouse
Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large historic house on Key West. Featuring a private heated pool, four private parking spaces, and a communal area with plenty of room for everyone, this seven-bedroom,...
Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table. Check out the history and architecture of Old Town. All these options and many more are yours...
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!
You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation...
Lazy Lane at Shipyard Condos
Grab your sunglasses, bathing suit, and sunscreen and get ready to dive into the beach lifestyle when you book this Key West condo. Boasting a shared pool to stay cool, this home gives you the chance to slip into vacation mode with ease.
This condo is just two...
View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!
Balmy breezes, brilliant sunrises, and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex. You'll spend most of your time overlooking...
Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental!
Located at the Shipyard Condominiums condo rental in Key West.
This downstairs 2 bedroom 1...
Situated on the second floor of a historic home, this spacious dog-friendly condo welcomes guests with great amenities and a private hot tub! Soak after a long day in the sunshine, and make full use of the back patio space.
You're right around the corner from Duval Street's...
A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old military
Hospital building. In the mid 80's it was purchased by a developer who renovated the entire property in keeping with the existing...
The Frontier Flat
Escape to the land of sea and sun for your next vacation with this fresh condo in Key West. Featuring one bedroom and one bathroom, entertainment, and an awesome location close to all the action on the waterfront, up to four guests will love it here! The family dog is also...
Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you!
When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside...
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Amenities & Details
About this property
Location, Location, Location!! Sunrise off Southard has it all! An upscale one bedroom home offers tropical beauty with all the comforts. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape...
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Amenities & Details
Private Outdoor Pool (Heated)
About this property
Enjoy the unbeatable location of this two-story home only a block away from Duval Street. Take advantage of the large open concept living room, kitchen, and dining spaces while relaxing indoors. You can also beat the Florida heat by cooling off in the pool. This home is ready-made for...
UGJ4XzNfYmhtother travellers have booked this property
Amenities & Details
Outdoor Dining Area
About this property
Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge...
Sunset at Harbour Place
Enjoy this spectacular condo with an oceanfront view of Key West harbor for your next getaway in the Key West! Located in Truman Annex, this home boasts beautiful water views from the balcony and all around the condo, you'll be sure to feel inspired during your stay! This...
It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.
This lovely Truman Annex condo rental in the...
You will love this charming townhome on the President's Walk in the Truman Annex, Key West's most exclusive gated community in the heart of Old Town. Come for the Spanish tile, then stay for the tropical garden extensive seashell collection. Enjoy the seamless indoor to outdoor living...
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.
The name says it all!
This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located...
This cozy Key West rental is ready to be your home away from home! Located on a tree-lined street in the Truman Annex community, this townhouse offers a full kitchen, patio, and a shared pool.
Just a half-mile away, experience the excitement of Duval Street for shopping, dining, and...
Four Flowers Guesthouse
Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of four condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could...
Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.
Wonderful for larger groups or family get togethers, The Dolphin House offers a roomy vacation home and quaint guest house with a pool and outdoor living...
Start planning your Key West vacation when you book this three-bedroom, two-bathroom home. Up to eight guests will spend their vacation days lounging by the private pool, strolling the streets of downtown, and soaking up the Florida sun on soft sand beaches. The family dog is also...
Located in Shipyard Condos Truman Annex and is available for weekly or monthly rental.
The ideal location of this super-comfortable, 2nd floor, corner property makes it the perfect blend of convenience, tranquility, and tropical Key West scenery. Sit back and relax as you sip cocktails on the...
You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods. You’ll quickly see why its moniker fits, when you notice the purplish-pink walls and African art that adorn the living...
Curry House Bed & Breakfast
Looking for the perfect Key West vacation rental to host your family reunion or corporate retreat? Your search stops with Curry House Bed & Breakfast, a nine-bedroom, nine-bathroom getaway with historic charm, modern comforts, a private swimming pool, and room for up to...
Very private gated compound sleeping eight guests right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing...
Location, Beauty and Comfort! Kokomo Korner has what you are looking for! This upscale home has been meticulously designed with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the...
Feel the tropical allure of this spacious home in the center-of-it-all community of the historic Truman Annex!
The recently updated 3-bedroom, 3-bath town home, is the tranquil escape you have been looking for. Decorated with Key West charm and unique artwork, stunning orchids surround this home...
Curry House Room 5
Experience a piece of Key West's past when you book a stay at this charming ground-floor suite in the historic Curry House Bed & Breakfast! Up to two guests will enjoy a shared on-site pool, home comforts, and a convenient location in the heart of the city.
Curry House sits...
Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amazing furniture, artwork and amenities that give you the tropical, old town feel you seek when visiting Key West. The smallest details have not been missed, high thread count...
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....
Key West Suites Hotel 205
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...
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About this property
Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy!
If we find that the house has been left excessively dirty,...
Searching for an affordable monthly vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Then just tune into the Windchime! This lovely studio for two comes with all the comforts you need for an extended stay away from home,...
Curry House Room 2
Experience a piece of Key West history when you rent this charming Curry House suite, which features a private en suite bathroom, a semi-private balcony, a shared pool, and room for up to two guests!
Located in a quiet neighborhood three blocks from Duval Street, Curry House...
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...
Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else Old Town Key West has to offer.
Step out on the deck of Mary's Trio and breathe in the ocean breeze! This well-furnished home provides plenty of space to relax - ideal for families or...