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From $978 per night (USD)
VRBO
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $978 per night (USD)
VRBO
Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For Pricing
Expedia
From $281 per night (USD)
VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $281 per night (USD)
VRBO
Click For Pricing
Expedia
Galleon Resort efficiency
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
Click For Pricing
Expedia
From $1289 per night (USD)
VRBO
Steps from Duval with Private Pool – Coconut Palm
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Step into the heart of Key West at Coconut Palm! Just one block from Duval Street, this tropical gem features a ...
From $1289 per night (USD)
VRBO
From $1182 per night (USD)
Expedia
Parking & Shared Pool - Casa Key West
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: - Located on the south end of Duval Street steps from the Southernmost Point! - Large open-concept condo with p ...
From $1182 per night (USD)
Expedia
From $654 per night (USD)
VRBO
Private Parking & Near Downtown - Sea Breeze
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Sea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart of ...
From $654 per night (USD)
VRBO
From $1260 per night (USD)
Expedia
Coastal Comfort; Waterfront Luxury Home with private pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1260 per night (USD)
Expedia
From $703 per night (USD)
VRBO
Panoramic Ocean: Beach from every window
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $703 per night (USD)
VRBO
$Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR\/2BA in Old Town!$
From $339 per night (USD)
Expedia
Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR\/2BA in Old Town!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*** Located in the Old Town neighborhood. This exclusive residential area of Old Town Key West is really an extension of ...
From $339 per night (USD)
Expedia
From $628 per night (USD)
VRBO
Penthouse Beach Ocean Views- Live the Dream
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $628 per night (USD)
VRBO
From $1105 per night (USD)
Expedia
Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...
From $1105 per night (USD)
Expedia
From $703 per night (USD)
VRBO
Beach Penthouse: Ocean Views from every room Tropical Excellence
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 throug ...
From $703 per night (USD)
VRBO
From $1283 per night (USD)
Expedia
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...
From $1283 per night (USD)
Expedia
From $609 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Perfectly positioned townhouse in Truman Annex At Historic Foundry building. Hemingway Hideaway in Truman Annex is a de ...
From $609 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
If you are looking to stay in accommodations of high standards. This is the one for you! As you enter this large one bed ...
From $361 per night (USD)
Expedia
From $205 per night (USD)
VRBO
Conch House in the Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $205 per night (USD)
VRBO
Click For Pricing
Expedia
ISLAND SPA in the Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...
Click For Pricing
Expedia
$Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View$
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VRBO
Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
Click For Pricing
VRBO
From $364 per night (USD)
Expedia
BLUE HEAVEN at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $364 per night (USD)
Expedia
From $327 per night (USD)
VRBO
A Bella Capri in Key West by the Beach! *Monthly rental*
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $327 per night (USD)
VRBO
From $273 per night (USD)
Expedia
OYSTER'S PEARL at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $273 per night (USD)
Expedia
$**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..$
From $2414 per night (USD)
VRBO
**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..
Bedrooms:
8
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $2414 per night (USD)
VRBO
From $520 per night (USD)
Expedia
A LATITUDE ADJUSTMENT at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renov ...
From $520 per night (USD)
Expedia
From $454 per night (USD)
VRBO
ANOTHER DAY IN PARADISE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $454 per night (USD)
VRBO
From $943 per night (USD)
Expedia
A SUNSET BREEZE Beautiful private home with pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $943 per night (USD)
Expedia
From $417 per night (USD)
VRBO
A SUNSET POOLSIDE in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing FIRST FLOOR end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $417 per night (USD)
VRBO
From $441 per night (USD)
Expedia
ARCHIPELAGO ll at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining ...
From $441 per night (USD)
Expedia
From $273 per night (USD)
VRBO
ALHAMBRA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $273 per night (USD)
VRBO
From $444 per night (USD)
Expedia
SAILOR'S STORY at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $444 per night (USD)
Expedia
From $408 per night (USD)
VRBO
AQUA OASIS at The Truman Annex in Key West..
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $408 per night (USD)
VRBO
From $388 per night (USD)
Expedia
CONCH ISLAND at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $388 per night (USD)
Expedia
$*Casa-Amelia-Key-West* 1\/2 block off Duval Street$
From $645 per night (USD)
VRBO
*Casa-Amelia-Key-West* 1\/2 block off Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up ...
From $645 per night (USD)
VRBO
$Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony$
From $690 per night (USD)
Expedia
Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunset at Harbour Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $690 per night (USD)
Expedia
From $210 per night (USD)
VRBO
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $210 per night (USD)
VRBO
From $1073 per night (USD)
Expedia
Commodore's Cove - Epic Location 1 Block to Duval
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of home. Up to 12 can stay ...
From $1073 per night (USD)
Expedia
From $2501 per night (USD)
VRBO
Commodore's Compound - Epic Location Near Duval
Bedrooms:
7
Bathrooms:
10
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $2501 per night (USD)
VRBO
From $1391 per night (USD)
Expedia
Steps from Duval, Private Hot Tub - Seaport Suite
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: Located in the heart of Old Town Key West, Seaport Suite is the ideal getaway for large groups of up to 12 gues ...
From $1391 per night (USD)
Expedia
From $451 per night (USD)
VRBO
SEASCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $451 per night (USD)
VRBO
From $288 per night (USD)
Expedia
TROPICAL VINEYARD at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $288 per night (USD)
Expedia
Click For Pricing
VRBO
Old Town Island House Near a grocery store, beach, bike rental shop, Restaurants
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two Story Apartment in central Old Town Key West location. Only a 5 min bike ride to Duval. 1 King size bed on 3rd flo ...
Click For Pricing
VRBO
From $364 per night (USD)
Expedia
GREEN SPOT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastef ...
From $364 per night (USD)
Expedia
From $364 per night (USD)
VRBO
ANOTHER THREE HOUR TOUR at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $364 per night (USD)
VRBO
From $298 per night (USD)
Expedia
CONCH RETREAT Truman Annex Condo - 2 decks, pool, 2 Bikes, Free parking and WIFI
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! This is a Saturday-Saturday weekly condo for the rest of 2025. ...
From $298 per night (USD)
Expedia
From $395 per night (USD)
VRBO
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Spanning an e ...
From $395 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Private Heated Pool, Cabana, & Prime Key West Location Near Truman Annex!
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
This beautiful home has 3 bedrooms and 3 baths in the main house with a bonus cabana. There is a private and heated po ...
From $510 per night (USD)
Expedia
From $1805 per night (USD)
VRBO
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + LAST KEY SERVICES…
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $1805 per night (USD)
VRBO
From $388 per night (USD)
Expedia
ADRIFT in Key West at the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completel ...
From $388 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Luxurious Key West Pool Home block from Duval! Pool & Patio Recently Renovated!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Histo ...
From $225 per night (USD)
VRBO
From $496 per night (USD)
Expedia
FOREVER YOUNG at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $496 per night (USD)
Expedia
From $393 per night (USD)
VRBO
ABOUT TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $393 per night (USD)
VRBO
From $381 per night (USD)
Expedia
HAVANA VIEWS at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $381 per night (USD)
Expedia
From $347 per night (USD)
VRBO
SAND CRAB CABANA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $347 per night (USD)
VRBO
From $659 per night (USD)
Expedia
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $659 per night (USD)
Expedia
$Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n$
From $561 per night (USD)
VRBO
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all ...
From $561 per night (USD)
VRBO
From $271 per night (USD)
Expedia
The Estela, Old Town Key West Monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tucked away just 1 block from the action of Duval Street lies our newest space located at 613 Fleming Street. Find your ...
From $271 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Direct Ocean View from Your Condo-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom ...
From $368 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $398 per night (USD)
Expedia
From $273 per night (USD)
VRBO
A PLEASANT STAY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $273 per night (USD)
VRBO
Click For Pricing
Expedia
ANGEL FISH at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Tropically decorated 2 bedroom 2 bathroom townhouse in secluded area of Truman Annex, complete with updated appliances, ...
Click For Pricing
Expedia
From $493 per night (USD)
VRBO
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $493 per night (USD)
VRBO
From $660 per night (USD)
Expedia
TROPICAL EXECUTIVE at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $660 per night (USD)
Expedia
$Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking$
From $693 per night (USD)
VRBO
Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $693 per night (USD)
VRBO
$Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking$
From $878 per night (USD)
Expedia
Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $878 per night (USD)
Expedia
From $767 per night (USD)
VRBO
Washer & Dryer, Near Downtown - Mesa House, Dos
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Whether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Mes ...
From $767 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $326 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Steps To The Beach And The Sunrise-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnis ...
From $333 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Stone Throw Famous Duval Street Location-No Contact Check-In
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
House is located just steps from famous Dvual Street. Duval Street stretches from the Atlantic Ocean to the Gulf of Mexi ...
From $236 per night (USD)
Expedia
From $803 per night (USD)
VRBO
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunday to Sunday WEEK available to book. Limited Boat Slip available onsite. Must be reserved in advance after reserva ...
From $803 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Historic District-Pool View-Duval Street-Beach Nearby-No Contact Check-In
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in ...
From $314 per night (USD)
Expedia
Click For Pricing
VRBO
2 BR at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium ...
Click For Pricing
VRBO
$Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $862 per night (USD)
Expedia
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $862 per night (USD)
Expedia
$Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $643 per night (USD)
VRBO
Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $643 per night (USD)
VRBO
From $317 per night (USD)
Expedia
SUN, SEA, AND SKY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sun Sea and Sky is blocks from bustling Duval Street, the heart of Old Town Key West, and an easy walk to restaurants, s ...
From $317 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Private Home- Sun-filled Pool- Neighborhood Water Inlet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and c ...
From $221 per night (USD)
VRBO
From $408 per night (USD)
Expedia
ANGLER'S RETREAT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A stay in Anglers Retreat is more then just a rental, but will be part of your Key West vacation experience. In addition ...
From $408 per night (USD)
Expedia
From $388 per night (USD)
VRBO
A Seaglass Paradise at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $388 per night (USD)
VRBO
From $375 per night (USD)
Expedia
GREEN BAMBOO at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Paradise! This 2 bedroom townhouse, one bedroom is a king and the second bedroom features twin beds which can ...
From $375 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Balcony & Shared Pool - Island Time
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: "Island Time" is a newly renovated, 2 bed 2 bath condo located in the gated La Brisa Condominium complex. Situa ...
From $613 per night (USD)
VRBO
From $516 per night (USD)
Expedia
CAPTAINS WHEEL at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home feat ...
From $516 per night (USD)
Expedia
From $774 per night (USD)
VRBO
**WALKING ON SUNSHINE @ THE BEACH** Ocean Condo & Large Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $774 per night (USD)
VRBO
From $393 per night (USD)
Expedia
A LOW TIDE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award winning gated community of the T ...
From $393 per night (USD)
Expedia
Click For Pricing
VRBO
Private luxury retreat all included.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
All included in this large home has a huge master bedroom with 2 walking closets, opens to large wrap around balcony ove ...
Click For Pricing
VRBO
$Key West Retreat Near Duval Street | Scenic Resort w\/ Outdoor Pool$
From $871 per night (USD)
VRBO
Key West Retreat Near Duval Street | Scenic Resort w\/ Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $871 per night (USD)
VRBO
From $2780 per night (USD)
VRBO
Steps from Duval with Private Pool – Southern Palms
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Summary: Welcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, or ...
From $2780 per night (USD)
VRBO
From $739 per night (USD)
VRBO
Sunsplashed Tropical Gem! Two Amazing Rooms with Breathtaking Views in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $739 per night (USD)
VRBO
$Your Next Getaway is Here! Three Premium Ocean View (w\/ 2 Queens Each), Pool$
From $1029 per night (USD)
VRBO
Your Next Getaway is Here! Three Premium Ocean View (w\/ 2 Queens Each), Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1029 per night (USD)
VRBO
From $556 per night (USD)
VRBO
Escape To Paradise in Key West! 2 Relaxing Spaces, Minutes Away From The Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $556 per night (USD)
VRBO
$Close to Nearest Beach! Four Premium Ocean View Rooms (w\/ 2 Queen Beds), Pool$
From $1445 per night (USD)
VRBO
Close to Nearest Beach! Four Premium Ocean View Rooms (w\/ 2 Queen Beds), Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1445 per night (USD)
VRBO
From $659 per night (USD)
VRBO
Amazing Stay in the Keywest! Two Deluxe Pool View Two Queen Beds
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $659 per night (USD)
VRBO
From $1373 per night (USD)
VRBO
Perfect Staycation! Four Fantastic Ocean View Rooms, Outdoor Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1373 per night (USD)
VRBO
From $948 per night (USD)
VRBO
Delight In The Florida Sun! 3 Gorgeous Units In Sun Soaked Key West, Onsite Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $948 per night (USD)
VRBO
From $1006 per night (USD)
VRBO
3x Deluxe Pool View Two Queen Beds at 24 North Hotel Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1006 per night (USD)
VRBO
From $686 per night (USD)
VRBO
Your Next Beach Getaway is Here! Two Premium Ocean View Rooms, Close to Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $686 per night (USD)
VRBO
$Close to the Nearest Beach! Four Amazing Rooms w\/ Pool View$
From $1340 per night (USD)
VRBO
Close to the Nearest Beach! Four Amazing Rooms w\/ Pool View
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1340 per night (USD)
VRBO
From $927 per night (USD)
VRBO
Perfect Beach Getaway! 3 Amazing Rooms Rooms, Driving Distance to the Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $927 per night (USD)
VRBO
From $786 per night (USD)
VRBO
Key West Vacation! 3 Comfortable Units, Onsite Pool, Close to Smathers Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $786 per night (USD)
VRBO
From $1112 per night (USD)
VRBO
Amazing Stay Perfect for the Whole Family! Four Convenient Rooms, Outdoor Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1112 per night (USD)
VRBO
$Two Amazing Rooms (w\/ 2 Queen Beds), Outdoor Pool, Close to Nearest Beach$
From $586 per night (USD)
VRBO
Two Amazing Rooms (w\/ 2 Queen Beds), Outdoor Pool, Close to Nearest Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $586 per night (USD)
VRBO
$You Found it! Amazing Stay w\/ 4 Deluxe Pool View (w\/ Two Queen Beds Each)$
From $1244 per night (USD)
VRBO
You Found it! Amazing Stay w\/ 4 Deluxe Pool View (w\/ Two Queen Beds Each)
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1244 per night (USD)
VRBO

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