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From $401 per night (USD)
VRBO
A Bella Capri in Key West by the Beach! *Monthly rental*
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $401 per night (USD)
VRBO
From $410 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 $410 per night (USD)
Expedia
From $1915 per night (USD)
VRBO
**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $1915 per night (USD)
VRBO
From $590 per night (USD)
Expedia
A LATITUDE ADJUSTMENT at the Truman Annex in Key West
Bedrooms:
2
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 $590 per night (USD)
Expedia
From $460 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 $460 per night (USD)
VRBO
From $969 per night (USD)
Expedia
A SUNSET BREEZE Beautiful private home with pool!
Bedrooms:
2
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 $969 per night (USD)
Expedia
From $472 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 $472 per night (USD)
VRBO
From $457 per night (USD)
Expedia
ARCHIPELAGO ll at The Truman Annex in Key West
Bedrooms:
2
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 $457 per night (USD)
Expedia
From $290 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 $290 per night (USD)
VRBO
From $474 per night (USD)
Expedia
SAILOR'S STORY at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $474 per night (USD)
Expedia
From $330 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 $330 per night (USD)
VRBO
From $451 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 $451 per night (USD)
Expedia
From $587 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 $587 per night (USD)
VRBO
From $552 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 $552 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Poolside Paradise in Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to the best of Key West! Poolside Paradise is located in the Key West Golf Club. Our townhome is located direc ...
From $211 per night (USD)
VRBO
From $1077 per night (USD)
Expedia
Epic location, Private Parking - Commodore's Cove
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of a home. Up to 12 can st ...
From $1077 per night (USD)
Expedia
From $2156 per night (USD)
VRBO
Epic Location Near Duval, Private Hot Tub, Parking
Bedrooms:
7
Bathrooms:
8
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $2156 per night (USD)
VRBO
From $1060 per night (USD)
Expedia
Steps from Duval, Private Hot Tub - Seaport Suite
Bedrooms:
3
Bathrooms:
4
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 $1060 per night (USD)
Expedia
From $469 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 $469 per night (USD)
VRBO
From $298 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 $298 per night (USD)
Expedia
From $237 per night (USD)
VRBO
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 $237 per night (USD)
VRBO
From $440 per night (USD)
Expedia
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Spanning an e ...
From $440 per night (USD)
Expedia
From $489 per night (USD)
VRBO
Peachy Keen Private Heated Pool, Cabana, & Prime Location Truman Annex!
Bedrooms:
3
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 $489 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $642 per night (USD)
Expedia
From $1236 per night (USD)
VRBO
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $1236 per night (USD)
VRBO
From $425 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 $425 per night (USD)
Expedia
From $207 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 $207 per night (USD)
VRBO
From $582 per night (USD)
Expedia
FOREVER YOUNG at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $582 per night (USD)
Expedia
From $419 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 $419 per night (USD)
VRBO
From $431 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 $431 per night (USD)
Expedia
From $363 per night (USD)
VRBO
SAND CRAB CABANA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $363 per night (USD)
VRBO
$Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n$
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $378 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 $378 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $328 per night (USD)
Expedia
From $261 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 $261 per night (USD)
VRBO
From $290 per night (USD)
Expedia
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 $290 per night (USD)
Expedia
From $496 per night (USD)
VRBO
ANGEL FISH at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropically decorated 2 bedroom 2 bathroom townhouse in secluded area of Truman Annex, complete with updated appliances, ...
From $496 per night (USD)
VRBO
From $541 per night (USD)
Expedia
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
2
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 $541 per night (USD)
Expedia
From $677 per night (USD)
VRBO
TROPICAL EXECUTIVE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $677 per night (USD)
VRBO
From $650 per night (USD)
Expedia
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 $650 per night (USD)
Expedia
From $838 per night (USD)
VRBO
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 $838 per night (USD)
VRBO
From $550 per night (USD)
Expedia
Washer & Dryer, Near Downtown - Mesa House, Dos
Bedrooms:
1
Bathrooms:
2
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 $550 per night (USD)
Expedia
From $324 per night (USD)
VRBO
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 $324 per night (USD)
VRBO
From $300 per night (USD)
Expedia
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 $300 per night (USD)
Expedia
From $225 per night (USD)
VRBO
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 $225 per night (USD)
VRBO
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 $281 per night (USD)
VRBO
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 $281 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $796 per night (USD)
VRBO
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 $796 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
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 $538 per night (USD)
Expedia
From $313 per night (USD)
VRBO
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 $313 per night (USD)
VRBO
From $409 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 $409 per night (USD)
Expedia
From $396 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 $396 per night (USD)
VRBO
From $391 per night (USD)
Expedia
GREEN BAMBOO at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Paradise! This 2 bedroom townhouse, featuring one bedroom with a king and the second bedroom features twin be ...
From $391 per night (USD)
Expedia
From $512 per night (USD)
VRBO
Island Time | Luxury Beach Condo w/ Pool & Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: "Island Time" is a newly renovated, 2 bed 2 bath condo located in the gated La Brisa Condominium complex. Situa ...
From $512 per night (USD)
VRBO
From $572 per night (USD)
Expedia
CAPTAINS WHEEL at The Truman Annex in Key West
Bedrooms:
2
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 $572 per night (USD)
Expedia
From $716 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 $716 per night (USD)
VRBO
From $409 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 $409 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
From $1783 per night (USD)
Expedia
Steps from Duval with Private Pool – Southern Palms
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Summary: Welcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, or ...
From $1783 per night (USD)
Expedia
From $462 per night (USD)
VRBO
PELICAN'S PERCH at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town neighborhood ...
From $462 per night (USD)
VRBO
From $751 per night (USD)
Expedia
A SUNSET AND A HARBOUR VIEW at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Exceptional accommodations, spectacular location and first class amenities await you and your group! This two bedroom, ...
From $751 per night (USD)
Expedia
From $435 per night (USD)
VRBO
ANNIE'S HIDEAWAY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large cover ...
From $435 per night (USD)
VRBO
From $1082 per night (USD)
Expedia
3-Story spacious conch style home w/ private pool & dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $1082 per night (USD)
Expedia
Click For Pricing
Expedia
KEY WEST - Weekly Stay Only - 2 Bedroom 2 Bathrooms Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Coconut Mallory Marina and Resort is located in the southernmost city in the continental United States. Key West, Fl ...
Click For Pricing
Expedia
From $373 per night (USD)
Expedia
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Single family home. (Not a condo.) We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. ...
From $373 per night (USD)
Expedia
From $347 per night (USD)
VRBO
Carriage House at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $347 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Bunk Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $336 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Unique Home with loft @ Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $283 per night (USD)
VRBO
From $467 per night (USD)
Expedia
MARLIN BLUE in the Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...
From $467 per night (USD)
Expedia
From $404 per night (USD)
VRBO
COOL BREEZE @ the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** This community is loc ...
From $404 per night (USD)
VRBO
From $380 per night (USD)
Expedia
TROPICAL BREEZES 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 $380 per night (USD)
Expedia
From $442 per night (USD)
VRBO
MANATEE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
'Manatee' is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ...
From $442 per night (USD)
VRBO
From $380 per night (USD)
Expedia
ISLAND 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 $380 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Petronia Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $235 per night (USD)
VRBO
Click For Pricing
Expedia
Classic Key West condo w/ private parking, covered porches, & shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Cool Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
Expedia
From $680 per night (USD)
VRBO
**LAYOVER in PARADISE @ CASA MARINA** New Home / Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! A home design ...
From $680 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Aah PARADISE at the Truman Annex in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AAH PARADISE This Foundry townhome is a Bostonian style 3 level home located in Old Town Key West. This home has been re ...
From $603 per night (USD)
Expedia
From $471 per night (USD)
VRBO
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Note: In 2026, bookings will require a minimum stay of 28 days, starting on the first of the month. I can adjust the dat ...
From $471 per night (USD)
VRBO
From $565 per night (USD)
Expedia
A LICENSE TO CHILL in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The historic Foundry, known as building #11, features three story townhomes, located in the award-winning residential ne ...
From $565 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental ...
From $192 per night (USD)
VRBO
From $1148 per night (USD)
Expedia
DOLPHIN WATCH in Key West @ The Truman Annex Compass Realty
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attrac ...
From $1148 per night (USD)
Expedia
From $411 per night (USD)
VRBO
AMBERJACK at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $411 per night (USD)
VRBO
From $1173 per night (USD)
Expedia
CATCH OF THE DAY at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
View passing ships and sunsets from your own first floor, large deck with plenty of seating for a large family in the Tr ...
From $1173 per night (USD)
Expedia
From $438 per night (USD)
VRBO
SOUTHARD COMFORT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOCATION, LOCATION, LOCATION! Southard Comfort is on Southard Street in the TRUMAN ANNEX, which is one of the most beau ...
From $438 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Luxury Waterfront at Galion Resort in Old Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $669 per night (USD)
Expedia
From $377 per night (USD)
VRBO
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! DOCKSIDE DAYD ...
From $377 per night (USD)
VRBO
From $713 per night (USD)
Expedia
PARADISE ON THE OCEANat The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $713 per night (USD)
Expedia
From $467 per night (USD)
VRBO
A SUNRISE COTTAGE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool an ...
From $467 per night (USD)
VRBO
From $414 per night (USD)
Expedia
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***This unit holds a City of Key West Transient License and will be permitted to continue offering weekly rentals in 202 ...
From $414 per night (USD)
Expedia
From $351 per night (USD)
VRBO
ALMOST 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 $351 per night (USD)
VRBO
From $2584 per night (USD)
Expedia
Private Heated Pool & Near Duval - The Curry House
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $2584 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 6
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Curry House offers three stories of historic Conch house charm, perfect for your getaway. This guesthouse featu ...
From $285 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Balcony, Pool, Near Duval - Curry House Room 3 + 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Curry House offers three stories of historic charm, transporting you back in time. The guesthouse features priv ...
From $389 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guesth ...
From $285 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 8
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $280 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 7
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $280 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $290 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 9
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $284 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Curry House | Heated Pool, King Bed, 1st Floor
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $285 per night (USD)
Expedia

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