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From $705 per night (USD)
VRBO
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 $705 per night (USD)
VRBO
From $415 per night (USD)
Expedia
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 $415 per night (USD)
Expedia
From $798 per night (USD)
VRBO
Exquisite Elegance in Old Town Key West: Your Stylish Sanctuary Awaits
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This stylish Conch home is tucked away on a quiet lane in Old Town Key West. Newly remodeled, impressively decorated 3 B ...
From $798 per night (USD)
VRBO
From $323 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 $323 per night (USD)
Expedia
From $372 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 $372 per night (USD)
VRBO
From $334 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 $334 per night (USD)
Expedia
From $279 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 $279 per night (USD)
VRBO
From $1087 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 $1087 per night (USD)
Expedia
From $218 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 $218 per night (USD)
VRBO
From $427 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 $427 per night (USD)
Expedia
From $371 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 $371 per night (USD)
VRBO
From $345 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 $345 per night (USD)
Expedia
From $417 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 $417 per night (USD)
VRBO
From $345 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 $345 per night (USD)
Expedia
From $343 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 $343 per night (USD)
VRBO
From $581 per night (USD)
Expedia
AAH PARADISE at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AAH PARADISE This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been r ...
From $581 per night (USD)
Expedia
From $460 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 $460 per night (USD)
VRBO
From $545 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 $545 per night (USD)
Expedia
From $605 per night (USD)
VRBO
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 ...
From $605 per night (USD)
VRBO
From $202 per night (USD)
Expedia
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 $202 per night (USD)
Expedia
From $1169 per night (USD)
VRBO
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 $1169 per night (USD)
VRBO
From $436 per night (USD)
Expedia
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 $436 per night (USD)
Expedia
From $1072 per night (USD)
VRBO
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 $1072 per night (USD)
VRBO
From $421 per night (USD)
Expedia
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 $421 per night (USD)
Expedia
$Colorful cottage w\/shared pool, central AC, washer\/dryer$
Click For Pricing
VRBO
Colorful cottage w\/shared pool, central AC, washer\/dryer
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Grinnell Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For Pricing
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 $354 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 $354 per night (USD)
VRBO
From $684 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 $684 per night (USD)
Expedia
From $469 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 $469 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to "Cocktails & Dreams," an impeccably updated second-floor condo located in the coveted Shipyard Condominiums! ...
From $399 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 $2787 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 $2787 per night (USD)
Expedia
From $332 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 $332 per night (USD)
VRBO
From $517 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 $517 per night (USD)
Expedia
From $324 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 $324 per night (USD)
VRBO
From $327 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 $327 per night (USD)
Expedia
From $323 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 $323 per night (USD)
VRBO
From $311 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 $311 per night (USD)
Expedia
From $303 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 $303 per night (USD)
VRBO
From $313 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 $313 per night (USD)
Expedia
From $958 per night (USD)
VRBO
Sweet Caroline | Banana's Foster Guesthouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $958 per night (USD)
VRBO
From $422 per night (USD)
Expedia
KeyLime Cottage | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $422 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Sugar Pie Suite | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $375 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Honeybun Hideaway at Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $386 per night (USD)
Expedia
From $512 per night (USD)
VRBO
Banana Split | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $512 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Creme Brulee Suite | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $423 per night (USD)
Expedia
From $826 per night (USD)
VRBO
Pool, Parking, & Pet Friendly - Sunnyside Up
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Sunnyside Up is a charming Conch-style home on United Street, just steps from Key West’s "Old Town." With an op ...
From $826 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Atlantic Paradise Escape | Luxury Oceanfront Condo in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $196 per night (USD)
Expedia
From $345 per night (USD)
VRBO
Lovely 2 bedroom, 2 bathroom steps from the beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Key West at La Brisa, a gated Condo community, just steps from the beach on Key West's Atlantic coast. Walk in ...
From $345 per night (USD)
VRBO
From $518 per night (USD)
Expedia
COLORFUL COCKTAIL in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Shipyard unit is a two level condominium which has a private courtyard with a deck to enjoy the beautiful weather a ...
From $518 per night (USD)
Expedia
From $689 per night (USD)
VRBO
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + 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! When explorin ...
From $689 per night (USD)
VRBO
From $640 per night (USD)
Expedia
A PALM OASIS at The Truman Annex in Key West.....
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
NEW LISTING!!! This charming two bedroom, two and one half bath townhome has recently been updated and added to our rent ...
From $640 per night (USD)
Expedia
From $548 per night (USD)
VRBO
Coastal Inspired Cottage in Bahama Village Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Bahama Dreams, a fully renovated 3 bedroom/ 2 bath eyebrow style home just two blocks off iconic Duval Street ...
From $548 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Atlantic Parrot Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $546 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Bright Keys Cottage with Enclosed Yard, Deck, Porch, Partial, AC, & WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Key Rest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $217 per night (USD)
VRBO
From $407 per night (USD)
Expedia
MONTHLY RENTAL, T-giving 25 open, block to Duval, POOL, your own personal resort
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to "Shipwrecked in Paradise"! Historic Key West Eyebrow House with private pool..... ONE block to Duval, the He ...
From $407 per night (USD)
Expedia
From $334 per night (USD)
VRBO
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You don’t oft ...
From $334 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautifully home with quaint charm has a one month minimum stay requirement because of local zoning regulation. Col ...
From $235 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Extended Summer Stays for 2025- Open 6 months from April 1st onwards
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $171 per night (USD)
VRBO
From $542 per night (USD)
Expedia
**THE BEAMING BARRACUDA @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERV
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE BEAMING B ...
From $542 per night (USD)
Expedia
From $626 per night (USD)
VRBO
Hyatt Beach House! Quiet Key West Location! Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $626 per night (USD)
VRBO
From $797 per night (USD)
Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $797 per night (USD)
Expedia
From $307 per night (USD)
VRBO
ISLAND TIME at Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Time***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***This is a beautiful, private two-story open plan townhome back ...
From $307 per night (USD)
VRBO
From $425 per night (USD)
Expedia
~LA MAISONNETTE~ Gated condominium 1 block from the allure of Duval Street.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Location, location, location, is what this chic condominium is all about! From here you can walk 1 block t ...
From $425 per night (USD)
Expedia
From $394 per night (USD)
VRBO
The Galleon Resort Best Resort Location in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $394 per night (USD)
VRBO
From $308 per night (USD)
Expedia
TAILGATE KEY at the Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $308 per night (USD)
Expedia
From $508 per night (USD)
VRBO
SWEET'S SPOT at The Truman Annex in Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $508 per night (USD)
VRBO
Click For Pricing
Expedia
Studio at Hyatt Residence Club Key West, Sunset Harbor.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Seth Nock Licensed Broker, Selling Timeshares INC. Studio at Hyatt Residence Club Key West, Sunset Harbor. Check-in: ...
Click For Pricing
Expedia
From $304 per night (USD)
VRBO
Anchors Away - Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $304 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Red Room 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 $335 per night (USD)
Expedia
From $437 per night (USD)
VRBO
Shared Pool & Near Duval - Road's End
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Located just a stone's throw from Mile Marker Zero, "Road's End" is a charming 1-bedroom, 1.5-bath townhome in ...
From $437 per night (USD)
VRBO
From $356 per night (USD)
Expedia
BEST TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This newly renovated shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautif ...
From $356 per night (USD)
Expedia
From $396 per night (USD)
VRBO
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! The moment yo ...
From $396 per night (USD)
VRBO
From $394 per night (USD)
Expedia
POOLSIDE HANGOVER at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy yo ...
From $394 per night (USD)
Expedia
From $1313 per night (USD)
VRBO
A Place on Emma at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1313 per night (USD)
VRBO
From $378 per night (USD)
Expedia
A DUCK ON THE GREEN at the Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $378 per night (USD)
Expedia
From $380 per night (USD)
VRBO
SOUTHERNMOST SANCTUARY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...
From $380 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $200 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $192 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $421 per night (USD)
Expedia
From $1185 per night (USD)
VRBO
Oversized home for the whole family w/private pool & dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1185 per night (USD)
VRBO
From $430 per night (USD)
Expedia
HIGH TIDE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaura ...
From $430 per night (USD)
Expedia
From $424 per night (USD)
VRBO
A CONCH ESCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...
From $424 per night (USD)
VRBO
From $407 per night (USD)
Expedia
A SUNSET VIEW at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $407 per night (USD)
Expedia
From $1082 per night (USD)
VRBO
Spacious home with pool & balcony - 1 block from Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1082 per night (USD)
VRBO
Click For Pricing
Expedia
Charming home in Old Town, walk to shops & restaurants - yard
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Gingerbread Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
Expedia
From $436 per night (USD)
VRBO
ARCHIPELAGO l 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 $436 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Old Town Charm Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming Old Town cottage is a short walk to Duval Street nightlife, restaurants, shops and culture… and a walk or ...
From $291 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Location, Beauty & Comfort @ Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $410 per night (USD)
VRBO
From $805 per night (USD)
Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $805 per night (USD)
Expedia
From $730 per night (USD)
VRBO
Oceanfront 4-Bed 3-Bath home with pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views p ...
From $730 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Alluring corner unit w/ full kitchen & pool - close to beach/ nightlife
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Seaclusion Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $456 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Wonderful Condo in Key West w/Free WiFi, Lanai, A/C, Shared Hot Tub & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tradewinds at Smathers Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $272 per night (USD)
VRBO
From $465 per night (USD)
Expedia
Steps from Duval, Shared Pool – Sky Loft Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $465 per night (USD)
Expedia
From $839 per night (USD)
VRBO
BLUE LAGOON at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $839 per night (USD)
VRBO
$**SUGARPOPPY COTTAGE** Cozy Cottage \/ Private Pool + LAST KEY SERVICES$
From $356 per night (USD)
Expedia
**SUGARPOPPY COTTAGE** Cozy Cottage \/ Private Pool + 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! Look for the ...
From $356 per night (USD)
Expedia
From $368 per night (USD)
VRBO
NEW LISTING 2nd Fl Condo w/private outdoor deck overlooking historic Fleming St.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Airy sun-filled apartment above an art gallery in 100 year old Old Town Conch home. Private cozy quiet & romantic hideaw ...
From $368 per night (USD)
VRBO
From $1751 per night (USD)
Expedia
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $1751 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Sailor's Sanctuary - A Renovated Condo in Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Renovated ground floor apartment in Truman Annex. Steps from Duval Street! Enjoy all that the beautiful gated community ...
From $227 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Hidden Beach - the perfect place to stay in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hidden Beach Unit 3 - In Old Town, just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. ...
From $444 per night (USD)
Expedia

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