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VRBO
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
Click For Pricing
VRBO
From $494 per night (USD)
Expedia
Free Parking, Pool, & Pet Friendly - The Trinidad
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $494 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Rent a Piece of Paradise, Best Location on the Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $285 per night (USD)
VRBO
From $353 per night (USD)
Expedia
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambianc ...
From $353 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $450 per night (USD)
VRBO
From $499 per night (USD)
Expedia
The Palms...A beautiful space in the perfect place.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $499 per night (USD)
Expedia
From $1932 per night (USD)
VRBO
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
Bedrooms:
4
Bathrooms:
8
Sleeps:
20
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...
From $1932 per night (USD)
VRBO
From $520 per night (USD)
Expedia
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** 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! For a month i ...
From $520 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Eleanor's Place Key West - Historic Old Town Cottage Dog Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Eleanor's Place is a charming Key West Cottage in the heart of Key West! Featured on HGTV's Island Life, our renovated c ...
From $286 per night (USD)
VRBO
From $327 per night (USD)
VRBO
~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $327 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Dreamworks Conch Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PEACEFUL RETREAT... A quintessential Key West cottage in the heart of Old Town and only a few blocks away from Higgs Bea ...
From $205 per night (USD)
VRBO
From $162 per night (USD)
VRBO
Seaside Condo, 2 pools, close to Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Upon waking in the morning we hear the murmuring of tropical birds , feel the gentle sea breezes and the fragrance of j ...
From $162 per night (USD)
VRBO
From $432 per night (USD)
VRBO
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion ...
From $432 per night (USD)
VRBO
From $546 per night (USD)
Expedia
EBB AND FLO ~ Newly Renovated Retreat in Old Town with Incredible Pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
OLD TOWN KEY WEST… Surround yourself in this newly renovated gem located in the desirable Casa Marina neighborhood neari ...
From $546 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Studio overlooking historic Key West waterfront.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathr ...
From $203 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Pool, Free Parking & Pet Friendly - The Barbados
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. Just 1 mile from the b ...
From $504 per night (USD)
Expedia
$Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!$
From $1832 per night (USD)
VRBO
Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Octopus’s Garden — Top-Rated Key West Rental with 150+ 5-Star Reviews! Location: Steps from Duval Street & Ernest Hemin ...
From $1832 per night (USD)
VRBO
From $809 per night (USD)
Expedia
Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $809 per night (USD)
Expedia
From $809 per night (USD)
VRBO
Oceanfront Property - 2BR/2BA - Near Smather's Beach - Poolside Bar and Grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
★Excellent Key West Location - Oceanside Resort - Two Bedroom - Two Bath - Sleeps 6 ★Very Clean - Very Nice Property. T ...
From $809 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Atlantic Ocean Breezes Tropical Island Key West Sunrises
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $185 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Tropical 2BR Condo w/ Pool, Tennis, Near Beach & Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our piece of paradise in Key West! Our beautifully maintained, fully tiled 2-bedroom condo is your perfect ho ...
From $300 per night (USD)
VRBO
From $998 per night (USD)
Expedia
ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $998 per night (USD)
Expedia
From $1441 per night (USD)
VRBO
NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis
Bedrooms:
0
Bathrooms:
2
Sleeps:
4
( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely ...
From $1441 per night (USD)
VRBO
From $2811 per night (USD)
Expedia
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $2811 per night (USD)
Expedia
From $582 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming Historic Bungalow with Private Pool & Detached Cottage – Steps from Duval Street! Experience the best of Key W ...
From $582 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Key West Cabana-Old Town Key West- Steps to Duval Street w/ Pool & Tiki Bar
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience the Best of Key West at Key West Cabana — Your Charming 2-Bedroom, 2-Bathroom Retreat in Old Town Welcome to ...
From $474 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Happy’s Houseboat Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $581 per night (USD)
VRBO
From $242 per night (USD)
Expedia
OUR HAPPY PLACE ~ Adorable 2 Bedroom, 2 Bath Condo Steps from the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $242 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Private Paradise with Heated Waterfall Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $319 per night (USD)
VRBO
From $501 per night (USD)
VRBO
Gorgeous beach bungalow just steps from the beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just seconds away from the ocean, this 3 bedroom 2 bath home with a large backyard and patio is ready for you and your f ...
From $501 per night (USD)
VRBO
From $145 per night (USD)
VRBO
A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Caroline's Cottage KW Welcome to Caroline’s Cottage steps away from the world’s famous Duval Street in Key West Fla. Yo ...
From $145 per night (USD)
VRBO
From $1634 per night (USD)
Expedia
Sublime Sunsets Waterfront Condo at The Truman Annex in Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $1634 per night (USD)
Expedia
From $161 per night (USD)
VRBO
Centrally located cottage apartment with patio - walk to beach & dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $161 per night (USD)
VRBO
From $163 per night (USD)
Expedia
Cozy cottage apartment with front porch & upgraded finishes - close to beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Borrowed Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $163 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $211 per night (USD)
VRBO
From $267 per night (USD)
Expedia
GOOD FEELIN ~ Charming 2 BR/2 Ba Home Conveniently Located w/ Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SPOIL YOURSELF… Come unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of sw ...
From $267 per night (USD)
Expedia
From $223 per night (USD)
VRBO
POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w/ Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOST ON ISLAND TIME… Treasure your time together within this charming Key West cottage tucked away on this peaceful and ...
From $223 per night (USD)
VRBO
From $385 per night (USD)
Expedia
GOOD VIBES ~ 2 Cottages w/ 4 BR/3 Ba, Outdoor Oasis and Parking!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
MEMORIES TO LAST A LIFETIME… This unique set of 2 charming, Conch style homes provide the perfect compound setting for y ...
From $385 per night (USD)
Expedia
From $281 per night (USD)
VRBO
A+ Location in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $281 per night (USD)
VRBO
From $882 per night (USD)
Expedia
AFTERNOON DELIGHT at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $882 per night (USD)
Expedia
From $2357 per night (USD)
VRBO
**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
Bedrooms:
9
Bathrooms:
8
Sleeps:
20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $2357 per night (USD)
VRBO
From $293 per night (USD)
VRBO
Julia's Secret
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $293 per night (USD)
VRBO
From $1411 per night (USD)
VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1411 per night (USD)
VRBO
From $625 per night (USD)
Expedia
Stunning Historic Estate – 20% Off Summer Bookings, Heated Pool & Bikes Included
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Discover a delightful four-bedroom getaway nestled within the historic district of Key West. Nestled just a 13-minute wa ...
From $625 per night (USD)
Expedia
From $3258 per night (USD)
VRBO
1 Block to Duval St | Banana's Foster Guesthouse
Bedrooms:
7
Bathrooms:
7
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $3258 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $603 per night (USD)
Expedia
From $276 per night (USD)
VRBO
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $276 per night (USD)
VRBO
From $342 per night (USD)
Expedia
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $342 per night (USD)
Expedia
From $1529 per night (USD)
VRBO
Heated Pool, Steps to Duval St - Poolside Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home c ...
From $1529 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Shared Heated Pool, Near Duval - Poolside Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $368 per night (USD)
Expedia
From $1534 per night (USD)
VRBO
Old Town Retreat near Upper Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1534 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Dog-friendly condo with pool & hot tub - walk or bike to beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $340 per night (USD)
Expedia
From $503 per night (USD)
VRBO
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. This is ...
From $503 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $445 per night (USD)
Expedia
From $134 per night (USD)
VRBO
Conch Republic Studio - Key West Millionaires Row
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In the center of Key West's prestigious "Millionaires Row," Conch Republic Studio is a tranquil getaway for one or a cou ...
From $134 per night (USD)
VRBO
From $375 per night (USD)
Expedia
'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Hist ...
From $375 per night (USD)
Expedia
From $585 per night (USD)
VRBO
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $585 per night (USD)
VRBO
From $390 per night (USD)
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, ...
From $390 per night (USD)
Expedia
From $804 per night (USD)
VRBO
Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $804 per night (USD)
VRBO
Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For Pricing
Expedia
From $1089 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 $1089 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 $408 per night (USD)
VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
3
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 $408 per night (USD)
VRBO
From $916 per night (USD)
VRBO
★2BR Resort Villa at Heart of Old Town Key West- Sleeps 6!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $916 per night (USD)
VRBO
From $1231 per night (USD)
VRBO
Steps from Duval with Private Pool – Coconut Palm
Bedrooms:
2
Bathrooms:
3
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 $1231 per night (USD)
VRBO
From $746 per night (USD)
Expedia
Private Parking & Near Downtown - Sea Breeze
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Sea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart of ...
From $746 per night (USD)
Expedia
From $976 per night (USD)
VRBO
Waterfront Luxury Home with private pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $976 per night (USD)
VRBO
From $560 per night (USD)
Expedia
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 $560 per night (USD)
Expedia
From $339 per night (USD)
VRBO
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)
VRBO
From $459 per night (USD)
VRBO
Key West Oceanfront Condo - 'The Sea Jay'
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The condo is quite large at over 1150 square feet and looks directly at beautiful Smathers Beach. The 'Sea Jay' is loca ...
From $459 per night (USD)
VRBO
From $554 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 $554 per night (USD)
VRBO
From $1248 per night (USD)
Expedia
Spacious Waterfront 4 Bedroom Home
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 $1248 per night (USD)
Expedia
From $815 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 $815 per night (USD)
VRBO
From $1113 per night (USD)
Expedia
Oceanview 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 $1113 per night (USD)
Expedia
From $659 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry Building Discover your perfect Key West ret ...
From $659 per night (USD)
VRBO
From $710 per night (USD)
VRBO
Discover the lure of Casa Catalina, a blend of Key West charm and modern comfort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Casa Catalina – Your Key West Oasis! Step into the enchanting world of Key West with a stay at the newly ren ...
From $710 per night (USD)
VRBO
From $371 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 $371 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $456 per night (USD)
VRBO
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 $456 per night (USD)
VRBO
From $401 per night (USD)
Expedia
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 $401 per night (USD)
Expedia
From $323 per night (USD)
VRBO
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 $323 per night (USD)
VRBO
From $508 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 $508 per night (USD)
Expedia
From $496 per night (USD)
VRBO
BELLA VITA ~ 2/1.5 located in the Truman Annex with a community pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
IDEAL LOCATION IN GREAT COMMUNITY... Enjoy your stay at the President's Walk at Truman Annex. This well manicured commu ...
From $496 per night (USD)
VRBO
From $675 per night (USD)
VRBO
Hyatt Sunset Harbor, 2BD overlooking the stunning and beautiful Gulf of Mexico!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor! **Reservations are available in weekly (7 ni ...
From $675 per night (USD)
VRBO
From $256 per night (USD)
VRBO
Quiet Conch House in Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $256 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
Click For Pricing
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 $443 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 $443 per night (USD)
Expedia
From $1034 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 $1034 per night (USD)
VRBO
From $374 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 $374 per night (USD)
Expedia
From $1810 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 $1810 per night (USD)
VRBO
From $688 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 $688 per night (USD)
Expedia
From $500 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 $500 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
BIlly's Blue Heaven is fresh, clean and Pristine. We have updated the condo with all new paint, a new Smart Tv in the ...
From $378 per night (USD)
Expedia
From $1039 per night (USD)
VRBO
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 $1039 per night (USD)
VRBO
From $555 per night (USD)
Expedia
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 $555 per night (USD)
Expedia
From $500 per night (USD)
VRBO
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 $500 per night (USD)
VRBO
From $398 per night (USD)
Expedia
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 $398 per night (USD)
Expedia
From $578 per night (USD)
VRBO
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 $578 per night (USD)
VRBO
From $438 per night (USD)
Expedia
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 $438 per night (USD)
Expedia

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