
Key West National Wildlife Refuge Rentals

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VRBO
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
Click For PricingVRBO
- From $429 per night (USD)
Expedia
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Secret Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $429 per night (USD)Expedia
- From $571 per night (USD)
VRBO
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Key Lime Calypso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $571 per night (USD)VRBO
- From $525 per night (USD)
Expedia
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $525 per night (USD)Expedia
- From $254 per night (USD)
VRBO
Elegant Condo with Entertainment & Private Parking - Great Central Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $254 per night (USD)VRBO
- From $340 per night (USD)
Expedia
Sunny Tropical Condo with WiFi & Pool - Close to Beachside Action
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Seashore at the Shipyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $340 per night (USD)Expedia
- From $502 per night (USD)
VRBO
**CONCH GET ENOUGH at The Truman Annex in Key West**
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $502 per night (USD)VRBO
- From $2397 per night (USD)
Expedia
Key West Oasis - Truman Annex Estate
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Key West Oasis! This beautiful and sophisticated estate checks all the boxes and is located on one of the mos ...
From $2397 per night (USD)Expedia
- From $476 per night (USD)
VRBO
Heart of Downtown Key West Cottage With Off-Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minut ...
From $476 per night (USD)VRBO
- From $918 per night (USD)
Expedia
Balcony & Near Downtown - Sky Suite on Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $918 per night (USD)Expedia
- From $776 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $776 per night (USD)VRBO
- From $798 per night (USD)
Expedia
Balcony on Duval - Duval Dream Loft
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $798 per night (USD)Expedia
- From $885 per night (USD)
VRBO
Balcony on Duval - The Collins on Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $885 per night (USD)VRBO
- From $798 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $798 per night (USD)Expedia
- From $409 per night (USD)
VRBO
A BLUE BEAUTY at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stunning, Modern 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completely renovated. Fu ...
From $409 per night (USD)VRBO
- From $1439 per night (USD)
Expedia
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool & Balcony over Duval + LAST KEY
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1439 per night (USD)Expedia
- From $1941 per night (USD)
VRBO
Balcony on Duval - Duval's Duet on Duval
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $1941 per night (USD)VRBO
- From $812 per night (USD)
Expedia
Largest Shipyard Condo in the Truman Annex - over twice the size with a loft!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Shipyard PENTHOUSE! This unit was supposed to be 2 units but it was built as one larger unit plus two lofts were added. ...
From $812 per night (USD)Expedia
- From $723 per night (USD)
VRBO
5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $723 per night (USD)VRBO
- From $580 per night (USD)
Expedia
ISLAND OASIS in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $580 per night (USD)Expedia
- From $644 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w/ balcony at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $644 per night (USD)VRBO
- From $535 per night (USD)
Expedia
~The Escape ~ Your own tropical escape on private island!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $535 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Truman Annex 2 bedroom 2.5 bath Townhouse- steps from Duval Street with pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Full renovation completed in August 2024. This beautiful townhouse has a perfect location in Truman Annex. Truman Annex ...
From $500 per night (USD)VRBO
- From $439 per night (USD)
Expedia
Yellow 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 $439 per night (USD)Expedia
- From $416 per night (USD)
VRBO
Blue 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 $416 per night (USD)VRBO
- From $362 per night (USD)
Expedia
Green 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 $362 per night (USD)Expedia
- From $316 per night (USD)
VRBO
One Bedroom Deck Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $316 per night (USD)VRBO
- From $553 per night (USD)
Expedia
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $553 per night (USD)Expedia
- From $538 per night (USD)
VRBO
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $538 per night (USD)VRBO
- From $731 per night (USD)
VRBO
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
From $731 per night (USD)VRBO
- From $394 per night (USD)
VRBO
AWAY FROM IT ALL @ The Truman Annex
- 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 $394 per night (USD)VRBO
- From $478 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $478 per night (USD)Expedia
- From $420 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $420 per night (USD)VRBO
- From $1174 per night (USD)
Expedia
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $1174 per night (USD)Expedia
- From $357 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w/ a patio at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $357 per night (USD)VRBO
- From $236 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex 2 bedroom 2 bath Shipyard Condo at MM 0!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 2 bath {queen and ...
From $236 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 $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 $320 per night (USD)
VRBO
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 $320 per night (USD)VRBO
- From $360 per night (USD)
Expedia
SOUTHARD SUNSET~2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
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 $360 per night (USD)Expedia
- From $2804 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 $2804 per night (USD)VRBO
- From $234 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 $234 per night (USD)VRBO
- From $854 per night (USD)
VRBO
Amazing Penthouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing penthouse condo has one of the best view in Key West. Located in historic Mills Place in the main part of T ...
From $854 per night (USD)VRBO
- From $315 per night (USD)
Expedia
KEY LIME COTTAGE ~ Renovated 3 Bedroom, 2 Bathroom Home with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BAHAMA VILLAGE TREASURE... This Key West charmer is just a short stroll away from the award winning restaurants and deli ...
From $315 per night (USD)Expedia
- From $1011 per night (USD)
VRBO
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $1011 per night (USD)VRBO
- From $2059 per night (USD)
Expedia
Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to OCTOPUS GARDEN! The TOP Key West rental with 150+ 5-STAR reviews! Perfectly located and fully remodeled, Oc ...
From $2059 per night (USD)Expedia
- From $960 per night (USD)
VRBO
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 $960 per night (USD)VRBO
- From $469 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
Key West Cabana welcomes you to our quaint 2 bedroom, 2 bathroom home with large private pool, assigned parking for 2 ca ...
From $469 per night (USD)Expedia
- From $1553 per night (USD)
VRBO
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 $1553 per night (USD)VRBO
- From $800 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 $800 per night (USD)Expedia
- From $2934 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 $2934 per night (USD)VRBO
- From $274 per night (USD)
Expedia
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 $274 per night (USD)Expedia
- From $411 per night (USD)
VRBO
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Galleria was once a haven for traveling artists who frequented Key West. With a tranquil pool area and spacious pati ...
From $411 per night (USD)VRBO
- From $431 per night (USD)
Expedia
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 $431 per night (USD)Expedia
- From $317 per night (USD)
VRBO
Galleon Resort Efficiency in the old town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size b ...
From $317 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 $790 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 $790 per night (USD)VRBO
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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 PricingExpedia
- Click For Pricing
VRBO
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 PricingVRBO
- 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 $532 per night (USD)
VRBO
Pet Friendly Studio Near Duval – Traveler's Palm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: Get ready to dive into the vibrant energy of Key West at Traveler's Palm! This recently updated, spacious secon ...
From $532 per night (USD)VRBO
- From $1092 per night (USD)
Expedia
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 $1092 per night (USD)Expedia
- From $635 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfectly positioned townhouse in Truman Annex At Historic Foundry building. Hemingway Hideaway in Truman Annex is a de ...
From $635 per night (USD)VRBO
- From $373 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 $373 per night (USD)Expedia
- From $380 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 $380 per night (USD)VRBO
- From $285 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 $285 per night (USD)Expedia
- Click For Pricing
VRBO
SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A TRUMAN ANNEX DREAM... Come discover this beautifully renovated condo within the desirable Shipyard neighborhood in the ...
Click For PricingVRBO
- From $176 per night (USD)
Expedia
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 $176 per night (USD)Expedia
- From $749 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 $749 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 PricingExpedia
- 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 PricingVRBO
- From $351 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 $351 per night (USD)Expedia
- From $410 per night (USD)
VRBO
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)VRBO
- From $1898 per night (USD)
Expedia
**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 $1898 per night (USD)Expedia
- From $597 per night (USD)
VRBO
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 $597 per night (USD)VRBO
- From $470 per night (USD)
Expedia
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 $470 per night (USD)Expedia
- From $344 per night (USD)
VRBO
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 $344 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 $307 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 $307 per night (USD)VRBO
- From $477 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 $477 per night (USD)Expedia
- From $325 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 $325 per night (USD)VRBO
- From $458 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 $458 per night (USD)Expedia
- From $872 per night (USD)
VRBO
SEAPORT SERENITY-Beach-Pool-King-BBQ-Hot Tub-Extra Entrance
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & UNOBSTRUCTED VIEWS OF KEY WEST HARBOR AND ...
From $872 per night (USD)VRBO
- From $547 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 $547 per night (USD)Expedia
- From $1272 per night (USD)
VRBO
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 $1272 per night (USD)VRBO
- From $2845 per night (USD)
Expedia
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 $2845 per night (USD)Expedia
- From $1410 per night (USD)
VRBO
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 $1410 per night (USD)VRBO
- From $469 per night (USD)
Expedia
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)Expedia
- From $306 per night (USD)
VRBO
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 $306 per night (USD)VRBO
- From $489 per night (USD)
Expedia
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)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 $430 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 $430 per night (USD)Expedia
- From $592 per night (USD)
VRBO
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 $592 per night (USD)VRBO
- From $423 per night (USD)
Expedia
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 $423 per night (USD)Expedia
- From $434 per night (USD)
VRBO
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 $434 per night (USD)VRBO
- From $363 per night (USD)
Expedia
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)Expedia
- From $259 per night (USD)
VRBO
Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, 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 $259 per night (USD)VRBO
- From $214 per night (USD)
VRBO
Shipyard end unit - NOW AVAILABLE SEPT 2025
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Change In Latitudes is a non-smoking, 1st floor end unit in the serene section of Shipyard, Truman Annex. All the ame ...
From $214 per night (USD)VRBO