Key West National Wildlife Refuge Rentals
From $233 per night (USD)VRBO
THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***PARDON OUR DUST! This building is being re-roofed beginning the week of 06/02/25 and the process will take 3-4 weeks ...
From $233 per night (USD)VRBO
From $1087 per night (USD)Expedia
STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...
From $1087 per night (USD)Expedia
From $2000 per night (USD)VRBO
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $2000 per night (USD)VRBO
From $1001 per night (USD)Expedia
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Annex Home w/Private Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $1001 per night (USD)Expedia
From $1063 per night (USD)VRBO
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $1063 per night (USD)VRBO
From $304 per night (USD)Expedia
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
COZY VALUE IN TRUMAN ANNEX… This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the ...
From $304 per night (USD)Expedia
From $852 per night (USD)VRBO
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $852 per night (USD)VRBO
From $402 per night (USD)VRBO
A Slice of Paradise! @ the Shipyard Palms!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Old Town, with the beautiful community of private homes and condominiums of Truman Annex, this Shipyard ...
From $402 per night (USD)VRBO
From $419 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $419 per night (USD)VRBO
From $476 per night (USD)Expedia
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
STEPS TO IT ALL... Peaceful surroundings of swaying palm trees and picturesque white picket fences invite you in to this ...
From $476 per night (USD)Expedia
From $406 per night (USD)VRBO
Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg/bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the Key West Shire! A sublime sanctuary where all your worldly troubles melt away and relaxation is paramoun ...
From $406 per night (USD)VRBO
From $549 per night (USD)VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $549 per night (USD)VRBO
From $1089 per night (USD)VRBO
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $1089 per night (USD)VRBO
From $1186 per night (USD)Expedia
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $1186 per night (USD)Expedia
From $150 per night (USD)VRBO
PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. One of ...
From $150 per night (USD)VRBO
From $1181 per night (USD)Expedia
Secret Villa I @ Old Town with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $1181 per night (USD)Expedia
From $722 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 $722 per night (USD)VRBO
From $2186 per night (USD)Expedia
Key West Suites Hotel # 205
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...
From $2186 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 $248 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 $248 per night (USD)VRBO
From $214 per night (USD)VRBO
Shipyard Truman Annex; 620 Thomas St. 1st Floor 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
From $608 per night (USD)VRBO
** Waterfront - Two Blocks From Duval Street & Mallory Square**
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo located right on the water in Building 5 (Unit 531) - top floor - at the Hyatt Sunset Harbor, is a 2 bedroom, ...
From $608 per night (USD)VRBO
From $296 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 $296 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $180 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 $180 per night (USD)VRBO
From $731 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 $731 per night (USD)VRBO
From $897 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 $897 per night (USD)VRBO
From $1958 per night (USD)Expedia
Perfect Location, Private Heated Pool & Pristine Luxury Home!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Perfectly located and fully remodeled, Octopus's Garden is steps from Duval Street and the home of Ernest Hemmingway. ...
From $1958 per night (USD)Expedia
From $662 per night (USD)VRBO
ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
QUINTESSENTIAL OLD TOWN CHARM… Imagine pulling up to a picture-perfect gated community, lined by white picket fences and ...
From $662 per night (USD)VRBO
From $2921 per night (USD)Expedia
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 $2921 per night (USD)Expedia
From $267 per night (USD)VRBO
Eleanor's Place Key West Cottage in Historic Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
"Eleanor's Place Key West" is a charming Key West cottage in the heart of historic Old Town! Featured on HGTV's Island L ...
From $267 per night (USD)VRBO
From $338 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 $338 per night (USD)VRBO
From $389 per night (USD)VRBO
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 $389 per night (USD)VRBO
From $339 per night (USD)Expedia
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 $339 per night (USD)Expedia
From $397 per night (USD)VRBO
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
IN THE HEART OF IT ALL… A perfect location within a peaceful setting, this updated home allows for extraordinary moments ...
From $397 per night (USD)VRBO
From $411 per night (USD)Expedia
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PICTURE PERFECT… Swaying palms and a picturesque white picket fence outline this tropical retreat luring you in to your ...
From $411 per night (USD)Expedia
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 $644 per night (USD)Expedia
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)Expedia
From $865 per night (USD)VRBO
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 $865 per night (USD)VRBO
From $636 per night (USD)Expedia
Namaste 'The Spirit Within Me Salutes The Spirit Within You'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $636 per night (USD)Expedia
From $374 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 $374 per night (USD)VRBO
From $185 per night (USD)VRBO
Banyan Court downtown condo- 2 bedroom, 2 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 $185 per night (USD)VRBO
From $386 per night (USD)VRBO
Shipyard 197-Condo in Truman Annex-2 bedroom 1 bath, close to Duval w/ pool
- Bedrooms:
- 1
- 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 $386 per night (USD)VRBO
From $409 per night (USD)VRBO
Truman Annex unit 254
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 ...
From $409 per night (USD)VRBO
From $777 per night (USD)VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please choose a Saturday check-in, all rentals will be in seven night increments. Bedding configuration may vary, depend ...
From $777 per night (USD)VRBO
From $991 per night (USD)VRBO
Hyatt Sunset Harbor Resort for ONLY Sunday to Sunday Week's stay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is for A WEEK'S Stay Only in a 2 Bedroom 2 Bathroom Villa for 6 People. Discover this relaxing oasis in the heart ...
From $991 per night (USD)VRBO
From $452 per night (USD)VRBO
Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 4 - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get wit ...
From $452 per night (USD)VRBO
From $649 per night (USD)VRBO
Hyatt Sunset Harbour Resort-Prime location on Key West!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
All rentals will be in seven-night increments with a Friday through Sunday for check-in. Thank you for choosing Dash R ...
From $649 per night (USD)VRBO
From $343 per night (USD)VRBO
Cozy Piece of Key West History
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECTLY located, 100 y-o "Conch" House, w AAA+ front-porch, and 3 full baths to go w 3 BRs... brand-new kitchen, compl ...
From $343 per night (USD)VRBO
From $305 per night (USD)Expedia
THE OLD SAPODILLA HOUSE ~ Pet Friendly Home in Historic Bahama Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECT GETAWAY JUST STEPS FROM DUVAL... Private family home with poolside cottage totals three bedrooms and three full ...
From $305 per night (USD)Expedia
From $283 per night (USD)VRBO
~ THE PINK HOUSE ~ Saline pool, lush privacy and 2 ensuites with balconies.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $283 per night (USD)VRBO
From $595 per night (USD)VRBO
~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WEEKLY RENTAL: This property has a 7 night minimum stay. **Beginning January, 2026, Fair Winds will be a MONTHLY (28 n ...
From $595 per night (USD)VRBO
From $1347 per night (USD)VRBO
~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
THE PROPERTY: If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. ...
From $1347 per night (USD)VRBO
From $253 per night (USD)VRBO
~ SEAS THE DAY ~ Nestled in a gated community by Fort Zachary Taylor beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Home is available September 1 for a monthly rental (only). 28 night minimum** WEEKLY RENTAL: This property has a 7 n ...
From $253 per night (USD)VRBO
From $1350 per night (USD)VRBO
Very Rare-The Galleon 3 King Bd, 3 Bath w/ 4th king bd in loft + sleeper sofa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very b ...
From $1350 per night (USD)VRBO
From $190 per night (USD)VRBO
2026 now available! SPARKLING Old Town PRIVATE 3BR Lagoon Pool& FIVE stars!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This colorful three bedroom, two full bath, private, and historic home is a wonderful spot to vacation, live like a loca ...
From $190 per night (USD)VRBO
From $391 per night (USD)VRBO
Key West Hen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Give me a call if you have any questions! 702-232-3750 ****The roof has been replaced and the gutters are being done as ...
From $391 per night (USD)VRBO
From $747 per night (USD)VRBO
Tropical State of Mind Key West FL
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition TV found in every bedroom in ...
From $747 per night (USD)VRBO
From $524 per night (USD)VRBO
Key West 44ft Sailboat Wild Thing-Summer Fun Sandbar Motorboat Trips
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Boats are located at the Perry Marina! Summer special starting 6/1/25 until 10/1/25 receive upon weather availability-a ...
From $524 per night (USD)VRBO
From $671 per night (USD)Expedia
Beautiful sunsets!! Harbour Place, Truman Annex. Walk or bike to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Harbor Place is one of the most prestigious properties in Key West! This unit offers breath taking water views overlook ...
From $671 per night (USD)Expedia
From $1156 per night (USD)VRBO
Waterfront Views from Dolphin Watch
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Dolphin Watch is located in prestigious Truman Annex and is one of the few private waterfront homes. We are less than tw ...
From $1156 per night (USD)VRBO
From $354 per night (USD)VRBO
Location, Location, Location!!! Downtown Key West - Truman Annex!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
All the amenities of a fantastic resort suite and free assigned parking in the middle of everything in Key West...2/1 th ...
From $354 per night (USD)VRBO
From $620 per night (USD)VRBO
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $620 per night (USD)VRBO
From $408 per night (USD)VRBO
Galleon Resort Efficiency Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You w ...
From $408 per night (USD)VRBO
From $784 per night (USD)VRBO
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $784 per night (USD)VRBO
From $367 per night (USD)VRBO
Large Floorplan & Yard, Sunny 2BR KING/twin, 1 Bath, Truman Annx, Grd Flr, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Amazing LOCATION! Truman Annex: SHABBY CHICKEN - come stay at the large & proud bird in town!! Large front yard and po ...
From $367 per night (USD)VRBO
From $1326 per night (USD)VRBO
Palm Trees Ocean Breeze Key West FL
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck over ...
From $1326 per night (USD)VRBO
From $373 per night (USD)VRBO
Truman Annex - Beautiful Townhome - President's Lane
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2-story townhouse; master bedroom with King Bed and double doors to deck; full bath; second bedroom with two t ...
From $373 per night (USD)VRBO
From $305 per night (USD)VRBO
Tranquil 2-BR Condo in Truman Annex, Steps to Pool & 5-Min Walk to Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our lovely condo which is located in the famed Truman Annex Complex right in the heart of fabulous Key West. ...
From $305 per night (USD)VRBO
From $281 per night (USD)Expedia
Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This condo has a unique location in the Gated Truman Annex. It is very quiet, but yet very close to all Key West has t ...
From $281 per night (USD)Expedia
From $295 per night (USD)VRBO
Truman Annex Best Location in Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We stick to a Saturday check in during the in season months (Jan-April) Greetings from Paradise, where the temperature ...
From $295 per night (USD)VRBO
From $287 per night (USD)VRBO
Villa Nomade at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. Th ...
From $287 per night (USD)VRBO
From $620 per night (USD)VRBO
Miami Vice Sailboat Used For TV Series with 2 Hour Sandbar Motor Boat Trip
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
*Our business is now in a pristine marina at the stock island division in Key West. Perry Marina has a shuttle that ru ...
From $620 per night (USD)VRBO
From $506 per night (USD)VRBO
Old Town Beauty built in 1883
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Enjoy the lovely Key West ocean breeze from your private Tree House. This is the quietest area of Old Town but only4 blo ...
From $506 per night (USD)VRBO
From $431 per night (USD)VRBO
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get wit ...
From $431 per night (USD)VRBO
From $330 per night (USD)Expedia
Villa Mer at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Mer in luxurious surroundings. Renovated in 2019 it has a fully equipped kitchen with bar seating. The li ...
From $330 per night (USD)Expedia
From $406 per night (USD)VRBO
A Touch Of Cuba In Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and sin ...
From $406 per night (USD)VRBO
From $418 per night (USD)VRBO
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $418 per night (USD)VRBO
From $534 per night (USD)VRBO
A Touch of Bermuda at Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping ...
From $534 per night (USD)VRBO
From $1979 per night (USD)Expedia
Key West Suites Hotel - Adam Scott Rote Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central ...
From $1979 per night (USD)Expedia
From $381 per night (USD)VRBO
Key West Rooster
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please call or text if you’d like to book our home 702 232... 3750 When booking our home please include a brief descri ...
From $381 per night (USD)VRBO
From $1212 per night (USD)VRBO
Rare Penthouse 2 bed/2bath additional King in loft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath ...
From $1212 per night (USD)VRBO
From $771 per night (USD)VRBO
The Galleon Resort in Beautiful Key West. Amazing Views! 2 bedroom villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at The Galleon Resort! **Reservations are available in weekly (7 nig ...
From $771 per night (USD)VRBO
From $639 per night (USD)VRBO
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $639 per night (USD)VRBO
From $287 per night (USD)VRBO
Villa Fleur at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and d ...
From $287 per night (USD)VRBO
From $1084 per night (USD)Expedia
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...
From $1084 per night (USD)Expedia
From $417 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 $417 per night (USD)VRBO
From $344 per night (USD)Expedia
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 $344 per night (USD)Expedia
From $355 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 $355 per night (USD)VRBO
From $444 per night (USD)Expedia
Washer & Dryer, Near Downtown - Mesa House, Uno
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Mesa House, Uno, is a charming condo in a prime location with a large front porch. Great for couples on a weeke ...
From $444 per night (USD)Expedia
From $250 per night (USD)VRBO
Steps from Duval, Pool on Site & Bikes Included!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
***Pool on Property and use of Free Bikes During your Stay!!!*** ***Contactless Check In and Check Out*** ***Enhanced Cl ...
From $250 per night (USD)VRBO
From $366 per night (USD)Expedia
Hot Tub & Pet Friendly - Royal Palm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Royal Palm is a beautiful newly updated studio cottage tucked away in the heart of Old Town Key West. There is ...
From $366 per night (USD)Expedia
From $290 per night (USD)VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $290 per night (USD)VRBO
From $291 per night (USD)Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $291 per night (USD)Expedia
From $327 per night (USD)VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $327 per night (USD)VRBO
From $316 per night (USD)Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $316 per night (USD)Expedia
From $326 per night (USD)VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $326 per night (USD)VRBO
From $285 per night (USD)Expedia
Classic King, Pool - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $285 per night (USD)Expedia
From $298 per night (USD)VRBO
Classic King, Pool - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $298 per night (USD)VRBO
From $328 per night (USD)Expedia
Classic King & Private Balcony - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $328 per night (USD)Expedia