Key West National Wildlife Refuge Rentals
- From $307 per night (USD)
VRBO
BEST TIME at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This Shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautiful weather and e ...
From $307 per night (USD)VRBO
- From $301 per night (USD)
Expedia
African Queen by Brightwild | GREAT Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: African Queen Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seapo ...
From $301 per night (USD)Expedia
- From $330 per night (USD)
VRBO
Pilar's Cottage by Brightwild | Studio w\/Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Pilar Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seaport distr ...
From $330 per night (USD)VRBO
- From $1308 per night (USD)
Expedia
Harborwalk Hideaways by Brightwild |Prime Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Harborwalk Hideaways is a stunning, newly-renovated vacation rental complex tucked away in the Historic Seaport ...
From $1308 per night (USD)Expedia
- From $350 per night (USD)
VRBO
POOLSIDE HANGOVER at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is an amazing two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away ...
From $350 per night (USD)VRBO
- From $1157 per night (USD)
Expedia
A Place on Emma at the Truman Annex in Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1157 per night (USD)Expedia
- From $307 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 $307 per night (USD)VRBO
- From $497 per night (USD)
Expedia
**THE BEAMING BARRACUDA @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERV
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE BEAMING B ...
From $497 per night (USD)Expedia
- From $518 per night (USD)
VRBO
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 $518 per night (USD)VRBO
- From $460 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 $460 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our con ...
From $250 per night (USD)VRBO
- From $370 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
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $370 per night (USD)Expedia
- From $364 per night (USD)
VRBO
HIGH TIDE at The Truman Annex in Key West
- Bedrooms:
- 2
- 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 $364 per night (USD)VRBO
- From $350 per night (USD)
Expedia
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 $350 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
Expedia
GYPSY'S PALACE at The Truman Annex in Key West - Stunning ocean views!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! ...
Click For PricingExpedia
- From $623 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 $623 per night (USD)VRBO
- From $550 per night (USD)
Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Like many of ...
From $550 per night (USD)Expedia
- From $334 per night (USD)
VRBO
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 $334 per night (USD)VRBO
- From $3000 per night (USD)
Expedia
Takeover at the Grand Maloney by Brightwild
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $3000 per night (USD)Expedia
- From $196 per night (USD)
VRBO
Claude Monet Suite by Brightwild | Pool & Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to the Claude Monet Suite! This colorful, tropically-themed 1st floor suite is tucked away in The Galle ...
From $196 per night (USD)VRBO
- From $736 per night (USD)
Expedia
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 $736 per night (USD)Expedia
- From $1500 per night (USD)
VRBO
Features.Key West Suites Hotel has an outdoor pool and fitness center
- 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 ...
From $1500 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Banyan Resort - 2 Blocks to Sunset Celebration
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Banyan Resort is the ultimate destination for a weekend get-a-way or long term accommodations in our well appointed ...
From $375 per night (USD)Expedia
- From $757 per night (USD)
VRBO
ARCHIPELAGO at The Truman Annex in Key West
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...
From $757 per night (USD)VRBO
- From $586 per night (USD)
Expedia
SUNSET DALITE at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...
From $586 per night (USD)Expedia
- From $586 per night (USD)
VRBO
AQUA BREEZE at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $586 per night (USD)VRBO
- From $307 per night (USD)
Expedia
SHADY NOOK at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Two blocks away from Duval Street with direct access to Thomas Street through the rear gate. Has free hook up for intern ...
From $307 per night (USD)Expedia
- From $307 per night (USD)
VRBO
ROYAL POINCIENA 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 $307 per night (USD)VRBO
- From $585 per night (USD)
Expedia
THE PLANTATION at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
‘The Plantation” is a Three Bedroom Town home located within the prestigious gated community of ‘Truman Annex’ in Key We ...
From $585 per night (USD)Expedia
- From $821 per night (USD)
VRBO
A GULFSTREAM DRIFT at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...
From $821 per night (USD)VRBO
- From $429 per night (USD)
Expedia
LIFE IN THE SLOW LANE at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on t ...
From $429 per night (USD)Expedia
- Click For Pricing
VRBO
SALTWATER ANGLER at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
Click For PricingVRBO
- From $307 per night (USD)
Expedia
Island Breezes at The Truman Annex in Key West@ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...
From $307 per night (USD)Expedia
- From $586 per night (USD)
VRBO
A HARBOUR ROOST at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $586 per night (USD)VRBO
- From $407 per night (USD)
Expedia
ASCENSION at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of ...
From $407 per night (USD)Expedia
- From $364 per night (USD)
VRBO
DANCING PALMS at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come stay at this bright and airy 2 bedroom, 2 full bath town home in the renowned Truman Annex in Old Town. Leave the c ...
From $364 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For PricingVRBO
- From $586 per night (USD)
VRBO
OCEAN BREEZE at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $586 per night (USD)VRBO
- From $379 per night (USD)
Expedia
SAGO PALM at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $379 per night (USD)Expedia
- From $201 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 $201 per night (USD)VRBO
- From $1546 per night (USD)
Expedia
Key West - Historic & Charming - Main House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
OVERVIEW The 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The ...
From $1546 per night (USD)Expedia
- From $126 per night (USD)
VRBO
The Bolivar, Old Town Key West Monthly vacation rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tuck upstairs in the back of a historic Conch house is a home away from home with private back porch. 1 Block walk from ...
From $126 per night (USD)VRBO
- From $379 per night (USD)
Expedia
ARCHIPELAGO l at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $379 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Location, Beauty & Comfort @ Truman Annex
- Bedrooms:
- 3
- 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 $385 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We want you to know that your safety and comfort while in Key West is our utmost priority. Cleaning supplies are availab ...
From $300 per night (USD)Expedia
- From $652 per night (USD)
VRBO
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $652 per night (USD)VRBO
- From $369 per night (USD)
Expedia
Best location in town. Walk or ride and cover the whole island.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Walk everywhere from this little part of Paradise, you will never need a car. Located in beautiful Old Town, you are vi ...
From $369 per night (USD)Expedia
- From $431 per night (USD)
VRBO
TUCKED AWAY OFF DUVAL - A contemporary home w\/ local color at your door step
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 9
Location, location, location! Tucked Away is set on a small lane just one block from Duval Street, 2 blocks to the Hemin ...
From $431 per night (USD)VRBO
- From $239 per night (USD)
Expedia
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nice quiet vacation landing a few blocks from the action on Duval Street. This Saturday-Saturday home in Key West has: - ...
From $239 per night (USD)Expedia
- From $599 per night (USD)
VRBO
1 BLOCK OFF DUVAL! PRIVATE POOL AND HOT TUB
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy one of Old Town's wonderful historic homes with private pool and hot tub. Casa Rosa one of only seventy five remai ...
From $599 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $300 per night (USD)Expedia
- From $252 per night (USD)
VRBO
**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR\/2BA Cottage + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You have many ...
From $252 per night (USD)VRBO
- From $526 per night (USD)
VRBO
Dream Vacation! Near Famous Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $526 per night (USD)VRBO
- From $266 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $266 per night (USD)VRBO
- From $287 per night (USD)
Expedia
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 $287 per night (USD)Expedia
- From $202 per night (USD)
VRBO
Gulf Getaway by Brightwild | Condo w\/Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $202 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $650 per night (USD)Expedia
- From $937 per night (USD)
VRBO
The Mesa House by Brightwild | Close to Duval!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $937 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck 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 $287 per night (USD)Expedia
- From $550 per night (USD)
VRBO
Elegantly Furnished Key West Condo in the Truman Annex.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Elegantly furnished Key West vacation condo in the historic Truman Annex in the heart of Old Town in Key West. The condo ...
From $550 per night (USD)VRBO
- Click For Pricing
Expedia
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For PricingExpedia
- From $525 per night (USD)
VRBO
Cloud Suite on Duval | Luxury Condo, Epic Location
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Cloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of w ...
From $525 per night (USD)VRBO
- From $320 per night (USD)
Expedia
A PEACE OF PARADISE at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with fla ...
From $320 per night (USD)Expedia
- From $384 per night (USD)
VRBO
**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SERENITY ON S ...
From $384 per night (USD)VRBO
- From $152 per night (USD)
Expedia
PEAK OF DUVAL | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $152 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Roosters Perch at Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $299 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $300 per night (USD)Expedia
- From $247 per night (USD)
VRBO
Pierre's Perch by Brightwild | Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Welcome to the Pierre's Perch - a recently renovated, budget-friendly studio a part of history laden Galleria S ...
From $247 per night (USD)VRBO
- From $222 per night (USD)
Expedia
Chagall's Studio by Brightwild | Newly Remodeled!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Welcome to Chagall's Studio, a hidden little gem located at The Galleria Guesthouse in the heart of Bahama Vill ...
From $222 per night (USD)Expedia
- From $1822 per night (USD)
VRBO
Authentic Key West Adventure! 3 Comfortable Units, 3 Pools, Pets Allowed!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1822 per night (USD)VRBO
- From $2408 per night (USD)
VRBO
Family and Friends Getaway! 4 Comfortable Units, 3 Pools, Onsite Dining!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2408 per night (USD)VRBO
- From $552 per night (USD)
VRBO
Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
'The Plantation' is a NO SMOKING or VAPING,3 bed 3 bath townhome located within the gated community of Truman Annex in K ...
From $552 per night (USD)VRBO
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- Click For Pricing
Expedia
Old Town Conch Cottage completely remodelled and updated
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the heart of Old Town, this rare home has it all. 3 Bedrooms with 3.5 Baths in the Main House. Completed ...
Click For PricingExpedia
- From $224 per night (USD)
Expedia
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W\/D
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $224 per night (USD)Expedia
- From $394 per night (USD)
VRBO
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! MODERN MAJEST ...
From $394 per night (USD)VRBO
- From $323 per night (USD)
Expedia
Southern Skies, Stylish Home in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart ...
From $323 per night (USD)Expedia
- From $595 per night (USD)
VRBO
KAMP by Brightwild | Rooftop Penthouse On Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $595 per night (USD)VRBO
- From $410 per night (USD)
VRBO
Sunset Serenade - Sunset Key
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
The first time you arrive to Key West everything indicates that you’ve reached the last tropical island along the ribbon ...
From $410 per night (USD)VRBO
- From $287 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 $287 per night (USD)VRBO
- From $145 per night (USD)
Expedia
Monkey House by AvantStay | Pool, by Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Monkey House is a two-bedroom Key West escape that ...
From $145 per night (USD)Expedia
- Click For Pricing
VRBO
1st year for this gorgeous 4Bd 4Ba all ensuite, 2 parking spots, backyard oasis!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Moveable Feast, a new monthly vacation rental in the heart of Bahama Village that sleeps 10 comfortably. Loca ...
Click For PricingVRBO
- From $732 per night (USD)
Expedia
Custom House Inn | Two 2nd Floor Suites On Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $732 per night (USD)Expedia
- From $605 per night (USD)
VRBO
Custom House Inn | Two Suites On Duval St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $605 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Studio Unit in quiet resort adjacent to Old Town Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
From $250 per night (USD)VRBO
- From $333 per night (USD)
VRBO
**THE COZY STARFISH @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICES…
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE COZY STAR ...
From $333 per night (USD)VRBO
- From $1345 per night (USD)
VRBO
Studio Sleeps 2 | Pool | Beachfront | RW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios h ...
From $1345 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Key West•Beachfront•Concierge•Fast WiFi•Luxury RW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $1500 per night (USD)VRBO
- From $995 per night (USD)
VRBO
1 HSH Keys, Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $995 per night (USD)VRBO
- From $800 per night (USD)
VRBO
2\/2 Sleeps 6 | Comfy Beds | Beach | Pool RW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $800 per night (USD)VRBO
- From $795 per night (USD)
VRBO
1\/1 Sleeps 2 | Pool | Hot Tub | Concierge RW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $795 per night (USD)VRBO
- From $376 per night (USD)
VRBO
Escape to Key West! And stay at the Rose Key Cottage so close to Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Rose Key Cottage Escape, to your slice of paradise in Key West! Situated just half a block from the iconi ...
From $376 per night (USD)VRBO
- From $419 per night (USD)
VRBO
Charm is on order at Rose Key Cottage! Come check it out!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your piece of paradise! Rose Key Cottage is a delightful, historic home nestled in the heart of Old Town Key ...
From $419 per night (USD)VRBO
- From $217 per night (USD)
VRBO
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $217 per night (USD)VRBO
- From $233 per night (USD)
VRBO
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CLASSIC UPDATED CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in the heart of Bah ...
From $233 per night (USD)VRBO
- From $888 per night (USD)
VRBO
Waterfront Sunset Harbor Resort Near Old Town+Amenities: 2BR FindingMeili
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to FindingMeili🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! An Additional Savings from $500 ...
From $888 per night (USD)VRBO
- From $262 per night (USD)
VRBO
SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR\/2 Ba Home w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
BAHAMA VILLAGE BEAUTY... This dream of a home is yours for the ultimate escape to southernmost paradise! Located in the ...
From $262 per night (USD)VRBO