
Key West National Wildlife Refuge Rentals

- From $317 per night (USD)
VRBO
Sweet Sunshine Garden Flat – Downtown Key West - 2 Blocks Off Duval w Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ever dream of vacationing in a sun-kissed Caribbean Cottage-style flat close to the beach, nestled behind a white picket ...
From $317 per night (USD)VRBO
- From $1051 per night (USD)
Expedia
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 $1051 per night (USD)Expedia
- From $900 per night (USD)
VRBO
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full ...
From $900 per night (USD)VRBO
- From $456 per night (USD)
Expedia
ARCHIPELAGO l at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $456 per night (USD)Expedia
- From $459 per night (USD)
VRBO
Location, Beauty & Comfort @ Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $459 per night (USD)VRBO
- From $821 per night (USD)
Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $821 per night (USD)Expedia
- From $429 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 $429 per night (USD)VRBO
- From $3045 per night (USD)
Expedia
Takeover at the Grand Maloney
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick, ...
From $3045 per night (USD)Expedia
- From $507 per night (USD)
VRBO
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 $507 per night (USD)VRBO
- From $921 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 $921 per night (USD)Expedia
- From $1123 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 $1123 per night (USD)VRBO
- From $185 per night (USD)
Expedia
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 $185 per night (USD)Expedia
- From $1959 per night (USD)
VRBO
Historic Old Town Key West - Main House, 4 beds, 1 Sleeper Sofa, Accommodates 8
- 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 $1959 per night (USD)VRBO
- From $952 per night (USD)
Expedia
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Key West Wabi Sabi is a quintessential 1930s cottage that embodies the beauty and simplicity of island-life charm. If yo ...
From $952 per night (USD)Expedia
- From $1135 per night (USD)
VRBO
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a ha ...
From $1135 per night (USD)VRBO
- From $1751 per night (USD)
Expedia
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 $1751 per night (USD)Expedia
- From $879 per night (USD)
VRBO
ARCHIPELAGO in the Truman Annex
- Bedrooms:
- 4
- 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 $879 per night (USD)VRBO
- From $677 per night (USD)
Expedia
SUNSET DALITE at The Truman Annex in Key West
- Bedrooms:
- 2
- 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 $677 per night (USD)Expedia
- From $720 per night (USD)
VRBO
AQUA BREEZE at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $720 per night (USD)VRBO
- From $434 per night (USD)
Expedia
SHADY NOOK at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 2 bedroom, 1 bath condo is a blend of Key West charm, modern comfort and unbeatable location! You'll enjoy bright, ...
From $434 per night (USD)Expedia
- From $411 per night (USD)
VRBO
ROYAL POINCIENA at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled in the heart of Old Town within the sought-after Shipyard community, this inviting second-floor condo offers the ...
From $411 per night (USD)VRBO
- From $930 per night (USD)
Expedia
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 $930 per night (USD)Expedia
- From $506 per night (USD)
VRBO
LIFE IN THE SLOW LANE at the Truman Annex in Key West
- Bedrooms:
- 2
- 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 $506 per night (USD)VRBO
- From $686 per night (USD)
Expedia
SALTWATER ANGLER at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $686 per night (USD)Expedia
- From $392 per night (USD)
VRBO
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 $392 per night (USD)VRBO
- From $780 per night (USD)
Expedia
A HARBOUR ROOST 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 $780 per night (USD)Expedia
- From $466 per night (USD)
VRBO
**ASCENSION** @ The Truman Annex Compass Realty
- 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 $466 per night (USD)VRBO
- From $455 per night (USD)
Expedia
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 $455 per night (USD)Expedia
- 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 $704 per night (USD)
Expedia
OCEAN BREEZE at The Truman Annex in Key West
- Bedrooms:
- 2
- 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 $704 per night (USD)Expedia
- From $493 per night (USD)
VRBO
SAGO PALM at The Truman Annex in Key West
- Bedrooms:
- 2
- 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 $493 per night (USD)VRBO
- From $390 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 $390 per night (USD)VRBO
- From $554 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 $554 per night (USD)VRBO
- From $599 per night (USD)
Expedia
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
- Bedrooms:
- 1
- 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 $599 per night (USD)Expedia
- From $291 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 $291 per night (USD)VRBO
- From $321 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 $321 per night (USD)Expedia
- From $336 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 $336 per night (USD)VRBO
- From $340 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 $340 per night (USD)Expedia
- From $369 per night (USD)
VRBO
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 $369 per night (USD)VRBO
- From $329 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 $329 per night (USD)Expedia
- From $331 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 $331 per night (USD)VRBO
- From $323 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 $323 per night (USD)Expedia
- From $361 per night (USD)
VRBO
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 $361 per night (USD)VRBO
- From $359 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 $359 per night (USD)Expedia
- From $329 per night (USD)
VRBO
Deluxe King, Pet Friendly & - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $329 per night (USD)VRBO
- From $291 per night (USD)
Expedia
King Bed + Sleeper Sofa & Balcony -James House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $291 per night (USD)Expedia
- From $284 per night (USD)
VRBO
King Suite with Balcony - The James House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $284 per night (USD)VRBO
- From $370 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 $370 per night (USD)Expedia
- From $322 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 $322 per night (USD)VRBO
- From $371 per night (USD)
Expedia
King Bed + Sleeper Sofa & Balcony -James House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $371 per night (USD)Expedia
- From $359 per night (USD)
VRBO
King Suite + 2 Twins & Balcony – The James House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $359 per night (USD)VRBO
- From $348 per night (USD)
Expedia
King Suite, Pet Friendly & Shared Pool
- 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 $348 per night (USD)Expedia
- From $348 per night (USD)
VRBO
King Suite, Pet Friendly & Shared Pool
- 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 $348 per night (USD)VRBO
- From $356 per night (USD)
Expedia
King Suite with Balcony - The James House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $356 per night (USD)Expedia
- From $263 per night (USD)
VRBO
Classic Queen, Pet Friendly - 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 $263 per night (USD)VRBO
- From $360 per night (USD)
Expedia
King Suite with Balcony - The James House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $360 per night (USD)Expedia
- From $281 per night (USD)
VRBO
Classic Queen, Pet Friendly - 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 $281 per night (USD)VRBO
- From $325 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 $325 per night (USD)Expedia
- From $282 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 $282 per night (USD)VRBO
- From $331 per night (USD)
Expedia
Deluxe King, Pet Friendly & - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $331 per night (USD)Expedia
- From $358 per night (USD)
VRBO
King Suite with Balcony - The James House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $358 per night (USD)VRBO
- From $312 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 $312 per night (USD)Expedia
- From $458 per night (USD)
VRBO
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 $458 per night (USD)VRBO
- From $360 per night (USD)
Expedia
King Suite + 2 Twins & Balcony – The James House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $360 per night (USD)Expedia
- From $1002 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 $1002 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Prime location, stunning views from 2 decks—walk or ride to explore the island!
- Bedrooms:
- 1
- 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 $400 per night (USD)Expedia
- From $202 per night (USD)
VRBO
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nice quiet landing a few blocks from the action on Duval Street. This is a Saturday-Saturday weekly home for the rest of ...
From $202 per night (USD)VRBO
- From $439 per night (USD)
Expedia
Historic house near Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This private home is located on a secluded lane just behind the Key West Lighthouse across from the Hemingway Home Museu ...
From $439 per night (USD)Expedia
- From $1554 per night (USD)
VRBO
**ELEGANT ESCAPE @ THE ANNEX** Lavish Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! There’s no be ...
From $1554 per night (USD)VRBO
- From $371 per night (USD)
Expedia
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 $371 per night (USD)Expedia
- From $294 per night (USD)
VRBO
Blue Bayou: Ideal Key West Location W/ Shared Pool, Steps from Beach, Duval Street & Mallory Square!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Homeowners' Association (HOA) mandates a minimum rental period of 30 nights, with no exceptions. Please review additiona ...
From $294 per night (USD)VRBO
- From $311 per night (USD)
Expedia
70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latitudes Restaurant!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Homeowners' Association (HOA) mandates a minimum rental period of 30 nights, and no exceptions can be made. Please revie ...
From $311 per night (USD)Expedia
- From $426 per night (USD)
VRBO
Studio Near Downtown - The Bartlum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, lo ...
From $426 per night (USD)VRBO
- From $885 per night (USD)
Expedia
Casa Rosa: 4BR/4BA house, pool, near Duval
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida. *Saturday-to-Saturday ...
From $885 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
- Bedrooms:
- 2
- 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 $450 per night (USD)VRBO
- From $293 per night (USD)
Expedia
**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 60 days prior to your arrival! You have many ...
From $293 per night (USD)Expedia
- From $461 per night (USD)
VRBO
Foundry 7 - Historic Luxury in the Heart of Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Foundry 7 – A Rare Gem in Key West’s Prestigious Truman Annex! Step into paradise at Foundry 7, a spectacula ...
From $461 per night (USD)VRBO
- From $231 per night (USD)
Expedia
THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!
- 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 $231 per night (USD)Expedia
- From $2818 per night (USD)
VRBO
Southern snowbird-friendly house with pool, stunning backyard & great location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Southernmost Comfort House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $2818 per night (USD)VRBO
- From $365 per night (USD)
Expedia
AHOY MATE! New Shipyard Listing!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly updated condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled w ...
From $365 per night (USD)Expedia
- From $1079 per night (USD)
VRBO
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 $1079 per night (USD)VRBO
- From $2302 per night (USD)
Expedia
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 $2302 per night (USD)Expedia
- From $698 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Annex Home w/Private Heated Pool!
- 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 $698 per night (USD)VRBO
- From $1220 per night (USD)
Expedia
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 $1220 per night (USD)Expedia
- From $1895 per night (USD)
VRBO
Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in t ...
From $1895 per night (USD)VRBO
- From $357 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 $357 per night (USD)Expedia
- From $292 per night (USD)
VRBO
Gulf Getaway | Condo w/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $292 per night (USD)VRBO
- From $705 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
- Bedrooms:
- 2
- 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 $705 per night (USD)Expedia
- From $1106 per night (USD)
VRBO
Washer & Dryer, Near Downtown - The Mesa House
- 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 $1106 per night (USD)VRBO
- From $324 per night (USD)
Expedia
Lavender Jungle by AvantStay | Great Location w/ Patio & Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $324 per night (USD)Expedia
- From $682 per night (USD)
VRBO
Truman's Hideaway by AvantStay | Great Location w/ Patio, Outdoor Dining & BBQ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $682 per night (USD)VRBO
- From $356 per night (USD)
Expedia
Conch Adventure by AvantStay | Great Location w/ Patio, Outdoor Dining
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $356 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Sundown Refuge by AvantStay | Great Location w/ Outdoor Dining & Shared Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $495 per night (USD)VRBO
- From $427 per night (USD)
Expedia
Linger Longer by AvantStay | Key West Walkable | Gated Community, Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $427 per night (USD)Expedia
- From $200 per night (USD)
VRBO
La Casita by AvantStay | Steps to Duval Street | Month Long Stays Only
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* The location of La Casita cannot be beaten -- right ...
From $200 per night (USD)VRBO
- From $406 per night (USD)
Expedia
Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $406 per night (USD)Expedia
- From $173 per night (USD)
VRBO
Emma's Secret by AvantStay | Heart of Old Town | Month Long Stays Only
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Located in one of Key West’s historic and most cult ...
From $173 per night (USD)VRBO
- From $820 per night (USD)
Expedia
Easy Livin' by AvantStay | Key West Home w/ Pool & BBQ | Week Long Stays Only
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $820 per night (USD)Expedia
- From $429 per night (USD)
VRBO
Parrot Perch by AvantStay | Old Town Key West w/ Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $429 per night (USD)VRBO
- From $456 per night (USD)
Expedia
Artist Garden by AvantStay | Great Location w/ Balcony, Shared Pool & BBQ!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $456 per night (USD)Expedia