Special offers and Exclusive deals

Search Hotels

2026-11-11
2026-11-12
Guests

Filter Results

Hotels by class

Hotel name

Price per night

Accommodation type

Districts

Attractions

Thematic hotels

Review rating

Hotel facilities

Room facilities

Apply Filters
Clear Filters

Key West holiday rentals

Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock

915 Eisenhower Drive, Key West, United States View map

The 2-bedroom Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock Key West villa, located approximately 5 minutes' walk from the Wreckers Sloop Mary, can host up to 8 guests. This accommodation… More

Book Now

The Crestwood House - Private Heated Pool & Parking

Shoreline Road 17, Key West, United States View map

The 6-bedroom The Crestwood House - Private Heated Pool & Parking Villa Key West entices active guests with access to a fitness room and is located just 11 minutes' walk from FYT Fitness Center. More

From US$ 2726 Book Now

Petes West Cottage

505 Louisa Street, Key West, United States View map

Featuring a heated swimming pool, the 2-bedroom Petes West Cottage Key West is located only a 6-minute walk from the even Southernmost Point and is suitable for up to 4 guests. This holiday home… More

From US$ 928 Book Now

Good Vibrations By Last Key Realty

524 Dupont Lane, Key West, United States View map

Situated only a few steps from the Key West Lighthouse and Keeper's Quarters Museum, Good Vibrations By Last Key Realty Key West villa offers easy access to numerous tourist spots in the area. More

Book Now

Casa De Cubana

512 Amelia Street, Key West, United States View map

The 2-bedroom Casa De Cubana Villa Key West accommodates up to 4 guests and offers proximity to the Key West Butterfly and Nature Conservatory, located only a 7-minute walk away. More

From US$ 2269 Book Now

Jasmine Place

919 Whitehead Street, Key West, United States View map

During the stay at Jasmine Place Key West villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the 19 - acre Key West Cemetery, located a 13-minute walk away. More

Book Now

Hideaway @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Located only 400 metres from the South Beach, the comfortable Hideaway @ Speakeasy Inn Key West! offers Wi-Fi in the rooms and a car park. This Key West guest house lies in the Downtown Key West… More

From US$ 467 Book Now

Egret Suite | Bright Retreat, Hot Tubs, Steps From Duval!

1330 Simonton Street #1, Key West, United States View map

The 1-bedroom Egret Suite | Bright Retreat, Hot Tubs, Steps From Duval! Key West villa hosts up to 4 guests and provides proximity to the Key West Butterfly and Nature Conservatory, situated… More

From US$ 354 Book Now

Renovated Corner Unit

620 Thomas Unit 150, Key West, United States View map

Situated approximately a 5-minute walk from the Alan S Maltz Gallery, the 2-bedroom Renovated Corner Unit Villa Key West entices guests to explore various tourist attractions in the area. More

Book Now

New The Altair House - Fire Pit Pool & Hot Tub

Mangrove Lane 13, Key West, United States View map

Featuring a private pool, the 6-bedroom New The Altair House - Fire Pit Pool & Hot Tub Villa Key West is suitable for up to 14 people and is located about a 15-minute walk from the Key West Tropical… More

From US$ 4188 Book Now

Ibis By Avantstay

714 Olivia #11, Key West, United States View map

Staying at the 0-bedroom Ibis By Avantstay Key West villa, guests can visit Mile Marker 0 Store, which is only 1 km away. More

Book Now

Catherine House

518 Catherine Street, Key West, United States View map

During the stay at Catherine House Key West villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Key West Aquarium, located a 16-minute walk away. Offering a private… More

From US$ 759 Book Now

Anchor Drop Key West

1800 Atlantic Blvd, Unit A307, Key West, United States View map

During the stay at Anchor Drop Key West Villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Higgs Beach, located a 19-minute walk away. The 2-bedroom holiday home offers… More

From US$ 870 Book Now

Smooth Sailing By Last Key Realty

1800 Atlantic Blvd #C334, Key West, United States View map

Offering a Jacuzzi, Smooth Sailing By Last Key Realty Key West villa is situated merely a 7-minute walk from the fully accredited Mel Fisher Maritime Heritage Museum and can accommodate 6 people. More

From US$ 1034 Book Now

Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo

915 Eisenhower Drive, Key West, United States View map

Welcome to Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo, where plush sophistication meets laid-back comfort in the heart of Key West. This exquisite two-bedroom condo boasts… More

From US$ 184 Book Now

Andros Suite

921 Center Street #6, Key West, United States View map

More

Book Now

Casita Angelita By Last Key Realty

421 Angela Street Unit A, Key West, United States View map

Casita Angelita By Last Key Realty Key West villa accommodates up to 6 guests and offers proximity to the downtown commercial zoned Duval Street, located merely a 7-minute walk away. More

From US$ 750 Book Now

Aquaria House -Pool & Boat Dock

Shoreline Road 14, Key West, United States View map

Situated just 1.8 km from Safe Harbor, the 4-bedroom Aquaria House -Pool & Boat Dock Villa Key West features a patio with views of the sea. Offering a private swimming pool, this property invites… More

From US$ 3784 Book Now

Barbuda Suite By Last Key Realty

329 William Street #4, Key West, United States View map

Offering a heated swimming pool, the 1-bedroom Barbuda Suite By Last Key Realty Key West villa is located 750 metres from the 19-acre Key West Cemetery and is ideal for up to 4 guests. More

Book Now

Smuggler'S Cove @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Featuring Wi-Fi in the rooms, the comfortable Smuggler'S Cove @ Speakeasy Inn Key West! is about a 20-minute walk from the Bayview Park. This guest house also includes a car park. More

From US$ 396 Book Now

Contra House -Luxury Home With Pool

Simonton Street 720, Key West, United States View map

Situated within 5 minutes' walk of the downtown commercial zoned Duval Street, the 4-bedroom Contra House -Luxury Home With Pool Key West offers opportunities for cycling and fishing in the area. More

From US$ 1909 Book Now

Ann Street Cottage

219 Ann Street #2, Key West, United States View map

Offering a swimming pool, the 1-bedroom Ann Street Cottage Key West is located just 650 m from the vintage parish "Saint Paul's Episcopal Church of Key West" and is ideal for up to 2 guests. This… More

From US$ 711 Book Now

Casa Serendipity By Last Key Realty

1101 Angela Street, Key West, United States View map

Casa Serendipity By Last Key Realty Key West accommodates up to 6 guests and offers proximity to the Fleming Street, located 9 minutes' walk away. More

From US$ 1544 Book Now

Casa Papa Del Mar

1800 Atlantic Blvd, Unit C438, Key West, United States View map

The 2-bedroom Casa Papa Del Mar Villa Key West, located nearly a 5-minute walk from The Key West Nature Preserve, entices guests with a swimming pool as well as a Jacuzzi and a sauna to relax in. At… More

From US$ 709 Book Now

Charming Key West Rental

3 Coral Way, Key West, United States View map

More

From US$ 680 Book Now

The Southern Cross Tropical Village

1400 Alberta St #B, Key West, United States View map

The 2-bedroom The Southern Cross Tropical Village Key West villa hosts up to 6 guests and provides proximity to the Higgs Beach, situated only 650 metres away. This Key West holiday home features… More

From US$ 576 Book Now

Tranquility By The Beach

1800 Atlantic Blvd C129, Key West, United States View map

Situated nearly 25 minutes' walk from Southernmost Point of the Continental US Monument, the 2-bedroom Tranquility By The Beach Key West villa boasts a sauna, as well as a spa salon for guests to… More

From US$ 760 Book Now

Villa Angelita By Last Key Realty

421 Angela Street Unit B, Key West, United States View map

The 3-bedroom Villa Angelita By Last Key Realty Key West is nestled a mere 5 minutes' walk from the Ernest Hemingway Home and Museum and can accommodate up to 7 guests. More

From US$ 957 Book Now

New! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking

Duval Street 1075, Key West, United States View map

**Welcome to Villa Positano - Duval Square Condo** Nestled in the vibrant heart of Duval, the Villa Positano presents an exquisite retreat blending contemporary elegance with a touch of coastal charm. More

From US$ 718 Book Now

Puerta Coralina By Last Key Realty

901 Grinnell Street, Key West, United States View map

Located 750 metres from the Fleming Street, Puerta Coralina By Last Key Realty Key West villa boasts a private pool and can accommodate up to 6. More

From US$ 1500 Book Now

Pelican Suite | Cozy Cottage, Hot Tubs, Close To D

1330 Simonton Street #5, Key West, United States View map

The 1-bedroom Pelican Suite | Cozy Cottage, Hot Tubs, Close To D Key West accommodates up to 4 guests and offers proximity to the even Southernmost Point, located just a 5-minute walk away. More

From US$ 620 Book Now

The Elizabeth Suite

1501 Truman Avenue 1, Key West, United States View map

Offering access to entertainment venues such as the White Street Pier, situated only 1.5 km away, the 1-bedroom The Elizabeth Suite Key West villa can host up to 4 guests. More

From US$ 383 Book Now

The Mesa House-Close To Duval!

Simonton Street 220, Key West, United States View map

Situated merely 1.3 km from Southernmost Point of the Continental US Monument, the 3-bedroom The Mesa House-Close To Duval! Key West villa features a patio with views of the city. This Key West… More

From US$ 1393 Book Now

Always Your Paradise By Avantstay

620 Thomas Street #164, Key West, United States View map

Situated only 450 metres from the downtown commercial zoned Duval Street, the 1-bedroom Always Your Paradise By Avantstay Key West villa has a swimming pool with a patio. Featuring access to a patio,… More

Book Now

Key West On My Mind

1800 Atlantic Blvd Unit A305, Key West, United States View map

Located only a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Key West On My Mind Villa features an outdoor swimming pool and can accommodate up to 6 guests. Offering a Jacuzzi and a… More

From US$ 583 Book Now

Andy'S Attic

1016 Howe St #12, Key West, United States View map

Andy'S Attic Villa Key West is located a 13-minute walk from the secluded pocket Dog Beach and invites guests to join snorkelling and fishing. More

From US$ 365 Book Now

Carey'S Corner

1016 Howe St #10, Key West, United States View map

The 1-bedroom Carey'S Corner Villa Key West, located just a 6-minute walk from Southernmost Point of the Continental US Monument, can host up to 2 guests. This holiday home features opportunities for… More

From US$ 406 Book Now

Casa Loca

535 Petronia Street, Key West, United States View map

At the 3-bedroom Casa Loca Villa Key West, guests can enjoy windsurfing, snorkelling, and canoeing as well as a location just 5 minutes' walk from the Ernest Hemingway Home and Museum. This holiday… More

Book Now

Brand New Catchlight House With Private Pool

Mangrove Lane 7, Key West, United States View map

Situated around a 25-minute walk from the Cozumel Park, the 6-bedroom Brand New Catchlight House With Private Pool Villa Key West invites guests to relax at a patio. Guests can enjoy fishing at this… More

Book Now

Leo'S Lodge

1016 Howe St #7, Key West, United States View map

Along with proximity to Southernmost Point of the Continental US Monument, only a 6-minute walk away, the 1-bedroom Leo'S Lodge Key West offers opportunities for snorkelling and fishing in the area. More

From US$ 392 Book Now

Toon Hall Tropical Village

1400 Alberta St #A, Key West, United States View map

Staying at the 3-bedroom Toon Hall Tropical Village Key West villa, guests can easily reach the arts theater "Red Barn Theatre", located approximately a 25-minute walk away. Guests can enjoy canoeing… More

From US$ 669 Book Now

Upper Sunset North

801 Eisenhower Dr. #8, 8, Key West, United States View map

**Experience Laid-Back Luxury at Upper Sunset North Villa Key West** Recreational amenities abound, with a lavish outdoor pool surrounded by lounge chairs and tables for ultimate relaxation. More

From US$ 884 Book Now

Sugar Palm Suite At Travelers Palm Inn Key West

815 Catherine St., Key West, United States View map

Located nearly 25 minutes' walk from the Harry S. Truman Little White House, the 1-bedroom Sugar Palm Suite At Travelers Palm Inn Key West villa has a swimming pool and is ideal for up to 4 guests. More

Book Now

Spirit Of Key West By Last Key Realty

1106 Petronia Street, Key West, United States View map

Spirit Of Key West By Last Key Realty villa is nestled a 9-minute walk from the Fleming Street and can accommodate up to 8 guests. More

Book Now

A Palm Tree Haven

118 Admirals Lane, Key West, United States View map

At the 4-bedroom A Palm Tree Haven Villa Key West, guests can enjoy snorkelling and fishing as well as a location a mere 8 minutes' walk from the Ripley's Believe It or Not. More

Book Now

Kw48 Hemingway

418 Whalton Lane, Key West, United States View map

Staying at Kw48 Hemingway'S View Villa Key West, guests can visit the even Southernmost Point, which is just 0.8 km away. Located in the Downtown Key West district of Key West, the Key West holiday… More

Book Now

Cabana At The Golf Club - Monthly Rental

Key West, Key West, United States View map

Situated about a 25-minute walk from Safe Harbor, the 2-bedroom Cabana At The Golf Club - Monthly Rental Key West entices guests to explore various tourist attractions in the area. More

Book Now

A Duck On The Green

10 Whistling Duck Lane, Key West, United States View map

More

Book Now

Sun, Sea, And Sky

202-5 Southard Street, Key West, United States View map

Situated only 7 minutes' walk from the downtown commercial zoned Duval Street, the 1-bedroom Sun, Sea, And Sky Villa Key West entices guests with snorkelling and fishing in the area. More

Book Now

Away From It All

620 Thomas St., #283, Key West, United States View map

Located just 6 minutes' walk from Mile Marker 0 Store, the 2-bedroom Away From It All Key West villa offers quick access to various city attractions in the vicinity. More

Book Now