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2026-06-03
2026-06-04
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Extended Stay in Key West

St John - Downtown Waterfront Penthouse Pool Parking Dock

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St John - Downtown Waterfront Penthouse Pool Parking Dock Villa Key West is located only 6 minutes' walk from the C. B. Harvey Rest Beach Park and offers guests to relish a patio as… More

From US$ 2344 Book Now

Petes West Cottage

505 Louisa Street, Key West, United States View map

The 1-bedroom Petes West Cottage Key West is located approximately a 15-minute walk from Memorial Sculpture Garden and welcomes its guests to enjoy windsurfing, snorkelling, and canoeing. More

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Paradise Place Duval Square

1075 Duval Street, Key West, United States View map

Paradise Place Duval Square Key West apartment is a great place to stay in the Downtown Key West district, a 15-minute walk from the Harry S. Truman Little White House. For those travelling by car… More

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Duval Street Retreat

1124 Duval Street A, Key West, United States View map

Located just 1.5 km from Memorial Sculpture Garden, the 1-bedroom Duval Street Retreat Villa Key West provides access to various tourist attractions in the vicinity. More

From US$ 515 Book Now

Villa Angelita By Last Key Realty

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

The 2-bedroom Villa Angelita By Last Key Realty Key West provides easy access to various city attractions, such as Duval Street, situated around 5 minutes' walk away. More

From US$ 957 Book Now

Claude Monet Suite

1016 Howe Street #3, Key West, United States View map

The 1-room Claude Monet Suite Key West lies in the Downtown Key West district and offers swift access to the Ernest Hemingway Home and Museum, which is only 5 minutes' walk away. More

From US$ 220 Book Now

Latitude Penthouse Key West

1800 Atlantic Blvd Unit B417, Key West, United States View map

The 143 m^2 Latitude Penthouse Key West Apartment is located 2.2 km from Duval Street and around a 25-minute walk from The Ernest Hemingway Home and Museum. While staying in this 2-bedroom apartment,… More

From US$ 685 Book Now

Duval Street Suite W Kitchen And Shared Heated Pool

824 Duval Street, Key West, United States View map

Located 15 minutes' walk from the Harry S. Truman Little White House, Duval Street Suite W Kitchen And Shared Heated Pool Key West overlooks the garden. Offering access to a swimming pool, this… More

From US$ 501 Book Now

Fleming-O

726 Fleming St, Key West, United States View map

Staying at the 1-bedroom Fleming-O Villa Key West, guests can visit Higgs Beach Dog Park, which is nearly a 25-minute walk away. This Key West holiday home is located in the Downtown Key West… More

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Casita Angelita By Last Key Realty

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

Staying at the 2-bedroom Casita Angelita By Last Key Realty Key West villa, guests can easily reach Key West Wildlife Center, located around 25 minutes' walk away. More

From US$ 750 Book Now

Mango Hideaway Eyebrow House

516 Olivia St Rear, Key West, United States View map

To enjoy your vacation in Key West, stay at the 1-room Mango Hideaway Eyebrow House Apartment Key West, which is a mere 0.8 km from the San Carlos Institute and about 300 metres from the historic Key… More

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Sundial On The Atlantic Ocean View

1800 Atlantic Blvd, Unit C328, Key West, United States View map

**Sundial On The Atlantic Ocean View is an idyllic retreat where luxury meets the vibrant spirit of Key West. Just 5 kilometers from Key West International, this stunning oceanfront haven offers… More

From US$ 561 Book Now

Harbor House Penthouse- B

423 Front Street, Key West, United States View map

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Brisa Del Mar By Avantstay

1901 S.Roosevelt Blvd 206E, Key West, United States View map

The welcoming Brisa Del Mar By Avantstay Key West villa is located a 10-minute drive from the Key West Firehouse Museum and provides a swimming pool, ensuring a relaxing stay. More

From US$ 615 Book Now

La Casa Cubana The Cuban Club

1108 Duval St #G, Key West, United States View map

The spacious 1-bedroom La Casa Cubana Apartment Key West is nestled in the Downtown Key West district, within 15 minutes' walk of the Memorial Sculpture Garden. Guests will benefit from private car… More

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Key West Light Suite

215 Eanes Lane, Key West, United States View map

The 1-bedroom Key West Light Suite villa provides easy access to various city attractions, such as the Ernest Hemingway Home and Museum, situated approximately 5 minutes' walk away. More

From US$ 853 Book Now

New The Windrose House - Pool & Pets

Shoreline Road 3, Key West, United States View map

The 6-bedroom New Windrose House By Brightwild - Pool & Pets Villa is at a 7 km distance from Key West Firehouse Museum and it takes 10 minutes to drive to Key West International airport. The… More

From US$ 2971 Book Now

New Private Pool & Docking - Floralee House

Mangrove Lane 11, Key West, United States View map

**Discover the Charm of New Private Pool & Docking - Floralee House Villa Key West** Nestled in the enchanting surroundings of Key West, New Private Pool & Docking - Floralee House invites you to… More

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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

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New Coastal Rose - Bright Loft With High Ceilings

Rose Lane 526, Key West, United States View map

The spacious 84 m² New Coastal Rose - Bright Loft With High Ceilings Apartment Key West offers a central location nearly 5 minutes' walk from the Vandenberg Wreck. At the 1-bedroom apartment, guests… More

From US$ 858 Book Now

New Rose Petal Petite Suite - Pool & Parking

Rose Lane 526, Key West, United States View map

Featuring an outdoor swimming pool and a patio, the spacious 74 m² New Rose Petal Petite Suite - Pool & Parking Key West is situated in a historic area, just 1.3 km from the Key West Firehouse Museum… More

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Pelican Suite - Southernmost Sanctuary

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

Located nearly 5 minutes' walk from Dog Beach, the 1-bedroom Pelican Suite - Southernmost Sanctuary Key West villa offers quick access to various city attractions in the vicinity. More

From US$ 483 Book Now

The Mesa House-Close To Duval!

Simonton Street 220, Key West, United States View map

The 3-bedroom Mesa House Villa is nearly 8 minutes on foot from Truman Little White House and walking distance from the bustling plaza "Mallory Square". A fully furnished kitchen with a microwave… More

From US$ 1379 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

Poolside Retreat

Center Street 832, Key West, United States View map

The welcoming Poolside Retreat Apartment Key West is located just 1.6 km from the Fort Zachary Taylor and 15 minutes' walk from the Key West Aquarium. Offering access to a swimming pool, this… More

From US$ 545 Book Now

Paradise On Porter

514 Porter Lane, Key West, United States View map

Nestled approximately 25 minutes' walk from the Audubon House and Tropical Gardens, the 2-room Paradise On Porter Key West apartment allows guests to explore numerous tourist destinations in the… More

From US$ 254 Book Now

Curry House Room 6

Fleming Street 806, Key West, United States View map

To enjoy your vacation in Key West, stay at the 1-room Curry House Room 6 Key West, which is only 350 metres from the performing arts theater "Red Barn Theatre" and nearly a 5-minute drive from the… More

From US$ 340 Book Now

The Elizabeth Suite

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

Situated just a 5-minute stroll from The Unitarian Universalist Fellowship of Key West, the 1-bedroom The Elizabeth Suite Key West villa offers easy access to numerous tourist spots in the area. More

From US$ 383 Book Now

Commodore'S Cove

Simonton Street 219, Key West, United States View map

The spacious 4-bedroom Commodore'S Cove Key West apartment is located in the Downtown Key West district of Key West, approximately a 5-minute walk from the performing arts theater "Red Barn Theatre".… More

From US$ 1749 Book Now

Vangogh Studio

1016 Howe Street, Key West, United States View map

The 1-room Vangogh Studio Key West is nestled in the Downtown Key West district, just 1.4 km from the bustling plaza "Mallory Square". More

From US$ 239 Book Now

Brand New Catchlight House With Private Pool

Mangrove Lane 7, Key West, United States View map

The 7-bedroom Brand New Catchlight House With Private Pool Villa Key West is located around a 25-minute walk from Key West Tropical Forest and Botanical Garden and provides fishing for active guests. More

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The Fleming Suite

1501 Truman Avenue 3, Key West, United States View map

Nestled a 20-minute walk from The Ernest Hemingway Home and Museum, The Fleming Suite Key West villa entices guests to explore various tourist destinations nearby. More

From US$ 357 Book Now

Salvador'S Seclusion

1016 Howe St #4, Key West, United States View map

Offering a location merely a 14-minute walk from Mel Fisher Maritime Heritage Museum, the 1-bedroom Salvador'S Seclusion Villa Key West gives access to various tourist spots in the area. More

From US$ 258 Book Now

Hemingways Atlantic Retreat

1800 Atlantic Blvd Unit C339, Key West, United States View map

The spacious Hemingways Atlantic Retreat Apartment Key West is located 5 minutes' walk from The Key West Nature Preserve and looks out onto the sea. Offering access to a swimming pool, this apartment… More

From US$ 404 Book Now

African Queen - Harbor Walk Hideaways

Greene Street, Key West, United States View map

Located only 650 metres from the arts theater "Red Barn Theatre", the 40 m² African Queen - Harbor Walk Hideaways Key West apartment is 0.9 km from a top family-friendly place like the Key West… More

From US$ 1001 Book Now

Welcome Matt'S - Truman @ Duval Unit B

Truman Avenue, Key West, United States View map

Located about 20 minutes' walk from the Fort Zachary Taylor, the 39 m² Welcome Matt'S - Truman @ Duval Unit B Key West apartment is 1.2 km from a top family-friendly place like the Key West Aquarium. More

From US$ 422 Book Now

Wahoo Way

1201 Duval Street 1, Key West, United States View map

**Wahoo Way Villa: A Caribbean Haven in Key West** Lastly, location is paramount at this exquisite villa. More

From US$ 227 Book Now

Follow The Sun By Last Key Realty

1800 Atlantic Blvd #C228, Key West, United States View map

The 2-room Follow The Sun By Last Key Realty Key West apartment is located in Key West, around 900 metres from the Edward B. Knight Pier, and pampers guests with a Jacuzzi. The apartment is 2.4 km… More

From US$ 786 Book Now

The Breeze

1901 South Roosevelt Blvd, Unit 301 East, Key West, United States View map

During the stay at The Breeze Villa Key West, guests can indulge in a sauna or visit the Higgs Beach Dog Park, located 14 minutes' walk away. More

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Curry House - Room 9

Fleming Street 806, Key West, United States View map

Nestled in the picturesque island of Key West, the Curry House offers a charming blend of tropical elegance and modern comfort. Just 10 km from the bustling Key West International Airport, this… More

From US$ 184 Book Now

Key West On My Mind

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

Located just a 9-minute walk from Higgs Beach Dog Park and The Key West Nature Preserve, the 126 m^2 Key West On My Mind Apartment features views of the sea. More

From US$ 660 Book Now

Osprey Suite - Southernmost Sanctuary

1330 Simonton Street #4, Key West, United States View map

The 1-bedroom Osprey Suite - Southernmost Sanctuary Key West villa offers proximity to such city sites as Dog Beach, located just a 5-minute walk away. More

From US$ 945 Book Now

Coconut Palm

Whitehead Street 729, Key West, United States View map

**Coconut Palm Villa Key West** invites guests to experience the vibrant ambiance of Duval Street, where island-inspired charm meets contemporary luxury. Nestled amid a lively backdrop, this oasis… More

From US$ 1683 Book Now

Matisse Studio The Galleria

1016 Howe Street, Key West, United States View map

To enjoy your vacation in Key West, stay at the 13 m² Matisse Studio The Galleria Key West, which is nearly 5 minutes on foot from the Key West Lighthouse and Keeper's Quarters Museum and only 1.4 km… More

From US$ 438 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

Toon Hall Tropical Village

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

Along with proximity to Higgs Beach, a mere 0.6 km away, the 2-bedroom Toon Hall Tropical Village Key West villa offers opportunities for canoeing, hiking, and cycling in the area. More

From US$ 1271 Book Now

Leo'S Lodge

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

Located just a few steps from Key West Lighthouse and Keeper's Quarters Museum, the 1-bedroom Leo'S Lodge Key West offers quick access to various city attractions in the vicinity. More

From US$ 392 Book Now

Abbey'S Attic - Truman @ Duval Unit E

Truman Avenue, Key West, United States View map

The 14 m² Abbey'S Attic - Truman @ Duval Unit E Key West apartment is situated merely 5 minutes' walk from the historical Key West Lighthouse and 5 km from Key West International airport. More

From US$ 350 Book Now

Joan'S Caribbean Hideaway

143 Golf Club Drive, Key West, United States View map

Conveniently situated, Joan's Caribbean Hideaway Villa serves as the perfect base for exploring Key West's myriad attractions. More

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The Grand Turk - Sunrise Suites

3625 Seaside Drive #404, Key West, United States View map

The 74 m² The Grand Turk - Sunrise Suites Key West is around a 25-minute walk from the Smathers Beach, giving access to numerous sites in the area. More

From US$ 879 Book Now