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2026-02-25
2026-02-26
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Private Villas in Key West

Rose Lane Villas

511 Eaton Street (Check-In Location), Key West, United States View map

Only 13 km from the 6-room Rose Lane Villas takes guests to Key West Butterfly and Nature Conservatory, while Key West Aquarium is less than a 5-minute walk away. This Key West villa has a fully… More

From US$ 682 Book Now

Key West Villas

512 Angela Street, Key West, United States View map

**Key West Villas is a tropical retreat located in the heart of historic Key West.** Nestled less than a kilometer from the vibrant Duval Street, the Villas allow you to bask in the enchanting aromas… More

From US$ 519 Book Now

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking

Seaside Drive 3625, Key West, United States View map

Set at a 4.9 km distance from The Ernest Hemingway Home and Museum and nearly 20 minutes' walk from State Harbor, the 2-bedroom Tortuga Suite 301 is located in Key West. A full kitchen with a… More

From US$ 595 Book Now

Leeward Isle

Key West, United States View map

Nestled in the vibrant heart of Key West, Leeward Isle impressively combines casual elegance with modern comforts. More

From US$ 423 Book Now

Amelia House

Key West Florida 33040, Key West, United States View map

The 3-bedroom Amelia House Villa is located near the downtown commercial zoned Duval Street, at a 1.2 km distance from the fully accredited Mel Fisher Maritime Heritage Museum. The property also has… More

From US$ 270 Book Now

Sea Breeze -Great Location!

Whitehead Street 1025, Key West, United States View map

The 2-bedroom Sea Breeze Villa is located near The Ernest Hemingway Home and Museum, at 750 metres from the secluded pocket Dog Beach. The property features a fully equipped kitchen with a microwave… More

From US$ 414 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

Hemingway'S View

Key West, United States View map

The 3-bedroom Hemingway'S View Villa is located near The Ernest Hemingway Home and Museum, only 0.6 km from Southernmost Point. The property features a kitchen with a microwave, coffee/tea making… More

From US$ 1175 Book Now

New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool

Duval Street 1075, Key West, United States View map

Situated in the Duval district, the 3-bedroom New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool right next to Key West Butterfly and Nature Conservatory and nearly 20 minutes' walk from the… More

From US$ 343 Book Now

Windward Isle

531 Olivia St, Key West, United States View map

Only 10 minutes' walk from the Harry S. Truman Little White House, Windward Isle Villa is just off The Ernest Hemingway Home and Museum. This villa comprises 2 bedrooms and 1 bathroom. More

From US$ 312 Book Now

Aruba - Downtown Waterfront 2X2 Dock & Pool Pet-Friendly

915 Eisenhower Drive, Key West, United States View map

**Welcome to Aruba - Downtown Waterfront 2X2 Dock & Pool, a serene retreat immersed in the vibrant spirit of Key West.** Situated just 5 km from Key West International Airport, this pet-friendly… More

From US$ 789 Book Now

Casa Key West-Pool & Free Parking

Duval Street 1075, Key West, United States View map

The 3-bedroom Casa Key West At Duval Square Villa in Key West is a mere 1.3 km from Higgs Beach. A fully furnished kitchen with a microwave, coffee/tea making facilities and fridges is included at… More

From US$ 1090 Book Now

Conch Casa

Key West, United States View map

The Ernest Hemingway Home and Museum is situated 5 minutes on foot from the 2-bedroom Conch Casa Villa. Set close to Duval Street, the property is within close distance of Key West Aquarium. More

From US$ 614 Book Now

Sky Loft In Key West

Southard Street 611, Key West, United States View map

Positioned in the heart of Duval, the Sky Loft in Key West is an exquisite blend of laid-back luxury and sophisticated charm. This unique villa captures the essence of Key West while providing guests… More

From US$ 759 Book Now

Beachfront 2Bdr Condo Pool Hot Tub W Ocean Views Papaya Place By Avantstay

110A 1800 Atlantic Blvd, Key West, United States View map

The 0-bedroom Beachfront 2Bdr Condo Pool Hot Tub W Ocean Views Papaya Place By Avantstay Key West villa is situated around 400 metres from The Key West Nature Preserve and offers guests to relax with… More

From US$ 556 Book Now

Key Lime Calypso

409 Petronia Ave, Key West, United States View map

Key Lime Calypso Villa is situated in Key West, within a 5-minute walk of the downtown commercial zoned Duval Street and 15 minutes on foot from the secluded pocket Dog Beach. While staying at the 2… More

From US$ 333 Book Now

New The Cottage At James House

512 Caroline Street, Key West, United States View map

Situated in the vibrant heart of Duval, New The Cottage At James House offers an inviting retreat, merging chic decor with a warm ambiance. This exquisite accommodation showcases stylish leather… More

From US$ 519 Book Now

Tradewinds

529 531 Olivia St, Key West, United States View map

Nestled in the vibrant heart of Duval, Tradewinds Villa Key West offers an idyllic retreat steeped in island charm. This enchanting property welcomes guests with its captivating design and a warm… More

From US$ 1031 Book Now

St Croix - Downtown 4X4 Waterfront Penthouse Pool Dock Pet

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St Croix - Downtown 4X4 Waterfront Penthouse Pool Dock Pet 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$ 2229 Book Now

Crawl To Duval W/ Hot Tub

415 Truman Avenue, Key West, United States View map

Crawl To Duval W/ Hot Tub Villa is an 8-minute stroll from the even Southernmost Point, and within 8 minutes' stroll of Southernmost Point of the Continental US Monument. The 1-bedroom villa… More

From US$ 1033 Book Now

Paradise Place By Avantstay Key West Old Town Condo W Shared Pool

905 White St #1, Key West, United States View map

The 1-bedroom Paradise Place By Avantstay Key West Old Town Condo W Shared Pool is located 15 minutes' walk from C. B. Harvey Rest Beach Park and offers quick access to the Minor Saint Mary Star of… More

From US$ 973 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

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 is nestled nearly a 5-minute walk from The Key West Nature Preserve and entices guests with a Jacuzzi and a sauna. Featuring a swimming pool, this… More

From US$ 709 Book Now

Key West'S Best

1800 Atlantic Blvd, Unit C326, Key West, United States View map

Located just a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Key West'S Best villa entices guests with a hot tub and a sauna. More

From US$ 644 Book Now

Tropical Dreaming By Avantstay 4 Blks To Beach Private Pool

607 Amelia St, Key West, United States View map

Set close to South Beach, the 2-bedroom Tropical Dreaming By Avantstay 4 Blks To Beach Private Pool is a mere 600 metres from Duval Street. Guests of this property can use a free car park, a patio… More

From US$ 2326 Book Now

Amelia Home By Avantstay In Historic Old Town W Pool

605 Amelia Street, Key West, United States View map

The 1-bedroom Amelia Home By Avantstay In Historic Old Town W Pool is a mere 1 km from Higgs Beach and it takes 10 minutes to drive to Key West International airport. Located in the Duval district… More

From US$ 903 Book Now

Key West Found By Avantstay Close To Shops W Patio Shared Pool Month Long Stays Only

101 Front St #13, Key West, United States View map

Located only a 5-minute walk from the Mel Fisher Maritime Heritage Museum, the welcoming Key West Found By Avantstay Close To Shops W Patio Shared Pool Month Long Stays Only villa offers a swimming… More

From US$ 544 Book Now

St Thomas - Waterfront Penthouse Sleeps 16 W Pool & Boat Dock

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St Thomas - Waterfront Penthouse Sleeps 16 W Pool & Boat Dock Villa Key West provides easy access to various city attractions, such as the Historic Charter Boat Row, situated a mere 6… More

From US$ 1741 Book Now

Curacao - Large 2X2 Waterfront Condo Great View Pool & Dock

915 Eisenhower Drive, Key West, United States View map

Nestled in the heart of a vibrant coastal paradise, the Curacao - Large 2X2 Waterfront Condo boasts breathtaking views that immediately capture your attention. Just 5 km from Key West International… More

From US$ 766 Book Now

Pool 2 Blocks To Duval St Gated Community Month Long Stays Shipyard Treasure By Avantstay

208-5 Southard St, Key West, United States View map

Offering pool views, the 0-bedroom Pool 2 Blocks To Duval St Gated Community Month Long Stays Shipyard Treasure By Avantstay Key West villa is situated a mere 5 minutes' walk from the Ernest… More

From US$ 438 Book Now

Duval Street Suite Overlooking Duval With Parking And Pool

824 Duval Street, Key West, United States View map

Located in the Duval district with The Ernest Hemingway Home and Museum nearby, the 1-bedroom Duval Street Suite Overlooking Duval With Parking And Pool lies a mere 10 minutes' stroll from South… More

From US$ 763 Book Now

Bahama Gardens - Conch House

710 Thomas Street, Key West, United States View map

Bahama Gardens - Conch House Villa is situated in Key West, within a 5-minute walk of The Ernest Hemingway Home and Museum and 1.1 km from Simonton Street. The 2-bedroom villa also comes with a fully… More

From US$ 599 Book Now

Grand Marina Suite -Waterfront Condo

Peninsular Avenue 6000, Key West, United States View map

**Discover Tranquility at Grand Marina Suites** More

From US$ 325 Book Now

Andros - Spacious 2X2 Waterfront Condo

Eisenhower Drive 915, Key West, United States View map

Situated approximately a 25-minute walk from the Southernmost Point of the Continental US, the 2-bedroom Andros - Spacious 2X2 Waterfront Condo Key West villa invites guests to relax at a patio. More

From US$ 876 Book Now

Coral Hammock Poolside Home

28 Coral Way, Key West, United States View map

Coral Hammock Poolside Home is located at a 7 km distance from The Ernest Hemingway Home and Museum and 5 minutes' walk from Key West Baptist Temple. There is an equipped kitchenette area with… More

From US$ 862 Book Now

Tom'S Chicken Coop Key West

1800 Atlantic Blvd Unit A403, Key West, United States View map

Situated only 650 metres from Higgs Beach Dog Park, the 2-bedroom Tom'S Chicken Coop Key West Villa provides guests with a hot tub and a sauna for additional relaxation. Featuring a swimming pool… More

From US$ 598 Book Now

Botanical Island Delight

1800 Atlantic Blvd, #C120, Key West, United States View map

The 1-bedroom Botanical Island Delight Villa is within 3 km of Front Street, and within 25 minutes' walk of The Ernest Hemingway Home and Museum. Offering a sauna, a golf course and a Jacuzzi, the… More

From US$ 520 Book Now

Mar Y Sol Ocean Front

1800 Atlantic Blvd #101, Key West, United States View map

Mar Y Sol Ocean Front Villa is at a 2 km distance from the even Southernmost Point and approximately 5 minutes' drive from from The Ernest Hemingway Home and Museum. While staying at the 3-bedroom… More

From US$ 900 Book Now

Duval Sea Turtle By Avantstay Great Location Close To Shops Shared Pool

1075-29 Duval Square, Key West, United States View map

This 2-bathroom villa is at 300 metres from The Ernest Hemingway Home and Museum and walking distance from the even Southernmost Point. The Key West villa also features a kitchen and amenities such… More

From US$ 551 Book Now

Mermaids Retreat At Coral Hammock

41 Coral Way, Key West, United States View map

Situated just 6 minutes' walk from FYT Fitness Center, the 3-bedroom Mermaids Retreat At Coral Hammock Key West villa offers easy access to numerous tourist spots in the area. More

From US$ 501 Book Now

Parrot Perch By Avantstay Old Town Key West W Shared Pool Month-Long Stays Only

620 Thomas St #249, Key West, United States View map

Located in the historical Downtown Key West district, merely 6 minutes' walk from Mile Marker 0 Store, the 2-bedroom Parrot Perch By Avantstay Old Town Key West W Shared Pool Month-Long Stays Only… More

From US$ 223 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$ 766 Book Now

Ibis Suite - Southernmost Sanctuary

1330 Simonton Street #3, Key West, United States View map

Conveniently located just steps from the vibrant nightlife and cultural attractions of Duval Street, the holiday home offers effortless transportation options. More

From US$ 766 Book Now

Julia Whitehead Guest Suites

1011 Whitehead St Master, Key West, United States View map

Julia Whitehead Guest Suites is situated in Key West, at 450 metres from Duval Street and merely 0.6 km from South Beach. The 3-bedroom villa also comes with a kitchen complete with a microwave oven,… More

From US$ 458 Book Now

Atlantic Paradise By Avantstay Great Location W Balcony Outdoor Dining Shared Pool Hot Tub

1800 Atlantic 108A, Key West, United States View map

This 1-bedroom villa is located merely 0.9 km from C. B. Harvey Rest Beach Park and 0.5 km from Key West International airport. The property features a fully equipped kitchen with coffee and tea… More

From US$ 1367 Book Now

Yellowfin Ledge

1201 Duval Street 2, Key West, United States View map

Situated around a 25-minute walk from White Street Pier, the 1-bedroom Yellowfin Ledge Key West villa provides access to numerous tourist attractions in the area. More

From US$ 802 Book Now

First Breath By Avantstay Close To Old Town W Pool Month Long Stays Only

1106 Eaton Street, Key West, United States View map

The 3-bedroom villa is just 1.2 km from Truman Little White House and less than 10 minutes on foot from from the Minor Saint Mary Star of the Sea Basilica. Guests, staying at this villa, can use an… More

Book Now

Oceanfront Oasis

1901 South Roosevelt Blvd, Unit 304, Key West, United States View map

Located a mere 5 minutes' stroll from the Higgs Beach Dog Park, the 2-bedroom Oceanfront Oasis Villa Key West comes with a heated swimming pool, a sauna. More

From US$ 550 Book Now

The Crestwood House - Private Heated Pool & Parking

Shoreline Road 17, Key West, United States View map

Set about 25 minutes' walk from Key West Golf Club and around 20 minutes' walk from Safe Harbor, the 7-bedroom The Crestwood House - Private Heated Pool & Parking Villa is located in Key West. Guests… More

From US$ 2075 Book Now

Evershore House -Pool, Parking, Dock!

Key Haven Terrace 2, Key West, United States View map

The 4-bedroom Coastal Bliss Villa is set in Key West, approximately 25 minutes' walk from Sheriff s Animal Farm and at a 3.8 km distance from Fort East Martello Museum. This Key West villa also… More

From US$ 1979 Book Now