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2026-06-29
2026-06-30
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Key West holiday rentals

6 Bedroom 6 Bath Guesthouse On Duval Street

824 Duval Street, Key West, United States View map

Located merely 500 metres from Southernmost Point of the Continental US Monument, the 6-bedroom 6 Bedroom 6 Bath Guesthouse On Duval Street Key West villa offers opportunities for cycling and fishing… More

From US$ 4873 Book Now

Keys Please!

Louisa Street 514, Key West, United States View map

The 3-bedroom Keys Please! Villa Key West is located about a 20-minute walk from the White Street Pier and provides cycling and fishing for active guests. Situated in Duval with unique, island… More

From US$ 1910 Book Now

Mar Y Sol Ocean Front

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

Mar Y Sol Ocean Front Villa Key West is located 25 minutes' walk from the downtown commercial zoned Duval Street and invites guests to join windsurfing, snorkelling, and fishing. Featuring a sauna… More

From US$ 871 Book Now

Nautical Adventures In Paradise

1800 Atlantic Blvd #C126, Key West, United States View map

**Nautical Adventures in Paradise Key West** Connected to the vibrant pulse of Key West, Nautical Adventures In Paradise is ideally situated just 2.5 km from the historic Southernmost Point and only… More

From US$ 732 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

Windward Isle

531 Olivia St, Key West, United States View map

Nestled a 15-minute walk from the fully accredited Mel Fisher Maritime Heritage Museum, Windward Isle Villa Key West entices guests to explore various tourist destinations nearby. More

From US$ 312 Book Now

Paradise Found Cayo Hueso

1800 Atlantic Blvd Unit A111, Key West, United States View map

Paradise Found Cayo Hueso villa provides an opportunity to stay a 5-minute walk from The Key West Nature Preserve and offers a Jacuzzi and a sauna, perfect for decompressing. The 2-bedroom holiday… More

From US$ 597 Book Now

Tropical Paradise Key West

1800 Atlantic Blvd Unit A113, Key West, United States View map

Up to 6 guests can stay at the 2-bedroom Tropical Paradise Key West villa and enjoy The Key West Nature Preserve, located approximately a 5-minute walk away. Featuring a sauna, the property is 2.3 km… More

From US$ 506 Book Now

Rooftop Penthouse

623 Duval Street Penthouse Suite, Key West, United States View map

The 2-bedroom Rooftop Penthouse Key West villa is nestled just 0.6 km from the downtown commercial zoned Duval Street and can accommodate up to 6 guests. More

From US$ 1123 Book Now

Tom'S Chicken Coop Key West

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

Situated only 650 metres from the Higgs Beach Dog Park, the 2-bedroom Tom'S Chicken Coop Key West Villa can welcome up to 6 guests and boasts a Jacuzzi and a sauna for a relaxing retreat. Located in… More

From US$ 598 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 quick access to such city attractions as the secluded pocket Dog Beach, located just a 5-minute walk away. More

From US$ 945 Book Now

Yellowfin Ledge

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

The 1-bedroom Yellowfin Ledge Key West villa, located merely a 6-minute walk from the historical Key West Lighthouse, can host up to 3 guests. More

From US$ 954 Book Now

Blue Moonshine On The Atlantic

1800 Atlantic Blvd, Unit A413, Key West, United States View map

Located only a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Blue Moonshine On The Atlantic Villa Key West boasts an outdoor swimming pool and can accommodate up to 6. This 2-bathroom… More

From US$ 602 Book Now

Bahama Gardens - Main House

704 Thomas Street, Key West, United States View map

Located in the Downtown Key West district, Bahama Gardens - Main House Villa Key West is an 18-minute walk from the bustling plaza "Mallory Square" and offers a Jacuzzi. The 4-bedroom holiday home… More

From US$ 2304 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

Key West Light Suite

215 Eanes Lane, Key West, United States View map

The 1-bedroom Key West Light Suite villa, located just 5 minutes' walk from the Ernest Hemingway Home and Museum, can host up to 4 guests. More

From US$ 853 Book Now

The Mellow Macaw By Last Key Realty

1025D Whitehead Street, Key West, United States View map

The 2-bedroom The Mellow Macaw 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

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The Geiger Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

Situated only 650 m from the Key West First Legal Rum Distillery, 2-bedroom The Geiger Suite At Inn On Fleming Key West! villa is ideal for up to 4 guests. More

From US$ 402 Book Now

New Grenada Suite - Parking Pool & Pets 209

Seaside Drive 3625, Key West, United States View map

During the stay at New Grenada Suite - Parking Pool & Pets 209 Key West villa, guests can indulge in cycling and fishing or visit the bustling plaza "Mallory Square", located a 15-minute drive away. More

From US$ 513 Book Now

Somewhere On The Beach

1800 Atlantic Blvd, Unit C238, Key West, United States View map

The 2-bedroom Somewhere On The Beach Key West villa accommodates up to 6 guests and offers proximity to the Higgs Beach Dog Park, located just 0.8 km away. The Key West holiday home features… More

From US$ 972 Book Now

Darling Of Duval By Last Key Realty

425 Caroline Street, Key West, United States View map

Located around a 5-minute stroll from the Vandenberg Wreck, the 2-bedroom Darling Of Duval By Last Key Realty Key West villa can accommodate up to 4 guests, providing them with a Jacuzzi for a… More

From US$ 1598 Book Now

Blue Haven Unit B416

1800 Atlantic Blvd, Unit B416, Key West, United States View map

Located just 600 metres from the Higgs Beach Dog Park, the 2-bedroom Blue Haven Unit B416 Villa Key West provides an outdoor swimming pool as well as windsurfing, snorkelling, and canoeing to… More

From US$ 1571 Book Now

Fleming-O

726 Fleming St, Key West, United States View map

Located merely 650 metres from the vintage parish "Saint Paul's Episcopal Church of Key West", the 2-bedroom Fleming-O Villa Key West offers opportunities for windsurfing, snorkelling, and canoeing… More

From US$ 1006 Book Now

Duval Street Retreat

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

The 2-bedroom Duval Street Retreat Villa Key West offers swift access to various city sites, such as the historic Key West Lighthouse, situated about a 5-minute walk away. More

From US$ 515 Book Now

First Breath By Avantstay

1106 Eaton Street, Key West, United States View map

Situated a 6-minute walk from the Papa's Pilar Rum Distillery, the welcoming First Breath By Avantstay Key West villa entices guests with views of the pool. More

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Duval Hideaway

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

**Discover the Duval Hideaway Villa in the Heart of Key West** Conveniently located, the villa is within walking distance to the bustling nightlife and unique shops that Duval Street is renowned for. More

From US$ 515 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

Oceanfront Oasis

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

The 2-bedroom Oceanfront Oasis Villa Key West entices guests to enjoy windsurfing, snorkelling, and canoeing and offers proximity to the Higgs Beach Dog Park, located approximately a 5-minute stroll… More

From US$ 550 Book Now

Evershore House -Pool, Parking, Dock!

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

Situated merely 1.6 km from Sheriff s Animal Farm, the 4-bedroom Evershore House -Pool, Parking, Dock! Key West villa features a patio with views of the sea. Offering a private swimming pool, the… More

From US$ 3115 Book Now

Petes East Cottage

507 Louisa Street, Key West, United States View map

Situated merely a 6-minute stroll from Southernmost Point of the Continental US Monument, the 2-bedroom Petes East Cottage Key West ensures a great leisure experience by offering windsurfing… More

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Last Minute

Key West, United States View map

More

From US$ 861 Book Now

Duval Breeze By Avantstay

1075 Duval St #30, Key West, United States View map

The welcoming Duval Breeze By Avantstay Key West villa provides easy access to various city attractions, such as the Key West Butterfly and Nature Conservatory, situated merely 6 minutes' walk away. More

From US$ 1572 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

Knowles House

1004 Eaton Street, Key West, United States View map

Located 1 km from the downtown commercial zoned Duval Street, Knowles House Villa Key West provides access to various tourist attractions in the vicinity. More

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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$ 579 Book Now

Harbor House Suite A

Front Street, Key West, United States View map

Harbor House Suite A Key West villa is nestled merely a 5-minute walk from the waterfront Mallory Square and can accommodate up to 12 guests. More

From US$ 1520 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

Tranquility By Avantstay

714-5 Olivia St, Key West, United States View map

Located in the Downtown Key West district of Key West, a mere 6 minutes' walk from the Minor Saint Mary Star of the Sea Basilica, the 0-bedroom Tranquility By Avantstay Key West villa offers patio… More

From US$ 448 Book Now

Nassau Suite Key West

921 Center Street #12, Key West, United States View map

**Nassau Suite Key West** is nestled in the vibrant heart of Duval, offering an enchanting retreat that perfectly blends luxury with a lively atmosphere. This striking suite boasts elegant leather… More

From US$ 431 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 windsurfing, snorkelling, and fishing or visit Southernmost Point of the Continental US Monument, located 25 minutes' stroll away. More

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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$ 1379 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

Hemingways Atlantic Retreat

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

Located 9 minutes' walk from the Higgs Beach Dog Park, Hemingways Atlantic Retreat Villa Key West is suitable for 6 guests and provides a sauna for a truly relaxing stay. The 2-bedroom holiday home… More

From US$ 404 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

Louisa House

521 Louisa Street, Key West, United States View map

**Welcome to Louisa House Villa Key West,** a vibrant oasis nestled in the heart of Duval Street. This enchanting retreat offers an unrivaled blend of island-inspired charm and modern amenities… More

From US$ 1399 Book Now

Kw335Wk Dancing Palms

606 Truman Ave 9, Key West, United States View map

Located only 6 minutes' walk from the Ernest Hemingway Home and Museum, Dancing Palms Villa Key West offers opportunities for cycling and fishing in the area. More

From US$ 533 Book Now

Southard Getaway By Avantstay

203 Southard #3, Key West, United States View map

The welcoming Southard Getaway By Avantstay Key West villa offers proximity to nearby tourist spots, such as the Vandenberg Wreck, situated 13 minutes' walk away. More

From US$ 612 Book Now

The Mallory Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

Situated around 5 minutes' walk from the Key West Historic Seaport, 1-bedroom The Mallory Suite At Inn On Fleming Key West! villa entices guests with windsurfing, snorkelling, and fishing in the area. More

From US$ 441 Book Now

Aria At Azul Mansion Key West

907 Truman Ave., Key West, United States View map

Along with proximity to the Minor Saint Mary Star of the Sea Basilica, just a 5-minute walk away, the 1-bedroom Aria At Azul Mansion Key West Villa offers opportunities for windsurfing, snorkelling… More

From US$ 889 Book Now

Soul Of Duval By Last Key Realty

615½ Duval Street, Unit 1, Key West, United States View map

Offering access to entertainment venues such as the Papa's Pilar Rum Distillery, situated only 1.4 km away, the 2-bedroom Soul Of Duval By Last Key Realty Key West villa can host up to 4 guests. More

From US$ 500 Book Now