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2026-11-05
2026-11-06
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Holiday Homes in Key West

Ocean Hideaway On The Atlantic

1800 Atlantic Blvd Suite A206, Key West, United States Show map

Situated approximately 25 minutes' walk from the even Southernmost Point, the 2-bedroom Ocean Hideaway On The Atlantic Villa Key West entices guests with a hot tub and a sauna, ensuring a more… More

From US$ 621 Book Now

Royal Palm Suite At Travelers Palm Inn Key West

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

Located just a 9-minute walk from Key West Butterfly and Nature Conservatory, the 1-bedroom Royal Palm Suite At Travelers Palm Inn Key West villa features an outdoor swimming pool and can accommodate… More

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Petes Cottages

505-507 Louisa Street, Key West, United States Show map

The 4-bedroom Petes Cottages Key West hosts up to 8 guests and provides proximity to The Ernest Hemingway Home and Museum, situated merely a 5-minute walk away. This Key West villa features… More

From US$ 937 Book Now

Bayview North One

801 Eisenhower Dr. #4, 4, Key West, United States Show map

Bayview North One Villa Key West, located about 5 minutes' walk from Wreckers Sloop Mary, can host up to 8 guests. This property features opportunities for snorkelling and fisheries in the area, just… More

From US$ 1220 Book Now

Two Duval Street Condos W Parking And Pool

Duval Street 824, Key West, United States Show map

Two Duval Street Condos W Parking And Pool Key West villa is located about a 15-minute walk from Key West First Legal Rum Distillery and provides cycling and fisheries for active guests. Located not… More

From US$ 834 Book Now

6 Bedroom 6 Bath Guesthouse On Duval Street

824 Duval Street, Key West, United States Show map

Situated around 5 minutes' walk from The Ernest Hemingway Home and Museum, the 6-bedroom 6 Bedroom 6 Bath Guesthouse On Duval Street Key West villa is ideal for up to 24 guests. The property features… More

From US$ 4873 Book Now

Casa De Cubana

512 Amelia Street, Key West, United States Show map

Offering a location approximately a 10-minute walk from San Carlos Institute, the 2-bedroom Casa De Cubana Villa Key West gives access to various tourist spots in the area. With a maximum capacity of… More

From US$ 2269 Book Now

Flaglers Oasis By Avantstay

2209 Flagler Ave Is #B, Key West, United States Show map

The 2-bedroom Flaglers Oasis By Avantstay Key West villa hosts up to 4 guests and is nestled only 1.4 km from natural sites such as Higgs Beach Dog Park. Located approximately a 10-minute drive from… More

From US$ 181 Book Now

Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo

915 Eisenhower Drive, Key West, United States Show map

Featuring a swimming pool, the 2-bedroom Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo Key West villa is located approximately 5 minutes' walk from Bayview Park and is suitable for… More

From US$ 184 Book Now

Poolside Breeze Retreat

1800 Atlantic Blvd Unit A103, Key West, United States Show map

Up to 6 guests can stay at the 2-bedroom Poolside Breeze Retreat Villa Key West and enjoy The Key West Nature Preserve, located about a 5-minute walk away. Featuring a sauna, the villa is merely 1.8… More

From US$ 1026 Book Now

Key West Found By Avantstay

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

Staying at the 2-bedroom Key West Found By Avantstay villa, guests can visit Saint Mary Star of the Sea Basilica, which is just 1.7 km away. Offering parking as well as Wi-Fi, the welcoming holiday… More

From US$ 544 Book Now

Absolutely Paradise

1011 Simonton Street #3, Key West, United States Show map

Located around 5 minutes on foot from The Ernest Hemingway Home and Museum, the 3-bedroom Absolutely Paradise Key West villa can accommodate up to 8 guests, providing them with a sauna for a relaxing… More

From US$ 1973 Book Now

Casa Serendipity By Last Key Realty

1101 Angela Street, Key West, United States Show map

The 3-bedroom Casa Serendipity By Last Key Realty Key West offers quick access to such city attractions as The Unitarian Universalist Fellowship of Key West, located only a 5-minute walk away. More

From US$ 1544 Book Now

New Grenada Suite - Parking Pool & Pets 209

Seaside Drive 3625, Key West, United States Show map

Situated a mere 1.9 km from Fort East Martello Museum, the 2-bedroom New Grenada Suite - Parking Pool & Pets 209 Key West villa entices guests with a Jacuzzi, ensuring a more relaxing stay. Offering… More

From US$ 513 Book Now

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

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

The 1-bedroom Egret Suite | Bright Retreat, Hot Tubs, Steps From Duval! Key West villa accommodates up to 4 guests and offers proximity to the even Southernmost Point, located merely a 5-minute walk… More

From US$ 354 Book Now

Casita Angelita By Last Key Realty

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

Located just a 5-minute walk from The Ernest Hemingway Home and Museum, Casita Angelita By Last Key Realty Key West villa is suitable for 6 guests and provides a swimming pool to relax in. Located… More

From US$ 750 Book Now

New The Altair House - Fire Pit Pool & Hot Tub

Mangrove Lane 13, Key West, United States Show map

Offering a patio and barbecue for guests' leisure, New The Altair House - Fire Pit Pool & Hot Tub Villa Key West is situated a 25-minute walk from Key West Golf Club. Located in the vicinity of Key… More

From US$ 4188 Book Now

Last Minute

Key West, United States Show map

Located just a 6-minute stroll from Key West First Legal Rum Distillery, Last Minute Key West villa gives easy access to various tourist attractions in the area. More

From US$ 861 Book Now

Bahama Gardens - Cigar House

712 Thomas Street, Key West, United States Show map

Located a few steps from Key West Lighthouse and Keeper's Quarters Museum, the 2-bedroom Bahama Gardens - Cigar House Villa Key West provides guests with a Jacuzzi. Located only a 7-minute walk from… More

From US$ 813 Book Now

Bootlegger Bay @ Speakeasy Inn Key West!

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

The 1-bedroom Bootlegger Bay @ Speakeasy Inn Key West! villa accommodates up to 2 guests and offers proximity to Southernmost Point of the Continental US Monument, located just 6 minutes' walk away. More

From US$ 570 Book Now

Soul Of Duval By Last Key Realty

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

The 2-bedroom Soul Of Duval By Last Key Realty Key West villa is situated nearly 5 minutes' walk from The Ernest Hemingway Home and Museum, featuring such comforts as Wi-Fi and private car parking. More

From US$ 500 Book Now

Contra House -Luxury Home With Pool

Simonton Street 720, Key West, United States Show map

Offering an outdoor swimming pool, the 4-bedroom Contra House -Luxury Home With Pool Key West is situated merely 7 minutes' walk from The Ernest Hemingway Home and Museum and can accommodate up to 12… More

From US$ 1909 Book Now

St John - Downtown Waterfront Penthouse Pool Parking Dock

915 Eisenhower Drive, Key West, United States Show map

The 4-bedroom St John - Downtown Waterfront Penthouse Pool Parking Dock Villa Key West provides easy access to various city attractions, such as Bayview Park, situated nearly 5 minutes' walk away. More

From US$ 2344 Book Now

Smuggler'S Cove @ Speakeasy Inn Key West!

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

Smuggler'S Cove @ Speakeasy Inn Key West! villa is located an 8-minute walk from Saint Mary Star of the Sea Basilica and invites guests to join snorkelling and fisheries. The 1-bedroom holiday home… More

From US$ 396 Book Now

Conch In The Treetops By Last Key Realty

1800 Atlantic Blvd #C125, Key West, United States Show map

Located about a 5-minute walk from Higgs Beach Dog Park, the 2-bedroom Conch In The Treetops By Last Key Realty Key West villa boasts a swimming pool and can accommodate up to 6. Providing guests… More

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Key West Large Waterfront Condo With Boat Slip, Sleeps 8

915 Eisenhower Drive, Key West, United States Show map

Staying at the 2-bedroom Key West Large Waterfront Condo With Boat Slip, Sleeps 8 villa, guests can visit the vintage parish "Saint Paul's Episcopal Church of Key West", which is nearly a 25-minute… More

From US$ 383 Book Now

Island Pearls

527 Fleming Street, Key West, United States Show map

The 2-bedroom Island Pearls Villa Key West accommodates up to 4 guests and offers proximity to Nancy Forrester's Secret Garden, located only a 9-minute walk away. The property features opportunities… More

From US$ 1551 Book Now

Anchor Drop Key West

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

Located only 0.8 km from Higgs Beach Dog Park, the 2-bedroom Anchor Drop Key West Villa offers a heated pool, a Jacuzzi and a sauna for a truly relaxing stay. Hosting up to 6 guests, this Key West… More

From US$ 870 Book Now

Hideaway @ Speakeasy Inn Key West!

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

The 1-bedroom Hideaway @ Speakeasy Inn Key West! villa offers quick access to such city attractions as Key West Lighthouse and Keeper's Quarters Museum, located nearly a 5-minute walk away. Providing… More

From US$ 467 Book Now

Andros Suite

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

Located just a 7-minute walk from Key West Butterfly and Nature Conservatory, the 1-bedroom Andros Suite Key West villa features a heated pool and can accommodate up to 4 guests. More

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Prime Downtown Location - Truman Little Cozy Cottage

910 Simonton Street 3, Key West, United States Show map

Offering access to entertainment venues such as Key West First Legal Rum Distillery, situated just 1.5 km away, Prime Downtown Location - Truman Little Cozy Cottage Key West can host up to 2 guests. More

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Upper Bayview South

801 Eisenhower Dr. #10, 10, Key West, United States Show map

Upper Bayview South Villa Key West offers quick access to such city attractions as Wreckers Sloop Mary, located nearly a 5-minute walk away. Providing guests with Wi-Fi and private parking, this… More

From US$ 1763 Book Now

Atlantic Sunrise Penthouse

1800 Atlantic Blvd, Unit C425, Key West, United States Show map

Suitable for 8 guests, the 3-bedroom Atlantic Sunrise Penthouse Villa Key West is located only a 9-minute walk from Higgs Beach Dog Park and provides a Jacuzzi and a sauna for a relaxing stay. This… More

From US$ 941 Book Now

Sundial On The Atlantic Ocean View

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

Boasting a sauna, the 2-bedroom Sundial On The Atlantic Ocean View Villa Key West is located only a 9-minute walk from Higgs Beach Dog Park and can accommodate 6 guests. This villa features… More

From US$ 561 Book Now

Petes West Cottage

505 Louisa Street, Key West, United States Show map

Featuring a swimming pool, Petes West Cottage Key West is suitable for up to 4 people and is located a 20-minute stroll from Fort Zachary Taylor. Providing guests with Wi-Fi and a car park, the 2… More

From US$ 928 Book Now

Duval Street Suite Overlooking Duval With Parking And Pool

824 Duval Street, Key West, United States Show map

The 1-bedroom Duval Street Suite Overlooking Duval With Parking And Pool Key West villa is located around a 15-minute walk from Key West Aquarium and provides cycling and fisheries for active guests.… More

From US$ 763 Book Now

Kw72A Old Town Garden Villas - Abaco Suite

921 Center St., Key West, United States Show map

Situated only 5 minutes' walk from the downtown commercial zoned Duval Street, the 1-bedroom Kw72A Old Town Garden Villas - Abaco Suite Key West is ideal for up to 4 guests. This villa features… More

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Mastway House -Pool & Dock!

Key Haven Terrace 4, Key West, United States Show map

Located 17 minutes' walk from Key Haven, the 4-bedroom Mastway House -Pool & Dock! Villa Key West offers fitness classes, as well as a fitness room for active guests. Offering a swimming pool, this 4… More

From US$ 3115 Book Now

Casa Papa Del Mar

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

Located just a 9-minute walk from Higgs Beach Dog Park, the 2-bedroom Casa Papa Del Mar Villa Key West is suitable for 6 guests and provides a swimming pool to relax in. This 2-bathroom villa… More

From US$ 709 Book Now

Kwss202 Sunrise Suites - Big Kahuna Suite 202

3625 Seaside Dr #202, Key West, United States Show map

The 2-bedroom Kwss202 Sunrise Suites - Big Kahuna Suite 202 Key West villa entices active guests with access to a fitness suite and is located nearly a 10-minute ride from the even Southernmost Point… More

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Belle Of The Beach By Last Key Realty

1815 Atlantic Boulevard, Key West, United States Show map

The 6-bedroom Belle Of The Beach By Last Key Realty Key West villa is located approximately a 25-minute walk from the even Southernmost Point and provides a heated pool, ensuring a relaxing stay. More

From US$ 2288 Book Now

Parking Pool & Dock - Shellstone House

16 Andrea Lane, Key West, United States Show map

The 8-bedroom Parking Pool & Dock - Shellstone House Villa Key West is located approximately a 15-minute walk from Key West Tropical Forest and Botanical Garden and provides fisheries for active… More

From US$ 4425 Book Now

Quiet Pour @ Speakeasy Inn Key West!

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

Situated merely a 6-minute stroll from Southernmost Point of the Continental US Monument, the 1-bedroom Quiet Pour @ Speakeasy Inn Key West! villa ensures a great leisure experience by offering… More

From US$ 493 Book Now

The Mallory Suite At Inn On Fleming Key West!

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

Located only a 9-minute walk from the very unusual Key West Cemetery, 1-bedroom The Mallory Suite At Inn On Fleming Key West! villa boasts an outdoor swimming pool and can accommodate up to 2. The… More

From US$ 441 Book Now

Blue Haven Unit B416

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

The 2-bedroom Blue Haven Unit B416 Villa Key West, located about 5 minutes' walk from The Key West Nature Preserve, entices guests with a heated pool as well as a sauna to relax in. This… More

From US$ 1571 Book Now

Harbor House Penthouse- B

423 Front Street, Key West, United States Show map

Located in the Duval district, merely a 5-minute walk from Key West Aquarium, Harbor House Penthouse- B Villa Key West offers city views. The 4-bedroom holiday home features opportunities for… More

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Duval Street Retreat

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

Up to 6 guests can stay at Duval Street Retreat Villa Key West and enjoy the even Southernmost Point, located 6 minutes' walk away. More

From US$ 515 Book Now

Ibis By Avantstay

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

Offering an outdoor swimming pool, the 1-bedroom Ibis By Avantstay Key West villa is situated merely 0.6 km from the downtown commercial zoned Duval Street and can accommodate up to 2 guests. More

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Villa Angelita By Last Key Realty

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

Located just around the corner from the downtown commercial zoned Duval Street, Villa Angelita By Last Key Realty Key West is suitable for 7 guests and provides a swimming pool to relax in. More

From US$ 957 Book Now

Catherine House

518 Catherine Street, Key West, United States Show map

The 2-bedroom Catherine House Key West villa offers quick access to such tourist spots as Key West Lighthouse and Keeper's Quarters Museum, situated only 5 minutes' walk away. Providing guests with… More

From US$ 759 Book Now