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2026-11-05
2026-11-06
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Luxury accommodations in Key West

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

Sunrise Suite 203

3625 Seaside Dr #203, Key West, United States Show map

To enjoy your vacation in Key West, stay at the spacious 74 m² Sunrise Suite 203 Key West, which is about a 10-minute ride from Higgs Beach Dog Park and merely 600 metres from Thompson Island. Guests… More

From US$ 718 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

Kw37 Oceana Suite

Key West, United States Show map

The 53 m² Kw37 Oceana Suite Key West is situated only 5 minutes' walk from the 19-acre Key West Cemetery and 5 km from Key West International airport. Offering access to an outdoor swimming pool… More

From US$ 286 Book Now

Poolside Suite

Olivia Street 517, Key West, United States Show map

The 2-bedroom Poolside Suite Key West is located 2.3 km from Higgs Beach Dog Park and about a 10-minute walk from South Beach. Offering access to a swimming pool, the spacious 60 m² apartment is… More

From US$ 914 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

Harveys Haven

611 Southard St #2, Key West, United States Show map

The spacious 44 m² Harveys Haven Apartment Key West is located only 0.8 km from the 19-acre Key West Cemetery and offers Wi-Fi for either business or leisure. Providing a prime setting in Key West… More

From US$ 375 Book Now

Beach Club Siesta #104

1500 Atlantic Blvd #104, Key West, United States Show map

To enjoy your vacation in Key West, stay at the spacious 2-bedroom Beach Club Siesta #104 Key West apartment, which is approximately 6 km from Smathers Beach and nearly 20 minutes' walk from Key West… More

From US$ 637 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

Walking On Sunshine By Last Key Realty

1800 Atlantic Blvd #A406, Key West, United States Show map

Located merely 1.3 km from Key West Garden Club, the 2-bedroom Walking On Sunshine By Last Key Realty Key West apartment is within a 10-minute drive of a top family-friendly place like Key West… More

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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

A Cuban Club Suite Cuban Club

1102 Duval St, Key West, United States Show map

Located in Duval with leather arm chairs and couches all surrounded by glimmering candles and chic decor, merely 6 minutes' walk from South Beach, the spacious 2-bedroom A Cuban Club Suite Cuban Club… More

From US$ 678 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

Cuban Paradise Cuban Club

1102 Duval St #D, Key West, United States Show map

If you want to stay in the Downtown Key West district of Key West, the spacious 2-bedroom Cuban Paradise Cuban Club Key West apartment is a good choice located, a mere 1.6 km from Fort Zachary Taylor… More

From US$ 666 Book Now

Shipyard Treasure By Avantstay

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

Set in the Downtown Key West district, a 7-minute walk from the downtown commercial zoned Duval Street, the welcoming Shipyard Treasure By Avantstay Key West apartment accommodates up to 4 guests. More

From US$ 438 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

Cloud Suite On Duval

Duval Street 718, Key West, United States Show map

The spacious 2-bedroom Cloud Suite On Duval Key West is around 15 minutes' walk from the shopping mall "Clinton Square Market". Situated just moments from the vintage parish "Saint Paul's Episcopal… More

From US$ 1044 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

Orchid Suite

921 Center St #4, Key West, United States Show map

The spacious Orchid Suite Key West features a prime location 14 minutes' walk from the fully accredited Mel Fisher Maritime Heritage Museum and hosts up to 4 guests. Offering access to a swimming… More

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Parrotville

606 Truman Ave #12, Key West, United States Show map

Featuring a swimming pool, the spacious 2-bedroom Parrotville Key West apartment is within 5 minutes' walk of The Ernest Hemingway Home and Museum. Also, windsurfing, snorkelling, and canyoning can… More

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Artist Condo Duval Square #7

1075 Duval Street, Key West, United States Show map

Featuring a prime location just moments from Key West Lighthouse and Keeper's Quarters Museum, Artist Condo Duval Square #7 Key West accommodates up to 6 guests. Offering access to a heated pool… More

From US$ 703 Book Now

Bonaire Suite

921 Center St #7, Key West, United States Show map

The 1-bedroom Bonaire Suite Key West is situated in Duval with one of Key West's top culinary experiences, just a 6-minute walk from the even Southernmost Point, and offers spa therapy and a dining… More

From US$ 515 Book Now

Suite Sanctuary By Last Key Realty

1800 Atlantic Blvd #C424, Key West, United States Show map

Offering a swimming pool, the 2-bedroom Suite Sanctuary By Last Key Realty Key West is situated around a 25-minute walk from the historic Key West Lighthouse. Boasting a convenient location, a few… More

From US$ 1420 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

Beach Club Seabreeze #103

1500 Atlantic Blvd #103, Key West, United States Show map

The 2-bedroom Beach Club Seabreeze #103 Key West apartment boasts a beachfront setting and in around a 5-minute walk from Higgs Beach Dog Park. This spacious apartment can host up to 5 guests. More

From US$ 784 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

The Margaret Suite

1501 Truman Avenue, Key West, United States Show map

The Margaret Suite Key West is located within a 300-metre distance of Wreckers Sloop Mary and 25 minutes' walk from Papa's Pilar Rum Distillery. Offering access to an outdoor swimming pool, the… More

From US$ 292 Book Now

Duval Street Suite W Kitchen And Shared Heated Pool

824 Duval Street, Key West, United States Show map

To enjoy your vacation in Key West, stay at the 1-bedroom Duval Street Suite W Kitchen And Shared Heated Pool Key West, which is approximately 5 minutes' drive from the natural history museum… More

From US$ 501 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