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2026-02-27
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Vacation Rentals in Key West

The Penthouse At Custom House Inn

124 Duval Street, Key West, United States View map

The spacious The Penthouse At Custom House Inn Key West is a great place to stay in the Downtown Key West district, 20 minutes' walk from Key West Butterfly and Nature Conservatory. More

From US$ 1271 Book Now

Casa Serendipity By Last Key Realty

1101 Angela Street, Key West, United States View map

Located 25 minutes' walk from Key West Butterfly and Nature Conservatory, Casa Serendipity By Last Key Realty Key West gives access to various tourist sites in the vicinity. More

From US$ 1544 Book Now

Bahama House

522 Bahama Street Key West Historic District, Key West, United States View map

Situated in Key West, within 350 metres of Southernmost Point, the 3-bedroom Bahama House Villa provides accommodation with free self parking, an outdoor swimming pool and a picnic area. This Key… More

From US$ 1218 Book Now

Old Town Garden Villas - Abaco Suite

921 Center St. #1, Key West, United States View map

To enjoy your vacation in Key West, stay at the 2-room Old Town Garden Villas - Abaco Suite Key West, which is only 9 minutes' walk from Mile Marker 0 Store and just 1.9 km from Key West Express. More

From US$ 453 Book Now

Villa The Watson House

525 Simonton Street, Key West, United States View map

Along with proximity to Key West First Legal Rum Distillery, just 650 metres away, the 4-bedroom Villa The Watson House Key West offers opportunities for windsurfing, snorkelling, and canoeing in the… More

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Aria At Azul Mansion Key West

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

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Flaglers Oasis By Avantstay Private Pool In Key West Month Long Stays Only

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

The 2-bedroom villa is nearly a 10-minute stroll from Smathers Beach and within walking distance of Peace Covenant Presbyterian Church. Guests, staying at the villa, can use an equipped kitchenette… More

From US$ 181 Book Now

The Mallory Suite At Inn On Fleming Key West!

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

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Suite Sanctuary By Last Key Realty

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

**Experience the Charm of Suite Sanctuary by Last Key Realty in Key West** Nestled in the vibrant heart of Key West, Suite Sanctuary by Last Key Realty offers an inviting escape for travelers seeking… More

From US$ 1420 Book Now

Dancing Palms

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

The enchanting Dancing Palms Villa is ideally nestled in the heart of Duval. This exquisite retreat seamlessly combines the vibrant energy of Key West with the tranquility you crave, making it a… More

From US$ 533 Book Now

Egret Suite - Southernmost Sanctuary

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

Situated just 5 minutes' stroll from the even Southernmost Point, the 1-bedroom Egret Suite - Southernmost Sanctuary Key West villa offers quick access to numerous city landmarks nearby. More

From US$ 354 Book Now

Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom

915 Eisenhower Drive, Key West, United States View map

The 2-bedroom Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom Key West villa is located around 5 minutes' walk from Wreckers Sloop Mary and offers guests to relish a patio as well as a… More

From US$ 776 Book Now

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

Seagrass Suite

1011 Whitehead St. # 2 (Upper Unit), Key West, United States View map

To enjoy your vacation in Key West, stay at the 1-room Seagrass Suite Key West, which is within 1 km of Red Barn Theatre and only 13 minutes on foot from the natural history museum "Florida Keys Eco… More

From US$ 289 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

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Claude Monet Suite

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

Located within a 500-metre distance of the even Southernmost Point, the 1-room Claude Monet Suite Key West is 1.2 km from a top family-friendly place like Key West Aquarium. Situated within close… More

From US$ 220 Book Now

Duval Street Suite W Kitchen And Shared Heated Pool

824 Duval Street, Key West, United States View map

Located 7 minutes' walk from Duval Street and The Ernest Hemingway Home and Museum, Duval Street Suite W Kitchen And Shared Heated Pool Key West features views of the city. Situated within close… 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

Shipyard Seaclusion

Key West, United States View map

Located about a 5-minute ride from Key West Historic Seaport, the 1-room Shipyard Seaclusion Apartment Key West is within 1 km of a top family-friendly place like Key West Aquarium. More

From US$ 500 Book Now

Seagate House -Waterfront W Dock

Shoreline Road 10, Key West, United States View map

The 4-bedroom Modern Keys Villa is situated at a 7 km distance from White Street Pier and approximately 10 minutes' drive from Fort East Martello Museum. This property also comes with a kitchen… More

From US$ 2225 Book Now

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

Brisa Del Mar By Avantstay Communal Pool Gated Community Ocean Front

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

The 2-bedroom villa offers accommodation only 1.2 km from Higgs Beach, while Key West Firehouse Museum is a 20-minute walk away. This villa also comes with a fully-fitted kitchen complete with… More

From US$ 615 Book Now

La Casa Cubana

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

The spacious 1-bedroom La Casa Cubana Apartment Key West is in the centre of Key West, only 7 minutes' walk from Key West Butterfly and Nature Conservatory. The presence of snorkelling, canoeing, and… More

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Four Flowers Guesthouse

521 Simonton St, Key West, United States View map

The 190 m^2 Four Flowers Guesthouse Key West is located 500 metres from Papa's Pilar Rum Distillery and just a 10-minute walk from The Ernest Hemingway Home and Museum. Staying in the apartment… More

From US$ 1196 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 Shared Pool Near Zachary Beach Month-Long Stays Only

620 Thomas Street #164, Key West, United States View map

Staying at the 1-bedroom Always Your Paradise By Avantstay Shared Pool Near Zachary Beach Month-Long Stays Only Key West villa, guests can visit the Key West Aquarium, which is just 1 km away. More

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New Rose Petal Petite Suite - Pool & Parking

Rose Lane 526, Key West, United States View map

To enjoy your vacation in Key West, stay at the spacious 74 m^2 New Rose Petal Petite Suite - Pool & Parking Key West, which is within a 5-minute drive of Higgs Beach Dog Park and just 650 metres… 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$ 379 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$ 458 Book Now

Paradise On Porter

514 Porter Lane, Key West, United States View map

Guests can stay at the spacious 2-bedroom Paradise On Porter Key West apartment, which is located in the centre of Key West and nearly 25 minutes' walk from Truman Little White House. Such activities… More

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The Trinidad -Pool & Parking

Seaside Drive 3625, Key West, United States View map

Southernmost Point is within 4.8 km of the 2-bedroom Trinidad Suite 105 and Key West International airport is 5 minutes' drive away. The accommodation features a kitchen with a coffeemaker, a… More

From US$ 336 Book Now

Curry House Room 6

Fleming Street 806, Key West, United States View map

The 1-room Curry House Room 6 Key West is situated in the Downtown Key West district of Key West, just 5 minutes' stroll from the performing arts theater "Red Barn Theatre". Set right near Key West… More

From US$ 340 Book Now

Sweet Caroline

Caroline Street 537, Key West, United States View map

Sweet Caroline Villa offers accommodation just 400 metres from Simonton Beach, while Key West Aquarium is about a 5-minute stroll away. This villa is equipped with 2 bedrooms plus a kitchen with a… More

From US$ 932 Book Now

Commodore'S Cove

Simonton Street 219, Key West, United States View map

Guests can stay at the spacious 4-bedroom Commodore'S Cove Apartment Key West, which is located right in the centre of Key West and approximately 15 minutes' walk from The Ernest Hemingway Home and… More

From US$ 1749 Book Now

Vangogh Studio

1016 Howe Street, Key West, United States View map

The 1-room Vangogh Studio Key West welcomes travellers in the centre of Key West, located just 1.5 km from Key West First Legal Rum Distillery. Situated in the vicinity of the downtown commercial… More

From US$ 454 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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New Grenada Suite - Parking Pool & Pets 209

Seaside Drive 3625, Key West, United States View map

New Grenada Suite - Parking Pool & Pets 209 is located at a 4.9 km distance from The Ernest Hemingway Home and Museum and 10 minutes' drive from Key West Firehouse Museum. This villa is equipped with… More

From US$ 513 Book Now

The Grande Vista

1800 Atlantic Blvd Unit C432, Key West, United States View map

The 2-room The Grande Vista Apartment Key West is located nearly 5 minutes' walk from The Key West Nature Preserve and overlooks the sea. Area attractions include South Beach, 2.5 km away, and Key… More

From US$ 818 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

Welcome Matt'S - Truman @ Duval Unit B

Truman Avenue, Key West, United States View map

The 39 m² Welcome Matt'S - Truman @ Duval Unit B Key West apartment is located in the Downtown Key West district of Key West, approximately a 5-minute walk from the Ernest Hemingway Home and Museum. More

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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

To enjoy your vacation in Key West, stay at the 2-room Follow The Sun By Last Key Realty Apartment Key West, which is approximately 3 km from Fort Zachary Taylor and about 10 minutes' drive from Key… More

From US$ 786 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$ 616 Book Now

Tranquility By Avantstay Close To Duval St W Bbq Shared Pool

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

Located in the Downtown Key West district with The Ernest Hemingway Home and Museum nearby, the 1-bedroom Tranquility By Avantstay Close To Duval St W Bbq Shared Pool lies a mere 1.2 km from Higgs… More

From US$ 400 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

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 a stone's throw from the Key West Lighthouse and Keeper's Quarters Museum and 5 km from Key West International airport. More

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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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