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2025-07-07
2025-07-08
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Key West holiday rentals

Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock

915 Eisenhower Drive, Key West, United States View map

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The St Martin -Hot Tub & Pool

Seaside Drive 3625, Key West, United States View map

Saint Martin Suite 207 offers accommodation 4.9 km from The Ernest Hemingway Home and Museum, while Key West Butterfly and Nature Conservatory is nearly 10 minutes away by car. Guests, staying at the… More

From US$ 435 Book Now

Anchor Drop Key West

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

Nearly 15 minutes' walk from Higgs Beach, Anchor Drop Key West Villa is just off Fort Zachary Taylor Historic State Park. While staying at the 2-bedroom villa, guests are welcome to use an equipped… More

From US$ 708 Book Now

Bahama Gardens - Cigar House

712 Thomas Street, Key West, United States View map

The 2-bedroom Bahama Gardens - Cigar House Villa in the Downtown Key West district of Key West offers a golf course, a Jacuzzi and a sundeck as well as the access to Truman Beach, which is just 900… More

From US$ 813 Book Now

Heron Suite - Southernmost Sanctuary

1330 Simonton Street #2, Key West, United States View map

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From US$ 219 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

Mangrove Lagoon

104 Admirals Ln, Key West, United States View map

Located in the Downtown Key West district with Key West Shipwreck Treasure Museum nearby, the 2-bedroom Mangrove Lagoon Villa lies only 1 km from the 19 - acre Key West Cemetery. The accommodation… More

From US$ 437 Book Now

Beach House Condo By Avantstay Communal Pool Gated Community Great Location

620 Thomas St, Key West, United States View map

Due to the villa's great location, The Ernest Hemingway Home and Museum and the natural history museum "Florida Keys Eco-Discovery Center" are quite easy to reach. Extras include a refrigerator, an… More

From US$ 388 Book Now

Southard Getaway By Avantstay W Covered Patio Great Location Shared Pool Week Long Stays

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

South Beach is 1.2 km from the 2-bedroom villa, while Key West Aquarium is less than a 10-minute stroll from here. Guests, staying at the villa, can use a full kitchen with a refrigerator, an oven… More

From US$ 607 Book Now

Conch In The Treetops By Last Key Realty

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

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Bahama Gardens - Main House

704 Thomas Street, Key West, United States View map

Bahama Gardens - Main House Villa is located merely 1.2 km from the secluded pocket Dog Beach and 15 minutes' drive to Key West International airport. Guests, staying at the 4-bedroom villa, can use… More

From US$ 1997 Book Now

Duke Of Catherine By Last Key Realty

512 Catherine Street #2, Key West, United States View map

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Tom'S Oceanfront Penthouse

1800 Atlantic Blvd Unit A401, Key West, United States View map

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From US$ 833 Book Now

Conch Adventure By Avantstay Great Location W Patio Outdoor Dining And Shared Pool Week Long Stays

104 Southard Street #3, Key West, United States View map

This 2-bedroom villa is sited a mere 550 metres from The Ernest Hemingway Home and Museum. Set close to Duval Street, the villa is a few minutes drive from the 19-acre Key West Cemetery. More

From US$ 369 Book Now

Smooth Sailing By Last Key Realty

1800 Atlantic Blvd #C334, Key West, United States View map

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From US$ 1398 Book Now

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

915 Eisenhower Drive, Key West, United States View map

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From US$ 1741 Book Now

Casa Atlantic

Key West, United States View map

Casa Atlantic Villa is approximately 15 minutes on foot from Southernmost Point and a 10-minute drive from from Key West Aquarium. While staying at the 3-bedroom villa, guests are welcome to use a… More

From US$ 258 Book Now

Trumans Hideaway By Avantstay Great Location W Patio Outdoor Dining Bbq Shared Pool Week Long Stays

113 Front St #108, Key West, United States View map

Simonton Street is 10 minutes' walk from the 2-bedroom villa, while Mallory Square is within a 5-minute walk of here. Guests, staying at the villa, can use a full kitchen with an oven, kitchenware… More

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Rooftop Penthouse

Key West, United States View map

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From US$ 1123 Book Now

Tom'S Chicken Coop Key West

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

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From US$ 715 Book Now

New The Cottage At James House

512 Caroline Street, Key West, United States View map

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From US$ 519 Book Now

A Place In Paradise By Avantstay Key West Walkable W Shared Pool Week Long Stays Only

526 Porter Lane, Key West, United States View map

This 1-bedroom villa is located near Duval Street, a mere 1 km from the Minor Saint Mary Star of the Sea Basilica. A kitchen with a dishwasher, coffee & tea makers and an oven is included at the… More

From US$ 644 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$ 447 Book Now

La Brisa Unit 105 North Building

South Roosevelt Boulevard 1901, Key West, United States View map

Higgs Beach is 1.2 km from La Brisa Unit 105 North Building Villa, while The Ernest Hemingway Home and Museum is a 10-minute drive from here. The 2-bedroom villa also comes with a kitchen, which is… More

From US$ 764 Book Now

The Headquarters

Key West, United States View map

The 2-bedroom Headquarters Villa is set in the Downtown Key West district, at a 0.7 km distance from Dog Beach and 5 minutes' drive from the bustling plaza "Mallory Square". This property also comes… More

From US$ 247 Book Now

Alligator Reef Light Suite

Key West, United States View map

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American Shoal Light Suite

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

Dancing Palms

Key West, United States View map

The 2-bedroom Dancing Palms Villa is within a few steps of The Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. Featuring a patio and a heated swimming pool… More

From US$ 578 Book Now

Egret Suite - Southernmost Sanctuary

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

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From US$ 354 Book Now

Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom

915 Eisenhower Drive, Key West, United States View map

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From US$ 650 Book Now

St John - Downtown Waterfront Penthouse Pool Parking Dock

915 Eisenhower Drive, Key West, United States View map

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From US$ 2344 Book Now

Duval Street Retreat

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

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Villa Angelita By Last Key Realty

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

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Leo'S Lodge

1016 Howe St #7, Key West, United States View map

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From US$ 244 Book Now

Flagler Station

Key West, United States View map

Situated merely 1.2 km from Smathers Beach in Key West, the 3-bedroom Flagler Station Villa stands close to C. B. Harvey Rest Beach Park. This Key West villa also features a full kitchen and… More

From US$ 290 Book Now

6 Bedroom 6 Bath Guesthouse On Duval Street

824 Duval Street, Key West, United States View map

The 5-bedroom 6 Bedroom 6 Bath Guesthouse On Duval Street is located 15 minutes on foot from Simonton Street and within 5 minutes' walk of The Ernest Hemingway Home and Museum. The Key West villa… More

From US$ 3636 Book Now

Mermaids Retreat At Coral Hammock

41 Coral Way, Key West, United States View map

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From US$ 735 Book Now

Casita Angelita By Last Key Realty

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

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From US$ 750 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$ 1880 Book Now

Sundial On The Atlantic Ocean View

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

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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

Key West Lighthouse Suite

215 Eanes Lane, Key West, United States View map

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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$ 2125 Book Now

New Private Pool & Docking - Floralee House

Mangrove Lane 11, Key West, United States View map

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Always Your Paradise By Avantstay Shared Pool Near Zachary Beach Week Long Stays Only

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

Situated merely 1 km from Southernmost Point of the Continental US Monument in Key West, the villa stands close to Duval Street. The Key West villa comes with 2 bedrooms and an equipped kitchen with… More

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Pelican Suite - Southernmost Sanctuary

1330 Simonton Street #5, Key West, United States View map

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From US$ 630 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$ 1037 Book Now

New! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking

Duval Street 1075, Key West, United States View map

About 10 minutes' walk from the 3-bedroom New Villa Duval By Brightwild - On Duval Street Pool & Parking takes guests to the secluded pocket Dog Beach, while Southernmost Point of the Continental US… More

From US$ 458 Book Now

Nassau Suite Key West

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

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From US$ 546 Book Now