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2026-03-23
2026-03-24
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Key West holiday rentals

The Mallory Suite At Inn On Fleming Key West!

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

Along with proximity to the 19 - acre Key West Cemetery, just a 9-minute walk away, The Mallory Suite At Inn On Fleming Key West! villa offers opportunities for windsurfing, snorkelling, and fishing… More

From US$ 441 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

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$ 2298 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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Latitude Penthouse Key West

1800 Atlantic Blvd Unit B417, Key West, United States View map

The 143 m^2 Latitude Penthouse Key West Apartment is located 2.2 km from Duval Street and around a 25-minute walk from The Ernest Hemingway Home and Museum. While staying in this 2-bedroom apartment,… More

From US$ 685 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

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

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

Duval Street Suite Overlooking Duval With Parking And Pool

824 Duval Street, Key West, United States View map

Located in the Duval district with The Ernest Hemingway Home and Museum nearby, the 1-bedroom Duval Street Suite Overlooking Duval With Parking And Pool lies a mere 10 minutes' stroll from South… More

From US$ 763 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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Dream Maker On The Atlantic

1800 Atlantic Blvd #C320, Key West, United States View map

The 2-room Dream Maker On The Atlantic Apartment Key West is located within 5 minutes' walk of The Key West Nature Preserve and overlooks the sea. The waterfront Mallory Square lies just a short… More

From US$ 813 Book Now

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

Parrot Perch By Avantstay Old Town Key West W Shared Pool Month-Long Stays Only

620 Thomas St #249, Key West, United States View map

Located in the historical Downtown Key West district, merely 6 minutes' walk from Mile Marker 0 Store, the 2-bedroom Parrot Perch By Avantstay Old Town Key West W Shared Pool Month-Long Stays Only… More

From US$ 223 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

Casa Key West-Pool & Free Parking

Duval Street 1075, Key West, United States View map

The 3-bedroom Casa Key West At Duval Square Villa in Key West is a mere 1.3 km from Higgs Beach. A fully furnished kitchen with a microwave, coffee/tea making facilities and fridges is included at… More

From US$ 1090 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

The Elizabeth Suite

1501 Truman Avenue 1, Key West, United States View map

Situated just a 5-minute stroll from The Unitarian Universalist Fellowship of Key West, the 1-bedroom The Elizabeth Suite Key West villa offers easy access to numerous tourist spots in the area. More

From US$ 383 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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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

Tradewinds

529 531 Olivia St, Key West, United States View map

Nestled in the vibrant heart of Duval, Tradewinds Villa Key West offers an idyllic retreat steeped in island charm. This enchanting property welcomes guests with its captivating design and a warm… More

From US$ 1031 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

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

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

Curry House - Room 9

Fleming Street 806, Key West, United States View map

Nestled in the picturesque island of Key West, the Curry House offers a charming blend of tropical elegance and modern comfort. Just 10 km from the bustling Key West International Airport, this… More

From US$ 184 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

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

The Fleming Suite

1501 Truman Avenue 3, Key West, United States View map

Nestled a 20-minute walk from The Ernest Hemingway Home and Museum, The Fleming Suite Key West villa entices guests to explore various tourist destinations nearby. More

From US$ 357 Book Now

Toon Hall Tropical Village

1400 Alberta St #A, Key West, United States View map

Along with proximity to Higgs Beach, a mere 0.6 km away, the 2-bedroom Toon Hall Tropical Village Key West villa offers opportunities for canoeing, hiking, and cycling in the area. More

From US$ 1271 Book Now

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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Julie At Scarlet Mango Inn Key West

603 Southard St., Key West, United States View map

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Olivias Nest

828 White Street #1, Key West, United States View map

The 1-bedroom Olivias Nest Villa Key West offers quick access to such tourist spots as Wreckers Sloop Mary, situated only a 5-minute walk away. Guests can enjoy windsurfing, snorkelling, and canoeing… More

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A Palm Tree Haven

118 Admirals Lane, Key West, United States View map

A Palm Tree Haven Villa Key West offers swift access to various city sites, such as the performing arts theater "Red Barn Theatre", situated just 6 minutes' walk away. More

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Antigua Suite By Last Key Realty

329 William Street #3, Key West, United States View map

**Discover the Charm of the Antigua Suite by Last Key Realty** More

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Bayview North One

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

Set in the vibrant heart of Key West, Bayview North One Villa offers an idyllic retreat for travelers seeking comfort and convenience. Just 2 kilometers from the picturesque shores of South Beach and… More

From US$ 1220 Book Now

Golf Course Oasis With Private Yard, 5 Mi To Duval!

28 Merganser Ln, Key West, United States View map

Situated approximately 5 minutes' walk from the Key Haven, the 2-bedroom Golf Course Oasis With Private Yard, 5 Mi To Duval! Villa Key West offers easy access to numerous tourist spots in the area. More

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Honey At Scarlet Mango Inn Key West

603 Southard St., Key West, United States View map

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Sun, Sea, And Sky

202-5 Southard Street, Key West, United States View map

Located only 7 minutes' walk from the downtown commercial zoned Duval Street, Sun, Sea, And Sky Villa Key West offers opportunities for snorkelling and fishing in the area. Situated in the Downtown… More

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Away From It All

620 Thomas St., #283, Key West, United States View map

Away From It All Key West villa offers easy access to such tourist spots as the US 1 Mile Marker 0, located just a 6-minute walk away. More

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Southern Skies, Stylish Home In Old Town Key West

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

Featuring a private swimming pool for guests' enjoyment, Southern Skies, Stylish Home In Old Town Key West is nestled in the centre of Key West, 1.2 km from Nancy Forrester's Secret Garden. More

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Bahamian Reed By Avantstay Walk To Everything W Community Pool Month Long Stays Only

510 Porter Lane, Key West, United States View map

The welcoming Bahamian Reed By Avantstay Walk To Everything W Community Pool Month Long Stays Only Key West villa offers proximity to such city sites as Fort Zachary Taylor State Park, located… More

From US$ 434 Book Now

Sublime Sunsets

107 Front St #214, Key West, United States View map

Offering a location about a 20-minute walk from the Key West Shipwreck Treasure Museum, Sublime Sunsets Villa Key West gives access to various tourist spots in the area. More

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A Beachy View

620 Thomas St #186, Key West, United States View map

A Beachy View Key West villa is located approximately a 15-minute walk from the Southernmost Point of the Continental US and provides snorkelling and fishing for active guests. More

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Coral Queen Palm

83 Palm Dr, Key West, United States View map

Guests can enjoy a seaside sea view from a terrace at Coral Queen Palm Key West villa, 3 km from Old Finds Bight. Guests can enjoy windsurfing, cycling, and fishing at the 2-bedroom holiday home… More

From US$ 302 Book Now

Sapphire Sabbatical

9 Sapphire Dr., Key West, United States View map

Set around a 10-minute walk from Shark Key Island and 10 minutes by car from Boca Chica Clothing Optional Beach, the 3-bedroom Sapphire Sabbatical Villa is located in Key West. This Key West villa… More

From US$ 191 Book Now