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2026-02-27
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Vacation Rentals in Key West

Lighthouse Suites Collection

419 Truman Avenue, Key West, United States View map

Featuring a swimming pool for guests' enjoyment, Lighthouse Suites Collection Key West villa is nestled in the very heart of Key West, just 1.8 km from the Bayview Park. More

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Vista Fresco

1800 Atlantic Blvd #139C, Key West, United States View map

The spacious Vista Fresco Apartment Key West is located in Key West, a 25-minute walk from the downtown commercial zoned Duval Street, and pampers guests with a hot tub. Offering access to a heated… More

From US$ 511 Book Now

Poolside Paradise Tropical Village

708 South St. #E, Key West, United States View map

The 31 m² Poolside Paradise Tropical Village Key West apartment is located 2.1 km from Curry Mansion and around a 25-minute walk from US 1 Mile Marker 0. Offering access to a heated pool, this… More

From US$ 376 Book Now

The Duke And The Duchess By Last Key Realty

512 Catherine Street #1 & #2, Key West, United States View map

**Experience the Elegance at The Duke And The Duchess By Last Key Realty** More

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Key West Conch

707 Simonton Street, Key West, United States View map

**Welcome to Key West Conch Villa**, a luxurious oasis nestled in the vibrant heart of Duval Street. This exquisite retreat is designed to provide guests with an unforgettable escape, seamlessly… More

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Seagull Suite - Southernmost Sanctuary

Simonton Street, Key West, United States View map

Situated just a 5-minute walk from Southernmost Point, Seagull Suite - Southernmost Sanctuary Key West villa entices guests to explore various tourist attractions in the area. More

From US$ 367 Book Now

Villa Olivietta By Last Key Realty

803 Olivia Street, Key West, United States View map

The 4-bedroom Villa Olivietta By Last Key Realty Key West offers proximity to such city sites as Key West Cemetery, located just 5 minutes' walk away. More

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Angelas Eclectic Gallery By Last Key Realty

1017 Angela Street, Key West, United States View map

Angelas Eclectic Gallery By Last Key Realty Key West villa provides an opportunity to stay a 5-minute walk from The Unitarian Universalist Fellowship of Key West and offers a Jacuzzi, perfect for… More

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Meyers Island Oasis On Atlantic

1800 Atlantic Blvd #B316, Key West, United States View map

Situated only 1.1 km from Higgs Beach in Key West, the 2-bedroom Meyers Island Oasis On Atlantic Villa stands close to Fort Zachary Taylor Historic State Park. An equipped kitchenette area with a… More

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Coastal Comfort

2851 Key Cove Dr., Key West, United States View map

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From US$ 1745 Book Now

Matisse Studio The Galleria

1016 Howe Street, Key West, United States View map

The 13 m² Matisse Studio The Galleria Key West is located only 1.3 km from Ripley's Believe It or Not Museum and offers Wi-Fi for either business or leisure. The apartment lies in the Downtown Key… More

From US$ 438 Book Now

Southern Comfort

2855 Key Cove Dr., Key West, United States View map

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Sunshine State At Custom House Inn

124 Duval Street #5, Key West, United States View map

The 1-room Sunshine State At Custom House Inn Key West is located only 600 metres from US 1 Mile Marker 0 and 1.3 km from Key West Lighthouse. More

From US$ 416 Book Now

Eisenhower Retreat

719 Eisenhower Dr. #1, #1, Key West, United States View map

Eisenhower Retreat Villa is ideally situated just 5 km from Key West International Airport and 1.5 km from the picturesque Rest Beach, allowing for easy exploration of the area's natural beauty. More

From US$ 1498 Book Now

The Grand Cayman | Beautifully Remodeled Key West Condo!

3625 Seaside Drive #309, Key West, United States View map

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From US$ 636 Book Now

Windsor Townhomes 4

917 Windsor Lane, Key West, United States View map

Located only 1.4 km from Mallory Square, Windsor Townhomes 4 Key West is 16 minutes' walk from a top family-friendly place like Key West Aquarium. More

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Serenity On Southard By Last Key Realty

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

Situated about 2 km from Truman Little White House, the 48 m^2 Serenity On Southard By Last Key Realty Apartment Key West provides guests with Wi-Fi for either business or leisure. Offering access to… More

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New The Altair House - Fire Pit Pool & Hot Tub

Mangrove Lane 13, Key West, United States View map

This 7-bedroom villa is located within 7 km of Key West Firehouse Museum and 10 km from Key West International airport. The property has 7 bedrooms and 7 bathrooms for the guests' convenience. More

From US$ 1549 Book Now

Catherine House

518 Catherine Street, Key West, United States View map

Catherine House Key West villa is located a 7-minute walk from Key West Butterfly and Nature Conservatory and offers guests to enjoy windsurfing, snorkelling, and canoeing. More

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Dos Casitas By Last Key Realty

512 Catherine #2 & 516 Catherine Street, Key West, United States View map

Dos Casitas By Last Key Realty Key West villa provides an opportunity to stay just near Key West Lighthouse and Keeper's Quarters Museum and offers a Jacuzzi, perfect for decompressing. More

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Conch Cove

720 Rr Simonton Lane, Key West, United States View map

Featuring a heated swimming pool for guests' relaxation, the 3-bedroom Conch Cove Villa Key West is located approximately a 25-minute stroll from Key West Wildlife Center. Offering a prime location… More

From US$ 1612 Book Now

Booty Caye

73 Golf Club Drive, Key West, United States View map

The 1-bedroom Booty Caye Villa Key West is located about a 5-minute stroll from Key Haven and features a swimming pool and a terrace for a relaxing stay. Featuring complimentary private parking, the… More

From US$ 179 Book Now

Chagall'S Corner

1016 Howe St #14, Key West, United States View map

**Chagall's Corner is Key West**, where tropical charm meets modern luxury. Nestled just a short drive away from Key West International Airport, this haven invites you to unwind amidst vibrant… More

From US$ 451 Book Now

Rigby House - Brand New With Private Pool

Simonton Street 218, Key West, United States View map

**Welcome to Rigby House - Brand New With Private Pool Villa Key West**, your ultimate tropical escape nestled in the vibrant heart of Duval Street. This stunning retreat is freshly established and… More

From US$ 3023 Book Now

Coconut Palm Suite At Travelers Palm Inn Key West

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

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Southernmost Bliss By Last Key Realty

518 Frances Street, Key West, United States View map

Situated merely a 12-minute walk from The Oldest House, the 5-bedroom Southernmost Bliss By Last Key Realty Key West villa provides access to numerous tourist attractions in the area. More

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Sea Breeze Villa

1219 Grinnell Street Unit B, Key West, United States View map

Located approximately 10 minutes' drive from Key West Shipwreck Treasure Museum, the 3-bedroom Sea Breeze Villa Key West provides access to various tourist attractions in the vicinity. More

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Southernmost View -Pool & Water Views

Whitehead Street 1315, Key West, United States View map

Located in the Duval district with South Beach nearby, the 4-bedroom Southernmost View Villa lies 1.2 km from the vintage parish "Saint Paul's Episcopal Church of Key West". Offering free parking and… More

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Thalias Retreat

1075 Duval St #R23, Key West, United States View map

Curry Mansion is 16 minutes' stroll from Thalias Retreat Apartment Key West, while The Ernest Hemingway Home and Museum is situated nearby. Active guests might as well try windsurfing, snorkelling… More

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The Contented Crane By Last Key Realty

909 Windsor Lane, Key West, United States View map

The 4-bedroom The Contented Crane By Last Key Realty Key West villa offers proximity to such city sites as Southernmost Point of the Continental US, located just a 6-minute walk away. More

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Escape On Fleming

1110 Fleming Street #1, Key West, United States View map

**Escape On Fleming: A Tranquil Retreat in the Heart of Key West** Situated in a prime location, Escape On Fleming is an excellent base for exploring the enchanting charms of Key West. More

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Three Duval Street Suites W Parking And Pool

824 Duval Street, Key West, United States View map

Situated only 250 metres from The Ernest Hemingway Home and Museum, the 3-bedroom Three Duval Street Suites W Parking And Pool Key West villa ensures a great leisure experience by offering cycling… More

From US$ 2562 Book Now

Chicken Water Cabana At Custom House Inn

124 Duval Street #1 & #2, Key West, United States View map

To enjoy your vacation in Key West, stay at the 2-room Chicken Water Cabana At Custom House Inn Key West, which is 2.7 km from Higgs Beach and nearly 20 minutes' walk from the even Southernmost Point. More

From US$ 786 Book Now

Tobago House

911 Center Street, Key West, United States View map

Southernmost Point of the Continental US is 6 minutes' walk from Tobago House Villa Key West, offering a hot tub for guests' relaxation. This 3-bedroom villa features opportunities for windsurfing… More

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Casa De Cuba

518 Virginia Street, Key West, United States View map

Situated merely 6 minutes' walk from the even Southernmost Point, the 2-bedroom Casa De Cuba Villa Key West entices guests with windsurfing, snorkelling, and canoeing in the area. More

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Land Of Love By Avantstay Pets Allowed Shared Pool Great Location Month Long Stays Only

611 Grinnell St #7, Key West, United States View map

This 2-bedroom and 1-bathroom villa is located in Key West, just 0.9 km from The Oldest House Historical Place Museum as well as within 15 minutes' walk of Simonton Street. The accommodation features… More

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Sea Captains Haven By Last Key Realty

413 Porter Court, Key West, United States View map

The 3-bedroom Sea Captains Haven By Last Key Realty Key West villa is located around a 25-minute walk from US 1 Mile Marker 0 and provides a Jacuzzi. More

From US$ 742 Book Now

Neptunes Penthouse By Last Key Realty

1800 Atlantic Blvd #C436, Key West, United States View map

Located just 5 minutes' walk from Higgs Beach Dog Park and The Key West Nature Preserve, the 2-room Neptunes Penthouse By Last Key Realty Apartment Key West features views of the sea. More

From US$ 608 Book Now

Poolside Hide-Away Palm Gardens

905 White St #2, Key West, United States View map

Welcome to Poolside Hide-Away Palm Gardens, a serene retreat nestled just 10 kilometers from the vibrant heart of Key West. This idyllic escape offers a perfect blend of tranquility and accessibility… More

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Casa De Cubana

512 Amelia Street, Key West, United States View map

Staying at the 2-bedroom Casa De Cubana Villa Key West, guests can visit the Fort Zachary Taylor, which is nearly a 20-minute walk away. More

From US$ 2269 Book Now

Starfish

803 Catherine Street, Key West, United States View map

The 2-bedroom Starfish Villa Key West entices guests to enjoy windsurfing, snorkelling, and canoeing and offers proximity to Higgs Beach, located only 8 minutes' stroll away. The Key West holiday… More

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The Whitehead Room At Inn On Fleming Key West!

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

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Ricky'S Retreat - Truman @ Duval Unit A

Truman Avenue, Key West, United States View map

To enjoy your vacation in Key West, stay at the 1-room Ricky'S Retreat - Truman @ Duval Unit A Apartment Key West, which is just 1.8 km from Fleming Street and 12 minutes' walk from Nancy Forrester's… More

From US$ 532 Book Now

Holly'S Hideaway - Truman @ Duval Unit D

Truman Avenue, Key West, United States View map

The 1-room Holly'S Hideaway - Truman @ Duval Unit D Key West apartment lies in the Downtown Key West district and offers swift access to the downtown commercial zoned Duval Street, which is just 0.6… More

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Conch Casa Grande By Last Key Realty

58 Front Street, Key West, United States View map

**Conch Casa is where Sunshine Meets Sophistication** Nestled in the vibrant heart of Key West, Conch Casa Grande By Last Key Realty provides an exquisite blend of luxury and comfort just 10… More

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Paradise Palms By Avantstay Great Location W Outdoor Dining Bbq Close To Higgs Beach Month Long Stays

1115 Packer Street, Key West, United States View map

Located in the Downtown Key West district with Key West Firehouse Museum nearby, this 2-bedroom and 2-bathroom villa lies 0.9 km from the historic fort "West Martello Tower". An equipped kitchenette… More

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Jasmine Jule By Last Key Realty

108 Admirals Lane, Key West, United States View map

Situated merely a 9-minute walk from the vintage parish "Saint Paul's Episcopal Church of Key West", the 3-bedroom Jasmine Jule By Last Key Realty Key West villa provides access to numerous tourist… More

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Sunset South

801 Eisenhower Dr. #1, 1, Key West, United States View map

**Experience the Allure of Sunset South Villa Key West** For those looking to explore beyond the comfort of the villa, popular attractions like Higgs Beach are just a short distance away. More

From US$ 474 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

The Southernmost Comfort House

Key West, United States View map

The 5-bedroom Southernmost Comfort House Villa is located near the downtown commercial zoned Duval Street, merely 1.4 km from South Beach. The property also has a fully equipped kitchen with a fridge… More

From US$ 3303 Book Now