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2026-02-26
2026-02-27
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Hotels in Key West near Jackson Square

The Conch House Heritage Inn

625 Truman Ave, Key West, United States View map

Located within 20 minutes' walk of Ripley's Believe It or Not Museum, the 3-star The Conch House Heritage Inn Key West features Wi-Fi in public areas and private parking nearby. The bed & breakfast… More

From US$ 417 Book Now

New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool

Duval Street 1075, Key West, United States View map

Situated in the Duval district, the 3-bedroom New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool right next to Key West Butterfly and Nature Conservatory and nearly 20 minutes' walk from the… More

From US$ 343 Book Now

Duval Sea Turtle By Avantstay Great Location Close To Shops Shared Pool

1075-29 Duval Square, Key West, United States View map

This 2-bathroom villa is at 300 metres from The Ernest Hemingway Home and Museum and walking distance from the even Southernmost Point. The Key West villa also features a kitchen and amenities such… More

From US$ 551 Book Now

Duval Breeze By Avantstay Great Location Close To Beach Nightlife Shared Pool Week Long Stays

1075 Duval St #30, Key West, United States View map

South Beach is a mere 500 metres from the 2-bedroom and 2-bathroom villa, set right in the centre of Key West. A full kitchen with coffee/tea making equipment, fridges and an oven is included at this… More

From US$ 1572 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

Sea Esta Suite - Duval Square

1075 Duval Street R11, Key West, United States View map

The 115 m² Sea Esta Suite - Duval Square Key West is situated merely a 6-minute walk from Southernmost Point of the Continental US Monument and 5 km from Key West International airport. More

From US$ 748 Book Now

Ecco Domani By Avantstay Gorgeous Home W Pool Balcony In Great Location Month Long Stays Only

1011-2 Simonton St, Key West, United States View map

The villa is set in Key West, 15 minutes' walk from the shopping mall "Clinton Square Market" and about 10 minutes' drive from Key West Garden Club. The Key West villa features 2 bathrooms and boasts… More

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Ole Olivia

716 Olivia Street, Key West, United States View map

Nestled just 10 km from the vibrant pulse of Key West, Ole Olivia Villa Key West is an idyllic retreat that masterfully blends luxury and comfort. This enchanting escape captivates guests with its… More

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Absolutely Paradise

1011 Simonton Street #3, Key West, United States View map

During the stay at Absolutely Paradise Key West villa, guests can indulge in canoeing, cycling, and fishing or visit the Fort Zachary Taylor, located 20 minutes' walk away. More

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Almost Southernmost

1100 Whitehead Street, Key West, United States View map

During the stay at Almost Southernmost Key West villa, guests can indulge in windsurfing, snorkelling, and fisheries or visit Ripley's Believe It or Not Museum, located a 17-minute walk away. More

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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

Pier House Resort & Spa

One Duval Street, Key West, United States View map

**Discover Tranquility at Pier House Resort & Spa Key West** More

From US$ 835 Book Now

Colony Poolside

714 Olivia Street, Key West, United States View map

**Colony Poolside Villa: A Coastal Sanctuary** Conveniently located, Colony Poolside serves as a gateway to the enchanting sites of Key West. More

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Breezy Retreat

606 Truman Avenue, Key West, United States View map

The 2-bedroom Breezy Retreat Villa Key West is located just 1.5 km from Key West First Legal Rum Distillery and provides a swimming pool, ensuring a relaxing stay. More

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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

Ocean Key Resort & Spa, A Noble House Resort

Zero Duval, Key West, United States View map

Positioned around a 25-minute walk from the Fort Zachary Taylor, the 4-star Ocean Key Resort & Spa, A Noble House Resort Key West presents a banquet hall ideal for different occasions. Featuring a… More

From US$ 369 Book Now

Parrotville

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

The spacious Parrotville Key West apartment is nestled in the Downtown Key West district, a 5-minute walk from the seafood restaurant Blackfin Bistro. The opportunity for windsurfing, snorkelling… More

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Windward Breeze

606 Truman Ave #7, Key West, United States View map

Located right in the centre of Key West, the 117 m² Windward Breeze Apartment Key West offers fast access to Fort Zachary Taylor about 20 minutes' walk away. Guests can make the most of their stay at… More

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Villa Cubana By Last Key Realty

606 Truman Avenue #5, Key West, United States View map

The 2-bedroom Villa Cubana By Last Key Realty Key West is located only a 12-minute walk from Southernmost Point of the Continental US, giving access to various tourist spots nearby. More

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Nyah - Adult Exclusive

420 Margaret Street, Key West, United States View map

Welcome to the exceptional experience awaiting at the Nyah - Adult Exclusive located near the culturally vibrant Duval Street on an island paradise filled with historical landmarks and exciting… More

From US$ 79 Book Now

Cuban Paradise Cuban Club

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

The spacious Cuban Paradise Cuban Club Key West apartment is nestled in the Downtown Key West district, a 5-minute walk from the seafood restaurant Nine One Five. The opportunity for windsurfing… More

From US$ 666 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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A Cuban Club Suite

1102 Duval St, Key West, United States View map

**Indulge in Sophistication at A Cuban Club Suite** Conveniently located, A Cuban Club Suite serves as an ideal base to explore the rich history, stunning beaches, and vibrant nightlife of Key West. More

From US$ 678 Book Now

Tumis Time Out By Avantstay Heart Of Old Town W Shared Pool Month Long Stays Only

606 Truman Ave #4, Key West, United States View map

Discover the charm of Tumis Time Out By Avantstay Heart Of Old Town, an exquisite retreat nestled in the vibrant heart of Duval. This enchanting accommodation beckons with its stylish interiors… More

From US$ 251 Book Now

Margaret Street Retreat

628 Margaret St, Key West, United States View map

The 2-bedroom Margaret Street Retreat Villa is located within 15 minutes' walk of South Beach and offers quick access to the downtown commercial zoned Duval Street. A fully equipped kitchen with… More

From US$ 615 Book Now

Margarets Magic Compound By Last Key Realty

515-517 Margaret Street, Key West, United States View map

Nestled in the vibrant heart of Key West, Margarets Magic Compound By Last Key Realty offers an enchanting retreat just 10 km from the bustling Key West International Airport. More

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Duval Delight

1108 Duval St, Key West, United States View map

Situated about a 20-minute walk from Key West Historic Seaport, the 1-bedroom Duval Delight Villa Key West provides access to numerous tourist attractions in the area. More

From US$ 1156 Book Now

The Marker Waterfront Resort

200 William Street, Key West, United States View map

The Marker Key West Harbor Resort is a tranquil hideaway connecting guests to the unique, eclectic charm of the Florida Keys filtered through a luxury resort experience. Tucked away in Old Town Key… More

From US$ 467 Book Now

The Marker Key West Harbor Resort

200 William Street, Key West, United States View map

The Marker Key West Harbor Resort, located in the Downtown Key West district, merely a 6-minute walk from the Papa's Pilar Rum Distillery, offers cars for rent. Boasting a location just around the… More

From US$ 928 Book Now

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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Casa Margarita

314 Margaret Street, Key West, United States View map

Casa Margarita Villa Key West is located just an 8-minute walk from Key West First Legal Rum Distillery and offers a Jacuzzi, ensuring guests a relaxing stay. This 3-bedroom villa features… More

From US$ 1354 Book Now

Chelsea House Hotel - Key West

709 Truman Ave, Key West, United States View map

The 3-star Chelsea House Hotel - Key West is situated in the historical district of Key West, 1.7 km from Key West Aquarium, which is highly recommended for a family visit. Located within close… More

From US$ 168 Book Now

Douglas House

419 Amelia Street, Key West, United States View map

**Douglas House is your idyllic retreat tucked away in the heart of Key West's Historic Old Town.** This charming inn, housed in a beautiful Victorian building, boasts a fantastic location just… More

From US$ 205 Book Now

Amelia House

Key West Florida 33040, Key West, United States View map

The 3-bedroom Amelia House Villa is located near the downtown commercial zoned Duval Street, at a 1.2 km distance from the fully accredited Mel Fisher Maritime Heritage Museum. The property also has… More

From US$ 270 Book Now

Hyatt Centric Key West Resort & Spa

601 Front Street, Key West, United States View map

**Experience the Essence of Key West at Hyatt Centric Key West Resort & Spa** More

From US$ 283 Book Now

Casa Grande By Avantstay Dt Key West Near South Beach W Pool

515 Amelia Street, Key West, United States View map

Key West Aquarium is 1.4 km from Casa Grande By Avantstay Dt Key West Near South Beach W Pool, while Higgs Beach is 15 minutes on foot from here. The villa comprises 5 bedrooms and a fully equipped… More

From US$ 1074 Book Now

Cabana Retreat

605 Virginia St Unit 16, Key West, United States View map

The 3-bedroom Cabana Retreat Villa is located in Key West, within 15 minutes' walk of Key West Aquarium as well as within 400 metres of The Ernest Hemingway Home and Museum. The property features a… More

From US$ 350 Book Now

Winslow'S Bungalows - Key West Historic Inns

725 Truman Avenue, Key West, United States View map

Comprising 85 rooms, the 4-star Winslow'S Bungalows - Key West Historic Inns is near an entertainment district, only 1.9 km from the Higgs Beach Dog Park. Situated within reach of the Ernest… More

From US$ 471 Book Now

La Casa De Luces

422 Amelia St Apt. 1, Key West, United States View map

The spacious 2-bedroom La Casa De Luces Apartment Key West lies in the Downtown Key West district of Key West and offers swift access to The Ernest Hemingway Home and Museum, which is nearly a 5… More

From US$ 654 Book Now

Duval Corner

Amelia Street 422, Key West, United States View map

The 1-bedroom Duval Corner Villa is situated in the centre of Key West only 1.5 km from Mallory Square. Located in the Duval district, this property provides guests with a fully equipped kitchen with… More

From US$ 676 Book Now

Casita Olivietta By Last Key Realty

805 Olivia Street, Key West, United States View map

Situated just a 13-minute walk from Key West Firehouse Museum, the 5-bedroom Casita Olivietta By Last Key Realty Key West villa provides access to numerous tourist attractions in the area. More

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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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Casa Oliviana By Last Key Realty

803 Olivia Street, Key West, United States View map

Staying at the 4-bedroom Casa Oliviana By Last Key Realty Key West, guests can visit Key West Cemetery, which is merely a 13-minute walk away. More

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Speakeasy Inn & Rum Bar

1117 Duval Street, Key West, United States View map

Set in Duval with unique, island inspired Small Plates with bold Caribbean spices and fresh local seafood, 1.5 km from the bustling plaza "Mallory Square", the quaint Speakeasy Inn & Rum Bar Key West… More

From US$ 179 Book Now

Speakeasy Inn (Adults Only)

1117 Duval Street, Key West, United States View map

Located 10 minutes by car from Smathers Beach, the 3-star Speakeasy Inn Key West offers spacious rooms 19 minutes' walk from the top family-friendly place like Key West Aquarium. This budget inn… More

From US$ 253 Book Now

The Speakeasy Inn And Rum Bar

1117 Duval Street, Key West, United States View map

The Speakeasy Inn And Rum Bar Key West offers a terrace, located merely 1.8 km from White Street Pier. Featuring 7 rooms with views of the city, the hotel is a few minutes' drive from Florida Keys… More

From US$ 189 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

Key To Paradise

903 Windsor Ln, Key West, United States View map

**Welcome to Key To Paradise Key West**, a serene escape that perfectly combines luxury with the vibrant charm of Florida's southernmost point. Situated just 5 km from Key West International Airport,… More

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Galleon Resort And Marina

617 Front Street, Key West, United States View map

The 3-star Galleon Resort And Marina Key West is located 10 km from Key West International airport and offers a swimming pool as well as a fitness club. Nestled in the Downtown Key West district of… More

From US$ 285 Book Now

Duval Hideaway

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

**Discover the Duval Hideaway Villa in the Heart of Key West** Conveniently located, the villa is within walking distance to the bustling nightlife and unique shops that Duval Street is renowned for. More

From US$ 1284 Book Now