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2026-06-27
2026-06-28
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Key West holiday rentals

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

Flor De Cana At Azul Mansion Key West

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

Featuring a swimming pool, the 1-bedroom Flor De Cana At Azul Mansion Key West villa is located approximately 5 minutes' walk from Saint Mary Star of the Sea Basilica and is suitable for up to 2… More

From US$ 200 Book Now

The Simonton Room At Inn On Fleming Key West

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

1-bedroom The Simonton Room At Inn On Fleming Key West villa is located only 1.4 km from the Ripley's Believe It or Not and allows guests to enjoy windsurfing, snorkelling, and fishing. The… More

From US$ 259 Book Now

Havana Vieja At Azul Mansion Key West

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

Up to 2 guests can stay at the 1-bedroom Havana Vieja At Azul Mansion Key West villa and enjoy the historic Saint Mary Star of the Sea Church, located approximately a 5-minute walk away. The property… More

From US$ 522 Book Now

Upper Bayview South

801 Eisenhower Dr. #10, 10, Key West, United States View map

**Discover Coastal Bliss at Upper Bayview South** With complimentary WiFi and private parking available onsite, exploring the captivating attractions around the area becomes effortless. More

From US$ 1763 Book Now

Leaward Isle Island Retreat

1800 Atlantic Blvd, Unit A105, Key West, United States View map

Situated around 25 minutes' walk from the even Southernmost Point, the 2-bedroom Leaward Isle Island Retreat Villa Key West offers a swimming pool, a spa salon for guests to relax in. This property… More

From US$ 529 Book Now

Harbor House Penthouse- B

423 Front Street, Key West, United States View map

Located about a 5-minute walk from the bustling plaza "Mallory Square", Harbor House Penthouse- B Villa Key West offers fishing to diversify guests' leisure. More

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Kwss403 Sunrise Suites Tierra Bomba Suite #403

Key West, United States View map

Offering a hot tub for a relaxing experience, Sunrise Suites Tierra Bomba Suite #403 Key West villa is located 25 minutes on foot from the Fort East Martello Museum. More

From US$ 159 Book Now

Two Duval Street Suites W Parking And Pool

Duval Street 824, Key West, United States View map

Situated in the vibrant heart of Duval Street, Two Duval offers an exceptional escape steeped in the spirit of the Florida Keys. This premier destination is designed to provide guests with an… More

From US$ 807 Book Now

Key West Large Waterfront Condo With Boat Slip, Sleeps 8

915 Eisenhower Drive, Key West, United States View map

**Abaco - Large Waterfront 2X2 End Unit With Boat Slip Villa** offers a charming blend of luxury and convenience, ideally situated just 5 kilometers from the vibrant Key West International Airport. More

From US$ 383 Book Now

Atlantic Paradise By Avantstay

1800 Atlantic 108A, Key West, United States View map

The welcoming Atlantic Paradise By Avantstay Key West villa offers swift access to various city sites, such as The Key West Nature Preserve, situated approximately 5 minutes' walk away. Staying at… More

From US$ 1367 Book Now

Flaglers Oasis By Avantstay

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

Guests can enjoy a seaside sea view from a terrace at the welcoming Flaglers Oasis By Avantstay Key West villa, 3 km from the Ripley's Believe It or Not. More

From US$ 181 Book Now

Sombrero Reef Light Suite

419 Truman Avenue #2F, Key West, United States View map

The 1-bedroom Sombrero Reef Light Suite Key West villa, located only a 6-minute walk from the even Southernmost Point, can host up to 4 guests. More

From US$ 429 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

Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom

915 Eisenhower Drive, Key West, United States View map

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

From US$ 776 Book Now

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

Ocean Hideaway On The Atlantic

1800 Atlantic Blvd Suite A206, Key West, United States View map

### Ocean Hideaway On The Atlantic - Your Coastal Retreat Nestled just minutes away from the stunning shores of Smathers Beach, Ocean Hideaway On The Atlantic is a serene and luxurious getaway for… More

From US$ 621 Book Now

Dream Maker On The Atlantic

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

Situated within 25 minutes' walk of the historic Key West Lighthouse, the 2-bedroom Dream Maker On The Atlantic Villa Key West boasts a Jacuzzi, as well as a spa salon for guests to relax in. Located… More

From US$ 813 Book Now

The Truman Room At Inn On Fleming Key West!

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

1-bedroom The Truman Room At Inn On Fleming Key West! villa hosts up to 2 guests and provides proximity to the 19-acre Key West Cemetery, situated only a 9-minute walk away. This Key West holiday… More

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Tortugas Harbor Lighthouse Suite

419 Truman Avenue, Key West, United States View map

**Welcome to Tortugas Harbor Lighthouse Suite**, an exquisite retreat nestled in the vibrant heart of Duval Street. This charming suite captures the whimsical spirit of Key West, where chic decor… More

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Two Duval Street Condos W Parking And Pool

Duval Street 824, Key West, United States View map

Nestled around a 10-minute walk from the even Southernmost Point, the 2-bedroom Two Duval Street Condos W Parking And Pool Key West villa entices guests to explore various tourist destinations nearby… More

From US$ 834 Book Now

Kwss310 Sunrise Suites Panama Suite #310

Key West, United States View map

Sunrise Suites Panama Suite #310 Key West villa is located 4.8 km from the even Southernmost Point and provides a Jacuzzi. More

From US$ 122 Book Now

Pescado Penthouse

1201 Duval Street, Key West, United States View map

The 3-bedroom Pescado Penthouse Villa Key West, located just a 6-minute walk from the historic Key West Lighthouse, can host up to 9 guests. More

From US$ 1172 Book Now

Bahama Gardens - Cigar House

712 Thomas Street, Key West, United States View map

Located in the Downtown Key West district of Key West and a mere 1.1 km from the Minor Saint Mary Star of the Sea Basilica, the 2-bedroom Bahama Gardens - Cigar House Villa Key West provides guests… More

From US$ 813 Book Now

Duke Of Catherine By Last Key Realty

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

During the stay at Duke Of Catherine By Last Key Realty Key West villa, guests can indulge in a Jacuzzi or visit the USCGC Ingham Maritime Museum, located a 14-minute walk away. More

From US$ 1203 Book Now

The Bahama House - Key West

508 Amelia Street, Key West, United States View map

Inviting guests to enjoy a terrace with a swimming pool, 3-bedroom The Bahama House - Key West Villa is located a mere 6 minutes' walk from the even Southernmost Point. More

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Breezy Retreat

606 Truman Avenue, Key West, United States View map

Featuring a swimming pool, the 2-bedroom Breezy Retreat Villa Key West is located about a 5-minute walk from the historical Key West Lighthouse and is suitable for up to 4 guests. The villa features… 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 windsurfing, snorkelling, and canoeing or visit the Fort Zachary Taylor, located 20 minutes' walk away. Situated in the… More

From US$ 1973 Book Now

Duval Sea Turtle By Avantstay

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

Located only 6 minutes' walk from the Key West Aquarium, the 1-bedroom Duval Sea Turtle By Avantstay Key West villa boasts a swimming pool, a hot tub for a relaxing experience. Offering Wi-Fi, this… More

From US$ 551 Book Now

Octopus Garden By Last Key Realty

55 Coral Way, Key West, United States View map

Octopus Garden By Last Key Realty Key West villa is located 18 minutes' walk from Safe Harbor and provides a heated swimming pool, ensuring a relaxing stay. More

From US$ 969 Book Now

Number Eleven At Scarlet Mango Inn Key West

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

The 1-bedroom Number Eleven At Scarlet Mango Inn Key West villa provides easy access to various city attractions, such as Nancy Forrester's Secret Garden, situated about a 5-minute walk away. Guests… More

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Namaste

219 Ann Street Rear, Key West, United States View map

Situated about a 25-minute walk from the White Street Pier, the 1-bedroom Namaste Villa Key West invites guests to relax at a patio. This 2-bathroom villa is located in Duval with unique, island… More

From US$ 828 Book Now

Prime Downtown Location - Truman Little Cozy Cottage

910 Simonton Street 3, Key West, United States View map

Up to 2 guests can stay at Prime Downtown Location - Truman Little Cozy Cottage Key West and enjoy Saint Mary Star of the Sea Basilica, located 6 minutes' walk away. More

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Mastway House -Pool & Dock!

Key Haven Terrace 4, Key West, United States View map

The 4-bedroom Mastway House -Pool & Dock! Villa Key West entices active guests with access to a fitness room and is located 3.8 km from Sigsbee Park Island. Featuring a patio, this holiday home is… More

From US$ 3115 Book Now

The Cornish Suite At Inn On Fleming Key West!

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

Situated only 5 minutes on foot from the Key West Historic Seaport, 2-bedroom The Cornish Suite At Inn On Fleming Key West! villa ensures a great leisure experience by offering windsurfing… More

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Atlantic Paradise Found

1800 Atlantic Blvd C232, Key West, United States View map

Welcome to Atlantic Paradise, a luxurious enclave nestled in the heart of Key West, where comfort meets coastal charm. Just a short 5 km from Key West International Airport, this exquisite retreat… More

From US$ 674 Book Now

Ambrosia At Azul Mansion Key West

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

Situated just 7 minutes' walk from the 19 - acre Key West Cemetery, the 1-bedroom Ambrosia At Azul Mansion Key West Villa entices guests with windsurfing, snorkelling, and fishing in the area. More

From US$ 448 Book Now

Conch Adventure By Avantstay

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

Situated merely a 6-minute walk from Mile Marker 0 Store, the 0-bedroom Conch Adventure By Avantstay Key West villa offers easy access to numerous tourist spots in the area. Located 2.1 km from The… More

From US$ 369 Book Now

Mermaids Retreat At Coral Hammock

41 Coral Way, Key West, United States View map

The 3-bedroom Mermaids Retreat At Coral Hammock Key West villa is located nearly 15 minutes' walk from the Key West Tropical Forest and Botanical Garden and welcomes its guests to enjoy snorkelling… More

From US$ 590 Book Now

Royal Palm Suite At Travelers Palm Inn Key West

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

Offering a swimming pool, the 1-bedroom Royal Palm Suite At Travelers Palm Inn Key West villa is located merely 9 minutes' walk from the Key West Butterfly and Nature Conservatory and is ideal for up… More

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Coastal Comfort

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

Coastal Comfort Key West villa offers proximity to such city sites as the Kelly's Aerial Arts & Fitness, located just 6 minutes' walk away. Staying at the property, which is around 3 km from the… More

From US$ 1745 Book Now

Key West Charming By Avantstay

210-7 Southard St, Key West, United States View map

The 0-bedroom Key West Charming: Poolside Retreat Near Fort Zachary Taylor villa offers proximity to such city sites as the San Carlos Institute, located merely a 7-minute walk away. More

From US$ 396 Book Now

Heron Suite - Southernmost Sanctuary

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

Offering access to entertainment venues such as the Papa's Pilar Rum Distillery, situated just 1.4 km away, the 1-bedroom Heron Suite - Southernmost Sanctuary Key West villa can host up to 4 guests. More

From US$ 219 Book Now

New The Windrose House - Pool & Pets

Shoreline Road 3, Key West, United States View map

The 6-bedroom New The Windrose House - Pool & Pets Villa Key West is located around 20 minutes' walk from Safe Harbor and provides a private pool, ensuring a relaxing stay. The holiday home hosts up… More

From US$ 2971 Book Now

Conch In The Treetops By Last Key Realty

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

Featuring a Jacuzzi, Conch In The Treetops By Last Key Realty Key West villa is located around 5 minutes' walk from the Higgs Beach Dog Park and can host up to 6 guests. More

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Kingfish Keep

1201 Duval Street 3, Key West, United States View map

Situated just a 5-minute walk from Southernmost Point of the Continental US Monument, Kingfish Keep Villa Key West is ideal for up to 4 guests. More

From US$ 421 Book Now

Villa The Watson House

525 Simonton Street, Key West, United States View map

The 4-bedroom Villa The Watson House Key West accommodates up to 8 guests and offers proximity to the Vandenberg Wreck, located merely a 5-minute walk away. The property features opportunities for… More

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Atlantic Sunrise Penthouse

1800 Atlantic Blvd, Unit C425, Key West, United States View map

The 3-bedroom Atlantic Sunrise Penthouse Villa Key West hosts up to 8 guests and provides proximity to the Higgs Beach Dog Park, situated only a 9-minute walk away. Featuring a Jacuzzi and a sauna… More

From US$ 1238 Book Now

Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock

915 Eisenhower Drive, Key West, United States View map

The 2-bedroom Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock Key West villa, located approximately 5 minutes' walk from the Wreckers Sloop Mary, can host up to 8 guests. This accommodation… More

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Tom'S Oceanfront Penthouse

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

Located approximately a 25-minute walk from the downtown commercial zoned Duval Street, the 3-bedroom Tom'S Oceanfront Penthouse Villa Key West has an outdoor swimming pool and is ideal for up to 8… More

From US$ 1057 Book Now