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2026-04-18
2026-04-19
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Private Villas in Key West

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 is located approximately 5 minutes' walk from the Wreckers Sloop Mary and features an outdoor swimming pool and… More

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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

Heron Suite - Southernmost Sanctuary

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

The 1-bedroom Heron Suite - Southernmost Sanctuary Key West villa offers proximity to such city sites as the even Southernmost Point, located only 350 metres away. More

From US$ 219 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

The Southern Cross Tropical Village

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

Along with proximity to Higgs Beach, only 650 metres away, the 2-bedroom The Southern Cross Tropical Village Key West villa offers opportunities for windsurfing, snorkelling, and canoeing in the area. More

From US$ 872 Book Now

Renovated Corner Unit

620 Thomas Unit 150, Key West, United States View map

Located about 20 minutes' walk from Higgs Beach, Renovated Corner Unit Villa Key West provides access to various tourist attractions in the vicinity. More

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

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

Nestled 17 minutes' walk from the Southernmost Point, the welcoming Southard Getaway By Avantstay W Covered Patio Great Location Shared Pool Month Long Stays Key West villa entices guests to explore… More

From US$ 612 Book Now

Number Eleven At Scarlet Mango Inn Key West

603 Southard St., 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$ 2304 Book Now

Sweet Caroline

Caroline Street 537, Key West, United States View map

Sweet Caroline Villa offers accommodation just 400 metres from Simonton Beach, while Key West Aquarium is about a 5-minute stroll away. This villa is equipped with 2 bedrooms plus a kitchen with a… More

From US$ 932 Book Now

Blue Haven Unit B416

1800 Atlantic Blvd, Unit B416, Key West, United States View map

Set at 600 metres from Higgs Beach Dog Park and a mere 0.9 km from C. B. Harvey Rest Beach Park, the 1-bedroom Atlantic Blues Island Escape Villa is located in Key West. A full kitchen with a… More

From US$ 1571 Book Now

Beachfront 2Bdr Condo Pool Hot Tub W Ocean Views Papaya Place By Avantstay

110A 1800 Atlantic Blvd, Key West, United States View map

The 0-bedroom Beachfront 2Bdr Condo Pool Hot Tub W Ocean Views Papaya Place By Avantstay Key West villa is situated around 400 metres from The Key West Nature Preserve and offers guests to relax with… More

From US$ 556 Book Now

Namaste

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

The 2-bedroom Namaste Villa Key West is located about a 25-minute walk from Southernmost Point and provides windsurfing, snorkelling, and canoeing for active guests. More

From US$ 828 Book Now

Duke Of Catherine By Last Key Realty

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

Offering guests to unwind in a Jacuzzi, Duke Of Catherine By Last Key Realty Key West villa is located 13 minutes' walk from the secluded pocket Dog Beach. More

From US$ 1203 Book Now

Blue Moonshine On The Atlantic

1800 Atlantic Blvd, Unit A413, Key West, United States View map

The 2-bedroom Blue Moonshine On The Atlantic Villa is situated just 200 metres from The Key West Nature Preserve and a mere 0.9 km from C. B. Harvey Rest Beach Park. This property features an… More

From US$ 685 Book Now

Tom'S Oceanfront Penthouse

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

The 2-bedroom Tom'S Oceanfront Penthouse Villa Key West is located only 5 minutes' walk from The Key West Nature Preserve and offers guests to relish a patio as well as a swimming pool. This holiday… More

From US$ 1057 Book Now

The Gato Room At Inn On Fleming Key West!

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

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From US$ 424 Book Now

Conch Adventure By Avantstay Great Location W Outdoor Dining Pool Access Month-Long Stays

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

Offering pool views, the 0-bedroom Conch Adventure By Avantstay Great Location W Outdoor Dining Pool Access Month-Long Stays Key West villa is situated a mere 10 minutes' walk from the Ernest… More

From US$ 369 Book Now

Royal Palm Suite At Travelers Palm Inn Key West

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

Situated in the Downtown Key West district of Key West, merely 14 minutes' walk from Nancy Forrester's Secret Garden, Royal Palm Suite At Travelers Palm Inn Key West villa comes with a swimming pool… More

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Jasmine Place

919 Whitehead Street, Key West, United States View map

Situated a 16-minute walk from Key West Aquarium, Jasmine Place Key West villa entices guests to explore various tourist attractions in the area. More

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Smooth Sailing By Last Key Realty

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

Smooth Sailing By Last Key Realty Key West villa is merely a 5-minute walk from The Key West Nature Preserve, offering guests to unwind at a Jacuzzi. More

From US$ 1398 Book Now

Ann Street Cottage

219 Ann Street #2, Key West, United States View map

The 2-bedroom Ann Street Cottage Key West is located only a 6-minute walk from The Studios of Key West Cultural Association and offers guests to relish a patio as well as a heated swimming pool. At… More

From US$ 711 Book Now

Two Duval Street Condos W Parking And Pool

Duval Street 824, Key West, United States View map

Boasting the location 1.2 km from Simonton Street, the 2-bedroom Two Duval Street Condos W Parking And Pool is also at 150 metres of The Ernest Hemingway Home and Museum. Located in the Duval… More

From US$ 834 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

Havana Vieja At Azul Mansion Key West

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

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From US$ 522 Book Now

Flor De Cana At Azul Mansion Key West

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

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The Truman Room At Inn On Fleming Key West!

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

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The Cornish Suite At Inn On Fleming Key West!

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

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Casa Serendipity By Last Key Realty

1101 Angela Street, Key West, United States View map

Located 25 minutes' walk from Key West Butterfly and Nature Conservatory, Casa Serendipity By Last Key Realty Key West gives access to various tourist sites in the vicinity. More

From US$ 1544 Book Now

Alligator Reef Light Suite

419 Truman Avenue #1 F, Key West, United States View map

The 1-bedroom Alligator Reef Light Suite Key West villa provides easy access to various city attractions, such as the downtown commercial zoned Duval Street, situated nearly 5 minutes' walk away. More

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Villa The Watson House

525 Simonton Street, Key West, United States View map

Along with proximity to Key West First Legal Rum Distillery, just 650 metres away, the 4-bedroom Villa The Watson House Key West offers opportunities for windsurfing, snorkelling, and canoeing in the… More

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Aria At Azul Mansion Key West

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

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From US$ 889 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 offers swift access to various city sites, such as Key West Lighthouse and Keeper's Quarters Museum, situated nearly 5 minutes' walk away. More

From US$ 429 Book Now

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

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

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$ 318 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

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$ 1691 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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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

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

Sandpiper On The Ocean

1800 Atlantic Blvd C420, Key West, United States View map

To enjoy your vacation in Key West, stay at the 2-room Sandpiper On The Ocean Apartment Key West, which is within a 3-km distance of Fort Zachary Taylor and around a 25-minute stroll from Key West… More

From US$ 695 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

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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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$ 483 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