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2026-06-28
2026-06-29
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Key West holiday rentals

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

Tropical Dreaming By Avantstay

607 Amelia St, Key West, United States View map

Nestled only a 12-minute walk from the San Carlos Institute, the welcoming Tropical Dreaming By Avantstay Key West villa features a swimming pool along with a patio to help guests unwind. Boasting… More

From US$ 2051 Book Now

The Gato Room At Inn On Fleming Key West!

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

Along with proximity to the very unusual Key West Cemetery, merely 0.7 km away, 1-bedroom The Gato Room At Inn On Fleming Key West! villa offers opportunities for windsurfing, snorkelling, and… More

From US$ 205 Book Now

Petes West Cottage

505 Louisa Street, Key West, United States View map

Featuring a heated swimming pool, the 2-bedroom Petes West Cottage Key West is located only a 6-minute walk from the even Southernmost Point and is suitable for up to 4 guests. This holiday home… More

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Casa De Cubana

512 Amelia Street, Key West, United States View map

The 2-bedroom Casa De Cubana Villa Key West accommodates up to 4 guests and offers proximity to the Key West Butterfly and Nature Conservatory, located only a 7-minute walk away. More

From US$ 2269 Book Now

Amelia Home By Avantstay

605 Amelia Street, Key West, United States View map

Located around 10 minutes' walk from the downtown commercial zoned Duval Street, the 0-bedroom Amelia Home By Avantstay Key West boasts a swimming pool with a patio for additional relaxation. More

From US$ 903 Book Now

Key West Lighthouse Suite

215 Eanes Lane, Key West, United States View map

**The Key West Lighthouse Suite is a serene oasis tucked away in the vibrant heart of Duval.** This beautifully designed retreat captures the spirit of the islands and offers an immersive experience,… More

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American Shoal Light Suite

419 Truman Avenue, Key West, United States View map

Located in Duval with one of Key West's top culinary experiences, a mere 5 minutes' walk from the historical Key West Lighthouse, American Shoal Light Suite Key West villa offers sea views. More

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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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Jasmine Place

919 Whitehead Street, Key West, United States View map

During the stay at Jasmine Place Key West villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the 19 - acre Key West Cemetery, located a 13-minute walk away. More

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New Butterfly Nest - Newly Decorated

Seaside Drive 3625, Key West, United States View map

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From US$ 373 Book Now

Egret Suite - Southernmost Sanctuary

1330 Simonton Street #1, Key West, United States View map

The 1-bedroom Egret Suite - Southernmost Sanctuary Key West villa hosts up to 4 guests and provides proximity to the Key West Butterfly and Nature Conservatory, situated approximately a 5-minute… More

From US$ 354 Book Now

Old Town Main House Guest House Close To Duval

614 Virginia Street, Key West, United States View map

Situated 1.6 km from the Harry S. Truman Little White House, Old Town Main House Guest House Close To Duval Key West villa invites guests to relax at a patio. More

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Renovated Corner Unit

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

Situated approximately a 5-minute walk from the Alan S Maltz Gallery, the 2-bedroom Renovated Corner Unit Villa Key West entices guests to explore various tourist attractions in the area. More

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New The Altair House - Fire Pit Pool & Hot Tub

Mangrove Lane 13, Key West, United States View map

Featuring a private pool, the 6-bedroom New The Altair House - Fire Pit Pool & Hot Tub Villa Key West is suitable for up to 14 people and is located about a 15-minute walk from the Key West Tropical… More

From US$ 4188 Book Now

Ibis By Avantstay

714 Olivia #11, Key West, United States View map

Staying at the 0-bedroom Ibis By Avantstay Key West villa, guests can visit Mile Marker 0 Store, which is only 1 km away. More

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Catherine House

518 Catherine Street, Key West, United States View map

During the stay at Catherine House Key West villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Key West Aquarium, located a 16-minute walk away. Offering a private… More

From US$ 759 Book Now

Alligator Reef Light Suite

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

The 2-bedroom Alligator Reef Light Suite Key West villa is located approximately a 15-minute walk from the shopping mall "Clinton Square Market" and invites guests to enjoy a sun terrace. More

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Anchor Drop Key West

1800 Atlantic Blvd, Unit A307, Key West, United States View map

During the stay at Anchor Drop Key West Villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Higgs Beach, located a 19-minute walk away. The 2-bedroom holiday home offers… More

From US$ 708 Book Now

Smooth Sailing By Last Key Realty

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

Offering a Jacuzzi, Smooth Sailing By Last Key Realty Key West villa is situated merely a 7-minute walk from the fully accredited Mel Fisher Maritime Heritage Museum and can accommodate 6 people. More

From US$ 1034 Book Now

Pilars Secret

716 Duval St Rear, Key West, United States View map

During the stay at Pilars Secret Villa Key West, guests can indulge in windsurfing, snorkelling, and canoeing or visit the natural history museum "Florida Keys Eco-Discovery Center", located a 13… More

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New! Cristbal Suite - Balcony, Parking & Pool!

Seaside Drive 3625, Key West, United States View map

Situated in Key West, about a 10-minute ride from Key West Butterfly and Nature Conservatory, the 2-bedroom New! Cristbal Suite - Balcony, Parking & Pool! provides accommodation with free parking and… More

From US$ 339 Book Now

Carey'S Corner

1016 Howe St #10, Key West, United States View map

The 1-bedroom Carey'S Corner Villa Key West, located just a 6-minute walk from Southernmost Point of the Continental US Monument, can host up to 2 guests. This holiday home features opportunities for… More

From US$ 358 Book Now

Casita Angelita By Last Key Realty

421 Angela Street Unit A, Key West, United States View map

Casita Angelita By Last Key Realty Key West villa accommodates up to 6 guests and offers proximity to the downtown commercial zoned Duval Street, located merely a 7-minute walk away. More

From US$ 750 Book Now

Aquaria House -Pool & Boat Dock

Shoreline Road 14, Key West, United States View map

Situated just 1.8 km from Safe Harbor, the 4-bedroom Aquaria House -Pool & Boat Dock Villa Key West features a patio with views of the sea. Offering a private swimming pool, this property invites… More

From US$ 3784 Book Now

Barbuda Suite By Last Key Realty

329 William Street #4, Key West, United States View map

Offering a heated swimming pool, the 1-bedroom Barbuda Suite By Last Key Realty Key West villa is located 750 metres from the 19-acre Key West Cemetery and is ideal for up to 4 guests. More

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Ann Street Cottage

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

Offering a swimming pool, the 1-bedroom Ann Street Cottage Key West is located just 650 m from the vintage parish "Saint Paul's Episcopal Church of Key West" and is ideal for up to 2 guests. This… More

From US$ 711 Book Now

Palms Resort Beach Key West - Guest House

15760 Old State Road 4A, 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

Casa Serendipity By Last Key Realty Key West accommodates up to 6 guests and offers proximity to the Fleming Street, located 9 minutes' walk away. More

From US$ 1544 Book Now

The Southern Cross Tropical Village

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

The 2-bedroom The Southern Cross Tropical Village Key West villa hosts up to 6 guests and provides proximity to the Higgs Beach, situated only 650 metres away. This Key West holiday home features… More

From US$ 872 Book Now

Villa Angelita By Last Key Realty

421 Angela Street Unit B, Key West, United States View map

The 3-bedroom Villa Angelita By Last Key Realty Key West is nestled a mere 5 minutes' walk from the Ernest Hemingway Home and Museum and can accommodate up to 7 guests. More

From US$ 957 Book Now

Cohiba At Azul Mansion Key West

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

The 1-bedroom Cohiba At Azul Mansion Key West Villa is located nearly 25 minutes' walk from the Smathers Beach and welcomes its guests to enjoy windsurfing, snorkelling, and fishing. More

From US$ 262 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$ 718 Book Now

Puerta Coralina By Last Key Realty

901 Grinnell Street, Key West, United States View map

Located 750 metres from the Fleming Street, Puerta Coralina By Last Key Realty Key West villa boasts a private pool and can accommodate up to 6. More

From US$ 1500 Book Now

Pelican Suite - Southernmost Sanctuary

1330 Simonton Street #5, Key West, United States View map

The 1-bedroom Pelican Suite - Southernmost Sanctuary Key West villa accommodates up to 4 guests and offers proximity to the even Southernmost Point, located just a 5-minute walk away. More

From US$ 620 Book Now

The Fleming Suite

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

The Fleming Suite Key West villa is nestled a 9-minute walk from the Fleming Street and can accommodate up to 4 guests. More

From US$ 357 Book Now

The Elizabeth Suite

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

Offering access to entertainment venues such as the White Street Pier, situated only 1.5 km away, the 1-bedroom The Elizabeth Suite Key West villa can host up to 4 guests. More

From US$ 383 Book Now

Parrot Perch By Avantstay

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

Located just 6 minutes' walk from the downtown commercial zoned Duval Street, the 2-bedroom Parrot Perch By Avantstay Key West villa offers a swimming pool for guests to relax by. More

From US$ 223 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

Always Your Paradise By Avantstay

620 Thomas Street #164, Key West, United States View map

Situated only 450 metres from the downtown commercial zoned Duval Street, the 1-bedroom Always Your Paradise By Avantstay Key West villa has a swimming pool with a patio. Featuring access to a patio,… 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-Pool & Free Parking Villa accommodates up to 8 guests and offers proximity to Southernmost Point of the Continental US Monument, located merely a 5-minute walk away. More

From US$ 1170 Book Now

Paradise Place By Avantstay

905 White St #1, Key West, United States View map

Featuring a swimming pool for guests' relaxation, the 1-bedroom Paradise Place By Avantstay Key West villa is located nearly 20 minutes' walk from the Higgs Beach. This welcoming holiday home in… More

From US$ 789 Book Now

Brand New Catchlight House With Private Pool

Mangrove Lane 7, Key West, United States View map

Situated around a 25-minute walk from the Cozumel Park, the 6-bedroom Brand New Catchlight House With Private Pool Villa Key West invites guests to relax at a patio. Guests can enjoy fishing at this… More

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Toon Hall Tropical Village

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

Staying at the 3-bedroom Toon Hall Tropical Village Key West villa, guests can easily reach the arts theater "Red Barn Theatre", located approximately a 25-minute walk away. Guests can enjoy canoeing… More

From US$ 1271 Book Now

The North Star

Key West, United States View map

The 2-bedroom North Star Villa offers accommodation in Key West, within 2.6 km of Boca Chica Clothing Optional Beach and within 2.6 km of Boca Chica Beach. 2 bedrooms and 2 bathrooms can be found at… More

From US$ 159 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

Colony Conch Casa

714 Olivia Street #10, Key West, United States View map

The 3-bedroom Colony Conch Casa Villa Key West offers swift access to various city sites, such as Key West Lighthouse and Keeper's Quarters Museum, situated nearly 5 minutes' walk away. Guests can… More

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La Grande Reunion By Last Key Realty

618 Whitehead Street, Key West, United States View map

Situated only a 6-minute stroll from Southernmost Point of the Continental US, the 6-bedroom La Grande Reunion By Last Key Realty Key West villa offers quick access to numerous city landmarks nearby. More

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Dolce Paradiso

804 Catherine Street, Key West, United States View map

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Spirit Of Key West By Last Key Realty

1106 Petronia Street, Key West, United States View map

Spirit Of Key West By Last Key Realty villa is nestled a 9-minute walk from the Fleming Street and can accommodate up to 8 guests. More

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