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2026-11-12
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Key West holiday rentals

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 Mellow Macaw By Last Key Realty

1025D Whitehead Street, Key West, United States View map

The 2-bedroom The Mellow Macaw 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

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Key West Large Waterfront Condo With Boat Slip, Sleeps 8

915 Eisenhower Drive, Key West, United States View map

During the stay at Key West Large Waterfront Condo With Boat Slip, Sleeps 8 villa, guests can indulge in cycling and fishing or visit the vintage parish "Saint Paul's Episcopal Church of Key West"… More

From US$ 383 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

New Grenada Suite - Parking Pool & Pets 209

Seaside Drive 3625, Key West, United States View map

During the stay at New Grenada Suite - Parking Pool & Pets 209 Key West villa, guests can indulge in cycling and fishing or visit the bustling plaza "Mallory Square", located a 15-minute drive away. More

From US$ 513 Book Now

Kw72A Old Town Garden Villas - Abaco Suite

921 Center St., Key West, United States View map

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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

Casa De Cuba

518 Virginia Street, Key West, United States View map

Situated about 5 minutes' walk from the Ernest Hemingway Home and Museum, the 3-bedroom Casa De Cuba Villa Key West entices guests with windsurfing, snorkelling, and canoeing in the area. More

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Parking Pool & Dock - Shellstone House

16 Andrea Lane, Key West, United States View map

Featuring a private swimming pool, the 8-bedroom Parking Pool & Dock - Shellstone House Villa Key West is suitable for up to 18 people and is located around 25 minutes' walk from the Key West Golf… More

From US$ 4425 Book Now

Quiet Pour @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Quiet Pour @ Speakeasy Inn Key West!, located merely an 8-minute walk from the historic Saint Mary Star of the Sea Church, features Wi-Fi in the rooms. The guest house also includes a car park. More

From US$ 493 Book Now

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

Somewhere On The Beach

1800 Atlantic Blvd, Unit C238, Key West, United States View map

The 2-bedroom Somewhere On The Beach Key West villa accommodates up to 6 guests and offers proximity to the Higgs Beach Dog Park, located just 0.8 km away. The Key West holiday home features… More

From US$ 972 Book Now

Poolside Breeze Retreat

1800 Atlantic Blvd Unit A103, Key West, United States View map

Situated merely 1.6 km from the Higgs Beach, the 2-bedroom Poolside Breeze Retreat Villa Key West boasts a sauna, as well as a spa salon for guests to relax in. Located about a 10-minute ride from… More

From US$ 1026 Book Now

Sailboat Stay And Resort Amenities

7005 Shrimp Road, Key West, United States View map

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Blue Haven Unit B416

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

Located just 600 metres from the Higgs Beach Dog Park, the 2-bedroom Blue Haven Unit B416 Villa Key West provides an outdoor swimming pool as well as windsurfing, snorkelling, and canoeing to… More

From US$ 1571 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

Andros - Spacious 2X2 Waterfront Condo

Eisenhower Drive 915, Key West, United States View map

Offering a patio overlooking the sea, the 2-bedroom Andros - Spacious 2X2 Waterfront Condo Key West villa is located only 5 minutes' walk from the Wreckers Sloop Mary. Providing guests with high… More

From US$ 876 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

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

Fleming-O

726 Fleming St, Key West, United States View map

Located merely 650 metres from the vintage parish "Saint Paul's Episcopal Church of Key West", the 2-bedroom Fleming-O Villa Key West offers opportunities for windsurfing, snorkelling, and canoeing… More

From US$ 1018 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$ 615 Book Now

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$ 835 Book Now

6 Bedroom 6 Bath Guesthouse On Duval Street

824 Duval Street, Key West, United States View map

Located merely 500 metres from Southernmost Point of the Continental US Monument, the 6-bedroom 6 Bedroom 6 Bath Guesthouse On Duval Street Key West villa offers opportunities for cycling and fishing… More

From US$ 4873 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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Island Pearls

527 Fleming Street, Key West, United States View map

The 2-bedroom Island Pearls Villa Key West entices guests to enjoy windsurfing, snorkelling, and fishing and offers proximity to the Vandenberg Wreck, located just 5 minutes' stroll away. The Key… More

From US$ 1551 Book Now

Duval Street Retreat

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

The 2-bedroom Duval Street Retreat Villa Key West offers swift access to various city sites, such as the historic Key West Lighthouse, situated about a 5-minute walk away. More

From US$ 515 Book Now

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

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

Sweet Home Angelita By Last Key Realty

421 Angela Street, Key West, United States View map

Sweet Home Angelita By Last Key Realty Key West, located a 6-minute walk from the historic Key West Lighthouse, can host up to 13 guests. More

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Atlantic Parrot

1800 Atlantic Boulevard #435C, Key West, United States View map

Located within 600 metres of the White Street Pier, Atlantic Parrot Villa Key West is suitable for 5 guests and provides an outdoor swimming pool to relax in. More

From US$ 554 Book Now

Kwss202 Sunrise Suites - Big Kahuna Suite 202

3625 Seaside Dr #202, Key West, United States View map

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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

Bootlegger Bay @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Situated nearly 5 minutes' walk from the comfortable Bootlegger Bay @ Speakeasy Inn Key West!, guests can reach the Key West Butterfly and Nature Conservatory in no time. This Key West guest house… More

From US$ 570 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 | Vibrant Retreat, Hot Tubs, Steps From Duval

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

Staying at the 1-bedroom Heron Suite | Vibrant Retreat, Hot Tubs, Steps From Duval Key West villa, guests can visit the downtown commercial zoned Duval Street, which is only 1 km away. Offering a… 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

Belle Of The Beach By Last Key Realty

1815 Atlantic Boulevard, Key West, United States View map

Situated only 8 minutes' walk from the Higgs Beach Dog Park, Belle Of The Beach By Last Key Realty Key West villa is ideal for up to 16 guests. More

From US$ 2288 Book Now

Duval Street Suite Overlooking Duval With Parking And Pool

824 Duval Street, Key West, United States View map

The 1-bedroom Duval Street Suite Overlooking Duval With Parking And Pool Key West villa is nestled about 5 minutes' walk from the downtown commercial zoned Duval Street and can accommodate up to 4… More

From US$ 763 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

Petes Cottages

505-507 Louisa Street, Key West, United States View map

During the stay at Petes Cottages Key West, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Harry S. Truman Little White House, located a 15-minute walk away. The 4-bedroom… More

From US$ 937 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$ 941 Book Now