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

Ashe Splashe

806 Ashe Street, Key West, United States View map

Nestled a 25-minute walk from Southernmost Point of the Continental US Monument, Ashe Splashe Key West villa entices guests to explore various tourist destinations nearby. More

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Key West Conch

707 Simonton Street, Key West, United States View map

**Welcome to Key West Conch Villa**, a luxurious oasis nestled in the vibrant heart of Duval Street. This exquisite retreat is designed to provide guests with an unforgettable escape, seamlessly… More

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Cozy On Caroline - Key West Seaport

616 Caroline Street #6, Key West, United States View map

Located nearly 5 minutes on foot from the Key West Historic Seaport, Cozy On Caroline - Key West Seaport Villa offers quick access to various city attractions in the vicinity. More

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Casa Suite Casa By Last Key Realty

731 Waddell Street, Key West, United States View map

### Welcome to Casa Suite Casa By Last Key Realty Nestled in the sunny paradise of Key West, Casa Suite Casa By Last Key Realty provides guests with the perfect blend of luxury and comfort. More

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The Beaming Barracuda By Last Key Realty

101 Front Street #9, Key West, United States View map

Located just a 5-minute stroll from the Audubon House and Tropical Gardens, The Beaming Barracuda By Last Key Realty Key West villa gives easy access to various tourist attractions in the area. More

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Archipelago II

241 Southard Street, Key West, United States View map

The 2-bedroom Archipelago II Key West villa accommodates up to 6 guests and offers proximity to the downtown commercial zoned Duval Street, located merely 8 minutes' walk away. More

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Paradise Palms By Avantstay

1115 Packer Street, Key West, United States View map

Paradise Palms: Beachside Getaway with Outdoor Living Key West villa enjoys a great location nearly a 5-minute walk from the Key West Firehouse Museum, and invites guests to spend time on a patio. More

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A Bird'S Eye View

102-7 Southard Street, Key West, United States View map

The 2-bedroom A Bird'S Eye View Villa Key West is nestled only an 8-minute walk from the downtown commercial zoned Duval Street and can accommodate up to 4 guests. This 1-bathroom villa features… More

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Cocomo Cottage

329 Peacon Lane, Key West, United States View map

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The Lime And The Coconut By Last Key Realty

421-423 Simonton Street, Key West, United States View map

Staying at The Lime And The Coconut By Last Key Realty Key West villa, guests can easily reach the waterfront Mallory Square, located only 1 km away. The Key West holiday home features a swimming… More

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Paradise Found

Blackbeard Lane, Key West, United States View map

The 3-bedroom Paradise Found Key West villa offers proximity to nearby tourist spots, such as the American Shoal Lighthouse, situated a mere 10 minutes' walk away. More

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Tropical Cottage Tropical Village

708 South St #C, Key West, United States View map

Tropical Cottage Tropical Village Key West is located an 8-minute walk from the Higgs Beach and offers guests to enjoy windsurfing, snorkelling, and canoeing. The 4-bedroom villa features a heated… More

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A Fish Bowl

620 Thomas Street #189, Key West, United States View map

A Fish Bowl Villa Key West is located 14 minutes' walk from the waterfront Mallory Square and provides snorkelling and fishing for active guests. More

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Twice As Nice On Duval Street

Key West, United States View map

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From US$ 1123 Book Now

Conch Cove

Simonton Lane 720, Key West, United States View map

Conch Cove Villa Key West offers proximity to such city sites as the San Carlos Institute, located only a 6-minute walk away. More

From US$ 2574 Book Now

The Enchanted Rose By Last Key Realty

1613 Rose Street, Key West, United States View map

Situated approximately 5 minutes' walk from the Higgs Beach Dog Park, the 3-bedroom The Enchanted Rose By Last Key Realty Key West villa is ideal for up to 10 guests. More

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Key Lime Cottage

1311 Catherine Street, Key West, United States View map

Offering a private swimming pool, the 2-bedroom Key Lime Cottage Key West is situated a mere 9 minutes' walk from the Fleming Street and can accommodate up to 4 guests. This villa features… More

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Casa Del Sol

1519 Johnson Street, Key West, United States View map

Offering a location nearly a 25-minute walk from the 19-acre Key West Cemetery, the 6-bedroom Casa Del Sol Villa Key West gives access to various tourist spots in the area. More

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Dance Of The Butterflies By Last Key Realty

1323 Whitehead Street, Key West, United States View map

Dance Of The Butterflies By Last Key Realty Key West villa provides easy access to various city attractions, such as the Key West Lighthouse and Keeper's Quarters Museum, situated approximately a 5… More

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Treasure Cove

Key West, United States View map

**Treasure Cove is an exquisite retreat nestled in the heart of Key West, offering a harmonious blend of luxury and coastal charm.** Just a short 10 km from Key West International Airport, this… More

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Conch House

330 Caroline Street, Key West, United States View map

The 4-bedroom Conch House Villa Key West entices guests to enjoy snorkelling and fishing and offers proximity to the downtown commercial zoned Duval Street, located approximately a 10-minute stroll… More

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The Conch-Out Cottage

821 Terry Ln, Key West, United States View map

The 2-bedroom The Conch-Out Cottage Key West is located nearly 5 minutes' walk from The Ernest Hemingway Home and Museum and features a private swimming pool as well as a terrace for guests' pleasure… More

From US$ 245 Book Now

Oyster'S Pearl

620 Thomas Street #169, Key West, United States View map

The 1-bedroom Oyster'S Pearl Villa Key West offers quick access to such city attractions as Mile Marker 0 Store, located merely a 6-minute walk away. More

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Calusa Suite By Last Key Realty

329 William Street #6, Key West, United States View map

Located a mere 5 minutes' walk from the Key West Historic Seaport, Calusa Suite By Last Key Realty Key West villa features a heated swimming pool and can accommodate up to 2 guests. More

From US$ 528 Book Now

Sweet'S Spot

109 Front Street #309, Key West, United States View map

Offering a swimming pool, the 3-bedroom Sweet'S Spot Villa Key West is situated about a 5-minute walk from the Front Street and can accommodate up to 6 guests. This holiday home features… More

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Harbor Walk Hideaways

Greene Street, Key West, United States View map

The 4-bedroom Harbor Walk Hideaways Villa Key West hosts up to 14 guests and provides proximity to the Key West Historic Seaport, situated nearly 5 minutes' walk away. More

From US$ 2171 Book Now

Paradise Found

711 William Street, Key West, United States View map

At the 2-bedroom Paradise Found Key West villa, guests can enjoy windsurfing, snorkelling, and canoeing as well as a location just 5 minutes' walk from the Ernest Hemingway Home and Museum. More

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Afternoon Delight

401 Emma Street Apt F, Key West, United States View map

Located just a 9-minute walk from the downtown commercial zoned Duval Street, the 2-bedroom Afternoon Delight Villa Key West features a swimming pool and can accommodate up to 4 guests. This 2… More

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About Time

620 Thomas Street Apt# 193, Key West, United States View map

Offering a swimming pool, the 2-bedroom About Time Villa Key West is situated only 0.6 km from the Ernest Hemingway Home and Museum and can accommodate up to 4 guests. More

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Captains Daughter

719 Eisenhower Dr. #3, #3, Key West, United States View map

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Charming 'Boho Breeze' Retreat W/ Pool Access

171 Golf Club Dr, Key West, United States View map

Nestled about 7 km from the Ernest Hemingway Home and Museum, the 2-bedroom Charming 'Boho Breeze' Retreat W/ Pool Access Key West villa entices guests to explore various tourist destinations nearby. More

From US$ 145 Book Now

Villa Olivietta By Last Key Realty

803 Olivia Street, Key West, United States View map

Located approximately 5 minutes' walk from Saint Mary Star of the Sea Basilica, the 4-bedroom Villa Olivietta By Last Key Realty Key West offers quick access to various city attractions in the… More

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Bahamian Bamboo By Last Key Realty

510 Emma Street, Key West, United States View map

Staying at Bahamian Bamboo By Last Key Realty Key West villa, guests can easily reach the Fort Zachary Taylor, located just 1.2 km away. More

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New Hidden Oasis- Waterfall Pool Close To Beach

Seidenberg Avenue 2026, Key West, United States View map

New Hidden Oasis - Waterfall Pool Close To Beach Villa is situated in Key West, approximately 15 minutes' walk from C. B. Harvey Rest Beach Park and at a 2.3 km distance from the historical Key West… More

From US$ 735 Book Now

My Southernmost Kentucky Home

920 Terry Lane, Key West, United States View map

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Island Time On The Green

19 Kingfisher Way, Key West, United States View map

Island Time On The Green Key West villa, located within 200 metres of FYT Fitness Center, can host up to 4 guests. More

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Salt Pond Hideaway - Monthly Rental

3675 Seaside Drive #133, Key West, United States View map

Nestled a 25-minute walk from the Smathers Beach, Salt Pond Hideaway - Monthly Rental Key West villa entices guests to explore various tourist destinations nearby. More

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Lighthouse Suites Collection

419 Truman Avenue, Key West, United States View map

Located in Duval with one of Key West's top culinary experiences, 6 minutes' walk from the even Southernmost Point, Lighthouse Suites Collection Key West villa offers sea views. The 8-bedroom holiday… More

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Mansion The Watson House

525 Simonton Street, Key West, United States View map

Mansion The Watson House Villa Key West is located 13 minutes' walk from the downtown commercial zoned Duval Street and provides windsurfing, snorkelling, and canoeing for active guests. More

From US$ 3105 Book Now

Conch Republic Cooler

840 Olivia Street, Key West, United States View map

Situated 750 metres from the Ernest Hemingway Home and Museum, the 3-bedroom Conch Republic Cooler Villa Key West is ideal for up to 6 guests. More

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Hidden Oasis Colony

714 Olivia St, Key West, United States View map

The 1-bedroom Hidden Oasis Colony Villa Key West hosts up to 4 guests and provides proximity to the Ernest Hemingway Home and Museum, situated nearly a 5-minute walk away. This holiday home features… More

From US$ 406 Book Now

Trumans Trove By Last Key Realty

110 Admirals Lane, Key West, United States View map

Trumans Trove By Last Key Realty Key West villa, located merely 5 minutes' walk from the Key West Shipwreck Treasure Museum, can host up to 6 guests. More

From US$ 1216 Book Now

Sombrero Reef Lighthouse Suite

419 Truman Avenue, Key West, United States View map

Set in the vibrant heart of Duval, the Sombrero Reef Lighthouse Suite embodies a unique blend of elegance and casual charm. Guests visiting this exquisite retreat will discover an inviting ambiance… More

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The Lighthouse Penthouse Suite

419 Truman Avenue, Key West, United States View map

The Lighthouse Penthouse Suite Key West villa, situated right in the centre of Key West, and within 500 metres of the even Southernmost Point, can accommodate up to 8 guests. More

From US$ 1303 Book Now

Tropical Treat

3708 Duck Ave, Key West, United States View map

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Island Hideaway

1216 Margaret St., Key West, United States View map

Situated merely 0.7 km from the Key West Butterfly and Nature Conservatory, Island Hideaway Villa Key West offers a private swimming pool with a patio. Featuring access to a patio, this Key West… More

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Colorful Cocktail

210-3 Southard Street, Key West, United States View map

The 2-bedroom Colorful Cocktail Villa Key West offers swift access to various city sites, such as Jackson Square, situated approximately a 5-minute walk away. Guests can enjoy snorkelling and fishing… More

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Conch Easy Livin'

617 Simonton Street, Key West, United States View map

Situated merely an 8-minute stroll from the Key West First Legal Rum Distillery, the 2-bedroom Conch Easy Livin' Villa Key West ensures a great leisure experience by offering windsurfing, snorkelling… More

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Tropical Breezes

620 Thomas Street #294, Key West, United States View map

Tropical Breezes Villa Key West is located a 16-minute walk from the Fort Zachary Taylor and provides snorkelling and fishing for active guests. The 2-bedroom holiday home features a swimming pool… More

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The Ospreys Nest By Last Key Realty

3625 Seaside Drive #411, Key West, United States View map

Located about a 25-minute walk from the Key West Golf Club, The Ospreys Nest By Last Key Realty Key West villa has a swimming pool and is ideal for up to 6 guests. The holiday home offers guests a… More

From US$ 719 Book Now