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2026-11-14
2026-11-15
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Hotels with indoor pool in Key West

Captiva At Azul Mansion Key West

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

The comfortable Captiva At Azul Mansion Key West hotel is located in Key West, approximately a 25-minute walk from the bustling plaza "Mallory Square", and offers a heated pool. The guest house also… More

From US$ 304 Book Now

Corona At Azul Mansion Key West

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

The comfortable Corona At Azul Mansion Key West hotel, located nearly 25 minutes' walk from the Smathers Beach, offers an outdoor swimming pool, Wi-Fi in the rooms. This Key West guest house lies in… More

From US$ 404 Book Now

Kw335Wk Dancing Palms

606 Truman Ave 9, Key West, United States View map

Located only 6 minutes' walk from the Ernest Hemingway Home and Museum, Dancing Palms Villa Key West offers opportunities for cycling and fishing in the area. More

From US$ 533 Book Now

Turtle Nest Condo - Pool - 2Nd Floor

907 White St 5, Key West, United States View map

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The Mallory Suite At Inn On Fleming Key West!

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

Situated around 5 minutes' walk from the Key West Historic Seaport, 1-bedroom The Mallory Suite At Inn On Fleming Key West! villa entices guests with windsurfing, snorkelling, and fishing in the area. More

From US$ 441 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$ 2344 Book Now

Runaway Bills

812 Johnson Lane, Key West, United States View map

Up to 6 guests can stay at the 3-bedroom Runaway Bills Key West villa and enjoy the Key West Lighthouse and Keeper's Quarters Museum, located a mere 5 minutes' walk away. More

From US$ 297 Book Now

Kw37 Oceana Suite

Key West, United States View map

Located 19 minutes' walk from the Harry S. Truman Little White House, Oceana Suite Key West is a mere 1.5 km from a top family-friendly place like the Key West Aquarium. Situated a short way from the… More

From US$ 286 Book Now

Bahama Gardens - Main House

704 Thomas Street, Key West, United States View map

Welcome to Bahama Gardens - Main House For leisure and convenience, Bahama Gardens - Main House offers a plethora of services, including guided tours and transportation arrangements to nearby… More

From US$ 2304 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

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

Botanical Island Delight

1800 Atlantic Blvd, #C120, Key West, United States View map

Featuring an outdoor swimming pool, the 2-bedroom Botanical Island Delight Villa Key West is located only 5 minutes' walk from The Key West Nature Preserve and is suitable for up to 4 guests. More

From US$ 455 Book Now

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

Curry House - Room 2

Fleming Street 806, Key West, United States View map

The 19 m² Curry House - Room 2 Key West lies in the Downtown Key West district of Key West and offers swift access to the US 1 Mile Marker 0, which is merely 5 minutes' walk away. Situated 350 metres… More

From US$ 342 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

The Margaret Suite

1501 Truman Avenue, Key West, United States View map

The Margaret Suite Key West offers easy access to such tourist sites as the C. B. Harvey Rest Beach Park, located nearly 5 minutes' walk away. Situated 0.7 km from the Key West Firehouse Museum, this… More

From US$ 292 Book Now

Lavender Jungle By Avantstay

104 Southard Street #1, Key West, United States View map

Lavender Jungle By Avantstay Key West villa offers proximity to nearby tourist spots, such as the Harry S. Truman Little White House, situated 8 minutes' walk away. Located just 1.7 km from the Key… More

From US$ 425 Book Now

Seas The Breeze, Poolside Condo Near The Beach

3625 Seaside Drive 25105, Key West, United States View map

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From US$ 1246 Book Now

Tropical Heron Hideaway With Hot Tub, Pool

907 White St 4, Key West, United States View map

Located nearly a 25-minute walk from the Key West First Legal Rum Distillery, the 58 m² Heron Hideaway Key West apartment is 2.3 km from a top family-friendly place like the Key West Aquarium. More

From US$ 608 Book Now

Key West'S Best

1800 Atlantic Blvd, Unit C326, Key West, United States View map

Located just a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Key West'S Best villa invites guests to enjoy a Jacuzzi and a sauna. The holiday home features opportunities for snorkelling… More

From US$ 644 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

Sailboat Stay And Resort Amenities

7005 Shrimp Road, Key West, United States View map

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New The Cottage At James House

512 Caroline Street, Key West, United States View map

Situated in the vibrant heart of Duval, New The Cottage At James House offers an inviting retreat, merging chic decor with a warm ambiance. This exquisite accommodation showcases stylish leather… More

From US$ 519 Book Now

Waterfront Boat Stay & Resort Amenities

7025 Shrimp Rd, Key West, United States View map

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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

Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-Friendly

915 Eisenhower Drive, Key West, United States View map

Offering a patio overlooking the sea, the 2-bedroom Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-Friendly Villa is located about a 5-minute walk from the Bayview Park. Providing guests… More

From US$ 1038 Book Now

Curacao - Large 2X2 Waterfront Condo Great View Pool & Dock

915 Eisenhower Drive, Key West, United States View map

Nestled in the heart of a vibrant coastal paradise, the Curacao - Large 2X2 Waterfront Condo boasts breathtaking views that immediately capture your attention. Just 5 km from Key West International… More

From US$ 949 Book Now

Duval Street Suite W Kitchen And Shared Heated Pool

824 Duval Street, Key West, United States View map

Located 15 minutes' walk from the Harry S. Truman Little White House, Duval Street Suite W Kitchen And Shared Heated Pool Key West overlooks the garden. Offering access to a swimming pool, this… More

From US$ 501 Book Now

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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A Siesta Bay By Avantstay

620 Thomas St #263, Key West, United States View map

The 1-bedroom A Siesta Bay By Avantstay Key West villa is located just 6 minutes on foot from the downtown commercial zoned Duval Street and features a swimming pool as well as a patio for guests'… More

From US$ 351 Book Now

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

Keys Please!

Louisa Street 514, Key West, United States View map

The 3-bedroom Keys Please! Villa Key West is located about a 20-minute walk from the White Street Pier and provides cycling and fishing for active guests. Situated in Duval with unique, island… More

From US$ 1910 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 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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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

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

First Breath By Avantstay

1106 Eaton Street, Key West, United States View map

Situated a 6-minute walk from the Papa's Pilar Rum Distillery, the welcoming First Breath By Avantstay Key West villa entices guests with views of the pool. More

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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

High Tide In Key West

1800 Atlantic Blvd #B117, Key West, United States View map

Situated merely a 9-minute walk from the Higgs Beach Dog Park, High Tide In Key West Villa offers a sauna and can accommodate up to 6 guests. The 2-bedroom holiday home features opportunities for… More

From US$ 522 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

Mar Y Sol Ocean Front

1800 Atlantic Blvd #101, Key West, United States View map

Mar Y Sol Ocean Front Villa Key West is located 25 minutes' walk from the downtown commercial zoned Duval Street and invites guests to join windsurfing, snorkelling, and fishing. Featuring a sauna… More

From US$ 871 Book Now

Duval Street Suite W Parking And Pool

824 Duval Street, Key West, United States View map

Located just 300 m from the downtown commercial zoned Duval Street and the Key West Lighthouse and Keeper's Quarters Museum, the 37 m² Duval Street Suite W Parking And Pool Key West features views of… More

From US$ 636 Book Now

St Kitts - Downtown Waterfront Penthouse Pool Dock Parking

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St Kitts - Downtown Waterfront Penthouse Pool Dock Parking Villa Key West is located approximately 20 minutes' walk from the Ernest Hemingway Home and Museum and provides cycling and… More

From US$ 547 Book Now

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