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2026-06-28
2026-06-29
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Hotels in Windley Key area of Islamorada

Drop Anchor Resort & Marina

84959 Overseas Highway, Islamorada, United States Show map

Featuring bicycle rentals, as well as Wi-Fi in public areas, the 3-star Drop Anchor Resort & Marina Islamorada is 3.2 km from the 45-acre Founders Park. Boasting a heated swimming pool, this lovely… More

From US$ 251 Book Now

Anglers Reef Getaway

135 Anglers Way, Islamorada, United States Show map

Situated 2.6 km from the Rain Barrel Village, Anglers Reef Getaway Villa Islamorada entices guests to explore various tourist attractions in the area. More

From US$ 450 Book Now

Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

135 Anglers Way, Islamorada, United States Show map

Located 6 km from the Michelle Nicole Lowe Art Gallery, Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina gives access to various… More

From US$ 394 Book Now

Anglers Reef Vacation Rental

109 Anglers Way, Islamorada, United States Show map

Situated a 6-minute walk from Windley Key Island, Anglers Reef Vacation Rental Islamorada villa entices guests with views of the garden. The 3-bedroom villa features opportunities for canoeing… More

From US$ 365 Book Now

Anglers Reef Paradise

110 Anglers Way 110, Islamorada, United States Show map

Situated about a 5-minute walk from the Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise Islamorada villa entices guests with snorkelling, diving, and cycling in the area. More

From US$ 382 Book Now

Anglers Reef Villa 1

110 Anglers Way, Islamorada, United States Show map

The 3-star Anglers Reef Villa 1 Islamorada hotel is located in Islamorada, within 6 km of Anne s Beach, and offers a heated pool. There is also parking. More

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Coconut Cove Resort & Marina

84801 Overseas Highway, Islamorada, United States Show map

Offering an outdoor swimming pool, the 2-star Coconut Cove Resort & Marina Islamorada is situated in a shopping district, 3.6 km from the 45-acre Founders Park. Featuring 20 rooms with views of the… More

From US$ 212 Book Now

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

84745 Old Hwy #6, Islamorada, United States Show map

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa is located merely a 7-minute walk from the Windley Key Fossil Reef Geological State Park and entices guests with a spa centre… More

From US$ 467 Book Now

Island Time - Oceanview Balconies- Dock- Htd Pool

84745 Old Hwy #12, Islamorada, United States Show map

Located just 8 minutes on foot from the Windley Key Fossil Reef Geological State Park, Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada includes a terrace with views of the sea. More

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Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool

84745 Old Hwy #14, Islamorada, United States Show map

Located merely 8 minutes' walk from the Windley Key Fossil Reef Geological State Park, Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa offers opportunities for snorkelling… More

From US$ 1403 Book Now

Islamorada Home, Ocean Views, Playroom, Near Tiki Bar, Pool, And Boat Dockage, Ultimate Keys Getaway Home

84745 Old Highway Unit A2, Islamorada, United States Show map

Located at a 500-metre distance from Windley Key Fossil Reef Geological State Park, the 3-bedroom Islamorada Home, Ocean Views, Playroom, Near Tiki Bar, Pool, And Boat Dockage, Ultimate Keys Getaway… More

From US$ 797 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Situated 650 metres from the Windley Key Fossil Reef Geological State Park, Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa offers guests to relax by a private swimming pool. More

From US$ 624 Book Now

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms

A1, 84745 Old Highway, Islamorada, United States Show map

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms Islamorada villa is situated within a 700-metre distance of the Windley Key Fossil Reef Geological State Park and… More

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The Ocean View Inn

84500 Overseas Highway, Islamorada, United States Show map

The 3-star The Ocean View Inn Islamorada sits 700 m from the Windley Key Fossil Reef Geological State Park and offers a restaurant. The hotel lies 4.8 km from the Hurricane Monument, and offers an… More

From US$ 226 Book Now

Smugglers Cove Resort And Marina

85500 Overseas Highway, Islamorada, United States Show map

Smugglers Cove Resort And Marina Islamorada offers 12 rooms 15 minutes' drive from the class museum "Florida Keys History and Discovery Center". Parking is available on site as well. More

From US$ 99 Book Now

Sunshine Place

84371 Overseas Hwy, Islamorada, United States Show map

Sunshine Place Islamorada villa is located 4.2 km from the 45 - acre Founders Park and provides snorkelling, diving, and bowling for active guests. More

From US$ 384 Book Now

Florida Keys Boat Charters

85920 Overseas Highway, Islamorada, United States Show map

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From US$ 324 Book Now

Snorkel In Islamorada'S Clear Blue Waters

85920 Overseas Highway, Islamorada, United States Show map

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Straight To The Islamorada Sandbar Charters

85920 Overseas Highway, Islamorada, United States Show map

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Florida Keys Boat Trips Multi Activity

85920 Overseas Highway, Islamorada, United States Show map

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From US$ 342 Book Now

Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida

10610 San Remo Dr, Islamorada, United States Show map

Staying at Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida, guests can visit the 45 - acre Founders Park, which is about a 20-minute stroll away. More

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Fl Keys Venetian Shores Waterfront With Ocean Access, Pool

141 Stromboli Drive, Islamorada, United States Show map

Located approximately 25 minutes' walk from the 45 - acre Founders Park, Fl Keys Venetian Shores Waterfront With Ocean Access, Pool Islamorada villa features a private pool, a hot tub, ensuring a… More

From US$ 1011 Book Now

Bella

109 Valencia Drive, Islamorada, United States Show map

Bella Villa Islamorada offers proximity to nearby tourist spots, such as the Windley Key Fossil Reef Geological State Park, situated nearly 15 minutes' walk away. More

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Comfortable, Spacious 3-Br, 2-Ba-1 Level Home- Deep Dock On Canal, Islamorada

106 Palermo Drive, Islamorada, United States Show map

Guests can enjoy a seaside sea view from a terrace at Comfortable, Spacious 3-Br, 2-Ba-1 Level Home- Deep Dock On Canal, Islamorada, 10 minutes' drive from the History of Diving Museum. More

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La Dolce Vita Villa

116 Stromboli Dr, Islamorada, United States Show map

Staying at La Dolce Vita Villa Islamorada, guests can easily reach the class museum "Florida Keys History and Discovery Center", located approximately 7 km away. More

From US$ 333 Book Now

Lyons Landing

105 Severino Drive, Islamorada, United States Show map

The 3-bedroom Lyons Landing Villa Islamorada is located approximately 20 minutes' walk from the Rain Barrel Village, giving access to various tourist spots nearby. Guests can enjoy windsurfing… More

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Venetian House

101 San Marco Drive, Islamorada, United States Show map

Guests of Venetian House Villa Islamorada hotel can enjoy access to Windley Key Fossil Reef Geological State Park, located 15 minutes' walk away. This hotel offers Wi-Fi throughout the property. More

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Beautiful Home Located In Venetian Shores Neighborhood Home

Islamorada, United States Show map

Offering a Jacuzzi for a relaxing experience, Beautiful Home Located In Venetian Shores Neighborhood Home is located merely 1.9 km from Rain Barrel Sculpture Gallery. Providing guests with Wi-Fi and… More

From US$ 277 Book Now

Harbor House

101 San Juan Dr, Islamorada, United States Show map

Situated about a 25-minute walk from Windley Key, the 3-bedroom Harbor House Villa provides access to numerous tourist attractions in the area. Guests can enjoy water sports activities, windsurfing… More

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Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States Show map

Located about 5 minutes' walk from the Whale Harbor Marina, the oceanfront Chesapeake Beach Resort Islamorada offers 45 rooms with views of the pool. Boasting a swimming pool, the 3-star hotel is… More

From US$ 149 Book Now

Islamorada Beach - Beachfront, Fire Pit & Pool

83407 Old Highway, Islamorada, United States Show map

Offering a terrace overlooking the sea, Islamorada Beach - Beachfront, Fire Pit & Pool villa is located about 10 minutes' walk from Island Community Church. Located approximately 3 km from the… More

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Bungalow House

32 Park Road, Islamorada, United States Show map

Located around a 10-minute walk from the History of Diving Museum, Bungalow House Islamorada provides access to various tourist attractions in the vicinity. More

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Treasure Harbor Hideaway - Upper

105 Galleon Rd A, Islamorada, United States Show map

Located a mere 5 minutes' walk from Rain Barrel Sculpture Gallery, the 3-bedroom Treasure Harbor Hideaway - Upper Villa offers opportunities for windsurfing, cycling, and fishing in the area. More

From US$ 353 Book Now

Ragged Edge Resort & Marina

243 Treasure Harbor Drive, Islamorada, United States Show map

Ragged Edge Resort & Marina Islamorada, located approximately 10 minutes on foot from Bluewater In The Keys, offers an outdoor swimming pool and Wi-Fi throughout the property. The resort is a good… More

From US$ 339 Book Now

Treasure Harbor

200 Treasure Harbor Drive, Islamorada, United States Show map

Treasure Harbor Hotel Islamorada, located a mere 5 minutes' walk from the Rain Barrel Village and 2.5 km from Windley Key Island, features an outdoor swimming pool for guests to take a dip in. The… More

From US$ 171 Book Now

Islamorada Retreat For 2

164 Coral Road, Islamorada, United States Show map

Situated about a 5-minute walk from Founders Park, the 76 m² Islamorada Retreat For 2 apartment offers guests easy access to various tourist attractions nearby. More

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Beacon Reef #204

83201 Old Highway, Islamorada, United States Show map

The 118 m² Beacon Reef #204 Apartment Islamorada offers setting in a beach area of Islamorada, merely 5 minutes' walk from the History of Diving Museum. Featuring a Jacuzzi and a sauna, this 2… More

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Beacon Reef 501

83201 Old Highway #501, Islamorada, United States Show map

Beacon Reef 501 Villa Islamorada is situated just a 5-minute walk from the History of Diving Museum and provides a hot tub for additional comfort. Located fairly close to Island Community Church… More

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Beacon Reef 406

83201 Old Hwy Unit #406, Islamorada, United States Show map

Located about 5 minutes' walk from the History of Diving Museum, the 2-bedroom Beacon Reef 406 Villa Islamorada offers windsurfing, snorkelling, and bowling to diversify guests' leisure. Offering a… More

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Beacon Reef Condo Oceanside

83201 Old Highway #204, Islamorada, United States Show map

Lobster Trap Art Gift Shop and Gallery is within a 2-km distance of the spacious 2-bedroom Beacon Reef Condo Oceanside, while Island Community Church is situated nearby. Offering views of the sea… More

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Beacon Reef 503

83201 Old Highway #503, Islamorada, United States Show map

Offering a hot tub for a relaxing experience, Beacon Reef 503 Villa Islamorada is located an 18-minute walk from the class museum "Florida Keys History and Discovery Center". The 2-bedroom holiday… More

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Beacon Reef 301

83201 Old Hwy Unit 301, Islamorada, United States Show map

The beachfront Beacon Reef 301 Villa Islamorada provides an opportunity to stay a 5-minute walk from Island Community Church and offers a Jacuzzi, perfect for decompressing. Guests can enjoy… More

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Beacon Reef 307

83201 Old Hwy #307, Islamorada, United States Show map

Located about a 5-minute walk from the History of Diving Museum, the 2-bedroom Beacon Reef 307 Villa Islamorada entices guests with a Jacuzzi. Guests can enjoy windsurfing, snorkelling, and diving at… More

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Beacon Reef 222

83201 Old Highway Unit 222, Islamorada, United States Show map

Located 300 m from the History of Diving Museum, the 2-bedroom Beacon Reef 222 Villa Islamorada offers snorkelling to diversify guests' leisure. More

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Beacon Reef 306

83201 Old Hwy Unit 306, Islamorada, United States Show map

The 2-bedroom Beacon Reef 306 Villa Islamorada is located within 5 minutes' walk of Island Community Church and offers a hot tub for guests' relaxation. At this Islamorada holiday home, located 2.6… More

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Beacon Reef 310

83201 Old Highway #310, Islamorada, United States Show map

During the stay at Beacon Reef 310 Villa Islamorada, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Lobster Trap Art Gift Shop and Gallery, located 20 minutes' walk away. More

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