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2026-08-12
2026-08-13
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Hotels in Windley Key area of Islamorada

Drop Anchor Resort & Marina

84959 Overseas Highway, Islamorada, United States Show map

The 3-star Drop Anchor Resort & Marina Islamorada offers air-conditioned rooms around a 20-minute walk from Wilson Key. Located 2.8 km from the Rain Barrel Sculpture Gallery, this lovely resort… More

From US$ 221 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

Offering live performances for a delightful experience, Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina is located just an 8-minute… 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 2-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 situated within 6 km of the Hurricane Monument, which is an excellent place to improve cultural awareness. Guests can swim in a heated swimming… More

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Coconut Cove Resort & Marina

84801 Overseas Highway, Islamorada, United States Show map

Offering air-conditioned rooms and Wi-Fi in public areas, the 2-star Coconut Cove Resort & Marina Islamorada is 10 minutes' drive from the Rain Barrel Sculpture Gallery and 3.7 km from the Islamorada… More

From US$ 245 Book Now

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

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

Located merely a 7-minute walk from the Windley Key Fossil Reef Geological State Park, At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa offers snorkelling, ping pong, and… More

From US$ 467 Book Now

Island Time - Oceanview Balconies- Dock- Htd Pool

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

Situated just 8 minutes on foot from the Windley Key Fossil Reef Geological State Park, the 3-bedroom Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada ensures a great leisure… More

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

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

Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa accommodates up to 6 guests and offers proximity to the Windley Key Fossil Reef Geological State Park, located merely an 8… More

From US$ 1403 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Offering sea views, Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is situated 650 metres from the Windley Key Fossil Reef Geological State Park. The 3-bedroom holiday home hosts… 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

Offering karaoke for a delightful experience, Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms Islamorada villa is located within a 700-metre distance of the Windley… More

From US$ 723 Book Now

Paradise Palms Islamorada

84745 Old Highway Unit 9, Closest To The Ocean!, Islamorada, United States Show map

During the stay at Paradise Palms Islamorada villa, guests can indulge in snorkelling, canoeing, and ping pong or visit the Michelle Nicole Lowe Art Gallery, located 4.5 km away. Located within a 10… More

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The Ocean View Inn

84500 Overseas Highway, Islamorada, United States Show map

Featuring a restaurant, the comfortable The Ocean View Inn Islamorada lies 700 m from the Windley Key Fossil Reef Geological State Park. This 3-star hotel, overlooking Islamorada, offers an American… More

From US$ 345 Book Now

Smugglers Cove Resort And Marina

85500 Overseas Highway, Islamorada, United States Show map

Smugglers Cove Resort And Marina Islamorada offers 12 rooms a 10-minute drive from the Rain Barrel Village. Parking is available on site as well. More

From US$ 99 Book Now

Sunshine Place

84371 Overseas Hwy, Islamorada, United States Show map

Accommodating up to 3 guests, the 1-bedroom Sunshine Place Islamorada villa is situated 3.8 km from renowned cultural sites such as the Rain Barrel Sculpture Gallery. The property features… 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

The 3-bedroom Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida is located about a 20-minute stroll from the 45-acre Founders Park and allows guests to enjoy diving… 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 has a swimming pool and is ideal for up to 8 guests.… More

From US$ 1011 Book Now

Bella

109 Valencia Drive, Islamorada, United States Show map

Hosting up to 9 guests, Bella Villa Islamorada is nestled in a business area, about 15 minutes' walk from the Windley Key Fossil Reef Geological State Park. Guests can enjoy bowling and pool at the… More

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La Dolce Vita Villa

116 Stromboli Dr, Islamorada, United States Show map

Staying at the 3-bedroom La Dolce Vita Villa Islamorada, guests can easily reach the Lobster Trap Art Gift Shop and Gallery, located approximately 6 km away. This Islamorada holiday home is suitable… More

From US$ 333 Book Now

Lyons Landing

105 Severino Drive, Islamorada, United States Show map

The 4-bedroom Lyons Landing Villa Islamorada is located approximately 20 minutes' walk from the Rain Barrel Village and welcomes its guests to enjoy windsurfing, snorkelling, and diving. More

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Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States Show map

The oceanfront Chesapeake Beach Resort Islamorada enjoys a private location about 5 minutes' walk from the Whale Harbor Marina and offers 45 rooms with views of the pool. Featuring a heated pool, the… More

From US$ 149 Book Now

Ragged Edge Resort & Marina

243 Treasure Harbor Drive, Islamorada, United States Show map

Located approximately 10 minutes on foot from Bluewater In The Keys, the comfortable Ragged Edge Resort & Marina Islamorada features Wi-Fi throughout the property and a private parking lot on site. More

From US$ 360 Book Now

Treasure Harbor

200 Treasure Harbor Drive, Islamorada, United States Show map

The 3-star Treasure Harbor Hotel Islamorada offers its guests comfortable rooms a mere 5 minutes' walk from the Rain Barrel Village. This comfortable hotel also includes a car park. More

From US$ 171 Book Now

Beacon Reef #204

83201 Old Highway, Islamorada, United States Show map

The 118 m² Beacon Reef #204 Apartment Islamorada is nestled in a beach area of Islamorada, about 10 minutes by car from the Windley Key Fossil Reef Geological State Park and 2.7 km from the Gallery… 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 offers a hot tub, ensuring a more relaxing stay. This 2-bedroom villa features opportunities… More

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Beacon Reef 406

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

Featuring a Jacuzzi, the 2-bedroom Beacon Reef 406 Villa Islamorada is located about 5 minutes' walk from the History of Diving Museum and can host up to 4 guests. Providing guests with Wi-Fi and… More

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Beacon Reef 503

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

During the stay at Beacon Reef 503 Villa Islamorada, guests can indulge in a hot tub or visit the class museum "Florida Keys History and Discovery Center", located an 18-minute walk away. The 2… 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 is suitable for 4 guests and provides a Jacuzzi for a truly relaxing stay. Guests can… More

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Beacon Reef 222

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

Situated 300 m from the History of Diving Museum, the 2-bedroom Beacon Reef 222 Villa Islamorada is ideal for up to 4 guests. This 2-bathroom villa features opportunities for snorkelling in the area,… More

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Beacon Reef 306

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

Located around 300 metres from the History of Diving Museum, the 2-bedroom Beacon Reef 306 Villa Islamorada is suitable for 4 guests and offers a Jacuzzi to relax in. Offering Wi-Fi, this Islamorada… More

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Beacon Reef 310

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

Offering guests to unwind in a Jacuzzi, Beacon Reef 310 Villa Islamorada is located 25 minutes' walk from the Upper Matecumbe Key. Guests can enjoy windsurfing, snorkelling, and canoeing at the 2… More

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