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2026-11-10
2026-11-11
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Holiday Homes in Islamorada

Peninsula Villa Boat Dock Heated Pool Sunset Point

76414 Overseas Highway, Islamorada, United States Show map

Offering a swimming pool, the 6-bedroom Peninsula Villa Boat Dock Heated Pool Sunset Point Islamorada is situated within easy reach of Lower Matecumbe Key Island and can accommodate up to 12 guests. More

From US$ 1939 Book Now

Is17Flr - Executive Bay Club Condo

87200 Overseas Highway Unit M-1, Islamorada, United States Show map

Along with proximity to Islamorada, located only 300 metres away, the 2-bedroom Is17Flr - Executive Bay Club Condo Islamorada villa provides access to a fitness club. Located around 25 minutes on… More

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Little Bay Cottage

82246 Overseas Hwy, Islamorada, United States Show map

During the stay at Little Bay Cottage Islamorada, guests can indulge in windsurfing, snorkelling, and diving or visit Michelle Nicole Lowe Art Gallery, located 15 minutes' walk away. Located 950… More

From US$ 549 Book Now

Sirens Cove - Ocean Views, Game Room, Pool And Dock Access

84745 Old Hwy, Islamorada, United States Show map

The 3-bedroom Sirens Cove - Ocean Views, Game Room, Pool And Dock Access Islamorada villa hosts up to 8 guests and provides proximity to Windley Key Fossil Reef Geological State Park, situated only 8… More

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Tea Table Key

79775 Overseas Highway, Islamorada, United States Show map

During the stay at the 6-bedroom Tea Table Key Villa Islamorada, guests can indulge in a Jacuzzi or visit the world-class museum "Florida Keys History and Discovery Center", located 4.4 km away. More

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Little Bay Compound

82246 Overseas Highway, Islamorada, United States Show map

The 6-bedroom Little Bay Compound Villa Islamorada entices guests to enjoy windsurfing, snorkelling, and diving and offers proximity to Keys History & Discovery Center, located nearly a 10-minute… More

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Oceanside Anglers Reef Home With Beach Pool And Kayaks

119 Anglers Way, Islamorada, United States Show map

Oceanside Anglers Reef Home With Beach Pool And Kayaks Islamorada is located a 5-minute walk from Windley Key Fossil Reef Geological State Park and offers guests to enjoy fisheries. The 2-bedroom… More

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Beacon Reef 406

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

Featuring an aqua park and spa therapy for a delightful experience, Beacon Reef 406 Villa Islamorada offers a beachfront location merely a 5-minute walk from Island Community Church. Located 6 km… More

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