Islamorada Romantic Holidays
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Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,288 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, Hot tub
Travellers say...
For a five star hotel, the grounds should be kept up better
Reviewed on 14 Jan 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,632 reviews)
Couples like: bar, on the beach
Travellers say...
Friendly and helpful staff especially Xixi at the front desk. Rooms were clean and beds comfortable.
Reviewed on 15 Jan 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,262 reviews)
Couples like: restaurant with ocean view, on the beach, romance packages available
Travellers say...
Great Location, Friendly Staff
Reviewed on 12 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
