Islamorada Romantic Holidays
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Top Romantic Islamorada Hotels
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! (1,301 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, Hot tub
Travellers say...
This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.
Reviewed on 22 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! (1,652 reviews)
Couples like: bar, on the beach
Travellers say...
Awesome place!!
Reviewed on 30 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! (1,276 reviews)
Couples like: restaurant with ocean view, on the beach, romance packages available
Travellers say...
We enjoyed our stay and found the staff to be courteous and responsive. Our room was a generous size, clean and well appointed (as is often the case we wouldn’t have said no to a couple of more outlets lol). The beach and pool areas had plenty of seating and multiple things to do—ping pong, cornhole, ...
Reviewed on 26 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
