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! (1,267 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, Hot tub
Travellers say...
Everything was awsome
Reviewed on 7 Dec 2025
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! (1,586 reviews)
Couples like: bar, on the beach
Travellers say...
Breakfast was great every day. Chef Chris was so friendly and made us feel welcome.
Reviewed on 10 Dec 2025
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! (1,266 reviews)
Couples like: restaurant with ocean view, on the beach, romance packages available
Travellers say...
Friendly staff and beautiful property !
Reviewed on 15 Dec 2025
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.
