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! (1,305 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, Hot tub
Travellers say...
Place was great! Staff was amazing. Jessica at the front desk is a Rockstar! Property was beautiful!
Reviewed on 15 Feb 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! (1,662 reviews)
Couples like: bar, on the beach
Travellers say...
Clean rooms, beautiful scenery, gorgeous sunrise, delicious breakfast. Loved this place.
Reviewed on 16 Feb 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! (1,256 reviews)
Couples like: restaurant with ocean view, on the beach, romance packages available
Travellers say...
room was clean people were nice . was concerned being on the fifth floor and drone flying outside every day. felt weird like invasion of privacy.
Reviewed on 16 Feb 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.
