Islamorada Romantic Holidays

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Top Romantic Islamorada Hotels

Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
  • 8 min drive from Theater of the Sea
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 ...
9/10 Wonderful! (1,110 reviews)

Couples like: full-service spa, couples spa treatments, beachfront dining, Hot tub

Great Family weekend
"Great Resort. Family loved it ! Gary the server in Sushi restaurant was awesome."

Reviewed on 29 Jun 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
  • 22 min walk from Theater of the Sea
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their ...
9/10 Wonderful! (1,476 reviews)

Couples like: bar, on the beach

Travellers say...
"Super nice staff! Great place to stay!"

Reviewed on 2 Jul 2025

Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
  • 12 min drive from Theater of the Sea
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the bar in their reviews. ...
8.8/10 Excellent! (1,223 reviews)

Couples like: beachfront dining, on the beach, romance packages available

Travellers say...
"Place was clean and the amenities are really nice. This is our third time in this hotel and we missed the store to buy essentials and souvenirs and we missed also the ice creams options, the ice cream fridge was empty."

Reviewed on 30 Jun 2025

Amara Cay Resort
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.