Islamorada Romantic Vacations
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Top Romantic Islamorada Hotels
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fall in love again at this upscale resort. You and your special someone are sure to love the hot tub, spa, and in-room massages. You'll also appreciate the ocean-view ...
9.2/10 Wonderful! (1,284 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub
Travelers say...
Fantastic resort, will definitely be heading back!
Reviewed on Jan 4, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
A private beach and premium mattresses await at this romantic hotel, which also offers 2 outdoor pools and a white sand beach.
9.2/10 Wonderful! (1,625 reviews)
Couples like: bar, on the beach
Travelers say...
The resort is a great family friendly atmosphere. The staff was extremely hospitable. The beach is clean and lots of fun activities to do. Only wish we had more time!
Reviewed on Jan 6, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Ocean-view dining, a garden, and happy hours await visiting couples at this romantic resort. The property also offers a private beach and romance packages.
8.8/10 Excellent! (1,271 reviews)
Couples like: restaurant with ocean view, on the beach, romance packages available
Travelers say...
Was very nice , Did order cookies and brownies for the room Christmas night and that never happened! Fishing pole rental was ridiculous Food was great and good Keylime dessert !
Reviewed on Dec 28, 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.
