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! (1,288 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub
Travelers say...
Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family
Reviewed on Jan 11, 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! (1,631 reviews)
Couples like: bar, on the beach
Travelers say...
The check in was easy. The front desk employee was very kind. Our room was spotless. We spent the afternoon on the beach and used the kayak. We enjoyed breakfast. The omelet chef was awesome. Overall I was very happy with my stay
Reviewed on Jan 12, 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! (1,260 reviews)
Couples like: restaurant with ocean view, on the beach, romance packages available
Travelers say...
This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back
Reviewed on Jan 10, 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.
