Islamorada Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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! (1,328 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub
Travelers say...
Beautiful!!!
Reviewed on May 7, 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! (1,727 reviews)
Couples like: bar, on the beach
Travelers say...
Wow just wow Booked a king with ocean view They had a problem with door card reader. When I was checking in they were repairing it. So they upgraded me to a villa and holy cow now I know how rich people live!!! The staff were really friendly and knowledgeable about the area around the hotel. My wife ...
Reviewed on May 8, 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! (1,275 reviews)
Couples like: restaurant with ocean view, on the beach, romance packages available
Travelers say...
I enjoyed my proximity to the beach into the pool area and the room was nicely appointed!
Reviewed on May 7, 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.
