Islamorada Romantic Vacations
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Top Romantic Islamorada Hotels
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, 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 ...
9/10 Wonderful! (1,221 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub
Travelers say...
"room were cleaned every morning; we were able to park under the room drinks were pricy"
Reviewed on Oct 9, 2025
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! (1,539 reviews)
Couples like: bar, on the beach
Beautiful views
"Check in person was very friendly and included a glass of champagne! Beautiful resort location!"
Reviewed on Oct 12, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Ocean-view dining, a garden, and a private beach await visiting couples at this romantic resort. The property also offers romance packages and premium ...
8.8/10 Excellent! (1,254 reviews)
Couples like: beachfront dining, on the beach, romance packages available
Travelers say...
"Room was spacious, clean with a great balcony."
Reviewed on Oct 7, 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.
