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! (1,153 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub
Travelers say...
"amazing stay"
Reviewed on Aug 21, 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.
9/10 Wonderful! (1,493 reviews)
Couples like: bar, on the beach
Travelers say...
"Morning breakfast was great. Staff was very attentive and pleasant. Room view was amazing. Very convenient for a person in our party that is disabled."
Reviewed on Aug 21, 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! (1,243 reviews)
Couples like: beachfront dining, on the beach, romance packages available
Travelers say...
"Very clean also beautiful pool area"
Reviewed on Aug 20, 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.