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! (1,137 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub
Travelers say...
"Stayed here for one night. Unfortunately the weather wasn’t great so we didn’t get to experience the pool areas and such. We walked around the grounds at night in the rain and it was still breath taking. Would love to stay longer the next time I am back in the area."
Reviewed on Jul 20, 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! (1,480 reviews)
Couples like: bar, on the beach
Travelers say...
"Great view! Sweet ppl that work there!"
Reviewed on Jul 19, 2025
Large Screened Porch, Professional Cleaning, Wifi
Tavernier
A waterfront location and more await visiting couples at this romantic condo.
9.2/10 Wonderful! (63 reviews)
Awesome condo
"AMAZING! This condo has EVERYTHING that you are looking for in a short or extended stay! The property amenities are great and the balcony view is beautiful. The owner was extremely helpful with any questions we had and was very responsive. Will stay here again in the future."
Reviewed on Feb 2, 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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