Islamorada Romantic Holidays
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Top Romantic Islamorada Hotels
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,113 reviews)
"Amazing, we will be back as soon as possible. Luxury vacation!"
Reviewed on 4 Jul. 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (1,478 reviews)
"Super nice staff! Great place to stay!"
Reviewed on 2 Jul. 2025
Large Screened Porch, Professional Cleaning, Wifi
Tavernier
Book a stay at this beach condo in Tavernier. Enjoy private pools, a beach locale, and a sauna. Popular attractions Florida Keys Dive Center and Old Road Gallery ...
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 2 Feb. 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.