Islamorada Romantic Holidays
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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! (1,117 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, Hot tub
Travellers say...
"We enjoy our stays at this resort. We had two adjoining rooms this year and one room was very nice, while the second room was not. Lots of things damaged in the room, shower didn’t work, door handle to porch falling off. Hotel seems to need some maintenance done throughout. However, the staff is ..."
Reviewed on 6 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! (1,482 reviews)
Couples like: bar, on the beach
Travellers say...
"The property is nice. Water pressure was not great. Water stopped completely while in the shower on multiple occasions. It was not off long but it was completely off. It was nice that breakfast was served a bit later, but even by 9 some things were gone. Overall nice stay."
Reviewed on 6 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.