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Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$249 nightly
The price is $280 total per night from Jan 28 to Jan 29
$280 total
Jan 28 - Jan 29
Total with taxes and fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,625 reviews)
The resort is a great family friendly atmosphere. The staff was extremely hospitable. The beach is clean and lots of fun activities to do. Only wish we had more time!
Reviewed on Jan 6, 2026
Hawks Cay Resort
61 Hawks Cay Blvd Marathon FL
$343 nightly
The price is $384 total per night from Jan 29 to Jan 30
$384 total
Jan 29 - Jan 30
Total with taxes and fees
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8/10 Very Good! (1,015 reviews)
Overall a great stay. Very nice and clean condo with its own small pool. The property is beautiful and we enjoyed the tennis and pickleball facilities. Only areas for improvement were the initial delay in room being available from housekeeping and need for more service staff around the pool ...
Reviewed on Jan 4, 2026
Lime Tree Bay Resort
68500 Overseas Hwy Long Key FL
$169 nightly
The price is $190 total per night from Jan 11 to Jan 12
$190 total
Jan 11 - Jan 12
Total with taxes and fees
Book a stay at this beach resort in Long Key. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,128 reviews)
Great property for the price. Our first room was right next to a very noisy construction project, and smelled very strongly of cleaning liquid -- they were great about moving us to an upgraded room and we had an absolutely lovely stay other than that. If you're a strong kayaker or paddleboarder you ...
Reviewed on Jan 4, 2026
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.
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (122 reviews)
This place is super fun and unlike anywhere we've stayed before. Water lodges are well appointed with all the amenities needed and there are additional facilities around the main reception area.
Reviewed on Jan 6, 2026
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (606 reviews)
Great location and walkable to restaurants. Clean. Nice beach. Quiet. Pool was heated and warm. This was our first five day stay in a bungalow and we would stay again!
Reviewed on Jan 6, 2026
The Islands of Islamorada
82779 Old Hwy Islamorada FL
Book a stay at this beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.6/10 Exceptional! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort
Reviewed on Nov 25, 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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- Jacob's Aquatic Center
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- Crawl Key
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