Name: Islander Resort
Price range: CA $403
Rating: 9.4

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

CA $258

CA $369 total

Jul 14 - Jul 15

includes taxes & 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! (1,754 reviews)

"Everyone was friendly and room was nice."

Reviewed on Jun 13, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

CA $284

CA $422 total

Jul 8 - Jul 9

includes taxes & fees

Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (1,331 reviews)

"The room next to us had a domestic dispute that went on ALL night. We have two young children, and we could hear every word they were screaming. We called security twice, but nothing changed. As a result, we were unable to get any sleep."

Reviewed on Jun 14, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

CA $403

CA $548 total

Jun 28 - Jun 29

includes taxes & fees

Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...

9.4/10 Exceptional! (1,055 reviews)

"The property and room were clean. The staff were helpful. There were lots of activities to keep us busy. My only complaint was when I purchased on e drink from the bar there was an automatic 20% tip on the bill. If you’re going to automatically charge me just raise the price of the drink and pay ..."

Reviewed on Jun 14, 2026

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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.

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! (696 reviews)

"Excellent"

Reviewed on Jun 12, 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 Florida Keys ...

9.6/10 Exceptional! (76 reviews)

"I am not usually about leaving reviews however this property definitely needs it. Heard a lot about being pampered when I was checked in and that they will bring you anything and to let them know what our needs were. Property does not have any coffee shop or restaurant. We were told we could come ..."

Reviewed on May 18, 2026

Oceanfront Private Cottage!

Islamorada FL

Stay at this cottage in Islamorada. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions History of Diving Museum and Florida Keys Brewing ...

10/10 Exceptional! (117 reviews)

"Host was very responsive when we reached out and the place had everything we needed. The dock for the boat was very easy to get in and out of and we had plenty of room for the trailer. The place was also very clean."

Reviewed on Jun 11, 2026

See all properties in Upper Matecumbe Key

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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Stay near popular Upper Matecumbe Key attractions

Bud n' Mary's Dive Center

4.4/5 (504 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

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