Name: Chesapeake Beach Resort
Price range: RM818
Rating: 9.2

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

RM990

per night

19 Jul - 20 Jul

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 in their ...

9.2/10 Wonderful! (1,324 reviews)

"The decor was updated a bit but then dated in other areas. The balcony cushions had stains and the carpet needed to be replaced."

Reviewed on 23 Jun 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

RM776

per night

7 Jul - 8 Jul

Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...

8.8/10 Excellent! (1,283 reviews)

"Enjoyed the food & pool."

Reviewed on 24 Jun 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

RM818

per night

6 Jul - 7 Jul

Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...

9.2/10 Wonderful! (1,733 reviews)

"I thoroughly enjoyed my stay here! The room was immaculately clean! The staff was very attentive. I will definitely stay here again."

Reviewed on 25 Jun 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

Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...

8.8/10 Excellent! (702 reviews)

"Been coming here for over 30 years best place for the price and fishing !!"

Reviewed on 25 Jun 2026

The Islands of Islamorada

82779 Old Hwy Islamorada FL

Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...

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 18 May 2026

Treasure Harbor

200 Treasure Harbor Dr Islamorada FL

Stay at this houseboat in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...

9/10 Wonderful! (159 reviews)

"We highly recommend Treasure Harbor house boats, it was clean, the A/C was cold, water heater perfect, and close to everything we needed. It’s like a tiny house on water. Dallas, was accommodating and professional. Overall 5+ stars. We visit the keys often for scuba diving, we have now found our ..."

Reviewed on 7 Jun 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.

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Stay near popular Upper Matecumbe Key attractions

Bud n' Mary's Dive Center

8.8/5 (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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