Upper Matecumbe Key

Name: Chesapeake Beach Resort
Price range: P9,246
Rating: 9.2

Travel Guide

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

A pier extending into calm waters with a covered seating area and a sandy beach.

A pier with birds perched on poles, a sign, and a bridge in the background.

A calm lake with a reflection of trees and a cloudy sky.

Visit Upper Matecumbe Key

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

P9,120

P14,736 total

Aug 26 - Aug 27

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! (1,382 reviews)

"I"

Reviewed on Aug 14, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

P9,246

P13,844 total

Aug 26 - Aug 27

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! (1,742 reviews)

"Nice ocean/beach view. Good property. Easy to find. Definitely worth it. Free ok breakfast."

Reviewed on Aug 13, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

P10,288

P16,050 total

Aug 18 - Aug 19

includes taxes & fees

Book a 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 ...

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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 ...

Treasure Harbor

200 Treasure Harbor Dr Islamorada FL

Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...

9/10 Wonderful! (168 reviews)

"This place is a gem. It’s adorable. Great beds, plenty of space. Staff was amazing."

Reviewed on Aug 10, 2026

Island Bay Resort

92530 OVERSEAS HIGHWAY Tavernier FL

Book a stay at this beach aparthotel in Tavernier. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...

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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

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (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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