Upper Matecumbe Key Cheap Vacations

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Flight and Cheap hotel deals in Upper Matecumbe Key

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Bay Breeze Premium Apartments By Eskape Collection
MirabileCondoDwntown MIA Brickell w PRKG
The Retreat Collection at 1 Hotel & Homes South Beach
The Crosby Miami World Center
Fort Lauderdale Beach Resort by Vacatia
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5* Cheap holidays in Upper Matecumbe Key

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Andaz Miami Beach Resort & Spa
MirabileCondoDwntown MIA Brickell w PRKG
The Retreat Collection at 1 Hotel & Homes South Beach
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3 Night Cheap holidays in Upper Matecumbe Key

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The Crosby Miami World Center
The Retreat Collection at 1 Hotel & Homes South Beach
1 Hotel South Beach
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4 Night Cheap holidays in Upper Matecumbe Key

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Brickell Bay 3318
The W - Bayshore Unit 1003
Family Pool Home by Hollywood Beach
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Cheap Hotels in Upper Matecumbe Key

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
  • 10 min drive from Bud n' Mary's Dive Center
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! (1,729 reviews)
Kayak, pools and breakfast were awesome

Reviewed on May 17, 2026

Chesapeake Beach Resort
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.