Name: Chesapeake Beach Resort
Price range: $408 total
Rating: 9.2

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The Latest Upper Matecumbe Key vacation packages

Price found within the past 48 hours. Click for updated prices.

Hyatt Place Miami Airport-East

Palmer Lake

Save 100% on your flight

$503

per person

Apr 16 - Apr 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (2,247 reviews)

Room was nice, clean and beautiful view of the airport. A little noisy because of the airport but was nice. Never got to try the breakfast as we had an early flight. Easy check in process, will hold luggage so you don’t have to hold it till you get to check in.

Reviewed on Feb 3, 2026

Casablanca Miami Beach

North Beach

$643

per person

Apr 15 - Apr 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (311 reviews)

I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

Creekside Inn

Save 100% on your flight

$676

per person

Apr 20 - Apr 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

Ilios Rentals

Downtown Miami

$1,035

per person

Apr 16 - Apr 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

No reviews

Cavalier Hotel South Beach

South Beach

$686

per person

Mar 29 - Apr 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

Prime location within walking distance to all the hot spots. Included are 2 beach chairs with towels per day. Philip at the concierge received us warmly…checking us in early and giving us great recommendations. Room was a great size, A/C, with bathroom amenities. Overall, totally recommend.

Reviewed on Jan 31, 2026

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Discover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center

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 relaxing area.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

History of Diving Museum

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

Upper Matecumbe Key Hotel Deals

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$362 nightly

$408 total

Feb 11 - Feb 12

Total with taxes and fees

9.2/10 Wonderful! (1,665 reviews)

We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.

Reviewed on Feb 3, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$448 nightly

$505 total

Feb 10 - Feb 11

Total with taxes and fees

9.2/10 Wonderful! (1,294 reviews)

We stayed in Premiere ocean front king. The weather was unusually cold and windy so we didn't get to experience the resort as we had hoped. The staff at restaurants were very courteous and service prompt. Beach is lovely -- although not a natural sand beach. Gym could have been larger. We found spa ...

Reviewed on Feb 4, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

$303 nightly

$341 total

Feb 11 - Feb 12

Total with taxes and fees

8.8/10 Excellent! (1,263 reviews)

All good, nice bartender inside downstairs, and easy walk to fish and eat

Reviewed on Feb 5, 2026

See all 2,816 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.