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

$227

per person

Mar 16 - Mar 19

found 2 days 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

Creekside Inn

$644

per person

Mar 15 - Mar 20

found 2 days 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

Broadmore Miami Beach

North Beach

$283

per person

Mar 16 - Mar 20

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.6/10 (389 reviews)

What stood out the most is it’s an original hotel from the 1940’s. I cherish that. Elevator was very slow but its 60 plus years old. Admire the authenticity of this hotel. Key cards for the room are my ONLY complaint. Should be keys not cards. Staff is absolutely amazing. Right on the beach! Book it. You won’t be disappointed unless you want 5 star 2026. Thank you for everything broadmore!!!

Reviewed on Jan 31, 2026

The Penguin Hotel

South Beach

Save 100% on your flight

$458

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,491 reviews)

Muy buena atención y buen servicio super recomendable gracias

Reviewed on Feb 5, 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

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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! (1,658 reviews)

Spacious clean room. Good linens and towels with comfortable beds. Staff very helpful. Elevator was broken but staff carried bags up,

Reviewed on Feb 1, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$432 nightly

$487 total

Feb 11 - Feb 12

Total with taxes and fees

9.2/10 Wonderful! (1,293 reviews)

Everything about this resort is wonderful. Lots to do for the whole family, great restaurants, and gorgeous areas. We will definitely be going back.

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! (1,259 reviews)

We enjoyed our stay and found the staff to be courteous and responsive. Our room was a generous size, clean and well appointed (as is often the case we wouldn’t have said no to a couple of more outlets lol). The beach and pool areas had plenty of seating and multiple things to do—ping pong, cornhole, ...

Reviewed on Jan 26, 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.