Name: Chesapeake Beach Resort
Price range: $186 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.

Beach Place Hotel

North Beach

$506

per person

Jan 17 - Jan 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,007 reviews)

THe parking was very convenient,and well lit. There were shops close enough to walk but not so close that there were too many people. The best things is the proximity to the beach/park!

Reviewed on Oct 24, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$933

per person

Jan 22 - Jan 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (39 reviews)

Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back !

Reviewed on Nov 1, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$16,678

per person

Dec 22 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Bentley Hotel South Beach

South Beach

$949

per person

Dec 10 - Dec 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (390 reviews)

The staff was amazing and really helpful. Vanina helped us book a trip and Raenaldo was always most helpful, alingt with all the members of staff on duty for the week we stayed

Reviewed on Nov 2, 2025

President Hotel

South Beach

$863

per person

Dec 3 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,905 reviews)

The staff is very helpful with information specially Henry and the lady who works at the same desk when he is off duty. Even the guy who is parking cars offered a usufull information about the area.

Reviewed on Oct 29, 2025

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Discover the most popular places to visit in Upper Matecumbe Key

Florida Keys Brewing Co.

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

History of Diving Museum

4.5/5(51 reviews)

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.

Hurricane Monument

4/5(66 reviews)

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Fully refundableReserve now, pay when you stay

$259 nightly

$291 total

Nov 3 - Nov 4

Total with taxes and fees

9/10 Wonderful! (1,265 reviews)

Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff.

Reviewed on Oct 30, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$165 nightly

$186 total

Nov 5 - Nov 6

Total with taxes and fees

9.2/10 Wonderful! (1,548 reviews)

I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.

Reviewed on Oct 27, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$205 nightly

$231 total

Nov 30 - Dec 1

Total with taxes and fees

8.8/10 Excellent! (1,270 reviews)

We enjoyed our stay a beautiful place, but there was no free breakfast

Reviewed on Oct 24, 2025

See all 2,822 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.