Name: Chesapeake Beach Resort
Price range: $258 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.

1818 Meridian House Apartments and Suites by Eskape Collection

South Beach

Save 100% on your flight

$517

per person

May 18 - May 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (676 reviews)

The room was nice. It would use some better lighting, it was dark in the room with all the lights on. Flooring in front the the counter had large gaps in it. John was nice and helpful at check-in. It was pretty quiet both nights, with a few people getting home late and doors shutting.

Reviewed on Apr 5, 2026

Casablanca Miami Beach

North Beach

$1,542

per person

Jun 27 - Jun 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (322 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,433

per person

Jun 16 - Jun 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$686

per person

Jun 7 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Its my fourth time there and i loved it

Reviewed on Apr 6, 2026

Centric 40thFloor Brickell Condo FREE parking by Palermo Home Miami

Brickell

Save 100% on your flight

$1,361

per person

Jun 28 - Jul 3

found 19 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

8/10 Very Good! (1 review)

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Discover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center

4.5/5(142 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.

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.

Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$315 nightly

$354 total

Apr 29 - Apr 30

Total with taxes and fees

9.2/10 Wonderful! (1,310 reviews)

Amazing! Loved everything can’t wait to go back!!

Reviewed on Apr 5, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$230 nightly

$258 total

May 6 - May 7

Total with taxes and fees

9.2/10 Wonderful! (1,688 reviews)

Very clean, amazing breakfast, lovely staff.

Reviewed on Apr 7, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$288 nightly

$325 total

Apr 21 - Apr 22

Total with taxes and fees

8.8/10 Excellent! (1,267 reviews)

Great

Reviewed on Mar 30, 2026

See all 2,826 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.