Name: Chesapeake Beach Resort
Price range: $312 total
Rating: 9.2

Photo by Cameron Abbott

The Latest Upper Matecumbe Key vacation packages

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$754

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,007 reviews)

Everything was perfect . I would stay there again

Reviewed on Mar 16, 2026

Casablanca Miami Beach

North Beach

$1,943

per person

May 21 - May 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

5.8/10 (321 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

Creekside Inn

$999

per person

Apr 20 - Apr 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (1,027 reviews)

Older, but near our kayaking. On the canal & near several restaurants- walkable. Quiet, cool

Reviewed on Mar 16, 2026

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Discover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center

4.5/5(141 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

$436 nightly

$491 total

Apr 12 - Apr 13

Total with taxes and fees

9.2/10 Wonderful! (1,301 reviews)

Place was great!

Reviewed on Mar 19, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$277 nightly

$312 total

Apr 13 - Apr 14

Total with taxes and fees

9.2/10 Wonderful! (1,666 reviews)

Perfect

Reviewed on Mar 18, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$313 nightly

$353 total

Mar 22 - Mar 23

Total with taxes and fees

8.8/10 Excellent! (1,257 reviews)

Pool and beach area were extremely nice. The room was nice and clean, but you can tell it was an older hotel that they are working on remodeling. In some areas you could tell there was some deferred maintenance.

Reviewed on Mar 15, 2026

See all 2,795 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.