Name: Chesapeake Beach Resort
Price range: $420 total
Rating: 9.2

Photo by Cameron Abbott

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The Latest Upper Matecumbe Key vacation packages

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

Creekside Inn

$434

per person

Mar 17 - Mar 20

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

Casablanca Miami Beach

North Beach

$590

per person

Apr 12 - Apr 18

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

The Penguin Hotel

South Beach

$563

per person

May 1 - May 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Yes the WiFi wasn’t working though !

Reviewed on Feb 5, 2026

President Hotel

South Beach

$532

per person

May 1 - May 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,775 reviews)

It’s fine for me, I require no “perfect” room. but they should have coffee in the rooms, you can’t get it until 7AM on the hotel. The breakfast is edible and nutritious. It’s quiet which I loved the most, and staff is always available and friendly for when anything is not working in your room.

Reviewed on Feb 4, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,294

per person

Apr 12 - Apr 18

found 1 day ago

Roundtrip flight included

Boston (BOS) 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(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 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

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

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$373 nightly

$420 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

$309 nightly

$348 total

Feb 8 - Feb 9

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.