Name: Chesapeake Beach Resort
Price range: $217 total
Rating: 9

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The Latest Upper Matecumbe Key vacation packages

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

Park Central South Beach

South Beach

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (911 reviews)

The hotel is super clean, staff is very kind, especially Fernando who works at the front desk, restaurant staff like Hydagie was super helpful and kind, we enjoyed the view, pools, food and the beach activities right across the hotel, we will come back for sure!

Reviewed on Aug 12, 2025

Hotel Colonnade Coral Gables, Autograph Collection

Coral Gables Section

per person

Sep 13 - Sep 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,004 reviews)

I liked the property. Checking in staff was good. Check out staff not so good. Also hotel charge 25 dollar destination fee per day. As per Expedia u pay what u see on the booking. So not happy about that.

Reviewed on May 26, 2025

Riverside Hotel

East Fort Lauderdale

per person

Oct 13 - Oct 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (2,473 reviews)

This was one of the best hotels I’ve stayed at in a long time.

Reviewed on Aug 13, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Henrosa Hotel

South Beach

Save 100% on your flight

per person

Oct 15 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (809 reviews)

Good location, very walkable. Front desk staff is very nice.

Reviewed on Aug 8, 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

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

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

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$192 nightly

$217 total

Sep 11 - Sep 12

Total includes taxes and fees

9/10 Wonderful! (1,497 reviews)

"Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!"

Reviewed on Aug 11, 2025

Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

$209 nightly

$236 total

Aug 14 - Aug 15

Total includes taxes and fees

9/10 Wonderful! (1,146 reviews)

"Golf course could use just a little work. Everything else was great."

Reviewed on Aug 12, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$246 nightly

$276 total

Sep 1 - Sep 2

Total includes taxes and fees

8.8/10 Excellent! (1,239 reviews)

"The staff was very personable and accommodating.. it was our 32nd weeding anniversary and they had left a handwritten note and a treat in our room… it was appreciated… The grounds were nice and clean with the exception of the water area around the end of the property where the event area is located ..."

Reviewed on Aug 11, 2025

See all 2,764 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.