Name: Chesapeake Beach Resort
Price range: $179 total
Rating: 9

The Latest Upper Matecumbe Key vacation packages

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

Cavalier Hotel South Beach

South Beach

$554

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,000 reviews)

The staff greeted us wonderfully. The room is clean. The VIP perk was pleasant. Would definitely stay here again.

Reviewed on Sep 25, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,728

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

President Hotel

South Beach

$606

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,825 reviews)

Everyone was friendly and accommodating. Breakfast was great!

Reviewed on Sep 28, 2025

Bentley Hotel South Beach

South Beach

$834

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (334 reviews)

We had a very pleasant stay at this hotel. The property was clean and comfortable, and everything we needed was easily available. The highlight of our experience was the staff — they were extremely responsive, helpful, and made sure we felt well taken care of throughout our stay. Their attention and professionalism truly added to the overall experience. I would gladly stay here again and recommend it to others.

Reviewed on Sep 28, 2025

Ridley House - Key West Historic Inns

Key West Historic District

$873

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (819 reviews)

Everything was amazing. we arrived early and in a rain storm my two kids and I were soaked head to toe and the water even entered our luggage. they let us check in early got us en upgrade to. amazing staff and perfect spot close to all in Key West

Reviewed on Sep 25, 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

Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

$151 nightly

$170 total

Oct 6 - Oct 7

Total with taxes and fees

9/10 Wonderful! (1,216 reviews)

"Great resort for vacation.I liked everything about This place except for parking lots for beach bungalows rooms"

Reviewed on Sep 28, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$159 nightly

$179 total

Sep 30 - Oct 1

Total with taxes and fees

9/10 Wonderful! (1,534 reviews)

"Everything was perfect and beautiful"

Reviewed on Sep 23, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$227 nightly

$256 total

Oct 2 - Oct 3

Total with taxes and fees

8.8/10 Excellent! (1,258 reviews)

"The resort had free kayaking and paddle boarding which was a great addition."

Reviewed on Sep 22, 2025

See all 2,817 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.