Name: Chesapeake Beach Resort
Price range: $208 total
Rating: 9.2

The Latest Upper Matecumbe Key vacation packages

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

President Hotel

South Beach

$420

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,905 reviews)

Would like more variety in breakfast but overall very good. Thank you!

Reviewed on Nov 13, 2025

Hawks Cay Resort

$758

per person

Jan 19 - Jan 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,011 reviews)

Room was clean and spacious. Property did not have available microwave for guest. House keeping was good but did not replace soap or drinking glass. Gym not located in main hotel area and it closes at 5pm. Overall property is beautiful and good amenities.

Reviewed on Nov 7, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,310

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (39 reviews)

Lovely property. Staff service inconsistent overall. Room was not serviced one day. On the day there was construction above pool area, no notice was sent out. Pool area staff/manager and construction crew didn't seem to be on the same page.

Reviewed on Nov 13, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,094

per person

Dec 22 - Dec 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Cavalier Hotel South Beach

South Beach

$461

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,004 reviews)

Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.

Reviewed on Nov 4, 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

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.

Hurricane Monument

4/5(66 reviews)

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

$265 nightly

$299 total

Nov 30 - Dec 1

Total with taxes and fees

9/10 Wonderful! (1,259 reviews)

Beautiful grounds, immaculate rooms, divine sushi and meals! The pier is nonstop entertainment for kids, especially if they fish. There are activities for everyone in your family. Highly recommend this resort!

Reviewed on Nov 13, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$184 nightly

$208 total

Nov 16 - Nov 17

Total with taxes and fees

9.2/10 Wonderful! (1,564 reviews)

Nice place, good location, friendly staff, clean room, good food, beat views, easy access to pool and beach.

Reviewed on Nov 9, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$205 nightly

$231 total

Nov 30 - Dec 1

Total with taxes and fees

8.8/10 Excellent! (1,245 reviews)

The rooms were clean, staff was friendly and helpful, food was delicious, the property was beautiful and loved how there was connections to the other resorts through van transportation or the Rum runner boat! Would definitely stay again!

Reviewed on Nov 8, 2025

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.