Name: Chesapeake Beach Resort
Price range: $273 total
Rating: 9.2

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The Latest Upper Matecumbe Key vacation packages

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

Hyatt Place Miami Airport-East

Palmer Lake

$342

per person

Apr 5 - Apr 10

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (2,247 reviews)

Good hotel, but lights went and elevators didn't work.

Reviewed on Feb 1, 2026

Cavalier Hotel South Beach

South Beach

$432

per person

Apr 5 - Apr 10

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

Prime location within walking distance to all the hot spots. Included are 2 beach chairs with towels per day. Philip at the concierge received us warmly…checking us in early and giving us great recommendations. Room was a great size, A/C, with bathroom amenities. Overall, totally recommend.

Reviewed on Jan 31, 2026

Creekside Inn

$523

per person

Mar 23 - Mar 27

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

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,440

per person

Apr 5 - Apr 10

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Solé Miami, A Noble House Resort

Ocean Four

$657

per person

Apr 5 - Apr 10

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,935 reviews)

Was ok stay the hotel is nice but the pool area is very poor and the pool is not heated , the elevators are so slow other wise the rooms are clean and the staff is nice and helpful great locating on the beach

Reviewed on Feb 1, 2026

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Discover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center

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

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

$242 nightly

$273 total

Feb 3 - Feb 4

Total with taxes and fees

9.2/10 Wonderful! (1,658 reviews)

Spacious clean room. Good linens and towels with comfortable beds. Staff very helpful. Elevator was broken but staff carried bags up,

Reviewed on Feb 1, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$346 nightly

$390 total

Feb 3 - Feb 4

Total with taxes and fees

9.2/10 Wonderful! (1,289 reviews)

Great staff and beautiful property

Reviewed on Jan 29, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$306 nightly

$345 total

Feb 9 - Feb 10

Total with taxes and fees

8.8/10 Excellent! (1,259 reviews)

We enjoyed our stay and found the staff to be courteous and responsive. Our room was a generous size, clean and well appointed (as is often the case we wouldn’t have said no to a couple of more outlets lol). The beach and pool areas had plenty of seating and multiple things to do—ping pong, cornhole, ...

Reviewed on Jan 26, 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.