Name: Chesapeake Beach Resort
Price range: $304 total
Rating: 9.2

Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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

$361

per person

Apr 13 - Apr 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Room was nice, clean and beautiful view of the airport. A little noisy because of the airport but was nice. Never got to try the breakfast as we had an early flight. Easy check in process, will hold luggage so you don’t have to hold it till you get to check in.

Reviewed on Feb 3, 2026

Pelican Hotel

South Beach

$498

per person

Apr 5 - Apr 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (394 reviews)

A reasonably priced art deco hotel in a popular tourist area. Hotel and rooms are stylishly designed. Restaurant food was ok. Maria was a fabulous server. On the downside, there is no pool or fitness center.

Reviewed on Jan 12, 2026

Casablanca Miami Beach

North Beach

$488

per person

Apr 5 - Apr 10

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

Ilios Rentals

Downtown Miami

$1,035

per person

Apr 16 - Apr 21

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

No reviews

Bentley Hotel South Beach

South Beach

$1,145

per person

Apr 5 - Apr 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (466 reviews)

The room was clean and had all I needed. It was a bit small for the price but on New Years Eve, everything was overpriced. The kitchenette and supplies came in very handy. The balcony was not really usable as it faced an inside courtyard and elevator shaft that lacked privacy and much direct natural light. I would be interested in some of the other rooms if I return.

Reviewed on Feb 2, 2026

Don't see what you're looking for?

See all available trips from Columbus to Upper Matecumbe Key

View all trips

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

$270 nightly

$304 total

Feb 4 - Feb 5

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

$352 nightly

$397 total

Feb 4 - Feb 5

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

$304 nightly

$343 total

Feb 10 - Feb 11

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.