Name: Chesapeake Beach Resort
Price range: $249 total
Rating: 9.2

Photo by Cameron Abbott

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The Latest Upper Matecumbe Key vacation packages

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

Creekside Inn

$409

per person

Mar 5 - Mar 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

The guy at the front desk was very nice. The view from the room was great.

Reviewed on Dec 30, 2025

Miami Downtown Condos

Downtown Miami

$844

per person

Mar 25 - Mar 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (72 reviews)

Amazing customer service! Always there when you need them, no matter the time, or iinquiry! I had an amazing stay, and I’d highly recommend you stay!

Reviewed on Dec 28, 2025

Bay Breeze Premium Apartments By Eskape Collection

$570

per person

Mar 13 - Mar 18

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (189 reviews)

Our two bedroom apartment was very comfortable and quiet. We enjoyed our stay very much.

Reviewed on Dec 30, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,726

per person

Mar 9 - Mar 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

The Shelborne By Proper, a Member of Design Hotels

South Beach

$740

per person

Feb 6 - Feb 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (56 reviews)

Excellent amenities and great location

Reviewed on Dec 31, 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

$221 nightly

$249 total

Jan 14 - Jan 15

Total with taxes and fees

9.2/10 Wonderful! (1,609 reviews)

Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return.

Reviewed on Dec 31, 2025

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$277 nightly

$312 total

Jan 8 - Jan 9

Total with taxes and fees

8.8/10 Excellent! (1,271 reviews)

Was very nice , Did order cookies and brownies for the room Christmas night and that never happened! Fishing pole rental was ridiculous Food was great and good Keylime dessert !

Reviewed on Dec 28, 2025

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$322 nightly

$363 total

Jan 15 - Jan 16

Total with taxes and fees

9.2/10 Wonderful! (1,278 reviews)

Good property but a little dated and understaffed. They are trying and they are hospitable but not a 5 star experience. Still one of the nicer resorts in the area.

Reviewed on Dec 29, 2025

See all 2,808 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.