Name: Chesapeake Beach Resort
Price range: $185 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.

May-Dee Suites

Hollywood Hills

Save 100% on your flight

$325

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,381 reviews)

Highly recommend for a clean friendly quiet place to stay

Reviewed on Sep 12, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,788

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)

Henrosa Hotel

South Beach

Save 100% on your flight

$363

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (818 reviews)

Beach staff was rude.

Reviewed on Sep 8, 2025

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$391

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Great staff. Nice rooms close to beach

Reviewed on Sep 2, 2025

Sunset Cove Beach Resort

Save 100% on your flight

$614

per person

Nov 6 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (1,007 reviews)

We always love staying here. So relaxing and fun.

Reviewed on Sep 15, 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

$188 nightly

$212 total

Sep 21 - Sep 22

Total with taxes and fees

9/10 Wonderful! (1,197 reviews)

"Exceptional customer service, a plethora of activities and in a central location with many desirable businesses within a close reach."

Reviewed on Sep 16, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$164 nightly

$185 total

Sep 23 - Sep 24

Total with taxes and fees

9.2/10 Wonderful! (1,529 reviews)

Relaxation 😌

"Such a relaxing and fun spot. Enjoyed snorkeling every day at sunrise and sunset 😍 Can't wait for my next stay 🤗"

Reviewed on Sep 15, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$225 nightly

$254 total

Sep 21 - Sep 22

Total with taxes and fees

8.8/10 Excellent! (1,247 reviews)

"Great hotel with a perfect location and friendly staff."

Reviewed on Sep 13, 2025

See all 2,798 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.