Name: Chesapeake Beach Resort
Price range: $214 total

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.

Cavalier Hotel South Beach

South Beach

$515

per person

Jan 7 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,002 reviews)

Super unique and quaint property. Would absolutely go back again

Reviewed on Oct 26, 2026

Avi Lux Stay

East Fort Lauderdale

$751

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.6/10 Good! (10 reviews)

If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,232

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Broadway Suites Downtown by RocketStay

Coral Way

Save 100% on your flight

$808

per person

Jan 3 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (230 reviews)

Muy bien ubicado, limpio, buena relación precio calidad

Reviewed on Aug 9, 2026

Hotel Riu Plaza Miami Beach

Mid Beach

$630

per person

Jan 7 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

I would recommend to anyone and we will stay again

Reviewed on Oct 26, 2026

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Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 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.

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Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$207 nightly

$233 total

Nov 1 - Nov 2

Total with taxes and fees

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$190 nightly

$214 total

Nov 8 - Nov 9

Total with taxes and fees

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$222 nightly

$250 total

Nov 15 - Nov 16

Total with taxes and fees

8.8/10 Excellent! (1,326 reviews)

"Great property however the rooms could use an update."

Reviewed on Oct 25, 2026

See all 2,752 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.