Name: Chesapeake Beach Resort
Price range: $294 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.

Creekside Inn

$556

per person

May 18 - May 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

7.8/10 Good! (1,002 reviews)

Comfortable rooms right in town but also right on the canal

Reviewed on Apr 7, 2026

Casablanca Miami Beach

North Beach

$2,126

per person

Jun 17 - Jun 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

5.8/10 (322 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

President Hotel

South Beach

$1,256

per person

Jun 20 - Jun 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.4/10 Very Good! (2,145 reviews)

Nice and helpful front desk staff 1 block from Ocean Drive and the heart of South Beach Small touch for the birthday guest Full breakfast

Reviewed on Apr 7, 2026

Cavalier Hotel South Beach

South Beach

$1,584

per person

Jun 20 - Jun 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Its my fourth time there and i loved it

Reviewed on Apr 6, 2026

Carillon Miami Wellness Resort

North Beach

$745

per person

Jun 14 - Jun 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.8/10 Excellent! (788 reviews)

Everything about this place is just wonderful! It started with the staff on check in. The room was so nice and clean. The view was not right in front of the room, but still a great view. The housekeeping was fantastic. The health and spa check in was welcoming and the spa experience was a total removal from the everyday stress of life. My daughter and I also loved the pool and hot tub. Again the staff there was amazing as well. The beach is area from the beach and there is a boardwalk and fitness area to enjoy. Our Easter was extra special thanks to this experience.

Reviewed on Apr 7, 2026

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Discover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center

4.5/5(142 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 family-friendly 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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$315 nightly

$354 total

Apr 29 - Apr 30

Total with taxes and fees

9.2/10 Wonderful! (1,310 reviews)

Amazing! Loved everything can’t wait to go back!!

Reviewed on Apr 5, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$262 nightly

$294 total

May 4 - May 5

Total with taxes and fees

9.2/10 Wonderful! (1,690 reviews)

Beautiful property and the beach is nice, calm, and quiet. The made to order breakfasts every morning were absolutely amazing and delicious! My only complaint was that we explored Islamorada and did adventures during the day off the property. When we came back after dinnertime, we wanted to use some ...

Reviewed on Apr 7, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

$291 nightly

$328 total

Apr 20 - Apr 21

Total with taxes and fees

8.8/10 Excellent! (1,267 reviews)

Great

Reviewed on Mar 30, 2026

See all 2,826 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.