Name: Chesapeake Beach Resort
Price range: $273 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.

Flow Miami Hotel

Downtown Miami

$420

per person

Mar 16 - Mar 19

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (172 reviews)

Beautiful clean room/apartment. Loved the location and view at night. We walked to our cruise. Staff was also very friendly and helpful. Would stay here again!

Reviewed on Jan 25, 2026

Creekside Inn

$517

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

Bay Breeze Premium Apartments By Eskape Collection

$696

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (189 reviews)

The staff was courteous and helpful. The apartment was equipped with basic essentials. The area was quiet. I would suggest adding oven mittens in the kitchen as there was nothing to use to take the pan out of the oven with.

Reviewed on Jan 21, 2026

Casablanca Miami Beach

North Beach

$590

per person

Apr 12 - Apr 18

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$943

per person

Mar 14 - Mar 21

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Prime location within walking distance to all the hot spots. Included are 2 beach chairs with towels per day. Philip at the concierge received us warmly…checking us in early and giving us great recommendations. Room was a great size, A/C, with bathroom amenities. Overall, totally recommend.

Reviewed on Jan 31, 2026

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Discover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center

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

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

$242 nightly

$273 total

Feb 2 - Feb 3

Total with taxes and fees

9.2/10 Wonderful! (1,651 reviews)

Gorgeous view, very pleasant staff, clean room

Reviewed on Jan 30, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$346 nightly

$390 total

Feb 2 - Feb 3

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

Fully refundableReserve now, pay when you stay

$306 nightly

$345 total

Feb 8 - Feb 9

Total with taxes and fees

8.8/10 Excellent! (1,275 reviews)

The grounds are very well kept, the front desk staff were all very friendly and knowledgeable. The view from the ocen front room was just beautiful. The room and the halls could use a little love but other than that, a perfect stay.

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.