Name: Islander Resort
Price range: $281 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.

Brickell Bay 3505

Brickell

$615

per person

Jul 17 - Jul 20

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (2 reviews)

Great place and location! The pool was amazing.

Reviewed on May 9, 2026

3BR Pool House Sleeps 8

Driftwood

$873

per person

Jul 14 - Jul 19

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

No reviews

The W - Bayshore Unit 1003

East Fort Lauderdale

$744

per person

Jul 2 - Jul 6

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

6/10 (2 reviews)

MirabileCondoDwntown MIA Brickell w PRKG

Downtown Miami

$635

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

2/10 (2 reviews)

Casablanca Miami Beach

North Beach

$2,904

per person

Jul 23 - Jul 28

found 1 hour ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

5.8/10 (323 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

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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 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

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

$240 nightly

$270 total

May 21 - May 22

Total with taxes and fees

9.2/10 Wonderful! (1,738 reviews)

Just

Reviewed on May 12, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$304 nightly

$342 total

May 31 - Jun 1

Total with taxes and fees

9.2/10 Wonderful! (1,330 reviews)

Exelente service but the room need more clean and attention

Reviewed on May 11, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

$250 nightly

$281 total

May 19 - May 20

Total with taxes and fees

9.2/10 Wonderful! (1,013 reviews)

Everything about this property was excellent, from the wonderful staff to the kid-friendly atmosphere. We loved the breakfast brunch and the overall vibe of the place. However, dinner at The Drift was a letdown. For the price, the quality just wasn't there. I’d highly recommend the stay, but I suggest ...

Reviewed on May 10, 2026

See all 2,775 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.