Name: Islander Resort
Price range: $308 total
Rating: 9.4

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.

MirabileCondoDwntown MIA Brickell w PRKG

Downtown Miami

$403

per person

Jul 24 - Jul 26

found 1 hour ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

2/10 (2 reviews)

3BR Pool House Sleeps 8

Driftwood

$744

per person

Jul 15 - Jul 19

found 14 hours ago

Roundtrip flight included

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

No reviews

The W - Bayshore Unit 1003

East Fort Lauderdale

$583

per person

Jul 2 - Jul 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

6/10 (2 reviews)

I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.

Reviewed on May 20, 2026

Brickell Bay 3318

Brickell

$743

per person

Jul 8 - Jul 13

found 3 hours ago

Roundtrip flight included

New York (JFK) to Miami (MIA)

No reviews

Brickell Bay 3505

Brickell

$538

per person

Jul 13 - Jul 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.4/10 Exceptional! (3 reviews)

Great place and location! The pool was amazing.

Reviewed on May 9, 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

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$228 nightly

$257 total

May 28 - May 29

Total with taxes and fees

9.2/10 Wonderful! (1,731 reviews)

"Very noise…"

Reviewed on May 24, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$264 nightly

$297 total

May 26 - May 27

Total with taxes and fees

9.2/10 Wonderful! (1,313 reviews)

"Very efficient checkin, clean and spacious room and friendly staff. Convenient to everything Islamorada"

Reviewed on May 24, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$274 nightly

$308 total

Jun 7 - Jun 8

Total with taxes and fees

9.4/10 Exceptional! (1,017 reviews)

"Absolutely beautiful property, clean and well maintained. Staff was super friendly and there was lots of complimentary activities for the whole family. 10/10 we will absolutely be back."

Reviewed on May 24, 2026

See all 2,812 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.