Upper Matecumbe Key Vacation Packages 2026 from $886

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The Latest Upper Matecumbe Key vacation packages

Price found within the past 48 hours. Click for updated prices.

President Hotel Villa

South Beach

Save 100% on your flight

$886

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,000 reviews)

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$934

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,008 reviews)

The Local House

South Beach

Save 100% on your flight

$955

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,001 reviews)

The hotel has a great atmosphere. The check in lady was very nice she explained everything on details . Beach was just a block from the hotel . Love this hotel and definitely recommend it . Restaurant is downstairs too and very convenient

Reviewed on Oct 5, 2026

1 Hotel South Beach

South Beach

Save 100% on your flight

$2,584

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,654 reviews)

All good overall.

Reviewed on Oct 8, 2026

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$971

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Overall my stay here was great, easy access to the beach with beach chairs. Staff is helpful and welcoming. The room was okay, seemed a little old and in the shower the soap holder was broke. Great place to stay if you are looking for something with, pool and access to beach.

Reviewed on Oct 6, 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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Florida Keys Brewing Co.

9.2/10 (520 reviews)

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

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A building with a blue facade, a large mural of a diving scene, and a statue of a diver.

History of Diving Museum

9.0/10 (177 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.

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A stone monument with a relief sculpture, surrounded by palm trees and a clear blue sky.

Hurricane Monument

8.6/10 (250 reviews)

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

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Islamorada Brewery & Distillery

9.4/10 (8 reviews)

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

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MoradaWay Arts & Cultural District

Enjoy an outing to MoradaWay Arts & Cultural District during your stay in Islamorada.

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Lorelei Restaurant & Cabana Bar

After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.

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beach near Islamorada

Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?

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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

$186 nightly

$209 total

Oct 13 - Oct 14

Total with taxes and fees

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$185 nightly

$208 total

Oct 18 - Oct 19

Total with taxes and fees

Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$316 nightly

$355 total

Oct 20 - Oct 21

Total with taxes and fees

See all 2,714 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.