Upper Matecumbe Key Vacation Packages 2026 from $496

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The Latest Upper Matecumbe Key vacation packages

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$496

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,008 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,321

per person

Nov 15 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

President Hotel

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)

8.4/10 Very Good! (2,812 reviews)

Todo bien mi recomendación es q la piscina la cierren más tarde . Porque uno hace el chekin in a las 3 sin contar q no haiga personas x delante en la recepción mientras uno sube q la habitación se instala 4 y media 5 ! Y si sale a comer algo por lo del viaje q uno llega con hambre por ahí a las 6 llega ya no le da tiempo a uno de disfrutar la piscina porque la cierran a las 7 pues en mi caso q solo me hospede 1 dia ! Del resto todo bien gracias 🎉

Reviewed on Oct 7, 2026

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)

The Local House

South Beach

Save 100% on your flight

$955

per person

Dec 17 - Dec 23

found 12 hours 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

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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

9.2/10 Wonderful! (1,799 reviews)

"Boo"

Reviewed on Oct 7, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$317 nightly

$356 total

Oct 15 - Oct 16

Total with taxes and fees

9.4/10 Exceptional! (1,134 reviews)

"We got the poolside cabana king and it was perfect! Resort was immaculate! Already want to go back!"

Reviewed on Oct 6, 2026

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.