Upper Matecumbe Key Trip

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Top Upper Matecumbe Key Flight + Hotel Deals

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

Barcelona Studios Guesthouse

South Beach
Save 100% on your flight
₹45,745
per person
10 Nov - 16 Nov
found 24 hours ago
Return flight included
New York (JFK) to Miami (MIA)
9.4/10 Exceptional! (267 reviews)
Great but no tv in the room

Reviewed on 30 Sept 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
₹1,290,125
per person
21 Nov - 28 Nov
found 2 hours ago
Return direct flight included
Toronto (YYZ) 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 22 Jun 2016

Lyfe Resort & Residences

Lyfe Resort & Residences

Hollywood Beach
Save 100% on your flight
₹130,227
per person
21 Nov - 28 Nov
found 2 hours ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
7.8/10 Good! (36 reviews)
Miami Vacation Rentals - Downtown

Miami Vacation Rentals - Downtown

Downtown Miami
Save 100% on your flight
₹79,848
per person
10 Nov - 16 Nov
found 24 hours ago
Return flight included
New York (JFK) to Miami (MIA)
9/10 Wonderful! (92 reviews)
Beware! The parking is not as advertised and cost a fortune. The room was noisy at night making sleep difficult due to noisy air conditioner. The staff at the hotel was quite unfriendly and was quite unhelpful. And most of all getting in touch with Expedia was impossible to achieve, even as I write this review they have not responded to my claims.

Reviewed on 4 Oct 2026

EAST Miami

EAST Miami

Brickell
Save 100% on your flight
₹154,053
per person
10 Nov - 16 Nov
found 24 hours ago
Return flight included
New York (JFK) to Miami (MIA)
9.2/10 Wonderful! (4,151 reviews)
Great location and staff were very friendly.

Reviewed on 6 Oct 2026

Top hotels in Upper Matecumbe Key

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
₹15,836
₹24,859 total
19 Oct - 20 Oct
includes taxes & fees
9.2/10 Wonderful! (1,474 reviews)
"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"

Reviewed on 6 Oct 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
₹13,655
₹20,779 total
8 Oct - 9 Oct
includes taxes & fees
Chesapeake Beach Resort
Islander Resort

Islander Resort

82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
₹25,631
₹35,877 total
27 Oct - 28 Oct
includes taxes & fees
9.4/10 Exceptional! (1,133 reviews)
"Muy buenas condiciones , recomendado para una experiencia inolvidable"

Reviewed on 6 Oct 2026

Islander Resort
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.

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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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

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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Frequently asked questions

How much does an Upper Matecumbe Key holiday package cost?
Starting from a low ₹45,745, a package is your passport to low-cost travel. Custom make your Upper Matecumbe Key getaway by selecting from our huge range of hotels, airfares and rental cars.
How do I get a cheap travel package to Upper Matecumbe Key?
You'll save loads of cash if you combine your hotels, flights and car rentals into an Upper Matecumbe Key holiday package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, so you'll always have plenty of variety to choose from. Eager to save even more? Add some exciting activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
How far in advance should I book my Upper Matecumbe Key holiday?
While prices change frequently, we generally suggest booking your spot as soon as possible. Many international airfares are available on Expedia up to a year in advance. If you're booking late, you may still get lucky. Cheap tickets to Upper Matecumbe Key sometimes appear just weeks before departure.
What does an Expedia Upper Matecumbe Key travel package include?
Flights, car rentals and hotels — we connect you to the very best bargains. All you'll have to do is figure out your preferred combination. After you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it easy to put together an exciting Upper Matecumbe Key escape.
What should I know before booking an Upper Matecumbe Key travel package?
We already have low prices. However, you'll enjoy an even better deal if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and loads of choice.
Can I choose my airline with an Upper Matecumbe Key Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You're in control. We have access to more than 550 airline partners worldwide, so you have lots of choice when putting together your Upper Matecumbe Key adventure.
If I'm not able to travel, can I cancel my Upper Matecumbe Key holiday package?
You sure can, and we'll help you every step of the way. You may be able to amend or cancel your Upper Matecumbe Key holiday package for free within 24 hours of booking. However, you may be charged a fee by your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, look up our Customer Service Portal for more information.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.