Upper Matecumbe Key Holidays

Photo by Cameron Abbott

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Top Flight + Hotel Deals in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was €772, price is now €455 per person
€455
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Washington (DCA) to Miami (MIA)
8.6/10 Excellent! (1,012 reviews)
Restaurant customer service improves

Reviewed on 30 Jul 2026

Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Price was €1,471, price is now €787 per person
€787
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Washington (DCA) to Miami (MIA)
8.6/10 Excellent! (1,439 reviews)
Just beautiful!!

Reviewed on 31 Jul 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was €1,432, price is now €806 per person
€806
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Washington (DCA) to Miami (MIA)
8.2/10 Very good! (1,167 reviews)
Very good free breakfast , room was ready before the check in time

Reviewed on 28 Jul 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Price was €1,265, price is now €730 per person
€730
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Washington (DCA) to Miami (MIA)
8.4/10 Very good! (8,618 reviews)

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Ocean Four
Price was €864, price is now €511 per person
€511
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Washington (DCA) to Miami (MIA)
8.6/10 Excellent! (2,142 reviews)
Extremely nice staff.

Reviewed on 29 Jul 2026

Top hotels in Upper Matecumbe Key

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is €228 per night from 10 Aug to 11 Aug
€228
10 Aug - 11 Aug
includes taxes & fees
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is €196 per night from 5 Aug to 6 Aug
€196
5 Aug - 6 Aug
includes taxes & fees
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is €227 per night from 12 Aug to 13 Aug
€227
12 Aug - 13 Aug
includes taxes & fees
8.8/10 Excellent! (1,286 reviews)
"The property was beautiful"

Reviewed on 30 Jul 2026

Amara Cay Resort
See all 2,776 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 family-friendly area.
See properties

Frequently asked questions

How much does an Upper Matecumbe Key holiday package cost?
Starting from a low €455, 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.