Upper Matecumbe Key Holidays from AU$617

Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Upper Matecumbe Key Holiday Deals

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
Save 100% on your flight
Price was AU$1,155, price is now AU$617 per person
AU$617
per person
15 Aug - 19 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Miami (MIA)
8.6/10 Excellent! (1,009 reviews)
Park 15$ a day -

Reviewed on 13 July 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was AU$19,932, price is now AU$9,517 per person
AU$9,517
per person
15 Aug - 19 Aug
found 1 day ago
Return flight included
Atlanta (ATL) 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 June 2016

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Save 100% on your flight
Price was AU$1,164, price is now AU$665 per person
AU$665
per person
15 Aug - 19 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (481 reviews)
Nice place to stay. Comfortable and clean. Good breakfast. Great location.

Reviewed on 12 July 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was AU$2,720, price is now AU$1,564 per person
AU$1,564
per person
15 Aug - 19 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Miami (MIA)
9.4/10 Exceptional! (1,577 reviews)
Amazing

Reviewed on 12 July 2026

Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
Save 100% on your flight
Price was AU$1,000, price is now AU$625 per person
AU$625
per person
27 Sept - 1 Oct
found 1 day ago
Return flight included
New York (NYC) to Miami (MIA)
9.4/10 Exceptional! (228 reviews)
Your staying here for the location. Very old Florida. The a/c was very loud and hard to sleep through and the bed was flimsey and uncomfortable. All the toiletries are in the lobby which if you dont know that can be annoying. There are two cats that roam around very cute. And an adorable area in the back perfect for reading or having a glass of wine.

Reviewed on 13 July 2026

Upper Matecumbe Key Holiday

Upper Matecumbe Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)

Our pick of the best Upper Matecumbe Key Hotel Deals

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 AU$379 per night from 9 Aug to 10 Aug
AU$379
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,348 reviews)
"First visit to Cheeca was 2008. The property grounds are still gorgeous and the staff still lovely BUT the room and facilities are not what you would expect of a resort of this caliber and reputation. There was visible grime in our room, on walls, floorboards, mirrors, light switches and damaged ..."

Reviewed on 13 July 2026

Cheeca Lodge & Spa
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 AU$363 per night from 19 July to 20 July
AU$363
19 July - 20 July
includes taxes & fees
8.8/10 Excellent! (1,296 reviews)
"."

Reviewed on 13 July 2026

Amara Cay Resort
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 AU$348 per night from 3 Aug to 4 Aug
AU$348
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (1,760 reviews)
"The room was clean and we had plenty of towels and bathroom supplies. The made to order omelets were delicious and there were plenty of other options to choose from, however the staff doing the cooking was a bit on the slow side."

Reviewed on 13 July 2026

Chesapeake Beach Resort
See all 2,747 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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 AU$617, 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.

Explore a world of travel with Expedia

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