Upper Matecumbe Key Holidays from AU$2,126

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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
per person
16 Aug - 19 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.

Reviewed on 1 Jul. 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
16 Aug - 19 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (1,189 reviews)
The staff was incredibly nice, the property itself was beautiful. For the price of my stay, I believe some services and amenities should have been included.

Reviewed on 1 Jul. 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
per person
16 Aug - 19 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.4/10 Very Good! (1,596 reviews)
Stayed in the villa, premium king room. Convinient location. Close to the beach, transportation, shops, dinning. Beach towels nice touch, just need to upgrade inventory. The pool is not too big and not very clean. Pool bar should be considered. Breakfast overall was good, except scrambled eggs for 4 days. Perhaps give other options on alternating days. We requested clean towels after 48 hrs since nothing is drying in the room. No housekeeping issues. Hooks on the wall would be very handy to hang clothes and towels. Overall good vibe hotel.

Reviewed on 4 Jul. 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
per person
16 Aug - 19 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (3,178 reviews)
Loved the ambience, food, and drinks. We will definitely be coming back!

Reviewed on 2 Jul. 2025

Hilton Miami Airport Blue Lagoon

Hilton Miami Airport Blue Lagoon

4 out of 5
per person
16 Aug - 19 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8/10 Very Good! (3,160 reviews)
Great Hotel and will stay here again, however i will not book through Expedia.

Reviewed on 2 Jul. 2025

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

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$485 per night from 23 July to 24 July
AU$485
23 July - 24 July
includes taxes & fees
9/10 Wonderful! (1,483 reviews)
"The staff was amazing and attentive. The rooms were comfortable and clean. There was some debris just outside the pool area near the seasonal resident carports."

Reviewed on 30 Jun. 2025

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 AU$407 per night from 6 July to 7 July
AU$407
6 July - 7 July
includes taxes & fees
8.8/10 Excellent! (1,223 reviews)
"Place was clean and the amenities are really nice. This is our third time in this hotel and we missed the store to buy essentials and souvenirs and we missed also the ice creams options, the ice cream fridge was empty."

Reviewed on 30 Jun. 2025

Amara Cay Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$354 per night from 14 July to 15 July
AU$354
14 July - 15 July
includes taxes & fees
9/10 Wonderful! (1,118 reviews)
Great Family weekend
"Great Resort. Family loved it ! Gary the server in Sushi restaurant was awesome."

Reviewed on 29 Jun. 2025

Cheeca Lodge & Spa
See all 2,749 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

Frequently asked questions

How much does an Upper Matecumbe Key holiday package cost?
Starting from a low AU$2,126, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.