Upper Matecumbe Key Holidays from AU$3,954

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The Latest Upper Matecumbe Key Holiday Deals

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

President Hotel

3.5 out of 5
South Beach
Price was AU$6,078, price is now AU$3,954 per person
AU$3,954
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.4/10 Very Good! (1,825 reviews)
Rooms were clean and front desk staff was very friendly and accommodating on check in!

Reviewed on 13 Oct 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Save 100% on your flight
Price was AU$7,969, price is now AU$4,685 per person
AU$4,685
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.6/10 Excellent! (116 reviews)
Perfect stay!! Def will be going back!

Reviewed on 11 Oct 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Save 100% on your flight
Price was AU$7,913, price is now AU$4,664 per person
AU$4,664
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (334 reviews)
Staff was very nice and accommodating. They went up and beyond to help us.

Reviewed on 12 Oct 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Save 100% on your flight
Price was AU$8,348, price is now AU$5,218 per person
AU$5,218
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (3,369 reviews)
Loveddd everything here! The staffs and front desk were amazing and I loved the location of this hotel. It was my first time in Miami and I’m glad I booked here! I will be booked here again when I’m back!

Reviewed on 12 Oct 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was AU$6,160, price is now AU$3,987 per person
AU$3,987
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.2/10 Very Good! (1,440 reviews)
Always amazing stay at the penguin. Starbucks across street for morning quiet end of the strip and short walk to the other end. Free drinks during check in. We always stay here when coming down to South Beach!!!

Reviewed on 12 Oct 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

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$346 per night from 15 Oct to 16 Oct
AU$346
15 Oct - 16 Oct
includes taxes & fees
9/10 Wonderful! (1,214 reviews)
"Staff was extremely accommodating, Property is stunning with numerous activities."

Reviewed on 6 Oct 2025

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 AU$339 per night from 15 Oct to 16 Oct
AU$339
15 Oct - 16 Oct
includes taxes & fees
9.2/10 Wonderful! (1,536 reviews)
"I had a wonderful stay here with my pet! The hotel is super pet-friendly, which made our trip so easy and enjoyable. There’s plenty of parking, and the view from our room was amazing. I also loved that my favorite buffet was right in the parking lot next door — total bonus! Perfect spot for anyone ..."

Reviewed on 9 Oct 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$322 per night from 15 Oct to 16 Oct
AU$322
15 Oct - 16 Oct
includes taxes & fees
8.8/10 Excellent! (1,254 reviews)
"Room was spacious, clean with a great balcony."

Reviewed on 7 Oct 2025

Amara Cay Resort
See all 2,800 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.
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Frequently asked questions

Can I cancel my flight booking to Upper Matecumbe Key due to COVID-19?
Many airlines now provide more flexibility due to COVID-19. Our convenient Customer Service Portal will help solve most questions about which policies apply to your Upper Matecumbe Key flight. It's also worth scanning over the terms and conditions of your airfare — preferably before you make a booking!
What's the best way to find cheap flights to Upper Matecumbe Key that have flexible change policies?
At Expedia, we've been channeling our inner yogi to help you locate the most flexible fares around town. Just check the "No change fee" box right underneath the filter subheading "Flexible change policies" to find your perfect flight to Upper Matecumbe Key.
What are some of the general tips for travellers to Upper Matecumbe Key during the COVID-19 outbreak?
COVID-19 has brought about significant changes to how we travel. If you're planning a holiday in Upper Matecumbe Key, these tips will help you navigate travel's newest challenges:
  • Look into if any restrictions apply to both your origin and destination. You may not be able to travel depending on local circumstances, so be sure to check before you book.
  • When you go through airport checkpoints, do not remove your face mask. You will be asked to lower it briefly to confirm your identity. Those who refuse to wear a face mask may face civil penalties and may also be escorted from the terminal.
  • Instead of handing a TSA officer your boarding pass, position it straight on the scanner yourself. When that's done, hold it up for inspection.
  • One liquid hand sanitizer container is now permitted in your carry-on luggage. It must be no larger than 12 oz (350 ml), and you'll have to remove it from your bag for X-ray screening.
  • Put any personal items (phone, wallet and keys for example) in your carry-on rather than a bin to minimize handling during screening.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on makes it less likely that a TSA officer will need to open and touch your bag for inspection.

Which airlines fly to Upper Matecumbe Key?
Delta is a widely known airline servicing Upper Matecumbe Key. Book a ticket to Key West Intl. Airport (EYW) and you'll have 191 Delta flights per month to select from.
How can I find cheap tickets to Upper Matecumbe Key?
You'll always pick up a terrific deal with Expedia, but our "flexible dates" search function makes it that much easier. Enter your preferred travel date, then tick the flexible dates box above to see prices for nearby days. was the lowest price for a flight to Upper Matecumbe Key in the last seven days.
How much is a flight to Upper Matecumbe Key?
The price of a round-trip ticket to Upper Matecumbe Key in the last seven days ranged between and . If you were heading one way from (), you could have nabbed an affordable fare from just .
What are the most popular airports to fly into in Upper Matecumbe Key?
Key West Intl. Airport (EYW) is the main point of entry for those hoping to visit Upper Matecumbe Key. Around 1119 flights per month touch down here.
When is the cheapest time to fly to Upper Matecumbe Key?
If you'd rather spend your cash exploring Upper Matecumbe Key rather than on getting there, take off early in the week. The most economical day to fly is usually Tuesday, with Monday a close second. With many folks keeping their travel to weekends, Saturday often has the most expensive airfares.
How much is a plane ticket to Upper Matecumbe Key?
Airfares ranged from to in the last seven days. When you're ready to book, we'll be ready to help you secure the best price to Upper Matecumbe Key.
Which airlines with flights to Upper Matecumbe Key employ COVID-19 cleanliness policies?
In response to the global COVID-19 pandemic, the majority of airlines have introduced new precautionary measures to help their passengers and staff get back in the air. Here are some good examples:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.