Upper Matecumbe Key Holidays from AU$2,910

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The Latest Upper Matecumbe Key Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Miami International Airport Hotel

Miami International Airport Hotel

3 out of 5
Price was AU$3,474, price is now AU$2,910 per person
AU$2,910
per person
14 May - 18 May
found 7 hours ago
Return flight included
Melbourne (MEL) to Miami (MIA)
7.8/10 Good! (5,362 reviews)
Clean room. Staff this visit got me checked in and my room key. Nothing additional such as a smile, thank you or even a welcome, which is mostly the norm everywhere now. No extras such as water or coffee. But its perfect if you just need a bed for the night. Personally, i would stay again due to proximity.

Reviewed on 12 Apr 2026

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was AU$4,644, price is now AU$3,529 per person
AU$3,529
per person
14 May - 18 May
found 7 hours ago
Return flight included
Melbourne (MEL) to Miami (MIA)
9.4/10 Exceptional! (151 reviews)
While the hotel was great in all the different categories the staff going out of their way to help stood out the most. I had some issues with parking and really appreciated the efforts they went to resolve them!

Reviewed on 25 Mar 2026

Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Price was AU$4,264, price is now AU$3,336 per person
AU$3,336
per person
14 May - 18 May
found 7 hours ago
Return flight included
Melbourne (MEL) to Miami (MIA)
8.6/10 Excellent! (1,362 reviews)
The room was ok but someone knocked on our door at 12am and it was very unsettling

Reviewed on 11 Apr 2026

Gale Miami Hotel and Residences

Gale Miami Hotel and Residences

4 out of 5
Downtown Miami
Price was AU$3,562, price is now AU$2,940 per person
AU$2,940
per person
14 May - 18 May
found 7 hours ago
Return flight included
Melbourne (MEL) to Miami (MIA)
8.8/10 Excellent! (1,617 reviews)
I enjoyed my stay. It was clean. Parking is just a headache and costly. Food was expensive. Three breaks meals shouldn’t be almost $160. That’s ridiculous. Overall, I was comfortable in my suite because it was clean and fresh. Every hotel room should have a microwave by the way. That was the most disappointing thing.

Reviewed on 13 Apr 2026

Residence at the Four Seasons

Residence at the Four Seasons

3.5 out of 5
Brickell
Price was AU$4,848, price is now AU$4,064 per person
AU$4,064
per person
14 May - 18 May
found 7 hours ago
Return flight included
Melbourne (MEL) to Miami (MIA)
9.6/10 Exceptional! (5 reviews)
Unit, amenities, service, location - all top notch

Reviewed on 12 Apr 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$513 per night from 3 May to 4 May
AU$513
3 May - 4 May
includes taxes & fees
9.2/10 Wonderful! (1,316 reviews)
The rooms we were in were definitely tired with thin walls. You could hear everything in the room next door. The golf course lodging probably needs to be torn down and rebuilt. The property/location was great and the staff were super friendly.

Reviewed on 12 Apr 2026

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$368 per night from 14 May to 15 May
AU$368
14 May - 15 May
includes taxes & fees
9.2/10 Wonderful! (1,700 reviews)
Great location, access to the water front. Very nice and quiet atmosphere. Excellent made to order breakfast and other options.

Reviewed on 12 Apr 2026

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$548 per night from 3 May to 4 May
AU$548
3 May - 4 May
includes taxes & fees
8.8/10 Excellent! (1,276 reviews)
Great location. Eat at Lazy Days next door and Flagler Station if you want more upscale. They have a water taxi that unfortunately we didn’t get to go on because it was so windy but hope to go again and get on it next time.

Reviewed on 12 Apr 2026

Amara Cay Resort
See all 2,789 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.