Upper Matecumbe Key Holidays from NZ$2,791

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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
Price was NZ$4,242, price is now NZ$2,791 per person
NZ$2,791
per person
19 Feb - 23 Feb
found 24 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Main road in front of hotel was closed. When we arrived, the concierge had no idea where to tell us to park. If they were transparent about it, ok. I would be ok. Then they said they are out of the 'free' wine, but could charge me $8 for a Heineken. Then couldn't get the elevator to work (we were on the 2nd floor thank God) The room was in good shape. The parking is what set off the chain for me. It's not hard to update a website. Or at least tell your staff what to say. Ended up parking in the City parking garage. I'd give it like a 75/100.

Reviewed on 6 Jan 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 NZ$37,372, price is now NZ$19,614 per person
NZ$19,614
per person
19 Feb - 23 Feb
found 24 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
8/10 Very Good! (1 review)
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
Price was NZ$6,278, price is now NZ$4,023 per person
NZ$4,023
per person
19 Feb - 23 Feb
found 24 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
The holding fee is ridiculously high

Reviewed on 8 Jan 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was NZ$4,172, price is now NZ$2,914 per person
NZ$2,914
per person
19 Feb - 23 Feb
found 24 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Very nice staff, helpful. The only thing is you have to walk through the back alley to go to breakfast. Lol. But rather than that we enjoyed it very much! Will recommend to friends and family!

Reviewed on 9 Jan 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was NZ$3,911, price is now NZ$2,795 per person
NZ$2,795
per person
19 Feb - 23 Feb
found 24 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Overall is nice. However, i think it will be even better if there is toothbrush and paste

Reviewed on 8 Jan 2026

Upper Matecumbe Key Holiday

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 NZ$454 per night from 28 Jan to 29 Jan
NZ$454
28 Jan - 29 Jan
includes taxes & fees
9.2/10 Wonderful! (1,625 reviews)
The resort is a great family friendly atmosphere. The staff was extremely hospitable. The beach is clean and lots of fun activities to do. Only wish we had more time!

Reviewed on 6 Jan 2026

Chesapeake Beach Resort
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 NZ$639 per night from 29 Jan to 30 Jan
NZ$639
29 Jan - 30 Jan
includes taxes & fees
9.2/10 Wonderful! (1,283 reviews)
Fantastic resort, will definitely be heading back!

Reviewed on 4 Jan 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 NZ$533 per night from 22 Jan to 23 Jan
NZ$533
22 Jan - 23 Jan
includes taxes & fees
8.8/10 Excellent! (1,273 reviews)
All issues were addressed quickly and professionally. Room was large/ spacious. Views were gorgeous. Tiki bar staff was awesome.

Reviewed on 4 Jan 2026

Amara Cay Resort
See all 2,793 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.

Discover the most popular places to visit in Upper Matecumbe Key

History of Diving Museum

History of Diving Museum

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

History of Diving Museum

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.