Upper Matecumbe Key Holidays from £1,327

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Top Upper Matecumbe Key Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Save 100% on your flight
Price was £2,338, price is now £1,327 per person
£1,327
per person
22 Jun - 28 Jun
found 1 day ago
Return flight included
Aberdeen (ABZ) to Miami (MIA)
9/10 Wonderful! (2 reviews)
The room was clean, there was a problem at the check out time as all the guest have the same check out and all the elevators collapse, it took us more than an hour to get down. The parking is really a problem as we had to go up almost 20 floors. Location is pretty good.

Reviewed on 14 Apr 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 £29,832, price is now £13,892 per person
£13,892
per person
21 Jun - 28 Jun
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Miami (MIA)
8/10 Very Good! (1 review)
Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Save 100% on your flight
Price was £4,354, price is now £2,189 per person
£2,189
per person
21 Jun - 28 Jun
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Miami (MIA)
8.2/10 Very Good! (151 reviews)
The room was overall good order and clean. 5 Star is reserved for properties that go above and beyond with details and exceed expectations. This property was great with regards to cleanliness, but not 5 star. Minor details, small spots here and there and other fine details that can be overlooked but keeps it from a 5 star rating

Reviewed on 1 May 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was £3,286, price is now £1,870 per person
£1,870
per person
21 Jun - 28 Jun
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Miami (MIA)
8.6/10 Excellent! (1,003 reviews)
I spent 3 days and was amazing, the location was incredible, the room beautiful, air conditioned and elevator worked and was good, the only problem is that they gibe you chairs for the beach and then they force you to pay for umbrella, I would rather dont have anything but the sneaky way the umbrella people worked was not good. But to be honest I would go back to that hotel many many more times, it was as beautiful as it was on the pictures and more.

Reviewed on 29 Apr 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was £3,023, price is now £1,736 per person
£1,736
per person
21 Jun - 28 Jun
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Miami (MIA)
8.4/10 Very Good! (2,272 reviews)
Breakfast and location are great!

Reviewed on 2 May 2026

Upper Matecumbe Key Essential Information

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

Top hotels in Upper Matecumbe Key

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 £274 per night from 10 May to 11 May
£274
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (1,318 reviews)
Yes

Reviewed on 2 May 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 £189 per night from 4 May to 5 May
£189
4 May - 5 May
includes taxes & fees
9.2/10 Wonderful! (1,706 reviews)
Fantastic breakfast, not over crowded. Very relaxing

Reviewed on 2 May 2026

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is £208 per night from 26 May to 27 May
£208
26 May - 27 May
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Wonderful resort. Immaculate grounds. Just a very happy place.

Reviewed on 30 Apr 2026

Islander Resort
See all 2,810 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.

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. Flight-inclusive packages are ATOL protected.