Upper Matecumbe Key Holidays

Photo by Cameron Abbott

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Top Flight + Hotel Deals in Upper Matecumbe Key

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

President Hotel

3.5 out of 5
South Beach
Price was €1,725, price is now €1,010 per person
€1,010
per person
31 Jan - 7 Feb
found 19 hours ago
Return flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
A great location and friendly service.

Reviewed on 16 Dec 2025

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 €23,715, price is now €10,900 per person
€10,900
per person
31 Jan - 7 Feb
found 19 hours ago
Return flight included
Dublin (DUB) to Miami (MIA)
8/10 Very Good! (1 review)
EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Price was €3,898, price is now €2,166 per person
€2,166
per person
31 Jan - 7 Feb
found 19 hours ago
Return flight included
Dublin (DUB) to Miami (MIA)
9/10 Wonderful! (84 reviews)
Great location and hotel.

Reviewed on 8 Dec 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was €5,023, price is now €2,800 per person
€2,800
per person
31 Jan - 7 Feb
found 19 hours ago
Return flight included
Dublin (DUB) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
We love the 1 hotel! Staff are friendly and helpful and the facilities are immaculate. Room was gorgeous and the food on property was phenomenal. We loved being on the beach and having access to lounge chairs and towels- also so nice to have waiter service on the beach and at the pools!

Reviewed on 13 Dec 2025

EAST Miami

EAST Miami

5 out of 5
Brickell
Price was €3,296, price is now €1,849 per person
€1,849
per person
31 Jan - 7 Feb
found 19 hours ago
Return flight included
Dublin (DUB) to Miami (MIA)
9.2/10 Wonderful! (3,553 reviews)
I had a wonderful stay at East Miami hotel! The staff were incredibly friendly and helpful, always going above and beyond to make sure I had everything I needed. The food was delicious, with a great variety of options to choose from. Plus, the hotel was impeccably clean, which is always a huge plus. I highly recommend this hotel to anyone looking for an enjoyable getaway.

Reviewed on 15 Dec 2025

Top hotels in Upper Matecumbe Key

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 €184 per night from 17 Dec to 18 Dec
€184
17 Dec - 18 Dec
includes taxes & fees
9.2/10 Wonderful! (1,595 reviews)
Idyllic beautiful beach setting, clean comfortable rooms, lovely setting.

Reviewed on 14 Dec 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is €282 per night from 6 Jan to 7 Jan
€282
6 Jan - 7 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,265 reviews)
very nice staff, quiet and comfortable

Reviewed on 10 Dec 2025

Amara Cay 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 €267 per night from 18 Dec to 19 Dec
€267
18 Dec - 19 Dec
includes taxes & fees
9.2/10 Wonderful! (1,267 reviews)
Everything was awsome

Reviewed on 7 Dec 2025

Cheeca Lodge & Spa
See all 2,818 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.

Popular places to visit

Bud n' Mary's Dive Center

4.5/5(3 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

Bud n' Mary's Dive Center

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.