Upper Matecumbe Key Holidays

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Top Flight + Hotel Deals in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Price was €1,979, price is now €1,373 per person
€1,373
per person
25 Jul - 31 Jul
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very Good! (8,315 reviews)
Excellent hotel will Stay again

Reviewed on 15 Jun 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 €14,770, price is now €7,111 per person
€7,111
per person
26 Jul - 31 Jul
found 8 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8/10 Very Good! (1 review)
The Setai Private Luxury Residences

The Setai Private Luxury Residences

5 out of 5
South Beach
Price was €7,432, price is now €4,603 per person
€4,603
per person
26 Jul - 31 Jul
found 8 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
No reviews
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was €3,536, price is now €2,225 per person
€2,225
per person
25 Jul - 31 Jul
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.4/10 Exceptional! (1,545 reviews)
Room cleaning was very late in the afternoon!

Reviewed on 15 Jun 2026

EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Price was €2,406, price is now €1,725 per person
€1,725
per person
26 Jul - 31 Jul
found 8 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.2/10 Wonderful! (133 reviews)
This is my new hotel for Miami trip. Great location and everything was great! Love this place.

Reviewed on 8 Jun 2026

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 €232 per night from 18 Jun to 19 Jun
€232
18 Jun - 19 Jun
includes taxes & fees
9.2/10 Wonderful! (1,759 reviews)
"Staff was very helpful and friendly. 2 pools are great as is free kayaks and paddle boards. Breakfast cooked to order and delicious. 6&4 yr old grandkids had a ball. This is our 2nd time staying here."

Reviewed on 15 Jun 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 €295 per night from 13 Jul to 14 Jul
€295
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (1,333 reviews)
"We had a wonderful stay and really loved the resort. The room and balcony were absolutely perfect. My one suggestion would be to consider making one of the two beachfront pools adults-only. There is already an adults-only pool on the property, which is a nice option, but it’s located in the middle ..."

Reviewed on 15 Jun 2026

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is €307 per night from 22 Jun to 23 Jun
€307
22 Jun - 23 Jun
includes taxes & fees
9.4/10 Exceptional! (1,056 reviews)
"We were only there one night."

Reviewed on 15 Jun 2026

Islander Resort
See all 2,778 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.

Stay near popular Upper Matecumbe Key attractions

Islamorada_BudnMarysDiveCenter_6069243-0004

Bud n' Mary's Dive Center

8.8/5 (504 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.
See properties

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.