Upper Matecumbe Key Vacations from ₩2,680,548

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The Latest Upper Matecumbe Key Vacation Packages

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

President Hotel

3.5 out of 5
South Beach
Price was ₩3,459,599, price is now ₩2,680,548 per person
₩2,680,548
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Seoul (SEL) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Clean room, good location, close to ocean. Room was in a side building with card security on elevator. Nothing fancy, but met our needs for a pre-cruise place. Lots of fun restaurants a stroll away.

Reviewed on Feb 14, 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 ₩26,986,318, price is now ₩13,848,492 per person
₩13,848,492
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Seoul (SEL) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was ₩3,999,530, price is now ₩2,878,608 per person
₩2,878,608
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Seoul (SEL) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Bed was comfortable. Vibe was funky and cool. Staff was friendly and helpful.

Reviewed on Feb 12, 2026

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Price was ₩5,287,217, price is now ₩3,853,894 per person
₩3,853,894
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Seoul (SEL) to Miami (MIA)
9.2/10 Wonderful! (3,553 reviews)
Everything was amazing!

Reviewed on Feb 14, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ₩3,632,410, price is now ₩2,756,368 per person
₩2,756,368
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Seoul (SEL) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Great location and I messed up our reservation dates and they graciously worked with me to change to the correct dates

Reviewed on Feb 14, 2026

Find the Best Upper Matecumbe Key Vacation Packages

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 ₩547,208 per night from Feb 22 to Feb 23
₩547,208
₩721,203 total
Feb 22 - Feb 23
includes taxes & fees
9.2/10 Wonderful! (1,301 reviews)
Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs.

Reviewed on Feb 9, 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 ₩629,577 per night from Feb 17 to Feb 18
₩629,577
₩789,489 total
Feb 17 - Feb 18
includes taxes & fees
9.2/10 Wonderful! (1,654 reviews)
Just perfect

Reviewed on Feb 12, 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 ₩535,044 per night from Feb 25 to Feb 26
₩535,044
₩707,511 total
Feb 25 - Feb 26
includes taxes & fees
8.8/10 Excellent! (1,270 reviews)
Great staff, good view from room and breakfast was superb. Thanks.

Reviewed on Feb 10, 2026

Amara Cay Resort
See all 2,819 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.

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 travelers 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 vacation 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.