Upper Matecumbe Key Vacations from ￥328,984

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The Latest Upper Matecumbe Key Vacation Packages

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 ￥519,826, price is now ￥328,984 per person
￥328,984
per person
Mar 25 - Mar 31
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
AC - do not work or air movement- Only 1 channel for TV - Checking was long and felt distracting to do.

Reviewed on Jan 16, 2026

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Save 100% on your flight
Price was ￥748,328, price is now ￥479,143 per person
￥479,143
per person
Mar 25 - Mar 31
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (3,553 reviews)
I absolutely loved the place. Highly recommend.

Reviewed on Jan 15, 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ￥572,201, price is now ￥372,821 per person
￥372,821
per person
Mar 25 - Mar 31
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Average hotel. Noticed few things during our stay. - The staff outside the hotel is "valet only" staff. Don't expect anyone to help you with your bags. - One day, our room was not made up. Looks like they are "scheduled". Not sure if they do it daily by default. - Zero sound-proof. We heard literally everything our room neighbors said. - We didn't rent a car but if you do, expect a front parking of just 4-5 cars. So, don't take a car with you. - No late checkout available. Good things. - The pool is good.

Reviewed on Jan 12, 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ￥485,762, price is now ￥331,040 per person
￥331,040
per person
Mar 25 - Mar 31
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Overall, the stay was excellent. The breakfast was great and very convenient, and the valet parking service was also top-notch. The only minor drawback was the cracked windows, which allowed in a noticeable amount of street noise. If street noise doesn’t bother you, this is a great option, especially given its close proximity to the beach and Lummus Park.

Reviewed on Jan 17, 2026

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Price was ￥519,339, price is now ￥355,571 per person
￥355,571
per person
Mar 25 - Mar 31
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
A reasonably priced art deco hotel in a popular tourist area. Hotel and rooms are stylishly designed. Restaurant food was ok. Maria was a fabulous server. On the downside, there is no pool or fitness center.

Reviewed on Jan 12, 2026

Find the Best Upper Matecumbe Key Vacation Packages

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 ￥26,605 per night from Jan 29 to Jan 30
￥26,605
￥38,824 total
Jan 29 - Jan 30
includes taxes & fees
9.2/10 Wonderful! (1,631 reviews)
The check in was easy. The front desk employee was very kind. Our room was spotless. We spent the afternoon on the beach and used the kayak. We enjoyed breakfast. The omelet chef was awesome. Overall I was very happy with my stay

Reviewed on Jan 12, 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 ￥41,606 per night from Jan 22 to Jan 23
￥41,606
￥58,370 total
Jan 22 - Jan 23
includes taxes & fees
9.2/10 Wonderful! (1,288 reviews)
For a five star hotel, the grounds should be kept up better

Reviewed on Jan 14, 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 ￥31,324 per night from Jan 22 to Jan 23
￥31,324
￥46,803 total
Jan 22 - Jan 23
includes taxes & fees
8.8/10 Excellent! (1,263 reviews)
Amazing place to stay. Staff was great

Reviewed on Jan 16, 2026

Amara Cay Resort
See all 2,815 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.