Upper Matecumbe Key Vacations from ￥308,773

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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 ￥359,841, price is now ￥308,773 per person
￥308,773
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (2,048 reviews)
I really liked the location — it was very convenient. The room was pretty big and very clean, which made the stay comfortable. The staff was friendly and welcoming. The breakfast was okay, nothing special, but it was fine.

Reviewed on Mar 1, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was ￥368,872, price is now ￥310,742 per person
￥310,742
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back

Reviewed on Feb 24, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ￥362,840, price is now ￥310,161 per person
￥310,161
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,701 reviews)
The staff and service plus the location has made this my new Miami Beach place of stay. Luggage holding and early check in is a godsend with vacation traveling. The walk to the beach was short and near the Art Deco section of the beach. Police are near and keep the area relatively safe at night. Unlike other beach spots this area does calm down and able to sleep at night without a club jamming music

Reviewed on Mar 3, 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ￥386,294, price is now ￥331,908 per person
￥331,908
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1,151 reviews)
Room was okay. The beds were smaller than we expected and there were only flat sheets on the mattress rather than fitted sheets. Breakfast was very good, pool and beach access were great.

Reviewed on Mar 1, 2026

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Price was ￥383,820, price is now ￥333,556 per person
￥333,556
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (432 reviews)
The hotel was OK but pricey. Breakfast included but limited to three dishes. The access to the beach waa 2 blocks away. No coffee. The staff was very good. maker in the room. The hotel carpets were overused

Reviewed on Mar 3, 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 ￥70,491 per night from Mar 12 to Mar 13
￥70,491
￥90,781 total
Mar 12 - Mar 13
includes taxes & fees
9.2/10 Wonderful! (1,299 reviews)
This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.

Reviewed on Feb 25, 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 ￥48,715 per night from Mar 24 to Mar 25
￥48,715
￥63,633 total
Mar 24 - Mar 25
includes taxes & fees
9.2/10 Wonderful! (1,668 reviews)
Couldn't say enough good things about this place! Right on the water! Super clean facility - seemed new! Ready for the differentiator? The breakfast team! MADE TO ORDER OMELET OR EGGS! So awesome!! Salt Water and Fresh Water Pools! Hot tub! Yup, we will be back! March '26

Reviewed on Mar 5, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is ￥48,181 per night from Mar 8 to Mar 9
￥48,181
￥65,682 total
Mar 8 - Mar 9
includes taxes & fees
8.8/10 Excellent! (1,262 reviews)
Staff at reception are rude and unhelpful. They need to cheer up. Food is at best average and expensive.

Reviewed on Mar 4, 2026

Amara Cay Resort
See all 2,787 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.