Upper Matecumbe Key Vacations from ￥327,866

Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Upper Matecumbe Key Vacation Packages

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

Hotel AKA Brickell

5 out of 5
Brickell
Price was ￥405,086, price is now ￥327,866 per person
￥327,866
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9/10 Wonderful! (1,325 reviews)
Room fine Service not the best Elevators very bad

Reviewed on Jan 9, 2026

Pier Sixty-Six (Pier 66)

Pier Sixty-Six (Pier 66)

5 out of 5
East Fort Lauderdale
Price was ￥399,000, price is now ￥331,976 per person
￥331,976
per person
Apr 1 - Apr 5
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.8/10 Exceptional! (273 reviews)
Great stay. Great hotel staff. Enjoyed the spa. Room keepers could be more timely, but still got the job done.

Reviewed on Jan 9, 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 ￥3,695,406, price is now ￥1,825,400 per person
￥1,825,400
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8/10 Very Good! (1 review)
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Price was ￥434,352, price is now ￥336,070 per person
￥336,070
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8.2/10 Very Good! (7,303 reviews)
The room was spotless and polished. The hotel was amazing. I was in a conference for 2 days and 3 nights, and I never left the hotel. I would love to come back again when I have time to explore the complex and surrounding area.

Reviewed on Jan 11, 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 ￥28,655 per night from Jan 28 to Jan 29
￥28,655
￥41,119 total
Jan 28 - Jan 29
includes taxes & fees
9.2/10 Wonderful! (1,626 reviews)
Very clean and nice. Not a 5 star resort. But nice. Breakfast was good

Reviewed on Jan 11, 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 ￥38,539 per night from Jan 29 to Jan 30
￥38,539
￥54,903 total
Jan 29 - Jan 30
includes taxes & fees
9.2/10 Wonderful! (1,288 reviews)
Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 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 ￥32,297 per night from Jan 22 to Jan 23
￥32,297
￥47,880 total
Jan 22 - Jan 23
includes taxes & fees
8.8/10 Excellent! (1,260 reviews)
This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back

Reviewed on Jan 10, 2026

Amara Cay Resort
See all 2,796 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.

Explore a world of travel with Expedia

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