Upper Matecumbe Key Vacations from ￥290,526

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The Latest Upper Matecumbe Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Silver Spray Motel

Silver Spray Motel

3 out of 5
Hollywood Beach
Price was ￥309,536, price is now ￥290,526 per person
￥290,526
per person
Dec 27 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
6.8/10 (724 reviews)
Ce que je n'aime pas l'office de l'hôtel n'est pas ala même locale.

Reviewed on Sep 9, 2025

Costa Hollywood Beach Resort

Costa Hollywood Beach Resort

4 out of 5
Hollywood Beach
Price was ￥351,735, price is now ￥326,681 per person
￥326,681
per person
Dec 27 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9/10 Wonderful! (3,525 reviews)
Need to pay for valet parking!! $45 per night!

Reviewed on Oct 11, 2025

Downtown Hollywood Gardens Inn & Suites

Downtown Hollywood Gardens Inn & Suites

2 out of 5
Downtown Hollywood
Price was ￥338,238, price is now ￥314,466 per person
￥314,466
per person
Dec 27 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (910 reviews)
The rooms are safe and clean

Reviewed on Oct 4, 2025

Diplomat Beach Resort Hollywood, Curio Collection by Hilton

Diplomat Beach Resort Hollywood, Curio Collection by Hilton

4.5 out of 5
Hollywood Beach
Price was ￥361,519, price is now ￥341,930 per person
￥341,930
per person
Dec 27 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (3,140 reviews)
The place was absolutely amazing

Reviewed on Oct 10, 2025

Casa Del Mar Deluxe Studio 2

Casa Del Mar Deluxe Studio 2

2 out of 5
Hollywood Beach
Price was ￥367,514, price is now ￥348,634 per person
￥348,634
per person
Dec 27 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
No reviews

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, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ￥24,039 per night from Oct 19 to Oct 20
￥24,039
￥37,250 total
Oct 19 - Oct 20
includes taxes & fees
9/10 Wonderful! (1,220 reviews)
"room were cleaned every morning; we were able to park under the room drinks were pricy"

Reviewed on Oct 9, 2025

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 ￥22,153 per night from Oct 19 to Oct 20
￥22,153
￥33,426 total
Oct 19 - Oct 20
includes taxes & fees
9.2/10 Wonderful! (1,532 reviews)
"Quiet. Peaceful. Perfect getaway for couples. Excellent customer service. This was our second stay at Chesapeake. Chesapeake and Islamorada are our new favorite destinations in the Keys. Islamorada reminds us of the Key West we fell in love with 30 years ago. Low key and peaceful. Every day is perfect ..."

Reviewed on Oct 4, 2025

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 ￥19,293 per night from Oct 19 to Oct 20
￥19,293
￥31,741 total
Oct 19 - Oct 20
includes taxes & fees
8.8/10 Excellent! (1,253 reviews)
"We had a room with an ocean view and it was great. There was a beautiful double rainbow over the water one of the days we were there."

Reviewed on Oct 4, 2025

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.

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