Upper Matecumbe Key Vacation Packages

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Top Upper Matecumbe Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Hollywood Hills
Price was CA $2,570, price is now CA $1,190 per person
CA $1,190
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
No reviews
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was CA $4,558, price is now CA $1,454 per person
CA $1,454
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
6/10 (2 reviews)
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was CA $4,610, price is now CA $1,900 per person
CA $1,900
per person
Jul 19 - Jul 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
2/10 (2 reviews)
Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was CA $6,684, price is now CA $3,474 per person
CA $3,474
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Miami (MIA)
8.2/10 Very Good! (151 reviews)
This was an overall excellent experience. The room was nice and reasonably priced. There ended up being an ac issue where the room temperature wouldn’t drop below 77 degrees, which produced several sleepless nights. The communication with the rental temp was pretty horrid, we received a few ineffective ways to troubleshoot it; but nothing was ever fixed. We were even promised a follow up phone call the next day(post checkout) and were ghosted. This was pretty disappointing.

Reviewed on May 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 CA $23,260, price is now CA $12,146 per person
CA $12,146
per person
Jul 26 - Jul 31
found 4 hours ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)

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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 CA $264 per night from May 21 to May 22
CA $264
per night
May 21 - May 22
9.2/10 Wonderful! (1,328 reviews)
Beautiful!!!

Reviewed on May 7, 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 CA $239 per night from May 31 to Jun 1
CA $239
per night
May 31 - Jun 1
9.2/10 Wonderful! (1,728 reviews)
Wow just wow Booked a king with ocean view They had a problem with door card reader. When I was checking in they were repairing it. So they upgraded me to a villa and holy cow now I know how rich people live!!! The staff were really friendly and knowledgeable about the area around the hotel. My wife ...

Reviewed on May 8, 2026

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from May 17 to May 18
CA $245
per night
May 17 - May 18
9.2/10 Wonderful! (1,009 reviews)
The resort is truly a tropical paradise.

Reviewed on May 8, 2026

Islander Resort
See all 2,774 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.
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Discover the most popular places to visit in Upper Matecumbe Key

History of Diving Museum

History of Diving Museum

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

History of Diving Museum
Hurricane Monument

Hurricane Monument

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

Hurricane Monument

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.