Upper Matecumbe Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Upper Matecumbe Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was CA $2,065, price is now CA $880 per person
CA $880
per person
Jul 25 - Jul 28
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
2/10 (2 reviews)
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was CA $4,181, price is now CA $1,486 per person
CA $1,486
per person
Jul 13 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
7.4/10 Good! (3 reviews)
I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.

Reviewed on May 20, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $13,871, price is now CA $5,805 per person
CA $5,805
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was CA $1,847, price is now CA $884 per person
CA $884
per person
Jul 16 - Jul 19
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
No reviews
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 $16,869, price is now CA $8,923 per person
CA $8,923
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)

Ready to book your vacation to Upper Matecumbe Key?

 

Choose your dates

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 $332 per night from Jun 9 to Jun 10
CA $332
CA $475 total
Jun 9 - Jun 10
includes taxes & fees
9.2/10 Wonderful! (1,317 reviews)
"Cheeca Lodge is my absolute favorite place in The Keys The property is gorgeous, I love the amenities, the complimentary kayaking, bikes & champagne for Mother’s Day was such a nice touch The rooms are so cozy, just love it there. Ask for Rob at the pool bar, he makes a great drink!"

Reviewed on Jun 4, 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 $262 per night from Jul 1 to Jul 2
CA $262
CA $373 total
Jul 1 - Jul 2
includes taxes & fees
9.2/10 Wonderful! (1,738 reviews)
"Pros....Room was awesome and clean. Amazing views. Close to anything you may need. Cons....Property was a little rough. Cans and trash were kind of everywhere."

Reviewed on Jun 3, 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 $309 per night from Jun 18 to Jun 19
CA $309
CA $441 total
Jun 18 - Jun 19
includes taxes & fees
9.4/10 Exceptional! (1,031 reviews)
"Safety issue. All paddleboards were worn with cracks and fiberglass splinters in multiple areas. Can easily cut someone. Was not comfortable to use one. EVERYTHING ELSE FANTASTIC."

Reviewed on Jun 3, 2026

Islander Resort
See all 2,824 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Upper Matecumbe Key

Hurricane Monument

Hurricane Monument

4/5(1 review)

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
History of Diving Museum

History of Diving Museum

4/5(1 review)

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

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.