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.
The Club - Pool - Gym - Parking - Heart of Brickell

The Club - Pool - Gym - Parking - Heart of Brickell

4 out of 5
Brickell
Price was CA $2,693, price is now CA $1,394 per person
CA $1,394
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) 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 $48,281, price is now CA $23,323 per person
CA $23,323
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

District 225 - Rooftop Pool - Gym - Parking - Downtown Miami

District 225 - Rooftop Pool - Gym - Parking - Downtown Miami

4 out of 5
Downtown Miami
Price was CA $2,709, price is now CA $1,401 per person
CA $1,401
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
No reviews

Brickell Sea View 2BR Free Parking by Palermo Home

Brickell Sea View 2BR Free Parking by Palermo Home

2.5 out of 5
Brickell
Price was CA $3,466, price is now CA $1,878 per person
CA $1,878
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
10/10 Exceptional! (1 review)
Very nice stay

Reviewed on Mar 16, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was CA $2,905, price is now CA $1,616 per person
CA $1,616
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
I loved that it was an unique property & easily accessible to everything.

Reviewed on Nov 5, 2026

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 $256 per night from Nov 19 to Nov 20
CA $256
CA $391 total
Nov 19 - Nov 20
includes taxes & fees
9.2/10 Wonderful! (1,511 reviews)
"Perfect halfway stop off for trip to The Keys . Staff exceptionally helpful.. particularly ‘Fran’ I think that was her name on Front Desk. Great pools and loved the bikes ! Rooms were spacious and comfy beds. Recommend Lorelei Restaurant for something to eat off site ..! Great stay, definitely ..."

Reviewed on Nov 8, 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 $203 per night from Nov 10 to Nov 11
CA $203
CA $307 total
Nov 10 - Nov 11
includes taxes & fees
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 CA $235 per night from Nov 15 to Nov 16
CA $235
CA $368 total
Nov 15 - Nov 16
includes taxes & fees
Amara Cay Resort
See all 2,725 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

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
See properties

Frequently asked questions

How much does an Upper Matecumbe Key vacation package cost?
Starting from a low CA $1,394, a package is your passport to low-cost travel. Custom make your Upper Matecumbe Key getaway by selecting from our huge range of hotels, airfares and rental cars.
How do I get a cheap travel package to Upper Matecumbe Key?
You'll save loads of cash if you combine your hotels, flights and car rentals into an Upper Matecumbe Key vacation package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, so you'll always have plenty of variety to choose from. Eager to save even more? Add some exciting activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
How far in advance should I book my Upper Matecumbe Key vacation?
While prices change frequently, we generally suggest booking your spot as soon as possible. Many international airfares are available on Expedia up to a year in advance. If you're booking late, you may still get lucky. Cheap tickets to Upper Matecumbe Key sometimes appear just weeks before departure.
What does an Expedia Upper Matecumbe Key travel package include?
Flights, car rentals and hotels — we connect you to the very best bargains. All you'll have to do is figure out your preferred combination. After you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it easy to put together an exciting Upper Matecumbe Key escape.
What should I know before booking an Upper Matecumbe Key travel package?
We already have low prices. However, you'll enjoy an even better deal if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and loads of choice.
Can I choose my airline with an Upper Matecumbe Key Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You're in control. We have access to more than 550 airline partners worldwide, so you have lots of choice when putting together your Upper Matecumbe Key adventure.
If I'm not able to travel, can I cancel my Upper Matecumbe Key vacation package?
You sure can, and we'll help you every step of the way. You may be able to amend or cancel your Upper Matecumbe Key vacation package for free within 24 hours of booking. However, you may be charged a fee by your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, look up our Customer Service Portal for more information.

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.