Upper Matecumbe Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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.
May-Dee Suites
The Retreat Collection at 1 Hotel & Homes South Beach
Amara Cay Resort
Hawks Cay Resort
Casablanca Miami Beach

Ready to book your vacation to Upper Matecumbe Key?

 

Choose your dates

Upper Matecumbe Key Hotel Deals

Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from May 1 to May 2
CA $289
CA $403 total
includes taxes & fees
May 1 - May 2
9/10 Wonderful! (1,430 reviews)
"Good for the price and convenient for fishing trips. No frills, clean rooms good location."

Reviewed on Apr. 28, 2025

Chesapeake Beach Resort
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 CA $414 per night from May 5 to May 6
CA $414
CA $559 total
includes taxes & fees
May 5 - May 6
9/10 Wonderful! (1,066 reviews)
"Great spot. Restaurants on Location."

Reviewed on Apr. 24, 2025

Cheeca Lodge & Spa
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is CA $294 per night from May 14 to May 15
CA $294
CA $423 total
includes taxes & fees
May 14 - May 15
8.8/10 Excellent! (1,187 reviews)
"Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down."

Reviewed on Apr. 30, 2025

Amara Cay Resort
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

How much does an Upper Matecumbe Key vacation package cost?
Starting from a low CA $427, 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.

Discover the most popular places to visit in Upper Matecumbe Key

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