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.
B Ocean Resort Fort Lauderdale Beach
1 Hotel South Beach
Hawks Cay Resort
Henrosa Hotel
Villas At Hawks Cay Resort
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.

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, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $308 per night from Nov. 25 to Nov. 26
CA $308
CA $441 total
includes taxes & fees
Nov 25 - Nov 26
9/10 Wonderful! (1,002 reviews)
"Property was lovely. Staff was amazing. Breathtaking views, great restaurants and awesome tiki bar. Highly recommended."

Reviewed on Nov. 21, 2024

Cheeca Lodge & Spa
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 $261 per night from Dec. 3 to Dec. 4
CA $261
CA $387 total
includes taxes & fees
Dec 3 - Dec 4
8.8/10 Excellent! (1,211 reviews)
"My family truly enjoyed this resort. Extremely satisfied. We are your customers from now on. Thank you."

Reviewed on Nov. 20, 2024

Amara Cay Resort
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 $198 per night from Dec. 8 to Dec. 9
CA $198
CA $293 total
includes taxes & fees
Dec 8 - Dec 9
9/10 Wonderful! (1,366 reviews)
"The Staff was very accommodating. The room was clean and equipped with a microwave, refrigerator, and very comfortable Robes. We loved the view and the peacefulness."

Reviewed on Nov. 19, 2024

Chesapeake Beach 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 $1,150, 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.