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.
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
per person
Oct 5 - Oct 12
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (149 reviews)
We had a great time at the hotel and were impressed with the well-maintained and spacious rooms. The mix of renters, vacationers, and pets on-site created a lively and diverse atmosphere, with everyone being friendly and welcoming. However, there was one issue that I would like to bring to your attention. Some previous tenants or vacationers had let their pets urinate in the common areas, which was unpleasant. Additionally, we noticed a smell in our room’s living room carpet, which was a result of pet urine. As pet owners, we understand the strong odor of pet urine and appreciate it when guests take responsibility for cleaning up after their pets. I hope this feedback helps improve the experience for future guests.

Reviewed on Aug. 4, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Miami (MIA)
8/10 Very Good! (1 review)
Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
The location is great and the customer service was excellent

Reviewed on Aug. 12, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (911 reviews)
Loved everything about this property. Best stay I have had in South Beach Yet. We had the room with the ocean front balcony and did not regret it. Even stayed an extra day.

Reviewed on Aug. 12, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
The property was gorgeous. The staff was wonderful.

Reviewed on Aug. 12, 2025

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Upper Matecumbe Key Hotel Deals

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 $208 per night from Aug 17 to Aug 18
CA $208
CA $312 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,489 reviews)
"Great amenities"

Reviewed on Aug. 10, 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 $210 per night from Aug 14 to Aug 15
CA $210
CA $330 total
Aug 14 - Aug 15
includes taxes & fees
9/10 Wonderful! (1,142 reviews)
"Great all around!"

Reviewed on Aug. 8, 2025

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 $232 per night from Sep 1 to Sep 2
CA $232
CA $352 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,238 reviews)
"We had a very nice stay celebrating my wife’s birthday."

Reviewed on Aug. 10, 2025

Amara Cay Resort
See all 2,766 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 showing outdoor art and a 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

How much does an Upper Matecumbe Key vacation package cost?
Starting from a low CA $968, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.