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.
Avalon Hotel

Avalon Hotel

3.5 out of 5
South Beach
Price was CA $779, price is now CA $375 per person
CA $375
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.2/10 Wonderful! (1,018 reviews)
Cross street to the beach. Very popular and busy area. Staffs are nice.

Reviewed on Aug. 25, 2025

Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Price was CA $1,422, price is now CA $630 per person
CA $630
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (2,500 reviews)
Excellent corner room overlooking the river, great stay.

Reviewed on Aug. 25, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Price was CA $1,319, price is now CA $599 per person
CA $599
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.8/10 Excellent! (1,193 reviews)
I thoroughly enjoyed my seaside suite. Gorgeous view. Loved that the property is located on the beach. The outdoor beach service is immaculate. John provides wonderful service with a smile. Throughout the property, I found the staff to be kind and attentive. I also enjoyed the pool area and the rooftop spa- it’s small but the service was quality. All in all- I enjoyed my respite at The Pelican.

Reviewed on Aug. 24, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $1,171, price is now CA $555 per person
CA $555
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.2/10 Very Good! (930 reviews)
I appreciated the close location to the beach. We were literally a walk across the street to the beach. Everything was walkable. The staff were attentive & present. Very helpful and friendly & accommodating. The lobby area always was clean smelling. I liked they provided complimentary bikes to ride, beach chairs & bottled water. What I did not like were the little bit of channels available on the tv. The stations they did have did not have service so it did not work. Would also recommend a full length mirror.

Reviewed on Aug. 23, 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
Price was CA $22,347, price is now CA $11,054 per person
CA $11,054
per person
Nov 6 - Nov 9
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)

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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 $156 per night from Sep 25 to Sep 26
CA $156
CA $254 total
Sep 25 - Sep 26
includes taxes & fees
9/10 Wonderful! (1,499 reviews)
"Fresh new rooms. Location was right on the ocean. Great breakfast, made for you. Front desk staff was amazing. Super accommodating and great communication. The only thing I would have recommended is that during construction they should have instated a bathroom vanity. Would return there again!!"

Reviewed on Aug. 24, 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 $240 per night from Aug 26 to Aug 27
CA $240
CA $364 total
Aug 26 - Aug 27
includes taxes & fees
9/10 Wonderful! (1,155 reviews)
"Perfect experience from beginning to end. Greeted by friendly people at the gate that gave me excellent information on checking in and parking. The check in staff were very friendly and when asked if any upgrades to my room were avaliable she found me something nicer then I was able to. The room ..."

Reviewed on Aug. 23, 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 $353 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,237 reviews)
"Not the best hotel in the Florida Keys, but it’s OK for cooling off for a couple of days. For me the pool by the ocean and the tiki bar were the stars of the show. Rooms were meh"

Reviewed on Aug. 22, 2025

Amara Cay Resort
See all 2,764 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
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Beach Vacations
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Family Vacations
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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 $375, 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.