Upper Matecumbe Key Holidays

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Top Flight + Hotel Deals in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
Hilton Cabana Miami Beach Resort

Hilton Cabana Miami Beach Resort

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 20 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (292 reviews)
The hotel has potential, but cleanliness definitely needs improvement. Our bathroom had hair stuck to the ceiling of the shower and visible mold in some areas, which was off-putting. Additionally, the parking fees are excessive. Hilton charged $57 + tax for parking, while a lot just two minutes away on foot offered the same service for only $30. For guests already paying a premium to stay here, the parking costs feel unjustified. I’d strongly recommend lowering the price to be more competitive with the surrounding area.

Reviewed on 30 Jul 2025

The Gabriel Miami South Beach, Curio Collection by Hilton

The Gabriel Miami South Beach, Curio Collection by Hilton

4 out of 5
South Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 20 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!

Reviewed on 31 Jul 2025

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
per person
24 Oct - 28 Oct
found 20 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,786 reviews)
Quiet ,clean property. Nice stay

Reviewed on 31 Jul 2025

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 20 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,099 reviews)
Everything was good however same breakfast choices everyday.

Reviewed on 20 Jul 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 20 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
The best hotel in Miami.

Reviewed on 1 Aug 2025

Top hotels in Upper Matecumbe Key

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 €255 per night from 13 Aug to 14 Aug
€255
13 Aug - 14 Aug
includes taxes & fees
9/10 Wonderful! (1,145 reviews)
"So this is my first time visiting Cheeca Lodge- I have alway"

Reviewed on 28 Jul 2025

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 €198 per night from 10 Aug to 11 Aug
€198
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (1,496 reviews)
"Ac. Was not great at all. Wish there was more of a variety for food at bar area. We were starving had to order pizza. That was one reason for picking this resort. The breakfast was wonderful tho"

Reviewed on 28 Jul 2025

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is €264 per night from 11 Aug to 12 Aug
€264
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,027 reviews)
"Amazing resort and staff. Felt like I was on a tropical island and in a whole other world. Food was amazing! Rooms were beautiful and beds were super comfortable. Would definitely be coming back!"

Reviewed on 28 Jul 2025

Islander Resort
See all 2,747 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.

Popular places to visit

Bud n' Mary's Dive Center

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 family-friendly area.

Bud n' Mary's Dive Center

Frequently asked questions

How much does an Upper Matecumbe Key holiday package cost?
Starting from a low €354, 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 holiday 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 holiday?
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 holiday package?
Yes — that's one of the best things about an Expedia holiday 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 holiday 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 holiday 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.