Title: Beach Vacations in Upper Matecumbe Key 2026 | Expedia.ca

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# Upper Matecumbe Key Beach Vacations

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## Flight and Beach hotel deals in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.

![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/ff03be62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Solé Miami, A Noble House Resort

Ocean Four

CA $1,066

per person

May 31 - Jun 6

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

8.6/10 Excellent! (2,063 reviews)

Clean room, beautiful location. Restaurant was good. Pool was great!

Reviewed on Mar 17, 2026

![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Villas At Hawks Cay Resort

CA $2,800

per person

Apr 25 - May 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.4/10 Very Good! (174 reviews)

We had a great stay.

Reviewed on Mar 20, 2026

![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/75c6ca53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Carillon Miami Wellness Resort

North Beach

CA $2,083

per person

May 31 - Jun 6

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

8.8/10 Excellent! (787 reviews)

The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it

Reviewed on Feb 5, 2026

![Hyde Beach House Hollywood Pr Suites](https://images.trvl-media.com/lodging/47000000/46080000/46073700/46073630/067a1b6d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyde Beach House Hollywood Pr Suites

Hollywood Beach

CA $2,603

per person

Jun 2 - Jun 9

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

6.8/10 (14 reviews)

My family had a perfect vacation. Beautiful hotel very spacious and comfortable for my family of 5\. Also enjoyed the Beautiful pool and breathing view. Will definitely visit again.

Reviewed on Jun 28, 2024

Don't see what you're looking for?

See all available trips from Columbus to Upper Matecumbe Key

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## 5\* Beach holidays in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.

![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/75c6ca53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Carillon Miami Wellness Resort

North Beach

CA $2,083

per person

May 31 - Jun 6

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

8.8/10 Excellent! (787 reviews)

The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it

Reviewed on Feb 5, 2026

![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel South Beach

South Beach

CA $2,627

per person

Jun 1 - Jun 5

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

9.4/10 Exceptional! (1,464 reviews)

This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again!

Reviewed on Mar 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Upper Matecumbe Key

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## 3 Night Beach holidays in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.

![Eurostars Winter Haven](https://images.trvl-media.com/lodging/1000000/70000/63100/63080/7218bdc3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Winter Haven

South Beach

CA $605

per person

May 28 - May 31

found 14 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.8/10 Excellent! (201 reviews)

partly beach view. very clean room. friendly staffs

Reviewed on Mar 8, 2026

![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel South Beach

South Beach

CA $2,874

per person

Apr 23 - Apr 26

found 2 days ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

9.4/10 Exceptional! (1,464 reviews)

This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again!

Reviewed on Mar 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Upper Matecumbe Key

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Beach holidays in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

CA $989

per person

Apr 20 - Apr 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

7.8/10 Good! (1,027 reviews)

Kind of run down. Need updates bad

Reviewed on Mar 20, 2026

![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/f54c02bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casablanca Miami Beach

North Beach

CA $3,566

per person

Jun 7 - Jun 11

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

5.8/10 (321 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Upper Matecumbe Key

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Find the best beach vacations in Upper Matecumbe Key

####  What are some benefits when booking beach vacations in Upper Matecumbe Key? 

When you travel to the beach in Upper Matecumbe Key, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. 
  
####  How can I book the best beach vacations in Upper Matecumbe Key? 

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Upper Matecumbe Key trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. 

####  Can I book cheap beach vacations in Upper Matecumbe Key? 

There are quite a few things you can do to get cheap beach vacations in Upper Matecumbe Key. Prices range from CA $605, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. 

####  Can I book beach packages? 

Yes, and you'll find quite a few beach packages available in Upper Matecumbe Key. These package deals let you save by booking your accommodation and your flight together with savings of up to 37\. 

####  Why should I book family beach vacations? 

When you're travelling with the family to Upper Matecumbe Key, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. 

####  How can I find a beachfront vacation in Upper Matecumbe Key? 

It's easy to find a beachfront vacation accommodation in Upper Matecumbe Key using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

####  How can I book last-minute beach vacations? 

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Upper Matecumbe Key as your destination and see what's available. 

####  Can I find all-inclusive beach vacations ? 

Yes, all you have to do to find all-inclusive beach vacations in Upper Matecumbe Key is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. 

####  Can I book a beach trip that's fully refundable? 

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Islamorada. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

####  Why should I book beach vacations with Expedia? 

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

## Beach Hotels in Upper Matecumbe Key

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

- 10 min drive from Bud n' Mary's Dive Center

Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...

9.2/10 Wonderful! (1,670 reviews)

So I did like our stay. However, we didn’t sleep great because the air conditioner is right at the foot of the master bedroom and it blows wind in your face constantly. We reached out to the property manager and he didn’t help us because it was broken and wouldn’t work the way intended. So overall ...

Reviewed on Mar 20, 2026

[](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

- 5 min drive from Bud n' Mary's Dive Center

Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

[](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

- 12 min walk from Bud n' Mary's Dive Center

Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...

8.8/10 Excellent! (1,001 reviews)

We Love this place!

Reviewed on Mar 17, 2026

[](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information)

[See all 2,795 properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635975749648)

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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## More Vacations Ideas

[Flights to Upper Matecumbe Key

](https://expedia.ca/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[

Upper Matecumbe Key Hotels

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Upper Matecumbe Key Vacation Rentals

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Upper Matecumbe Key Car Rentals

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Upper Matecumbe Key Vacations

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

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