Title: Upper Matecumbe Key Vacation Packages & Trips 2026 from CA $1,293 | Expedia.ca

[Upper Matecumbe Key Travel Guide](https://expedia.ca/Upper-Matecumbe-Key.dx553248635975749648)[Hotels in Upper Matecumbe Key](https://expedia.ca/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[Vacation Rentals in Upper Matecumbe Key](https://expedia.ca/Upper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[Flights to Upper Matecumbe Key](https://expedia.ca/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[Upper Matecumbe Key Car Rentals](https://expedia.ca/Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648.Car-Rental-Guide)

![](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Upper Matecumbe Key Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.

![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cavalier Hotel South Beach

South Beach

CA $1,293

per person

Feb 19 - Feb 24

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

Perfect location and great bonus with beach towels and two free chairs on the beach.

Reviewed on Dec 27, 2025

![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/w2048h1535x0y1-af4622e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Miami Downtown Condos

Downtown Miami

CA $1,533

per person

Mar 25 - Mar 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.6/10 Excellent! (72 reviews)

Amazing customer service! Always there when you need them, no matter the time, or iinquiry! I had an amazing stay, and I’d highly recommend you stay!

Reviewed on Dec 28, 2025

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

CA $1,316

per person

Mar 6 - Mar 13

found 15 hours ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

The guy at the front desk was very nice. The view from the room was great.

Reviewed on Dec 30, 2025

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $18,890

per person

Mar 15 - Mar 22

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

8/10 Very Good! (1 review)

![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Shelborne By Proper, a Member of Design Hotels

South Beach

CA $2,211

per person

Feb 20 - Feb 24

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

9.4/10 Exceptional! (56 reviews)

Excellent amenities and great location

Reviewed on Dec 31, 2025

## Ready to book your vacation to Upper Matecumbe Key?

Choose your dates

## Upper Matecumbe Key Hotel Deals

![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

Fully refundableReserve now, pay when you stay

CA $242

CA $350 total

Jan 14 - Jan 15, 2026

includes taxes & fees

9.2/10 Wonderful! (1,597 reviews)

It was a great breakfast.... they had everything that i liked in particular. They had healthy options.. not a big place so it didnt seem overwhelmed with options just the right amount of options. Place i staid had an amazing ocean view :)

Reviewed on Dec 23, 2025

[](https://expedia.ca/Hotel-Search?startDate=14%2F01%2F2026&endDate=15%2F01%2F2026&selected=4170&PinnedHotelID=4170&HadPinnedHotel=true&regionId=553248635975749648)

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

CA $277

CA $412 total

Jan 13 - Jan 14, 2026

includes taxes & fees

8.8/10 Excellent! (1,271 reviews)

Was very nice , Did order cookies and brownies for the room Christmas night and that never happened! Fishing pole rental was ridiculous Food was great and good Keylime dessert !

Reviewed on Dec 28, 2025

[](https://expedia.ca/Hotel-Search?startDate=13%2F01%2F2026&endDate=14%2F01%2F2026&selected=61976&PinnedHotelID=61976&HadPinnedHotel=true&regionId=553248635975749648)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

CA $348

CA $492 total

Jan 29 - Jan 30, 2026

includes taxes & fees

9.2/10 Wonderful! (1,276 reviews)

It was over the top amazing

Reviewed on Dec 27, 2025

[](https://expedia.ca/Hotel-Search?startDate=29%2F01%2F2026&endDate=30%2F01%2F2026&selected=5780&PinnedHotelID=5780&HadPinnedHotel=true&regionId=553248635975749648)

[See all 2,805 properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Upper Matecumbe Key

![History of Diving Museum](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497744-history-of-diving-museum.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### History of Diving Museum

4/5(1 review)

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.

[](https://expedia.ca/History-Of-Diving-Museum-Matecumbe.d6069257.Vacation-Attraction)

![Hurricane Monument showing outdoor art and a monument](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63861-Islamorada.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Hurricane Monument

4/5(1 review)

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

[](https://expedia.ca/Hurricane-Monument-Matecumbe.d6063543.Vacation-Attraction)

## Frequently asked questions

### Can I cancel my flight booking to Upper Matecumbe Key due to COVID-19?

### What's the best way to find cheap flights to Upper Matecumbe Key that have flexible change policies?

### What are some of the general tips for travelers to Upper Matecumbe Key during the COVID-19 outbreak?

> - Look into if any restrictions apply to both your origin and destination. You may not be able to travel depending on local circumstances, so be sure to check before you book.
> - When you go through airport checkpoints, do not remove your face mask. You will be asked to lower it briefly to confirm your identity. Those who refuse to wear a face mask may face civil penalties and may also be escorted from the terminal.
> - Instead of handing a TSA officer your boarding pass, position it straight on the scanner yourself. When that's done, hold it up for inspection.
> - One liquid hand sanitizer container is now permitted in your carry-on luggage. It must be no larger than 12 oz (350 ml), and you'll have to remove it from your bag for X-ray screening.
> - Put any personal items (phone, wallet and keys for example) in your carry-on rather than a bin to minimize handling during screening.
> - Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on makes it less likely that a TSA officer will need to open and touch your bag for inspection.

### Which airlines fly to Upper Matecumbe Key?

### How can I find cheap tickets to Upper Matecumbe Key?

### How much is a flight to Upper Matecumbe Key?

### What are the most popular airports to fly into in Upper Matecumbe Key?

### When is the cheapest time to fly to Upper Matecumbe Key?

### How much is a plane ticket to Upper Matecumbe Key?

### Which airlines with flights to Upper Matecumbe Key employ COVID-19 cleanliness policies?

> - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
> - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
> - United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

## Explore a world of travel with Expedia

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- [Windley Key Fossil Reef Geological State Park ](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)

- [Alamo Rent A Car Rental Cars in Islamorada ](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Islamorada.d10768-c6.Car-Rental-Guide-Suppliers)
- [Car rental Islamorada ](https://www.expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)
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- [Luxury Car Rentals in Islamorada ](https://www.expedia.ca/Luxury-Car-Rentals-In-Islamorada.d10768-tLuxury.Car-Rental-Guide-Class)
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- [Islamorada Vacation Rentals ](https://www.expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)

- [Things to do in Islamorada ](https://www.expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)

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