Title: Upper Matecumbe Key Vacation Packages & Trips 2026 from CA $914 | 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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## Top Upper Matecumbe Key Vacation Deals

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

![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 $914

per person

Apr 10 - Apr 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

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

Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

![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 $19,627

per person

Mar 14 - Mar 21

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

8/10 Very Good! (1 review)

![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 $1,864

per person

Mar 14 - Mar 21

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

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

Courteous staff. Great location

Reviewed on Feb 7, 2026

![ABAE Hotel by Eskape Collection ](https://images.trvl-media.com/lodging/17000000/16040000/16037600/16037592/50112048_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### ABAE Hotel by Eskape Collection 

South Beach

CA $1,393

per person

Mar 27 - Apr 3

found 20 hours ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

8.8/10 Excellent! (1,000 reviews)

Great room and spotless

Reviewed on Jan 30, 2026

![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Vacation Club at Beach House, Key West

CA $1,351

per person

Apr 27 - May 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

This place is amazing! The property is beautiful and quiet. The pool area was clean and well cared for. Our room was spacious, very clean and had everything we needed. The staff was kind and always helpful. We would definitely go back.

Reviewed on Feb 5, 2026

## 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 $320

CA $437 total

Feb 11 - Feb 12

includes taxes & fees

9.2/10 Wonderful! (1,665 reviews)

We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.

Reviewed on Feb 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=4170&PinnedHotelID=4170&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 $518

CA $683 total

Feb 10 - Feb 11

includes taxes & fees

9.2/10 Wonderful! (1,296 reviews)

Paradise away from Home!! Thank you!

Reviewed on Feb 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=5780&PinnedHotelID=5780&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 $337

CA $480 total

Feb 11 - Feb 12

includes taxes & fees

8.8/10 Excellent! (1,264 reviews)

All good, nice bartender inside downstairs, and easy walk to fish and eat

Reviewed on Feb 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=61976&PinnedHotelID=61976&HadPinnedHotel=true&regionId=553248635975749648)

[See all 2,816 properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%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 showing heritage elements](https://images.trvl-media.com/place/6069257/3860ae1a-3cef-4809-8059-43794e9fe7f9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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.

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

![Hurricane Monument showing outdoor art and a monument](https://images.trvl-media.com/place/6063543/461255cf-b7dd-46e6-b190-1a13cf74e1c5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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.

[](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.

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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)

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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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