Title: Upper Matecumbe Key Vacation Packages & Trips 2026 from CA $566 | 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
- ###  
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.

![Hyatt Place Miami Airport-East](https://images.trvl-media.com/lodging/10000000/9520000/9517300/9517242/e322cfbb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Place Miami Airport-East

Palmer Lake

CA $566

per person

Apr 5 - Apr 10

found 19 hours ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8.2/10 Very Good! (2,247 reviews)

The staff was caring, helpful, and assisted with all of our needs

Reviewed on Jan 26, 2026

![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 $879

per person

Mar 15 - Mar 20

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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 Penguin Hotel](https://images.trvl-media.com/lodging/1000000/70000/62900/62824/d4ab7ebb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Penguin Hotel

South Beach

CA $1,023

per person

Mar 15 - Mar 21

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8.2/10 Very Good! (1,491 reviews)

Clean room, but very cold. Great location!

Reviewed on Jan 31, 2026

![President Hotel](https://images.trvl-media.com/lodging/1000000/580000/575900/575859/5a013cab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel

South Beach

CA $1,013

per person

Mar 15 - Mar 21

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8.4/10 Very Good! (1,775 reviews)

Staff was great, love the location!

Reviewed on Jan 28, 2026

![Embassy Suites by Hilton Fort Lauderdale 17th Street](https://images.trvl-media.com/lodging/1000000/20000/12000/11909/8d47bc21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Embassy Suites by Hilton Fort Lauderdale 17th Street

East Fort Lauderdale

CA $841

per person

Mar 22 - Mar 26

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8.8/10 Excellent! (674 reviews)

Kathy the front desk Manager was wonderful. The hotel is clean and walking distance to some stores and restaurants. A very short distance to the cruise terminal.

Reviewed on Jan 29, 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 $265

CA $375 total

Feb 2 - Feb 3

includes taxes & fees

9.2/10 Wonderful! (1,655 reviews)

Staff was very nice. Nice to use the complimentary clear bottom kayaks. Breakfast was good, Didi made a great omelette!

Reviewed on Jan 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%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 $383

CA $530 total

Feb 2 - Feb 3

includes taxes & fees

9.2/10 Wonderful! (1,301 reviews)

This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.

Reviewed on Jan 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%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 $323

CA $463 total

Feb 8 - Feb 9

includes taxes & fees

8.8/10 Excellent! (1,276 reviews)

We enjoyed our stay and found the staff to be courteous and responsive. Our room was a generous size, clean and well appointed (as is often the case we wouldn’t have said no to a couple of more outlets lol). The beach and pool areas had plenty of seating and multiple things to do—ping pong, cornhole, ...

Reviewed on Jan 26, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=61976&PinnedHotelID=61976&HadPinnedHotel=true&regionId=553248635975749648)

[See all 2,819 properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F02%2F2026&endDate=02%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)

- [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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