Title: Upper Matecumbe Key Vacation Rentals from CA $316: Short-Term Rentals for 2026 | 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)[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)[Upper Matecumbe Key Vacation Packages](https://expedia.ca/Upper-Matecumbe-Key.d553248635975749648.Destination-Travel-Guides)

![Florida Keys Brewing Co. showing signage](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Upper Matecumbe Key Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Upper Matecumbe Key vacation rentals

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/5e728c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98496c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Cottage](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/b8fa0acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

8.8/10

Excellent

(591)

"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Terry

CA $218

CA $316 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

![2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fa0090c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/531fe0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a93dc7d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

9.8/10

Exceptional

(70)

"Great for family vacation with kids. love it"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dixania

CA $833

CA $1,013 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/92a650b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/ee0752b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/1641bbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Houseboat in Islamorada

[](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information)

9.0/10

Wonderful

(117)

"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary

CA $209

CA $429 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information)

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/7f2e2269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/0514aa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Key Largo One-bedroom Cottage](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/29275608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Conch Key One-bedroom Cottage | Private kitchen](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/2180f342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Tavernier

[](https://www.expedia.ca/Tavernier-Hotels-Island-Bay-Resort.h13279636.Hotel-Information)

10/10

Exceptional

(141)

"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacob

CA $582

CA $655 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Island-Bay-Resort.h13279636.Hotel-Information)

![55-inch Smart TV with digital channels, books](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/96d842c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/f15964b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/c244835e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/a7f8b8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Houseboat in Key Largo

[](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information)

CA $1,723

CA $1,939 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08&regionId=553248635975749648&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=HOUSE_BOAT)

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## Top Upper Matecumbe Key Hotel Reviews

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg)

### Amara Cay Resort

10/10 Excellent

"Clean rooms! Great resort , fun activities , very nice and quiet area , made my anniversary with my girlfriend very special! "

[](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information)

![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg)

### Waterside Suites & Marina

10/10 Excellent

"Always a great experience every time we go to key largo we stay there "

[](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg)

### Cheeca Lodge & Spa

10/10 Excellent

"Fabulous waterfront, activities, and dining as well as the staff. "

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

![Pines & Palms Resort](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg)

### Pines & Palms Resort

10/10 Excellent

"Great room great place. Very clean easy to get to wonderful staff "

[](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information)

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg)

### Chesapeake Beach Resort

10/10 Excellent

"The breakfasts are great "

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

![La Jolla Resort](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92_y.jpg)

### La Jolla Resort

10/10 Excellent

"Very clean. Newly renovated."

[](https://expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information)

![Breezy Palms Resort](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg)

### Breezy Palms Resort

10/10 Excellent

"Spotless room- right on beach- really enjoyed "

[](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg)

### Islander Resort

10/10 Excellent

"The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful"

[](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information)

![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg)

### Marina Del Mar Resort and Marina

10/10 Excellent

"Room clean, beautiful setting, pleasant ambiance good restaurants! Staff friendly and courteous"

[](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information)

## Find out more about Upper Matecumbe Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upper Matecumbe Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Hotels in Vancouver](https://expedia.ca/Vancouver-Hotels.d178315.Travel-Guide-Hotels)
- [Hotels in Santa María Huatulco](https://expedia.ca/Santa-Maria-Huatulco-Hotels.d6051926.Travel-Guide-Hotels)
- [The Westin Ottawa](https://expedia.ca/Ottawa-Hotels-The-Westin-Ottawa.h9572.Hotel-Information)
- [All Inclusive Resorts and Hotels in Turks and Caicos](https://expedia.ca/Destinations-In-Turks-And-Caicos-All-Inclusive-Hotel.0-0-d184-tAllInclusiveHotel.Hotel-Filter-Destinations)
- [Staybridge Suites West Edmonton by IHG](https://expedia.ca/Edmonton-Hotels-Staybridge-Suites-West-Edmonton.h7749122.Hotel-Information)
- [Cheap Hotels in Chilliwack](https://expedia.ca/Chilliwack-Hotels-Cheap-Hotels.0-0-d6058408-tCheapHotels.Travel-Guide-Filter-Hotels)

Flights

- [Cheap Flights to Kelvington](https://expedia.ca/Cheap-Flights-To-Kelvington.d553248635922155871.Travel-Guide-Flights)
- [Cheap Flights from London (YXU) to Québec (YQB)](https://expedia.ca/lp/flights/yxu/yqb/london-to-quebec)
- [Cheap Flights from Canada](https://expedia.ca/lp/flights/31/flights-from-canada)
- [Cheap Flights from Québec (YQB) to Honolulu (HNL)](https://expedia.ca/lp/flights/yqb/hnl/quebec-to-honolulu)
- [Cheap Flights to Riyadh](https://expedia.ca/Cheap-Flights-To-Riyadh.d3051.Travel-Guide-Flights)
- [Cheap Flights from Delhi (DEL) to Vancouver (YVR)](https://expedia.ca/lp/flights/del/yvr/delhi-to-vancouver)
- [Emirates Toronto (YYZ) to Dubai (DXB) flights](https://expedia.ca/lp/flight-routes/emirates-from-pearson-intl-to-dubai-intl/ek/yyz/dxb)
- [Cheap Flights from Toronto (YYZ) to Calgary (YYC)](https://expedia.ca/lp/flights/yyz/yyc/toronto-to-calgary)
- [Air Canada](https://expedia.ca/Air-Canada-Flights.cAC.Travel-Guide-Airlines)
- [Cheap Flights to Vancouver](https://expedia.ca/Cheap-Flights-To-Vancouver.d178315.Travel-Guide-Flights)
- [Cheap Flights from Detroit (DTW) to Bridgetown (BGI)](https://expedia.ca/lp/flights/dtw/bgi/detroit-to-bridgetown)
- [Cheap Flights from Edmonton (YEG) to Mumbai (BOM)](https://expedia.ca/lp/flights/yeg/bom/edmonton-to-mumbai)
- [Cheap Flights from Stopover](https://expedia.ca/lp/flights/553248635975869605/flights-from-stopover)
- [Cheap Flights from Calgary (YYC) to Toronto (YYZ)](https://expedia.ca/lp/flights/yyc/yyz/calgary-to-toronto)
- [Cheap Flights from Toronto (YYZ) to Tokyo (TYO)](https://expedia.ca/lp/flights/yyz/tyo/toronto-to-tokyo)
- [Cheap Flights from Ottawa (YOW) to Singapore (SIN)](https://expedia.ca/lp/flights/yow/sin/ottawa-to-singapore)

Packages

- [Dominican Republic All-inclusive Vacation Packages](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic)
- [all inclusive vacations](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations)
- [Switzerland Vacations](https://expedia.ca/Switzerland.d174.Destination-Travel-Guides)

Vacation Rentals

- [Arizona Vacation Rentals](https://expedia.ca/Destinations-In-Arizona.d204.Vacation-Rental-Destinations)

General

- [Visit Tours](https://expedia.ca/Tours.dx3564)

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