Title: Upper Matecumbe Key Vacation Rentals from CA $311: 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)

![Islamorada Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Cameron Abbott

# Upper Matecumbe Key Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-05-08&endDate=2026-05-10&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/12000000/11950000/11945900/11945889/19240ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach towels](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/4550dbd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Economy Room](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/f0ed1fc9.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

(607 reviews)

"Property was nice and easy to navigate, ocean view room was extra nice to have!"

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

Lisa

CA $212

CA $311 total

includes taxes & fees

Jan 18 - Jan 19

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

![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/55a08207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a064415d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fcc01350.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 reviews)

"Amazing stay, can’t wait to stay there again!"

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

Anonymous traveller

CA $846

CA $1,028 total

includes taxes & fees

Jan 19 - Jan 20

[](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)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/17a61bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually decorated, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/e70c5d33.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)

### Houseboat in Islamorada

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

9.0/10

Wonderful

(124 reviews)

"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"

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

Nick

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

![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/dd2c750f.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)

![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/ab2c2d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/dc4f4949.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 $1,574

CA $1,771 total

includes taxes & fees

Jan 27 - Jan 28

[](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=2026-01-29&endDate=2026-01-30&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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=APART_HOTEL)

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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=VILLA)

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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=APARTMENT)

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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=VACATION_HOME)

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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=CONDO)

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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=HOUSE_BOAT)

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## Top Upper Matecumbe Key Hotel Reviews

![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg)

### Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent

"Everything about this place was perfect, location, staff, comfort, and amenities. Can’t wait to go back!"

[](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information)

![Lime Tree Bay Resort](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8_y.jpg)

### Lime Tree Bay Resort

10/10 Excellent

"Beautiful resort on the beach and everything was perfect ."

[](https://expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information)

![Hadley Resort and Marina](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd_y.jpg)

### Hadley Resort and Marina

10/10 Excellent

"Clean room and beautiful view. "

[](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information)

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

### Waterside Suites & Marina

10/10 Excellent

"Location was great. View of a well boat traveled canal. Local bar on the other side of the canal had live music we enjoyed from our balcony. Close to Key Largo attractions."

[](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.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 check in was easy. The front desk employee was very kind. Our room was spotless. We spent the afternoon on the beach and used the kayak. We enjoyed breakfast. The omelet chef was awesome. Overall I was very happy with my stay "

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

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg)

### La Siesta Resort & Villas

10/10 Excellent

"The kitchen had nothing in it, so plan ahead. No silverware at all. The room was as pictured, and the pool.and beach areas were very nice. Lots of restaurants super close. Shopping nearby as well"

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

"All the staff were friendly and helpful, and the property was clean and enjoyable! We truly enjoyed our stay! "

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

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg)

### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent

"We had a wonderfull time. Everyone was very attentive and helpful."

[](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information)

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg)

### Hawks Cay Resort

10/10 Excellent

"Overall great experience."

[](https://expedia.ca/Marathon-Hotels-Hawks-Cay-Resort.h6068.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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- [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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