Title: Upper Matecumbe Key Vacation Rentals from CA $272: 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 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Jan 8 - Jan 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-08&endDate=2026-01-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 9 - Jan 10](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-09&endDate=2026-01-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [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) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-16&endDate=2026-01-18&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) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.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) ![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 (606) "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 $179 CA $272 total includes taxes & fees Jan 14 - Jan 15 [](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/55000000/54780000/54774300/54774228/95dbc957.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) ### Villa in Matecumbe [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) 9.8/10 Exceptional (70) "Amazing stay, can’t wait to stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $766 CA $938 total includes taxes & fees Jan 12 - Jan 13 [](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) ![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) ![Front of property](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/13368841.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 (123) "Great spot! Will be back someday hopefully. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Diane CA $185 CA $403 total includes taxes & fees Jan 13 - Jan 14 [](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) ![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) ### Houseboat in Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information) CA $1,740 CA $1,957 total includes taxes & fees Jan 12 - Jan 13 [](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=2026-01-22&endDate=2026-01-23®ionId=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®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=APART_HOTEL) Villas [](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=VILLA) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=APARTMENT) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=HOUSE_BOAT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=COTTAGE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FUpper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals) ## Top Upper Matecumbe Key Hotel Reviews ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "The property is spectacular - absolutely beautiful, lit up at night with torches and lighting. The room was well appointed, clean and relaxing. The food was good, the service was excellent." [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.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 "Amazing place - so much variety" [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.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 "I would definitely stay here again. The property and staff are awesome. The pool hours could be extended. Closing at 5pm is very early. " [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.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 resort is a great family friendly atmosphere. The staff was extremely hospitable. The beach is clean and lots of fun activities to do. Only wish we had more time! " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.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 "The room was nicely prepared when we arrived and the maid service was excellent all week. The office staff were all very pleasant and helpful. The hotel is well situated close to restaurants and stores. The breakfast was simple but with a good selection and plentiful supply. The place was pretty quiet most of the time and we slept well in a comfy bed. The bathroom was old and in need of some TLC but everything worked just fine and we had no problems." [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Breezy Palms Resort](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg) ### Breezy Palms Resort 10/10 Excellent "The bungalow was quaint and well appointed. " [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.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 a great stay. Very nice and clean condo with its own small pool. The property is beautiful and we enjoyed the tennis and pickleball facilities. Only areas for improvement were the initial delay in room being available from housekeeping and need for more service staff around the pool area." [](https://expedia.ca/Marathon-Hotels-Hawks-Cay-Resort.h6068.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 "Room was very nice resort was clean" [](https://expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Rooms were clean, restaurant food was excellent, and service was friendly." [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.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. 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