Title: Upper Matecumbe Key Villas | 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)[Upper Matecumbe Key Vacation Packages](https://expedia.ca/Upper-Matecumbe-Key.d553248635975749648.Destination-Travel-Guides) ![Islamorada which includes a beach bar](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191196-Islamorada.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Upper Matecumbe Key Villa 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 Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Upper Matecumbe Key Villas ![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) ![Boating](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a93dc7d6.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) ### The Islands of Islamorada Matecumbe 9.8/10 Exceptional (66) "Absolutely outstanding resort. Legitimate 5 star property. " CA $772 CA $946 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75670000/75661400/75661357/1ab75f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75670000/75661400/75661357/82213b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/76000000/75670000/75661400/75661357/cb6fb9fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/76000000/75670000/75661400/75661357/dd8e00ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA Duck Key 9.2/10 Wonderful (18) "Property was very nice, everything as expected based on listing. Very good place for families." CA $315 CA $776 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Marathon-Hotels-Villa-5087-On-Duck-Key.h75661357.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/65000000/64570000/64560700/64560631/edeb3198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64570000/64560700/64560631/0946c24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/65000000/64570000/64560700/64560631/90-1b7387ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64570000/64560700/64560631/e09a4628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA Duck Key 9.6/10 Exceptional (54) "Very clean. " CA $332 CA $822 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Marathon-Hotels-Duck-Key-Villa.h64560631.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74090000/74080700/74080672/f8fb90b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74090000/74080700/74080672/9fd1e670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/75000000/74090000/74080700/74080672/99145898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74090000/74080700/74080672/4991ce1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA Marathon 9.2/10 Wonderful (29) "Wonderful experience, great views, clean rooms, great amount of space. Great price" CA $356 CA $849 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Marathon-Hotels-Villa-7075-On-Duck-Key.h74080672.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/111000000/110620000/110616000/110615911/050cedf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110620000/110616000/110615911/4a861100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/111000000/110620000/110616000/110615911/850d621e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110620000/110616000/110615911/68fd4471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seas the Keys Getaway Duck Key 9.6/10 Exceptional (8) "Heated dip pool/hot tub. On the canal, great hosts, prompt replies and great communication." CA $323 CA $647 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Marathon-Hotels-Seas-The-Keys-Getaway.h110615911.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120460000/120452600/120452598/bcbb17d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach towels](https://images.trvl-media.com/lodging/121000000/120460000/120452600/120452598/a1dd58b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120460000/120452600/120452598/2e6c385e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120460000/120452600/120452598/7d65007b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA Duck Key CA $322 CA $783 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Marathon-Hotels-Villa-5008-On-Duck-Key-Boat-Slip-Available-2BD-15BA.h120452598.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88250000/88243000/88242996/65d9b616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88250000/88243000/88242996/698559f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/89000000/88250000/88243000/88242996/4e7df35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88250000/88243000/88242996/062cc7ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun Duck Key 10/10 Exceptional (13) "We enjoyed our stay." CA $447 CA $973 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Marathon-Hotels-Waterfront-Villa-In-Paradise-Dipping-Pool-Middle-Keys-Soak-In-The-Sun.h88242996.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74050000/74045000/74044948/ae2a8b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach towels](https://images.trvl-media.com/lodging/75000000/74050000/74045000/74044948/7aadc845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74050000/74045000/74044948/e9c6e2be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74050000/74045000/74044948/561af59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA Duck Key 8.6/10 Excellent (25) "Great location! We enjoyed our time there." CA $288 CA $742 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Marathon-Hotels-Villa-5086-On-Duck-Key.h74044948.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83040000/83039300/83039248/3a1818d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/84000000/83040000/83039300/83039248/dd06207c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83040000/83039300/83039248/42718c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/84000000/83040000/83039300/83039248/14ed78a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA Duck Key 10/10 Exceptional (4) "Everything about the stay was nice. " CA $343 CA $810 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Marathon-Hotels-Villa-5034-On-Duck-Key-Boat-Slip-Available.h83039248.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92270000/92269900/92269883/197e92bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92270000/92269900/92269883/77d2a162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92270000/92269900/92269883/f3ec1fa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/93000000/92270000/92269900/92269883/09311c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA Duck Key 9.0/10 Wonderful (8) "Property was clean and comfortable with an excellent sunset view each evening." CA $343 CA $810 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Marathon-Hotels-Villa-5028-On-Duck-Key-BOAT-SLIP-Available.h92269883.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120460000/120452800/120452771/bc4c1594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120460000/120452800/120452771/f75bd6cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120460000/120452800/120452771/4f89dbb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120460000/120452800/120452771/6aba9095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA Duck Key CA $308 CA $766 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Marathon-Hotels-Villa-5021-On-Duck-Key-Boat-Slip-Available-2BD-25BA.h120452771.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120450000/120442900/120442882/ff464b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120450000/120442900/120442882/e36a502e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120450000/120442900/120442882/fc3ed5a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120450000/120442900/120442882/8bd69f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA Marathon CA $701 CA $1,471 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Marathon-Hotels-Villa-7071-Boat-Slip-Available.h120442882.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=2025-10-30&endDate=2025-10-31®ionId=553248635975749648&adults=2&lodging=VILLA&sort=RECOMMENDED&openPlayBack=true) ![](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-Villas.d553248635975749648-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpper-Matecumbe-Key-Villas.d553248635975749648-aaVillas.Travel-Guide-Accommodation) ## Top Upper Matecumbe Key Hotel Reviews ![Waterside Suites & Marina](//images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "This was right next to the departure point for Rainbow Reef's scuba diving boats, making it super easy to do a dive week without driving all over. The kitchen in the room was a nice addition as well." [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](//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 "Excellent hotel " [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "The pools where very clean and very comfy, the place is keep very clean. Thank you." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "It was great weekend! Clean room, nice service" [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "I went there this weekend to celebrate my birthday. Great place, well kept, nice service, rooms are pretty and clean. The pools are nice. Loved the resort. Hope to come back soon. They had a room for me right away. Check in was very pleasant. The paddle boarding, and canoes are free with the stay. I enjoyed my stay so much! Coming back home very relaxed! The only things I didn’t like were: my room didn’t have a shower cap or a shower mat, the fire pits were not on at night. Other than that everything was superb! They sent me a msg to see if everything was great and asked if I needed anything to let them know. I will be coming back! " [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Marina Del Mar Resort and Marina](//images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg) ### Marina Del Mar Resort and Marina 10/10 Excellent "Great views and ambience" [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Breezy Palms Resort](//images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg) ### Breezy Palms Resort 10/10 Excellent "The property is older, but very well maintained and renovated. The check in was wonderful. He gave us info about the room and recommended different things to do in the area. The room was very clean, updated, with an ocean view. The bed was very comfortable good morn" [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![La Siesta Resort & Villas](//images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "Excellent stay with great amenities." [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Amazing property! We’ve been going for years!!" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ## Find out more about Upper Matecumbe Key ## Upper Matecumbe Key Villas information | Number of reviews | | | --- | --- | | Accommodation | Villas | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [B&B in Coopertown](https://www.expedia.ca/Coopertown-Bed-And-Breakfast.d6177715-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Coopertown](https://www.expedia.ca/Coopertown-Guest-Houses.d6177715-aaGuestHouses.Travel-Guide-Accommodation) - [B&B in Elliott Key](https://www.expedia.ca/Elliott-Key-Bed-And-Breakfast.d553248621532652848-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Elliott Key](https://www.expedia.ca/Elliott-Key-Condos.d553248621532652848-aaCondos.Travel-Guide-Accommodation) - [Cottages in Elliott Key](https://www.expedia.ca/Elliott-Key-Cottages.d553248621532652848-aaCottages.Travel-Guide-Accommodation) - 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