Title: Book the Best PET FRIENDLY Hotels in Upper Matecumbe Key, FL from CA $236 - Upper Matecumbe Key Dog-Friendly Hotels | 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 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 # Find Pet-friendly Hotels in Upper Matecumbe Key, FL from CA $236 - ![](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 availability on Upper Matecumbe Key Pet-friendly Hotels Tonight [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-22&endDate=2025-12-23&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-23&endDate=2025-12-24&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upper Matecumbe Key pet-friendly hotels ![Private beach, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/12d77a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/fa9b6bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) Matecumbe 9.2/10 Wonderful (1601) "The entire resort was wonderful." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Mat CA $253 CA $363 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Outdoor pool, free cabanas](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/25606792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/711b38d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Double Beds, Kitchenette](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/4c5cb130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/0fad4f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn [](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information) Matecumbe 9.4/10 Exceptional (1000) "Room was clean and staff was helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $196 CA $236 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/0cb6bab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/b1df7837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach umbrellas, beach towels](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/658c83a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/2b7458ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sands of Islamorada [](https://www.expedia.ca/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information) Matecumbe 8.8/10 Excellent (392) "The rooms were recently remodeled and very nice. People are really nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammie CA $250 CA $300 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/6ec44483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/3ea0faf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/b513b652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1002) "The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa CA $371 CA $511 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Dock](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/61b3d4d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach towels, kayaking](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/8952c233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/00476fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hadley Resort and Marina [](https://www.expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) Matecumbe 7.6/10 Good (1001) "Comfortable stay. Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anand CA $205 CA $276 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite King](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/2f598fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Accessible Room King Bed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/1b5ced17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/28233e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Matecumbe 8.8/10 Excellent (1267) "Friendly staff and beautiful property !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ron CA $302 CA $432 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/7578de06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, Multiple Beds (Casa de Coco) | Dining room](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/9c557f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a11bb47b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) Matecumbe 8.8/10 Excellent (1001) "Great stay and beautiful space" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amir CA $259 CA $384 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/46d4fa27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/c40dc838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/w865h663x80y0-54866bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/w1009h683x7y0-80f60840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Morada [](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) Matecumbe 9.4/10 Exceptional (415) "always a pleasant stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert CA $579 CA $750 total includes taxes & fees Jan 22 - Jan 23, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Brand New Two King Bay Front | Private kitchen](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/4b05ab7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/29faa902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/641fc549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Villas by Islander Resort [](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) Matecumbe 8.8/10 Excellent (401) "Beautiful stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lakyne CA $403 CA $547 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/117520000/117513700/117513696/w792h683x116y0-7801bafe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117520000/117513700/117513696/w796h683x114y0-75fb9199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117520000/117513700/117513696/w585h683x219y0-7853365b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117520000/117513700/117513696/w865h663x80y0-e3c92120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Suite @Islamorada With Pool Access - Twilight Suite [](https://www.expedia.ca/Islamorada-Hotels-Charming-Suite-Islamorada-With-Pool-Access-Twilight-Suite.h117513696.Hotel-Information) Matecumbe CA $2,760 CA $3,484 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Charming-Suite-Islamorada-With-Pool-Access-Twilight-Suite.h117513696.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=2026-01-05&endDate=2026-01-06®ionId=553248635975749648&adults=2&amenities=PETS&sort=RECOMMENDED&openPlayBack=true) ## Top Upper Matecumbe Key Hotel Reviews ![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) ![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) ![Sands of Islamorada](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/0cb6bab7_y.jpg) ### Sands of Islamorada 10/10 Excellent "AC was very good kept the room at 68 and was very cold and comfortable. We didn’t cook but it appeared to be well stocked for those that would have " [](https://expedia.ca/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information) ![Bayside Villas by Islander Resort](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579_y.jpg) ### Bayside Villas by Islander Resort 10/10 Excellent "Beautiful stay!!!" [](https://expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ![Casa Morada](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/46d4fa27_y.jpg) ### Casa Morada 10/10 Excellent "Room was clean. Facility beautiful. Staff wonderful!" [](https://expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.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 "Comfortable stay. Great location. " [](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.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 "Great stay and beautiful space" [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Adults-Only-Resorts.0-n6240961-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Casino Hotels in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Casino-Hotel.0-n6240961-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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