Title: Book the Best PET FRIENDLY Hotels in Upper Matecumbe Key, FL - 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 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) # Find Pet-friendly Hotels in Upper Matecumbe Key, FL ![](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 [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-11&endDate=2025-10-12&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-12&endDate=2025-10-13&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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) ![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) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/43f5c138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort Matecumbe 9.2/10 Wonderful (1537) "Wonderful property, breakfast was awesome " CA $209 CA $314 total includes taxes & fees Oct 29 - Oct 30 [](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) ![Garden](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/92298919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Matecumbe 9.4/10 Exceptional (1003) "Great place to stay!" CA $156 CA $191 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.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) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/29faa902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/8ad54011.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 Matecumbe 8.8/10 Excellent (391) "Great place to stay" CA $305 CA $437 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.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) ![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) ![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) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1254) "Great hotel with a perfect location and friendly staff." CA $175 CA $290 total includes taxes & fees Oct 19 - Oct 20 [](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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a375b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas Matecumbe 8.6/10 Excellent (1004) "Great rooms" CA $149 CA $261 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.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) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/8f06ee9a.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) ### Hadley Resort and Marina Matecumbe 7.8/10 Good (1003) "Loved the rooms very spacious. Ocean view was amazing very close to restaurants " CA $137 CA $200 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.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) ![1 bedroom, premium bedding, in-room safe, desk](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) ![Islander Suite Ocean View Two Bedroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort Matecumbe 9.2/10 Wonderful (1008) "Stunning resort with great amenities and excellent service! " CA $277 CA $407 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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) ![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) ![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) ### Sands of Islamorada Matecumbe 8.8/10 Excellent (389) "The hotel was reasonably priced and while a little dated, the rooms were large and clean. The staff was SUPER nice. All in all, a great place to stay a couple nights in the keys at a reasonable price. Would definitely recommend!" CA $227 CA $274 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.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) ![Jungles Suite](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/w762h679x132y4-fc33a6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/b7eb418d.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 Matecumbe 9.4/10 Exceptional (409) "The marina was clean and convenient." CA $335 CA $415 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/117530000/117523100/117523098/w792h683x116y0-40905cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117530000/117523100/117523098/w796h683x114y0-41338ccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/118000000/117530000/117523100/117523098/w1009h683x7y0-57cf914a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117530000/117523100/117523098/w865h663x80y0-59e3e4fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite Matecumbe CA $1,401 CA $1,775 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-Peaceful-Garden-King-Suite-Islamorada-Gem-Gumbo-Limbo-Suite.h117523098.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=2025-10-25&endDate=2025-10-26®ionId=553248635975749648&adults=2&amenities=PETS&sort=RECOMMENDED&openPlayBack=true) ## Top Upper Matecumbe Key Hotel Reviews ![La Siesta Resort & Villas](//images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "Excelent service " [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Hadley Resort and Marina](//images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd_y.jpg) ### Hadley Resort and Marina 10/10 Excellent "Super " [](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "My son and his new wife had an amazing time on their honeymoon! They said everything was top notch and have gone on & on about what an amazing time they had! ⭐️⭐️⭐️⭐️⭐️" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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 "Excelent" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.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 "used tge dock very easy " [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Hampton Inn Key Largo Manatee Bay](//images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233_y.jpg) ### Hampton Inn Key Largo Manatee Bay 10/10 Excellent "The rooms are showing their age but all new remodeling starts soon. Staff very professional and met all our needs. Breakfast was great. Extremely convenient for our trip. We recommend and would stay there again." [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Bayside Villas by Islander Resort](//images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579_y.jpg) ### Bayside Villas by Islander Resort 10/10 Excellent "We loved our stay at Bayside Villas. We loved the access to both Bayside and Oceanside, the activities were great! Beautiful rooms, grounds! We will definitely return in the future. " [](https://expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ![Sands of Islamorada](//images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/0cb6bab7_y.jpg) ### Sands of Islamorada 10/10 Excellent "The hotel was reasonably priced and while a little dated, the rooms were large and clean. The staff was SUPER nice. All in all, a great place to stay a couple nights in the keys at a reasonable price. Would definitely recommend!" 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