Title: Pet-friendly Vacations in Upper Matecumbe Key 2026 | Expedia.ca ![](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Upper Matecumbe Key Pet-friendly Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Cameron Abbott - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Pet-friendly Hotels in Upper Matecumbe Key ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Beach Resort 83409 Overseas Hwy Islamorada FL - 10 min drive from Bud n' Mary's Dive Center Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ... 9.2/10 Wonderful! (1,668 reviews) Couldn't say enough good things about this place! Right on the water! Super clean facility - seemed new! Ready for the differentiator? The breakfast team! MADE TO ORDER OMELET OR EGGS! So awesome!! Salt Water and Fresh Water Pools! Hot tub! Yup, we will be back! March '26 Reviewed on Mar 5, 2026 [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Islander Resort 82100 Overseas Highway Islamorada FL - 6 min drive from Bud n' Mary's Dive Center Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ... 9.2/10 Wonderful! (1,009 reviews) Great boutique type hotel with good amenities. Excellent landscaping, lighting and access to amenities. Reviewed on Mar 2, 2026 [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Siesta Resort & Villas 80241 Overseas Highway Islamorada FL - 12 min walk from Bud n' Mary's Dive Center Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ... 8.8/10 Excellent! (1,003 reviews) Grrat view from room and location is awesome. Reviewed on Mar 4, 2026 [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) [See all 2,793 properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635975749648) 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## More Vacations Ideas [Flights to Upper Matecumbe Key ](https://expedia.ca/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[ Upper Matecumbe Key Hotels ](https://expedia.ca/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[ Upper Matecumbe Key Vacation Rentals ](https://expedia.ca/Upper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[ Upper Matecumbe Key Car Rentals ](https://expedia.ca/Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648.Car-Rental-Guide)[ Upper Matecumbe Key Vacations ](https://expedia.ca/Upper-Matecumbe-Key.d553248635975749648.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app