Title: Book the Best BOUTIQUE Hotels in Oakland Hills in 2025 | Expedia.ca [Vacation Rentals in Rotonda West](https://expedia.ca/Rotonda-West-Vacation-Rentals.d6341253.Travel-Guide-VacationRentals)[Flights to Rotonda West](https://expedia.ca/Cheap-Flights-To-Rotonda-West.d6341253.Travel-Guide-Flights)[Oakland Hills Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland-Hills.d553248635976470746.Car-Rental-Guide)[Oakland Hills Vacations](https://expedia.ca/Oakland-Hills.d553248635976470746.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/68575acfc5cb65bceeec32f9adbc2c9f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Oakland Hills, FL from CA $90 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Oakland Hills Boutique Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976470746&startDate=2025-10-01&endDate=2025-10-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976470746&startDate=2025-10-02&endDate=2025-10-03&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976470746&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976470746&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Hills Boutique Hotels ## Top Oakland Hills Hotel Reviews ![Four Points by Sheraton Punta Gorda Harborside](//images.trvl-media.com/lodging/3000000/2660000/2657300/2657255/277fe43e_y.jpg) ### Four Points by Sheraton Punta Gorda Harborside 10/10 Excellent "Nice" [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Four-Points-By-Sheraton-Punta-Gorda-Harborside.h2657255.Hotel-Information) ![Wyvern Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2200000/2193300/2193202/724bdd21_y.jpg) ### Wyvern Hotel, an Ascend Collection Hotel 10/10 Excellent "Room was wonderful and the rooftop amazing! Highly recommended " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Wyvern-Hotel.h2193202.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Oakland Hills? > After you've decided where to stay, consider what to do for fun during your trip. Attractions and activities to experience around Oakland Hills include Don Pedro Island Beach, Stump Pass Beach State Park, and Little Gasparilla Island Beach. 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