Find Boutique Hotels in Oakland Hills, FL

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Oakland Hills Boutique Hotels

Tonight
Aug 7 - Aug 8
Tomorrow
Aug 8 - Aug 9
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Oakland Hills Boutique Hotels

Top Oakland Hills Hotel Reviews

Four Points by Sheraton Punta Gorda Harborside

Four Points by Sheraton Punta Gorda Harborside

10/10 Excellent
"The rooms are really quiet."
Terry 3-night trip
Posted 3 days ago
Four Points by Sheraton Punta Gorda Harborside
Wyvern Hotel, Ascend Hotel Collection

Wyvern Hotel, Ascend Hotel Collection

10/10 Excellent
"Great views of harbor "
Walter Fenwick 2-night trip
Posted 4 days ago
Wyvern Hotel, Ascend Hotel Collection

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 Stump Pass Beach State Park, Little Gasparilla Island Beach, and Englewood Beach. For even more to see and do, make a stop at Boca Grande Beach, Blind Pass Beach, and Charlotte Sports Park.
#### When Should I Plan a Trip to Oakland Hills?\n
If you're curious about local weather, you can use this info to help you plan your escape to Oakland Hills: