Oakland Travel Guide
Winter Garden
Popular places to visit
Flamingo Crossings Town Center
You can find the perfect gifts to bring home at Flamingo Crossings Town Center during your stay in Winter Garden. Discover the top-notch restaurants and entertainment choices in this walkable area.
Disney's Magnolia Golf Course
Enjoy a round of golf in Winter Garden at Disney's Magnolia Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
Disney's Palm Golf Course
Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
Orange County National Golf Club
Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices.
Surfari Water Park
Enjoy the thrill rides with your children at Surfari Water Park as part of your trip to Four Corners. Make time for the shops and golf courses in this family-friendly area.
Disney's Oak Trail Golf Course
Enjoy a round of golf in Winter Garden at Disney's Oak Trail Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
Things to do
Universal Orlando Resort Theme Park Tickets
Old Town Kissimmee: Attraction & Meal Voucher
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Orlando: 7-D Dark Ride Entry Ticket
Top hotels in Oakland
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Great location lots of amenities, the pictures looked just like the Villas. We would stay here again.
Reviewed on 28 Apr 2026
Universal's Cabana Bay Beach Resort
Room was clean, staff was very willing to help. And seemed knowledgeable!
Reviewed on 28 Apr 2026
The Grove Resort & Water Park Orlando
Yes. Pool and slides were great for the price of the resort fee. The restaurant Valencia was unbearably slow. Plan to lose 2 hours there for a meal. The hallways were filthy (we were instructed to leave our trash in the hall. There was old trash debris scattered throughout the entirety of the hallway. ...
Reviewed on 28 Apr 2026
DoubleTree by Hilton at the Entrance to Universal Orlando
Great
Reviewed on 27 Apr 2026
Westgate Lakes Resort & Spa Universal Studios Area
Room service should come often
Reviewed on 28 Apr 2026
Rosen Inn at Pointe Orlando
Check in staff was amazing. So helpful and went above and beyond. Breakfast was good. Good variety. And lovely servers.
Reviewed on 28 Apr 2026
Other neighbourhoods around Oakland
Killarney
Killarney might not have many top sights, but Bella Collina Golf Club and West Orange Trail are two attractions nearby that you can check out.
Downtown Winter Garden
If you're spending some time in Downtown Winter Garden, West Orange Trail and Central Florida Railroad Museum are top sights worth seeing.
