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 Express Passes
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Walt Disney World® Resort Disney After Hours
Universal Orlando Resort Theme Park Tickets
Walt Disney World® Resort Theme Park Tickets
Top hotels in Oakland
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
While we were only there for 1 night, it was a great place to stay. The rooms are amazing and it was perfect for any family. Both the bed and sofabed were amazingly comfortable. The ONLY downside is if you like a firmer pillow, bring one as I felt they were almost too soft.
Reviewed on 29 Apr 2026
Universal's Cabana Bay Beach Resort
Fabulous
Reviewed on 29 Apr 2026
The Grove Resort & Water Park Orlando
My family and I loved everything about this resort! Next time we visit Orlando again this is where we’ll be staying!!
Reviewed on 29 Apr 2026
DoubleTree by Hilton at the Entrance to Universal Orlando
The pool was wonderful and the room was very clean
Reviewed on 29 Apr 2026
Westgate Lakes Resort & Spa Universal Studios Area
Beautiful property, lots of amenities and staff was friendly and helpful. Will definitely return
Reviewed on 30 Apr 2026
Rosen Inn at Pointe Orlando
Very convenient
Reviewed on 29 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.
