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.
Top hotels in Oakland
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
The room was immaculate and the property is amazing.
Reviewed on 4 May 2026
Universal's Cabana Bay Beach Resort
Everybody was super sweet and helpful
Reviewed on 3 May 2026
The Grove Resort & Water Park Orlando
We stayed here because it was selected by the person organizing our trip. Overall, I found it overpriced for what was offered. At check-in, we received a small pretzel and popcorn, but beyond that, there weren’t many amenities that justified the cost. It also felt like there were extra fees for everything. ...
Reviewed on 4 May 2026
DoubleTree by Hilton at the Entrance to Universal Orlando
We had a party of 12 and 3 rooms. Everything was great. The elevator situation was a little slow but it got you where you need to be.
Reviewed on 4 May 2026
Westgate Lakes Resort & Spa Universal Studios Area
Clean room, friendly staff, beautiful lake
Reviewed on 4 May 2026
Rosen Inn at Pointe Orlando
Didn't use the breakfast bar.
Reviewed on 3 May 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.
