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 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.
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.
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.
AdventHealth Winter Garden
If AdventHealth Winter Garden is what brings you to town, hopefully you'll have a chance to explore more of Winter Garden.
Things to do
Universal Orlando Resort Theme Park Tickets
Old Town Kissimmee: Attraction & Food/Drink Voucher
Orlando: 7-D Dark Ride Entry Ticket
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
Top hotels in Oakland
Universal's Cabana Bay Beach Resort
The mobile check-in counter representative was amazing. Everything about this hotel is remarkable…
Reviewed on 10 Jan 2026
Wyndham I-Drive Avanti Resort & Conference Center
10/10
Reviewed on 6 Jan 2026
The Grove Resort & Water Park Orlando
Nice room, great service
Reviewed on 12 Jan 2026
Rosen Inn at Pointe Orlando
The rooms are a little out dated. The television reception is HORRIBLE. called the front desk they would have someone come and look at TV HA ha ha. When the sound goes in and out and the picture is terrible and it's late no one is coming to fix the tv. This type of restort should have much better ...
Reviewed on 12 Jan 2026
DoubleTree by Hilton Hotel Orlando at SeaWorld
Beautiful hotel and friendly staff!
Reviewed on 8 Jan 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Excellent
Reviewed on 12 Jan 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.
