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 Express Passes
Universal Orlando Resort Theme Park Tickets
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
WonderWorks All Access After Dark
Wild Dolphin Exploration Boat Ride and Clearwater Beach Day
Top hotels in Oakland
Universal's Cabana Bay Beach Resort
Good
Reviewed on 4 Jan 2026
Wyndham I-Drive Avanti Resort & Conference Center
Everything was nice and neat
Reviewed on 31 Dec 2025
Rosen Inn at Pointe Orlando
Very good hotel. Affordable place for saving money and having a good night of sleeping.
Reviewed on 3 Jan 2026
The Grove Resort & Water Park Orlando
Very nice, 3 time at the grove and it doesn’t disappoint
Reviewed on 4 Jan 2026
DoubleTree by Hilton Hotel Orlando at SeaWorld
The breakfast food is amazing,the staff members are super nice and helpful. A very clean room nice area fun games.
Reviewed on 3 Jan 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Clean ,so good
Reviewed on 3 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.
