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.
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.
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.
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.
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.
Top hotels in Oakland
The Grove Resort & Water Park Orlando
Me and my family had a great experience!! My only ick was we never received blankets after requesting them twice but overall 10/10!
Reviewed on 4 Mar 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
We love to stay here for our run Disney race weekends. The resort staff is always kind and helpful. Our villa was clean, the grounds are very nice and well maintained.
Reviewed on 4 Mar 2026
DoubleTree by Hilton at the Entrance to Universal Orlando
It was a great location. There was mold in the shower and the sheets were dirty. The from desk staff were great.
Reviewed on 3 Mar 2026
Vacation Village Orlando, Celebration
Great resort to take your family very clean check in was a little long, but they got you in and out
Reviewed on 4 Mar 2026
Universal's Cabana Bay Beach Resort
We liked our family room suite- it was clean, quiet and dark when we slept. The beds were comfortable but the chairs in the room and throughout the resort are cheap and not comfy to sit in. The staff wasn’t very friendly, they were on the robotic side, just going through the motions. Check in was ...
Reviewed on 4 Mar 2026
Orlando International Drive North Hotel
It was great for traveling on a budget, but I like my rooms to be a bit cleaner; they need to mop a bit more thoroughly, but the bed was very clean.
Reviewed on 4 Mar 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.
