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.
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.
West Orange Trail
Enjoy a trip to West Orange Trail and popular activities such as taking adventure tours in Winter Garden. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.
Things to do
Universal Orlando Resort Theme Park Tickets
WonderWorks All Access After Dark
Orlando: 7-D Dark Ride Entry Ticket
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
Walt Disney World® Resort Theme Park Tickets
Top hotels in Oakland
DoubleTree by Hilton Hotel Orlando at SeaWorld
Great location friendly staff
Reviewed on 9 Dec, 2025
Universal's Cabana Bay Beach Resort
Excellent
Reviewed on 15 Dec, 2025
Rosen Inn at Pointe Orlando
The entire property was well-maintained and welcoming. The lobby and shops were beautifully decorated for Christmas and even had a “Letters to Santa” station set up. The rooms were clean and the bed and pillows extremely comfortable. You could not ask for a better centrally located area. We were ...
Reviewed on 11 Dec, 2025
DoubleTree by Hilton at the Entrance to Universal Orlando
The room was very clean, lots of towels and linens provided. The manager greeted us when we first walked in and had a great conversation (which I never do). It was a 15 minute walk from Universal. It was too cold for the pool, but it looked great! The game room was also a fun plus too!
Reviewed on 15 Dec, 2025
Wyndham I-Drive Avanti Resort & Conference Center
Upon arrival, our toilet overflowed and the bathtub was linking underneath. However, after we moved to another room, everything was great.
Reviewed on 14 Dec, 2025
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Great place I will definitely stay again
Reviewed on 15 Dec, 2025
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.
Oakland
- Walt Disney World® Resort
- Universal Studios Florida
- Universal Orlando Resort
- Magic Kingdom® Park
- Orange County Convention Center
- Disney's Animal Kingdom® Theme Park
- Epcot®
- Disney's Hollywood Studios®
- Kia Center
- ESPN Wide World of Sports Complex
- Universal’s Islands of Adventure
- Camping World Stadium
- Aquatica
- Mystic Dunes Golf Club
- Arnold Palmer's Bay Hill Golf Club
