Oakland, FL
Winter Garden
Popular places to visit
Flamingo Crossings Town Center
You can do some window-shopping at Flamingo Crossings Town Center during your visit to 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 a fun-filled day 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
Though AdventHealth Winter Garden might be what brings you to town, perhaps you'll have a chance to explore more of Winter Garden while you are here.
Things to do
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$36
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
$149
per traveler
86% of travellers recommend
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
$15
per adult
80% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
$12
per adult
90% of travellers recommend
WonderWorks All Access After Dark
$28
per traveler
88% of travellers recommend
Oakland Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
The price is $151 total per night from Jan 22 to Jan 23
$151 total
per night
Jan 22 - Jan 23
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (4,363 reviews)
Was a very nice room, with a great
Reviewed on Jan 20, 2026
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive Orlando FL
The price is $112 total per night from Feb 8 to Feb 9
$112 total
per night
Feb 8 - Feb 9
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.4/10 Good! (6,406 reviews)
The breakfast is good. The environment is quite.
Reviewed on Jan 18, 2026
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
The price is $85 total per night from Feb 8 to Feb 9
$85 total
per night
Feb 8 - Feb 9
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
8.4/10 Very Good! (5,571 reviews)
A nice room for the value. Very safe, and very quiet.
Reviewed on Jan 20, 2026
Orlando International Drive North Hotel
5859 American Way Orlando FL
The price is $84 total per night from Jan 27 to Jan 28
$84 total
per night
Jan 27 - Jan 28
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
7.2/10 Good! (2,709 reviews)
location, amenities
Reviewed on Jan 20, 2026
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
The price is $200 total per night from Jan 22 to Jan 23
$200 total
per night
Jan 22 - Jan 23
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (8,971 reviews)
Room was clean and the atmosphere was very enjoyable will love to return with better weather!
Reviewed on Jan 20, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
The price is $150 total per night from Jan 25 to Jan 26
$150 total
per night
Jan 25 - Jan 26
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (6,086 reviews)
Wonderful staff, even when the check-in lines were long, they were all super friendly. Room was clean, the location and amenities were fantastic. I’d make cabana bay my go to for any universal trip.
Reviewed on Jan 18, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other neighborhoods around Oakland
Killarney
If you're looking for some top things to see and do in Killarney and surrounding area, you can visit Bella Collina Golf Club and West Orange Trail.
Downtown Winter Garden
While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum.
Oakland, FL
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