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
5/5(1 review)
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
4/5(6 reviews)
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
4.5/5(25 reviews)
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
4.5/5(374 reviews)
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
$115 nightly
The price is $130 total per night from Feb 22 to Feb 23
$130 total
Feb 22 - Feb 23
Total with taxes and fees
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 at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
$116 nightly
The price is $131 total per night from Feb 24 to Feb 25
$131 total
Feb 24 - Feb 25
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (6,939 reviews)
Our room was clean and cozy, loved our stay. Staff was friendly and helpful as well
Reviewed on Jan 21, 2026
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
$75 nightly
The price is $85 total per night from Jan 27 to Jan 28
$85 total
Jan 27 - Jan 28
Total with taxes and fees
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
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
$84 nightly
The price is $94 total per night from Jan 27 to Jan 28
$94 total
Jan 27 - Jan 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the clean rooms in our ...
7.2/10 Good! (4,071 reviews)
It was ok
Reviewed on Jan 22, 2026
Orlando International Drive North Hotel
5859 American Way Orlando FL
$75 nightly
The price is $85 total per night from Jan 27 to Jan 28
$85 total
Jan 27 - Jan 28
Total with taxes and fees
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! (2,728 reviews)
Pros: Clean, Comfortable, Great Location (close to universal studios other attractions) Accessible, Splash Pad and Pool great & clean. Staff helpful and friendly! Overall I think this is a great hotel & very decently priced. Cons: You can hear everything going on outside of your room. People walking ...
Reviewed on Jan 22, 2026
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
$178 nightly
The price is $200 total per night from Jan 25 to Jan 26
$200 total
Jan 25 - Jan 26
Total with taxes and fees
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! (8,979 reviews)
This is about our 4th time at the resort and each time we have been highly impressed and satisfied. We will be back!
Reviewed on Jan 22, 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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