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.
Disney's Oak Trail Golf Course
Enjoy a round of golf in Winter Garden at Disney's Oak Trail Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
Things to do
Walt Disney World® Resort Disney After Hours
$191
per adult
100% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
$160
per traveler
80% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
$12
per adult
90% of travellers recommend
Orlando: Chocolate Kingdom Factory Adventure Tour
$24
per adult
100% of travellers recommend
Oakland Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
$127 nightly
The price is $142 total per night from Jun 1 to Jun 2
$142 total
Jun 1 - Jun 2
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (5,551 reviews)
"It was the perfect hotel villa for a family trip. The distance to Disney and Universal Studios wasn’t far, so we had such a wonderful and enjoyable vacation."
Reviewed on May 23, 2026
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
$212 nightly
The price is $239 total per night from Jun 10 to Jun 11
$239 total
Jun 10 - Jun 11
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! (9,941 reviews)
"There was roaches in our room."
Reviewed on May 23, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
$133 nightly
The price is $150 total per night from May 25 to May 26
$150 total
May 25 - May 26
Total with taxes and fees
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 ...
9/10 Wonderful! (6,830 reviews)
"Great experience! Bus service to Universal resorts was fast and easy. Close drive to Disney properties. Resort area was clean with plenty to do. Pools were great! Food service at resort was convenient. Food was average but worth it for ease. Conner and Kathryn were great at check in and throughout ..."
Reviewed on May 23, 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
7400 Canada Ave Orlando FL
$81 nightly
The price is $91 total per night from Jun 2 to Jun 3
$91 total
Jun 2 - Jun 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Popular attractions Universal’s Volcano ...
8.6/10 Excellent! (1,443 reviews)
"Bien"
Reviewed on May 23, 2026
B&B Hotel Orlando International Drive Near Universal - Newly Renovated!
6323 International Dr Orlando FL
$70 nightly
The price is $79 total per night from Jun 14 to Jun 15
$79 total
Jun 14 - Jun 15
Total with taxes and fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our reviews. ...
8.4/10 Very Good! (836 reviews)
"Very good very quiet and clean very close to universal and other spot for food tv not working tho"
Reviewed on May 22, 2026
Buena Vista Suites Orlando
8203 World Center Dr Orlando FL
$147 nightly
The price is $165 total per night from Jun 11 to Jun 12
$165 total
Jun 11 - Jun 12
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free breakfast, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,293 reviews)
"Layout of the rooms and value were phenomenal. Will stay again no doubt!"
Reviewed on May 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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