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
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travellers recommend
WonderWorks All Access After Dark
$28
per traveler
88% of travellers recommend
The Outta Control Magic Dinner Show
$39
per adult
86% of travellers recommend
Oakland Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
$125 nightly
The price is $141 total per night from Jun 4 to Jun 5
$141 total
Jun 4 - Jun 5
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! (5,532 reviews)
"ALL staff were polite and knowledgeable going out of there way to accommodate any and all of your needs. The grounds are beautiful and clean as are the rooms. This resort has numerous outdoor pools which were clean, warm and never really crowded. I would recommend this resort to anyone and would ..."
Reviewed on May 21, 2026
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
$214 nightly
The price is $241 total per night from May 25 to May 26
$241 total
May 25 - May 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! (9,923 reviews)
"We loved every second of our stay here, EXCEPT the outside doors slam so loudly and it is so hard to sleep early in the morning as doors are slamming from 5AM on."
Reviewed on May 21, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
$147 nightly
The price is $165 total per night from Jun 21 to Jun 22
$165 total
Jun 21 - Jun 22
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! (6,805 reviews)
"Very convenient. My son and I had a great time."
Reviewed on May 21, 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
7400 Canada Ave Orlando FL
$86 nightly
The price is $96 total per night from Jun 1 to Jun 2
$96 total
Jun 1 - Jun 2
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! (1,430 reviews)
"It was quiet and very beautiful"
Reviewed on May 21, 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! (823 reviews)
"El hotel estaba muy limpio , el personal muy atento , los utensilios todo funcionaba bien."
Reviewed on May 21, 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! (2,287 reviews)
"Clean room. Outdoor pool was ok. Breakfast is poor."
Reviewed on May 21, 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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