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! (5,531 reviews)
"My family and I had an amazing experience and will be back."
Reviewed on May 21, 2026
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
$209 nightly
The price is $235 total per night from May 27 to May 28
$235 total
May 27 - May 28
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! (9,920 reviews)
"Great overall experience."
Reviewed on May 21, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
$147 nightly
The price is $166 total per night from May 27 to May 28
$166 total
May 27 - May 28
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! (6,803 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
$87 nightly
The price is $98 total per night from Jun 1 to Jun 2
$98 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! (1,429 reviews)
"Roaches everywhere and strong smell of mold."
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! (822 reviews)
"Everything was perfect. Great hotel great ocation"
Reviewed on May 21, 2026
Buena Vista Suites Orlando
8203 World Center Dr Orlando FL
Fully refundableReserve now, pay when you stay
$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! (2,286 reviews)
"Traditional American breakfast buffet. Rooms and bathroom clean 4/5."
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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