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 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.
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.
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
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
$119 nightly
The price is $134 total per night from Jun 4 to Jun 5
$134 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! (5,463 reviews)
The parking fee is a little ridiculous after paying such value for the whole resort.
Reviewed on May 14, 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 21 to May 22
$241 total
May 21 - May 22
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! (9,847 reviews)
we loved the pools
Reviewed on May 14, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
$150 nightly
The price is $169 total per night from May 17 to May 18
$169 total
May 17 - May 18
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! (6,766 reviews)
Room was clean, food options great, pool was nice.
Reviewed on May 14, 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
7400 Canada Ave Orlando FL
$85 nightly
The price is $96 total per night from May 21 to May 22
$96 total
May 21 - May 22
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! (1,367 reviews)
well organized hotel and the layout of the rooms were well thought out. Location in relation to International drive was very good
Reviewed on May 14, 2026
B&B Hotel Orlando International Drive Near Universal - Newly Renovated!
6323 International Dr Orlando FL
$63 nightly
The price is $71 total per night from May 19 to May 20
$71 total
May 19 - May 20
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! (777 reviews)
The room had an unpleasant smell when we first entered. The rooms weren’t cleaned regularly; it was something that needed to be requested, and the employee provided me with incorrect information a day before my arrival at the property. Consequently, I ended up paying more money.
Reviewed on May 13, 2026
Buena Vista Suites Orlando
8203 World Center Dr Orlando FL
$142 nightly
The price is $160 total per night from May 31 to Jun 1
$160 total
May 31 - Jun 1
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! (2,262 reviews)
Staff was truly awesome. Pleasant, helpful, and welcoming!!!
Reviewed on May 13, 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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