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.
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.
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.
Things to do
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
$202
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
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
$133 nightly
The price is $150 total per night from Jan 6 to Jan 7
$150 total
Jan 6 - Jan 7, 2026
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 ...
8.8/10 Excellent! (5,868 reviews)
Stayed in the family suite. It was clean and met my expectations. I would recommend staying here.
Reviewed on Dec 27, 2025
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
$80 nightly
The price is $90 total per night from Jan 5 to Jan 6
$90 total
Jan 5 - Jan 6, 2026
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! (3,923 reviews)
Bathroom was small and outdated but it was convenient and close to great places
Reviewed on Dec 25, 2025
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
$84 nightly
The price is $95 total per night from Jan 14 to Jan 15
$95 total
Jan 14 - Jan 15, 2026
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! (5,450 reviews)
The breakfast was more expensive than we wanted to pay so we went elsewhere to eat.
Reviewed on Dec 28, 2025
Avanti International Resort
8738 International Dr Orlando FL
$97 nightly
The price is $109 total per night from Jan 27 to Jan 28
$109 total
Jan 27 - Jan 28, 2026
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
7.8/10 Good! (4,344 reviews)
Friendly staff, helpful.
Reviewed on Dec 27, 2025
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive Orlando FL
$106 nightly
The price is $119 total per night from Jan 5 to Jan 6
$119 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.4/10 Good! (6,317 reviews)
No vimos desayuno
Reviewed on Dec 27, 2025
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
$89 nightly
The price is $101 total per night from Jan 15 to Jan 16
$101 total
Jan 15 - Jan 16, 2026
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! (6,885 reviews)
Very clean room and very friendly staff alongside a wonderful dining experience. Will definitely be staying here again!
Reviewed on Dec 27, 2025
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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