Oakland, FL

Winter Garden

Photo by Gregg Yutko
Photo by Gregg Yutko

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 family-friendly area.

Flamingo Crossings Town Center

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 Palm Golf Course

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.

Orange County National Golf Club

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.

Disney's Magnolia Golf Course

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.

Surfari Water Park

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.

AdventHealth Winter Garden

Oakland Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando
4 out of 5
5780 Major Blvd, Orlando, FL
The price is ₩115,888 per night from Aug 4 to Aug 5
₩115,888
₩130,374 total
Aug 4 - Aug 5
includes taxes & fees
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.2/10 Very Good! (6,470 reviews)
"Excellent hotel , fresh towels everyday, clean room everyday. Excellent area right in front of universal studios.this hotel is the best"

Reviewed on Jul 14, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Marriott's Grande Vista
Marriott's Grande Vista
4 out of 5
5925 Avenida Vista, Orlando, FL
The price is ₩131,106 per night from Aug 4 to Aug 5
₩131,106
₩147,495 total
Aug 4 - Aug 5
includes taxes & fees
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (2,621 reviews)
"The hotel room was comfortable and spacious. The staff was friendly and helpful. This hotel is highly recommended and it’s also close to the attractions."

Reviewed on Jul 13, 2025

Marriott's Grande Vista
Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks
4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
The price is ₩107,694 per night from Aug 10 to Aug 11
₩107,694
₩138,813 total
Aug 10 - Aug 11
includes taxes & fees
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
9.4/10 Exceptional! (616 reviews)
"Great stay"

Reviewed on Jul 13, 2025

Kompose Boutique Resort at Theme Parks
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
The price is ₩205,197 per night from Jul 15 to Jul 16
₩205,197
₩292,819 total
Jul 15 - Jul 16
includes taxes & fees
Stay at this 4-star family-friendly resort in Four Corners. Enjoy 6 outdoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the pool and the helpful ...
7.8/10 Good! (8,115 reviews)
"HIGHLY RECOMMEND! I came here to celebrate my birthday and it exceeded expectations! Definitely will be back!"

Reviewed on Jul 13, 2025

The Grove Resort & Water Park Orlando
Universal's Cabana Bay Beach Resort
Universal's Cabana Bay Beach Resort
3.5 out of 5
6550 Adventure Way, Orlando, FL
The price is ₩218,968 per night from Aug 12 to Aug 13
₩218,968
₩246,339 total
Aug 12 - Aug 13
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (5,195 reviews)
"Wonderful place to stay! Perfect to access Volcano Bay!"

Reviewed on Jul 11, 2025

Universal's Cabana Bay Beach Resort
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4 out of 5
8800 Vistana Centre Dr, Orlando, FL
The price is ₩147,632 per night from Aug 4 to Aug 5
₩147,632
₩166,086 total
Aug 4 - Aug 5
includes taxes & fees
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (3,182 reviews)
"Very spacious rooms. Well maintained resort. Would go again"

Reviewed on Jul 12, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 38,567 properties in Oakland
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

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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 Resurrection Catholic Church.

Killarney
Love this tiny town, just 20 minutes from Walt Disney World. Inside #PlantStreetMarket you’ll find multiple vendors including local food, honey, coffee and desserts, and #crookedcanbrewing #wintergarden #lifeatexpedia

Downtown Winter Garden

While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum.

Downtown Winter Garden
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Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Vista del Lago

Oakland, FL