Oakland

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 walkable area.

Flamingo Crossings Town Center

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 Palm Golf Course

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 Magnolia Golf Course

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.

Orange County National Golf Club

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.

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

Things to do

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

P1,531
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

P4,282
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

P2,910
per traveler
82% of travellers recommend
Aquatica Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction and Meal Combo Offers

P1,685
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction and Meal Combo Offers
Indoor Karting

Andretti Indoor Karting & Games in Orlando

P1,735
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
WonderWorks All Access After Dark

WonderWorks All Access After Dark

P1,555
per traveler
86% of travellers recommend
WonderWorks All Access After Dark
See all activities in Winter Garden

Top hotels in Oakland

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 P6,606 per night from Jul 28 to Jul 29
P6,606
P7,432 total
Jul 28 - Jul 29
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! (3,106 reviews)
"great property"

Reviewed on Jun 24, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista
Marriott's Grande Vista
4 out of 5
5925 Avenida Vista, Orlando, FL
The price is P5,837 per night from Jul 20 to Jul 21
P5,837
P6,566 total
Jul 20 - Jul 21
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! (2,544 reviews)
"I had a fantastic stay!"

Reviewed on Jun 25, 2025

Marriott's Grande Vista
Rosen Inn at Pointe Orlando
Rosen Inn at Pointe Orlando
3 out of 5
9000 International Drive, Orlando, FL
The price is P6,334 per night from Jul 17 to Jul 18
P6,334
P7,126 total
Jul 17 - Jul 18
includes taxes & fees
Stay at this 3-star 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! (4,558 reviews)
"Friendly staff location was perfect for our trip."

Reviewed on Jun 26, 2025

Rosen Inn at Pointe Orlando
Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 out of 5
8442 Palm Parkway, Orlando, FL
The price is P3,990 per night from Jul 29 to Jul 30
P3,990
P4,488 total
Jul 29 - Jul 30
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.4/10 Very Good! (5,185 reviews)
"The beds are the only thing i dont like. They are like sleeping on a pile of sheets"

Reviewed on Jun 27, 2025

Rosen Inn Lake Buena Vista
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 P4,759 per night from Jul 28 to Jul 29
P4,759
P5,354 total
Jul 28 - Jul 29
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! (6,291 reviews)
"Great accommodations, rooms just needs to be renovated a bit"

Reviewed on Jun 26, 2025

DoubleTree by Hilton at the Entrance to Universal 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 P11,707 per night from Jul 29 to Jul 30
P11,707
P13,171 total
Jul 29 - Jul 30
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! (5,162 reviews)
"It was more than I expect"

Reviewed on Jun 26, 2025

Universal's Cabana Bay Beach Resort
See all 38,150 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 neighbourhoods 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 West Orange Trail.

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 Winter Garden Art Association and West Orange Trail.

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