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

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

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

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

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 P4,741 per night from Jul 28 to Jul 29
P4,741
P5,333 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! (6,316 reviews)
"Friendly Staff great location"

Reviewed on Jun 29, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
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 P6,580 per night from Jul 22 to Jul 23
P6,580
P7,403 total
Jul 22 - Jul 23
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! (3,138 reviews)
Wonderful time!
"Our stay was wonderful. Pools were great! Activities, restaurants, bars, arcade, basketball court. Lots to do and a great place for families."

Reviewed on Jul 1, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 P4,901 per night from Jul 13 to Jul 14
P4,901
P6,241 total
Jul 13 - Jul 14
includes taxes & fees
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Disney's Animal Kingdom® Theme ...
9.6/10 Exceptional! (434 reviews)
Excellent hotel
"Everything was very clean and employees very polite and professional. The only complaint I have is the strong smells of oils used in the air conditioning system. It is so strong it becomes very annoying."

Reviewed on Jun 30, 2025

Kompose Boutique Resort at Theme Parks
Universal's Cabana Bay Beach Resort
Universal's Cabana Bay Beach Resort
3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is P12,112 per night from Jul 29 to Jul 30
P12,112
P13,627 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! (5,179 reviews)
"Love it I celebrate my daughters birthday no complain the only thing food is really expensive inside the hotel"

Reviewed on Jun 29, 2025

Universal's Cabana Bay Beach Resort
Marriott's Grande Vista
Marriott's Grande Vista
4 out of 5
5925 Avenida Vista, Orlando, FL
The price is P5,814 per night from Jul 22 to Jul 23
P5,814
P6,541 total
Jul 22 - Jul 23
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! (2,558 reviews)
"Great place very big"

Reviewed on Jun 28, 2025

Marriott's Grande Vista
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 P9,521 per night from Jul 9 to Jul 10
P9,521
P13,246 total
Jul 9 - Jul 10
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! (8,008 reviews)
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Reviewed on Jul 2, 2025

The Grove Resort & Water Park Orlando
See all 38,194 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