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

P1,899
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

P3,770
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

P3,002
per traveler
82% of travellers recommend
Aquatica Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction and Meal Combo Offers

P836
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction and Meal Combo Offers
Indoor Karting

Andretti Indoor Karting & Games in Orlando

P1,619
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
WonderWorks All Access After Dark

WonderWorks All Access After Dark

P1,543
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
Fully refundableReserve now, pay when you stay
The price is P5,153 per night from Jun 15 to Jun 16
P5,153
P5,797 total
Jun 15 - Jun 16
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! (6,277 reviews)
"The staff was amazing. The only issue was checking in. We stood online for one hour because there was an event going on"

Reviewed on Jun 5, 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 P5,752 per night from Jul 6 to Jul 7
P5,752
P6,471 total
Jul 6 - Jul 7
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! (2,476 reviews)
"This place gets five stars. Everyone there was polite and friendly. The area was very clean and well kept. The room was nice and comfortable felt like you were at home."

Reviewed on Jun 4, 2025

Marriott's Grande Vista
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 P4,236 per night from Jul 6 to Jul 7
P4,236
P4,766 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this family-friendly 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! (2,988 reviews)
"Property is really nice, wish we had stayed longer to enjoy all the amenities. Staff is friendly and villa was clean. Driving around property is a little confusing but that was our only problem."

Reviewed on Jun 4, 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 P5,423 per night from Jun 8 to Jun 9
P5,423
P6,826 total
Jun 8 - Jun 9
includes taxes & fees
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
9.6/10 Exceptional! (224 reviews)
"The vibes here are immaculate. A very up beat, positive, friendly atmosphere. The staff are service driven and excellence minded. Highly recommend this resort!"

Reviewed on Jun 6, 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 P7,413 per night from Jun 8 to Jun 9
P7,413
P10,848 total
Jun 8 - Jun 9
includes taxes & fees
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy 6 outdoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the pool and the helpful ...
7.8/10 Good! (7,768 reviews)
"I really enjoyed the resort. It was so much to do!!!"

Reviewed on Jun 5, 2025

The Grove Resort & Water Park Orlando
Rosen Inn at Pointe Orlando
Rosen Inn at Pointe Orlando
3 out of 5
9000 International Drive, Orlando, FL
The price is P7,023 per night from Jun 8 to Jun 9
P7,023
P7,901 total
Jun 8 - Jun 9
includes taxes & fees
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (4,468 reviews)
"Close distance to many attractions. We did main event Aquatica and Dave &Busters. A lot of walking range dining and attractions. Great spot, in the heart of international drive"

Reviewed on Jun 5, 2025

Rosen Inn at Pointe Orlando
See all 37,846 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 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 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