Oakland

Winter Garden

Photo by Gregg Yutko
Photo by Gregg Yutko

Popular places to visit

Flamingo Crossings Town Center

You can find the perfect gifts to bring home at Flamingo Crossings Town Center during your stay in Winter Garden. Discover the top-notch restaurants and entertainment choices in this family-friendly 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

5/5(7 reviews)

Enjoy the thrill rides with your children 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

If AdventHealth Winter Garden is what brings you to town, hopefully you'll have a chance to explore more of Winter Garden.

AdventHealth Winter Garden

Things to do

Horseback Trail Ride

Horseback Trail Ride

S$127
per traveller
82% of travellers recommend
Horseback Trail Ride
Eco-Kayak Tour

Guided Eco-Paddle

S$75
per traveller
Guided Eco-Paddle
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

S$313
per traveller
86% of travellers recommend
Universal Orlando Resort Express Passes
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

S$69
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$108
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Exterior of WonderWorks

WonderWorks Orlando Admission Tickets

S$50
per adult
86% of travellers recommend
WonderWorks Orlando Admission Tickets
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 S$121 per night from 28 Jul to 29 Jul
S$121
28 Jul - 29 Jul
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! (6,400 reviews)
"Great lobby"

Reviewed on 7 Jul, 2025

DoubleTree by Hilton at the Entrance to Universal 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 S$129 per night from 7 Aug to 8 Aug
S$129
7 Aug - 8 Aug
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 ...
9.4/10 Exceptional! (536 reviews)
"Property was stunning, clean, modern, chic, and the room was incredible. Pro tips: If you call in the evening (I called 14 times between 1015pm and 145am due to my flight being delayed, ensuring I could check in passed their posted 2pm cutoff) they probably won't answer and when questioned about ..."

Reviewed on 7 Jul, 2025

Kompose Boutique Resort at Theme Parks
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
Fully refundableReserve now, pay when you stay
The price is S$168 per night from 29 Jul to 30 Jul
S$168
29 Jul - 30 Jul
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! (3,155 reviews)
"Water pressure could be a stronger, but otherwise great hotel. Conveniently located for theme parks. Clean and great service. Large rooms. Lacking kitchen frying pan and cookie sheet, in our room."

Reviewed on 6 Jul, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/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 S$235 per night from 5 Aug to 6 Aug
S$235
5 Aug - 6 Aug
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! (5,164 reviews)
"Retro"

Reviewed on 4 Jul, 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 S$149 per night from 28 Jul to 29 Jul
S$149
28 Jul - 29 Jul
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! (2,590 reviews)
"We absolutely loved the quiet area that we were in the villa was perfect. It was kept very clean and all the luxuries of a home. We hope to return in September loved it."

Reviewed on 6 Jul, 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 S$301 per night from 9 Jul to 10 Jul
S$301
9 Jul - 10 Jul
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! (8,039 reviews)
"It was everything we expected plus more."

Reviewed on 7 Jul, 2025

The Grove Resort & Water Park Orlando
See all 38,186 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

Killarney might not have many top sights, but Bella Collina Golf Club and Oakland Nature Preserve are two attractions nearby that you can check out.

Killarney
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Downtown Winter Garden

If you're spending some time in Downtown Winter Garden, West Orange Trail and Central Florida Railroad Museum are top sights worth seeing.

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