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 walkable area.

Flamingo Crossings Town Center

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 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

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

Surfari Water Park

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

Things to do

Eco-Kayak Tour

Guided Eco-Paddle

S$76
per traveller
Guided Eco-Paddle
Indoor Karting

Andretti Indoor Karting & Games in Orlando

S$40
per adult
82% of travellers recommend
Andretti Indoor Karting & Games in Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction & Food/Drink Voucher

S$19
per adult
74% of travellers recommend
Old Town Kissimmee: Attraction & Food/Drink Voucher
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

S$15
per adult
90% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
WonderWorks All Access After Dark

WonderWorks All Access After Dark

S$36
per traveller
84% of travellers recommend
WonderWorks All Access After Dark
Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

S$41
per adult
86% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
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$134 per night from 10 Sept to 11 Sept
S$134
10 Sept - 11 Sept
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 ...
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 S$126 per night from 18 Sept to 19 Sept
S$126
18 Sept - 19 Sept
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. ...
Marriott's Grande Vista
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$205 per night from 3 Sept to 4 Sept
S$205
3 Sept - 4 Sept
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 ...
Universal's Cabana Bay Beach Resort
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
The price is S$130 per night from 2 Sept to 3 Sept
S$130
2 Sept - 3 Sept
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 ...
Rosen Inn at Pointe Orlando
DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive, Orlando, FL
The price is S$124 per night from 3 Sept to 4 Sept
S$124
3 Sept - 4 Sept
includes taxes & fees
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.4/10 Good! (6,086 reviews)
"Everything about my visit was GREAT!!"

Reviewed on 26 Aug, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4 out of 5
12401 International Dr, Orlando, FL
The price is S$126 per night from 17 Sept to 18 Sept
S$126
17 Sept - 18 Sept
includes taxes & fees
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,104 reviews)
"Great spot for family , near everything"

Reviewed on 27 Aug, 2025

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
See all 38,664 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 West Orange Trail 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