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

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 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

Aquatica Orlando

Aquatica Orlando

HK$412
per traveller
84% of travellers recommend
Aquatica Orlando
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

HK$1,824
per traveller
86% of travellers recommend
Universal Orlando Resort Express Passes
I-RIDE Trolley Pass

I-RIDE Trolley Pass

HK$82
per traveller
86% of travellers recommend
I-RIDE Trolley Pass
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

HK$1,345
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
WonderWorks All Access After Dark

WonderWorks All Access After Dark

HK$215
per traveller
88% of travellers recommend
WonderWorks All Access After Dark
Old Town Kissimmee: Attraction & Food/Drink Voucher

Old Town Kissimmee: Attraction & Food/Drink Voucher

HK$117
per adult
74% of travellers recommend
Old Town Kissimmee: Attraction & Food/Drink Voucher
See all activities in Winter Garden

Top hotels in Oakland

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 HK$1,036 per night from 6 Jan to 7 Jan
HK$1,036
HK$1,166 total
6 Jan - 7 Jan
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
8.8/10 Excellent! (5,952 reviews)
Very good

Reviewed on 1 Jan 2026

Universal's Cabana Bay Beach Resort
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

3.5 out of 5
6515 International Drive Orlando FL
The price is HK$485 per night from 6 Jan to 7 Jan
HK$485
HK$704 total
6 Jan - 7 Jan
includes taxes & fees
Stay at this business-friendly hotel in Orlando. Enjoy free Wi-Fi, free parking and private pools. Our guests praise the pool and the clean rooms in their reviews. ...
7.2/10 Good! (3,996 reviews)
Room was nice and spacious!

Reviewed on 2 Jan 2026

Wyndham I-Drive Avanti Resort & Conference Center
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 HK$1,282 per night from 14 Jan to 15 Jan
HK$1,282
HK$1,872 total
14 Jan - 15 Jan
includes taxes & fees
Stay at this family-friendly resort in Four Corners. Enjoy free Wi-Fi, 6 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in ...
8/10 Very Good! (8,894 reviews)
Kind and helpful staff, clean rooms, pools and water parks were clean and maintained.

Reviewed on 2 Jan 2026

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 HK$597 per night from 27 Jan to 28 Jan
HK$597
HK$672 total
27 Jan - 28 Jan
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 3 outdoor pools and 2 coffee shops/cafes. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (5,470 reviews)
Yes

Reviewed on 30 Dec 2025

Rosen Inn at Pointe 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 HK$866 per night from 25 Jan to 26 Jan
HK$866
HK$975 total
25 Jan - 26 Jan
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 6 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in their ...
9.2/10 Wonderful! (4,220 reviews)
The room was spotless.

Reviewed on 2 Jan 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/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 HK$592 per night from 25 Jan to 26 Jan
HK$592
HK$885 total
25 Jan - 26 Jan
includes taxes & fees
Stay at this family-friendly resort in Orlando. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the breakfast and the pool in their reviews. ...
7.4/10 Good! (6,289 reviews)
Very nice hotel Lovely cookies and we are ready to go back!!!

Reviewed on 31 Dec 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
See all 39,750 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

Oakland