Oakland Travel Guide

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

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

Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

฿6,424
per traveller
86% of travellers recommend
Universal Orlando Resort Express Passes
Aquatica Orlando

Aquatica Orlando

฿1,680
per traveller
84% of travellers recommend
Aquatica Orlando
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

฿4,818
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Old Town Kissimmee: Attraction & Food/Drink Voucher

Old Town Kissimmee: Attraction & Food/Drink Voucher

฿476
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

฿381
per adult
90% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
The Hard Rock Cafe facade in Orlando.

Hard Rock Cafe Orlando

฿1,334
per traveller
Hard Rock Cafe Orlando
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 ฿4,128 per night from 6 Jan to 7 Jan
฿4,128
฿4,644 total
6 Jan - 7 Jan 2026
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! (5,907 reviews)
All great !

Reviewed on 29 Dec 2025

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 ฿1,972 per night from 5 Jan to 6 Jan
฿1,972
฿2,860 total
5 Jan - 6 Jan 2026
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! (3,924 reviews)
Bathroom was small and outdated but it was convenient and close to great places

Reviewed on 25 Dec 2025

Wyndham I-Drive Avanti Resort & Conference Center
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
The price is ฿2,489 per night from 28 Jan to 29 Jan
฿2,489
฿2,800 total
28 Jan - 29 Jan 2026
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! (5,451 reviews)
Clean

Reviewed on 29 Dec 2025

Rosen Inn at Pointe Orlando
Avanti International Resort

Avanti International Resort

4 out of 5
8738 International Dr Orlando FL
The price is ฿2,348 per night from 6 Jan to 7 Jan
฿2,348
฿3,270 total
6 Jan - 7 Jan 2026
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, an outdoor pool and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
7.8/10 Good! (4,342 reviews)
Great

Reviewed on 25 Dec 2025

Avanti International Resort
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 ฿2,267 per night from 6 Jan to 7 Jan
฿2,267
฿3,424 total
6 Jan - 7 Jan 2026
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! (6,325 reviews)
Clean room

Reviewed on 28 Dec 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
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 ฿2,829 per night from 15 Jan to 16 Jan
฿2,829
฿3,183 total
15 Jan - 16 Jan 2026
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the pool and the helpful staff in their ...
8.4/10 Very Good! (6,872 reviews)
Clean and tidy room with big windows

Reviewed on 26 Dec 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 39,712 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 Travel Guide