Oakland Travel Guide

Winter Garden

Oakland
Panoramic view of Lake Apopka and nature Florida.

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 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

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

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

Disney's Oak Trail Golf Course

Enjoy a round of golf in Winter Garden at Disney's Oak Trail Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Oak Trail Golf Course

Things to do

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

฿1,230
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Aquatica Orlando

Aquatica Orlando

฿1,690
per traveller
84% of travellers recommend
Aquatica Orlando
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

฿4,845
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Old Town Kissimmee: Attraction & Food/Drink Voucher

Old Town Kissimmee: Attraction & Meal Voucher

฿479
per adult
76% of travellers recommend
Old Town Kissimmee: Attraction & Meal Voucher
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

฿871
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

฿383
per adult
90% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
See all activities in Winter Garden

Top hotels in Oakland

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 ฿4,338 per night from 7 May to 8 May
฿4,338
฿4,880 total
7 May - 8 May
includes taxes & fees
Stay at this family-friendly aparthotel in Orlando. Enjoy free Wi-Fi, 6 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (5,309 reviews)
Like being back at Home. Can’t wait to return.

Reviewed on 28 Apr 2026

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 ฿4,856 per night from 3 May to 4 May
฿4,856
฿5,463 total
3 May - 4 May
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 ...
9/10 Wonderful! (6,711 reviews)
Had a great visit with the family! Love this resort and all it has to offer for different age groups!

Reviewed on 28 Apr 2026

Universal's Cabana Bay Beach Resort
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 ฿5,341 per night from 14 May to 15 May
฿5,341
฿7,793 total
14 May - 15 May
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! (9,699 reviews)
Good

Reviewed on 28 Apr 2026

The Grove Resort & Water Park Orlando
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 ฿2,999 per night from 17 May to 18 May
฿2,999
฿3,374 total
17 May - 18 May
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! (6,886 reviews)
Great

Reviewed on 27 Apr 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd Orlando FL
The price is ฿3,156 per night from 29 Apr to 30 Apr
฿3,156
฿4,643 total
29 Apr - 30 Apr
includes taxes & fees
Stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
8.4/10 Very Good! (6,271 reviews)
It’s a great place to travel to especially when you’re with kids, everything you could need is in the resort. I loved it! My son loved it

Reviewed on 28 Apr 2026

Westgate Lakes Resort & Spa Universal Studios Area
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
The price is ฿3,496 per night from 29 Apr to 30 Apr
฿3,496
฿3,933 total
29 Apr - 30 Apr
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 ...
8.6/10 Excellent! (6,418 reviews)
Very family friendly and clean areas! We enjoyed our time at the hotel

Reviewed on 28 Apr 2026

Rosen Inn at Pointe Orlando
See all 39,775 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

Panoramic view of Lake Apopka and nature Florida.

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
March 25, 2023, Winter Garden, FL: The West Orange bicycle trail through Winter Garden, Florida

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