Oakland

Winter Garden

Photo by Gregg Yutko
Photo by Gregg Yutko

Popular places to visit

Flamingo Crossings Town Center

You can do some window-shopping at Flamingo Crossings Town Center during your visit to Winter Garden. Discover the top-notch restaurants and entertainment choices in this family-friendly 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

Though AdventHealth Winter Garden might be what brings you to town, perhaps you'll have a chance to explore more of Winter Garden while you are here.

AdventHealth Winter Garden

Surfari Water Park

Enjoy a fun-filled day 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

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

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

P1,449
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

P3,053
per traveler
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

P3,765
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

P1,751
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction & Food/Drink Voucher

P850
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction & Food/Drink Voucher
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

P680
per adult
88% of travellers recommend
Orlando: 7-D Dark Ride Entry 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 P5,298 per night from Aug 6 to Aug 7
P5,298
P5,960 total
Aug 6 - Aug 7
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! (6,507 reviews)
"This is literally outside of the universal entrance. Very clean. It was just my husband and I but it’s also a wonderful place for little kids too. We plan on coming back and bringing our children. Clean property with friendly staff."

Reviewed on Jul 26, 2025

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 P4,986 per night from Aug 18 to Aug 19
P4,986
P5,609 total
Aug 18 - Aug 19
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! (2,694 reviews)
Nice stay
"Wonderful resort like hotel with great service and equally great accommodations. Qould highly recommend."

Reviewed on Jul 26, 2025

Marriott's Grande Vista
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 P3,846 per night from Aug 26 to Aug 27
P3,846
P5,055 total
Aug 26 - Aug 27
includes taxes & fees
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
9.4/10 Exceptional! (839 reviews)
"Everything it was excellent."

Reviewed on Jul 29, 2025

Kompose Boutique Resort at Theme Parks
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 P9,091 per night from Aug 26 to Aug 27
P9,091
P10,228 total
Aug 26 - Aug 27
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! (5,170 reviews)
"Excellent stay"

Reviewed on Jul 27, 2025

Universal's Cabana Bay Beach Resort
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 out of 5
14500 Continental Gateway, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is P3,713 per night from Jul 31 to Aug 1
P3,713
P8,356 total
Jul 31 - Aug 1
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
7/10 Good! (3,775 reviews)
"Had a great stay! The room was clean and comfortable, and the staff was super friendly and helpful. We had a small issue with our bedding, but they were quick to accommodate us in another unit, which we really appreciated. The location was convenient and everything else went smoothly. Would definitely ..."

Reviewed on Jul 27, 2025

Holiday Inn Resort Orlando Suites - Waterpark by IHG
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
The price is P6,264 per night from Aug 11 to Aug 12
P6,264
P7,047 total
Aug 11 - Aug 12
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winter Garden. Enjoy free breakfast, a free theme park shuttle, and a 24-hour fitness center. Our guests praise ...
9.2/10 Wonderful! (4,369 reviews)
"The only that I would change will be the breakfast hour.! Too early. I think that should be until 10:00 am at least. Cause if you are on vacation, you don’t want to wake up so early."

Reviewed on Jul 29, 2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
See all 38,479 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

If you're looking for some top things to see and do in Killarney and surrounding area, you can visit Bella Collina Golf Club and West Orange Trail.

Killarney
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Downtown Winter Garden

While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum.

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