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

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

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

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

P1,563
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

P3,877
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

P2,840
per traveler
82% of travellers recommend
Aquatica Orlando
WonderWorks All Access After Dark

WonderWorks All Access After Dark

P1,587
per traveler
88% of travellers recommend
WonderWorks All Access After Dark
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction and Meal Combo Offers

P860
per adult
78% of travellers recommend
Old Town Kissimmee: Attraction and Meal Combo Offers
Orlando: Chocolate Kingdom Factory Adventure Tour

Orlando: Chocolate Kingdom Factory Adventure Tour

P1,377
per adult
98% of travellers recommend
Orlando: Chocolate Kingdom Factory Adventure Tour
See all activities in Winter Garden

Top hotels in Oakland

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
The price is P4,482 per night from 5 May to 6 May
P4,482
P7,823 total
includes taxes & fees
May 5 - May 6
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 ...
7.2/10 Good! (2,682 reviews)
"Great accommodation really close to all attractions"

Reviewed on Apr 17, 2025

Holiday Inn Resort Orlando Suites - Waterpark by IHG
Rosen Inn at Pointe Orlando
Rosen Inn at Pointe Orlando
3 out of 5
9000 International Drive, Orlando, FL
The price is P4,774 per night from 21 Apr to 22 Apr
P4,774
P5,371 total
includes taxes & fees
Apr 21 - Apr 22
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (4,189 reviews)
Clean and small.
"It’s not too bad. The rooms are in the small side. There were stains on the bedding and towels and one towel had a huge hole. No wash clothes. The room seemed pretty clean and didn’t smell musty like most Florida hotels. All staff we come across were nice. The girls trying to sell stuff next to the ..."

Reviewed on Apr 19, 2025

Rosen Inn at Pointe 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 P9,305 per night from 21 Apr to 22 Apr
P9,305
P10,468 total
includes taxes & fees
Apr 21 - Apr 22
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! (5,186 reviews)
"Pools were clean, staff was great, shuttles were also helpful. The dinning options were really good and fresh"

Reviewed on Apr 17, 2025

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
Fully refundableReserve now, pay when you stay
The price is P10,723 per night from 27 Apr to 28 Apr
P10,723
P15,255 total
includes taxes & fees
Apr 27 - Apr 28
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful ...
8/10 Very Good! (7,467 reviews)
"Room itself was excellent. Parking ramp was congested for larger vehicles. Very confusing layout with limited signage and dirty elevators"

Reviewed on Apr 18, 2025

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 P5,813 per night from 22 Apr to 23 Apr
P5,813
P6,540 total
includes taxes & fees
Apr 22 - Apr 23
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! (6,253 reviews)
"Confirmed hotel"

Reviewed on Apr 18, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Caribe Royale Orlando
Caribe Royale Orlando
4.5 out of 5
8101 World Center Dr, Orlando, FL
The price is P10,156 per night from 21 Apr to 22 Apr
P10,156
P13,851 total
includes taxes & fees
Apr 21 - Apr 22
Book a stay at this luxury hotel in Orlando. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the restaurant in our ...
9/10 Wonderful! (3,990 reviews)
"I’m a returning guest. Love the hotel even though now parking fee is a bit high per night."

Reviewed on Apr 18, 2025

Caribe Royale Orlando
See all 37,360 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 Resurrection Catholic Church.

Killarney
Love this tiny town, just 20 minutes from Walt Disney World. Inside #PlantStreetMarket you’ll find multiple vendors including local food, honey, coffee and desserts, and #crookedcanbrewing #wintergarden #lifeatexpedia

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