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 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 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

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Aquatica Orlando

฿1,747
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

฿2,154
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

฿1,002
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

฿487
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction & Food/Drink Voucher
Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

฿1,036
per adult
84% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
WonderWorks All Access After Dark

WonderWorks All Access After Dark

฿898
per traveller
86% of travellers recommend
WonderWorks All Access After Dark
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 ฿2,726 per night from 10 Aug to 11 Aug
฿2,726
฿3,066 total
10 Aug - 11 Aug
includes taxes & fees
Stay at this 4-star 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 ...
8.2/10 Very Good! (6,438 reviews)
"goo"

Reviewed on 19 Jul 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 ฿3,084 per night from 10 Aug to 11 Aug
฿3,084
฿3,469 total
10 Aug - 11 Aug
includes taxes & fees
Stay at this 4-star spa hotel in Orlando. Enjoy free Wi-Fi, 4 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
8.8/10 Excellent! (2,637 reviews)
"Enjoyed are stay."

Reviewed on 18 Jul 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 ฿2,406 per night from 10 Aug to 11 Aug
฿2,406
฿3,121 total
10 Aug - 11 Aug
includes taxes & fees
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free Wi-Fi and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
9.4/10 Exceptional! (713 reviews)
"Absolutely loved my stay at this boutique hotel! Everything feels either newly built or freshly renovated-modern, chic, and thoughtfully designed from top to bottom. The atmosphere is upscale yet welcoming, and the attention to detail is hard to miss. One of the first things I noticed was how amazing ..."

Reviewed on 20 Jul 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 ฿5,053 per night from 20 Aug to 21 Aug
฿5,053
฿5,684 total
20 Aug - 21 Aug
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (5,128 reviews)
"I liked the variety of food and the convenient of transportation."

Reviewed on 19 Jul 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
The price is ฿4,826 per night from 22 Jul to 23 Jul
฿4,826
฿6,887 total
22 Jul - 23 Jul
includes taxes & fees
Stay at this 4-star family-friendly resort in Four Corners. Enjoy 6 outdoor pools, 3 restaurants and 2 hot tubs. Our guests praise the pool and the helpful staff ...
7.8/10 Good! (8,111 reviews)
"Front desk Robert was very pleasant and helpful property had system issues but Robert was so amazing helping us with our check in possess.."

Reviewed on 19 Jul 2025

The Grove Resort & Water Park Orlando
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 ฿2,105 per night from 27 Jul to 28 Jul
฿2,105
฿4,737 total
27 Jul - 28 Jul
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! (3,700 reviews)
"Overall, hotel was good and kids had a great time. However , I did not have a good experience with the guest service since my card was overcharged 2 times due to a system error ."

Reviewed on 21 Jul 2025

Holiday Inn Resort Orlando Suites - Waterpark by IHG
See all 38,684 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 Resurrection Catholic Church 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
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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 Travel Guide