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

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

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

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

Things to do

Aquatica Orlando

Aquatica Orlando

฿1,727
per traveller
82% of travellers recommend
Aquatica Orlando
Indoor Karting

Andretti Indoor Karting & Games in Orlando

฿991
per adult
82% of travellers recommend
Andretti Indoor Karting & Games in Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction & Food/Drink Voucher

฿481
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

฿385
per adult
90% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
WonderWorks All Access After Dark

WonderWorks All Access After Dark

฿888
per traveller
84% of travellers recommend
WonderWorks All Access After Dark
Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

฿956
per adult
86% of travellers recommend
Orlando: Museum of Illusions Admission 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 ฿3,262 per night from 12 Oct to 13 Oct
฿3,262
฿3,670 total
12 Oct - 13 Oct
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 ...
8.4/10 Very Good! (6,697 reviews)
"The hotel was really nice. The room was nice room service was good. It was clean. The hot tub did not work. The pool is amazing cause it was 9 feet deep. I love that and it wasn’t super cold but the restaurant in the hotel gave me moldy cheese. They did try to accommodate me afterwards but they’re ..."

Reviewed on 24 Sept 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 ฿2,812 per night from 26 Oct to 27 Oct
฿2,812
฿3,163 total
26 Oct - 27 Oct
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! (3,179 reviews)
"Always a beautiful and great family stay at the Marriott Grande Vista!! Great for families, very clean, awesome pools and restaurants. Staff is exceptionally friendly. Can’t wait to return!"

Reviewed on 23 Sept 2025

Marriott's Grande Vista
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 ฿4,289 per night from 30 Sept to 1 Oct
฿4,289
฿4,825 total
30 Sept - 1 Oct
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! (5,305 reviews)
"Clean and so fun. People are great! Everything and everyone has been wonderful and we are frequent Disney Resort visitors and Holiday Inn resort owners, but this place beats both!"

Reviewed on 25 Sept 2025

Universal's Cabana Bay Beach 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 ฿2,442 per night from 10 Oct to 11 Oct
฿2,442
฿3,655 total
10 Oct - 11 Oct
includes taxes & fees
Stay at this 4-star 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 ...
7.4/10 Good! (6,148 reviews)
"Good"

Reviewed on 24 Sept 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4 out of 5
12401 International Dr, Orlando, FL
The price is ฿3,096 per night from 19 Oct to 20 Oct
฿3,096
฿3,483 total
19 Oct - 20 Oct
includes taxes & fees
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free Wi-Fi, 5 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,319 reviews)
"Staff is always helpful/ accommodating. Got a free room upgrade. Very quiet and family friendly"

Reviewed on 25 Sept 2025

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
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 ฿3,199 per night from 27 Oct to 28 Oct
฿3,199
฿3,599 total
27 Oct - 28 Oct
includes taxes & fees
Stay at this 4-star eco-certified hotel 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! (3,568 reviews)
"An amazing stay,with the family.spacious room and super clean.definitely we will stay here again! Oh and also less than 10 minutes from the parks !!"

Reviewed on 25 Sept 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 39,250 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
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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