Oakland

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

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

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

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

RM333
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

RM716
per traveller
84% of travellers recommend
Universal Orlando Resort Express Passes
Aquatica Orlando

Aquatica Orlando

RM217
per traveller
82% of travellers recommend
Aquatica Orlando
HALLOWEEN HORROR NIGHTS at Universal Orlando Resort

HALLOWEEN HORROR NIGHTS at Universal Orlando Resort

RM402
per traveller
86% of travellers recommend
HALLOWEEN HORROR NIGHTS at Universal Orlando Resort
Orlando: Jet Ski Rentals from Lake Buena Vista Area

Orlando: Jet Ski Rentals from Lake Buena Vista Area

RM332
per traveller
100% of travellers recommend
Orlando: Jet Ski Rentals from Lake Buena Vista Area
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

RM571
per adult
74% of travellers recommend
Universal Orlando Resort Theme Park Tickets
See all activities in Winter Garden

Top hotels in Oakland

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 RM293 per night from 30 Oct to 31 Oct
RM293
RM449 total
30 Oct - 31 Oct
includes taxes & fees
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.4/10 Good! (6,212 reviews)
"Best hotel. Close to everything. Best breakfast buffet!!"

Reviewed on 15 Oct 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
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 RM562 per night from 5 Nov to 6 Nov
RM562
RM632 total
5 Nov - 6 Nov
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! (5,413 reviews)
"We had a great stay here. They have nightly movies by the pool for kids and adults. The food wasn’t the best, but other than that, it was great."

Reviewed on 15 Oct 2025

Universal's Cabana Bay Beach Resort
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
The price is RM395 per night from 27 Oct to 28 Oct
RM395
RM444 total
27 Oct - 28 Oct
includes taxes & fees
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
8.4/10 Very Good! (5,099 reviews)
"Nice staff, clean rooms"

Reviewed on 15 Oct 2025

Rosen Inn at Pointe 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 RM385 per night from 17 Nov to 18 Nov
RM385
RM434 total
17 Nov - 18 Nov
includes taxes & fees
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (3,720 reviews)
"Clean and nice size room"

Reviewed on 16 Oct 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 RM841 per night from 30 Oct to 31 Oct
RM841
RM1,136 total
30 Oct - 31 Oct
includes taxes & fees
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
7.8/10 Good! (8,658 reviews)
"Very clean"

Reviewed on 15 Oct 2025

The Grove Resort & Water Park Orlando
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

3.5 out of 5
6515 International Drive, Orlando, FL
The price is RM210 per night from 5 Nov to 6 Nov
RM210
RM322 total
5 Nov - 6 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the clean rooms in our ...
7.2/10 Good! (3,722 reviews)
"Clean room, nice pool, very convenient location."

Reviewed on 16 Oct 2025

Wyndham I-Drive Avanti Resort & Conference Center
See all 39,313 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