Oakland Travel Guide

Winter Garden

Oakland
Panoramic view of Lake Apopka and nature Florida.

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

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

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

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

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

Disney's Oak Trail Golf Course

Enjoy a round of golf in Winter Garden at Disney's Oak Trail Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Oak Trail Golf Course

Top hotels in Oakland

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 3.530.096 ₫ per night from 6 May to 7 May
3.530.096 ₫
3.971.357 ₫ total
6 May - 7 May
includes taxes & fees
Stay at this family-friendly aparthotel 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! (5,296 reviews)
The checkin process was very long in terms of waiting time.

Reviewed on 27 Apr 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/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 3.503.752 ₫ per night from 25 May to 26 May
3.503.752 ₫
3.941.853 ₫ total
25 May - 26 May
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
9/10 Wonderful! (6,695 reviews)
The relaxing weekend I needed

Reviewed on 27 Apr 2026

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 4.346.760 ₫ per night from 14 May to 15 May
4.346.760 ₫
6.342.318 ₫ total
14 May - 15 May
includes taxes & fees
Stay at this family-friendly resort in Four Corners. Enjoy free Wi-Fi, 6 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in ...
8/10 Very Good! (9,679 reviews)
This property is conveniently located to all of the theme parks, Without the hustle of being in the middle of them. The staff was friendly at check-in. Our condo was nice and had a good view of the pool and lake. It was frustrating that our dryer did not work in our condo and housekeeping never came ...

Reviewed on 27 Apr 2026

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
Fully refundableReserve now, pay when you stay
The price is 2.440.772 ₫ per night from 17 May to 18 May
2.440.772 ₫
2.745.836 ₫ total
17 May - 18 May
includes taxes & fees
Stay at this 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 their ...
8.4/10 Very Good! (6,880 reviews)
It meets standards

Reviewed on 27 Apr 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd Orlando FL
The price is 2.568.671 ₫ per night from 30 Apr to 1 May
2.568.671 ₫
3.778.603 ₫ total
30 Apr - 1 May
includes taxes & fees
Stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
8.4/10 Very Good! (6,243 reviews)
Close to a lot of attractions. Nice place to stay.

Reviewed on 27 Apr 2026

Westgate Lakes Resort & Spa Universal Studios Area
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
The price is 2.844.889 ₫ per night from 28 Apr to 29 Apr
2.844.889 ₫
3.200.533 ₫ total
28 Apr - 29 Apr
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 3 outdoor pools and 2 coffee shops/cafes. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (6,398 reviews)
mj

Reviewed on 27 Apr 2026

Rosen Inn at Pointe Orlando
See all 39,735 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

Panoramic view of Lake Apopka and nature Florida.

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
March 25, 2023, Winter Garden, FL: The West Orange bicycle trail through Winter Garden, Florida

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

Oakland Travel Guide

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