Oakland, FL

Winter Garden

At the Oakland Preserve. Nice Boardwalk plus an animal sanctuary
Panoramic view of Lake Apopka and nature Florida.

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

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

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

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

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

Oakland Hotel Deals

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 ₩252,516 per night from Mar 25 to Mar 26
₩252,516
₩366,447 total
Mar 25 - Mar 26
includes taxes & fees
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (9,206 reviews)
We enjoyed our stay, clean rooms, great amenities!

Reviewed on Mar 20, 2026

The Grove Resort & Water Park 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 ₩191,255 per night from Apr 20 to Apr 21
₩191,255
₩215,162 total
Apr 20 - Apr 21
includes taxes & fees
Book a stay at this family-friendly condo 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! (4,928 reviews)
Wonderful property and amenities. Almost no need to leave to enjoy a vacation

Reviewed on Mar 20, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
The price is ₩144,024 per night from Mar 30 to Mar 31
₩144,024
₩162,027 total
Mar 30 - Mar 31
includes taxes & fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
8.6/10 Excellent! (6,055 reviews)
Make parking slots mandatory and a small free breakfast. Cereal banana ect.

Reviewed on Mar 20, 2026

Rosen Inn at Pointe Orlando
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
The price is ₩109,653 per night from Mar 22 to Mar 23
₩109,653
₩190,580 total
Mar 22 - Mar 23
includes taxes & fees
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ...
9.4/10 Exceptional! (3,184 reviews)
Beautiful and modern resort a lot of amenities and the staff is amazing. Great place

Reviewed on Mar 20, 2026

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 ₩225,570 per night from Apr 21 to Apr 22
₩225,570
₩253,766 total
Apr 21 - Apr 22
includes taxes & fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (6,438 reviews)
Convenient to the parks

Reviewed on Mar 20, 2026

Universal's Cabana Bay Beach Resort
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 ₩168,558 per night from Apr 13 to Apr 14
₩168,558
₩240,040 total
Apr 13 - Apr 14
includes taxes & fees
Book a 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 our ...
8.4/10 Very Good! (5,947 reviews)
Clean rooms, welcoming staff, property was clean and pleasant. Will be going back

Reviewed on Mar 20, 2026

Westgate Lakes Resort & Spa Universal Studios Area
See all 39,348 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 neighborhoods around Oakland

Panoramic view of Lake Apopka and nature Florida.

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 West Orange Trail.

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

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

Oakland, FL