Oakland, FL

Winter Garden

Photo by Gregg Yutko
Photo by Gregg Yutko

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 walkable 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

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 ₩106,771 per night from Jan 3 to Jan 4
₩106,771
₩161,645 total
Jan 3 - Jan 4, 2026
includes taxes & fees
Book a stay at this 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! (6,276 reviews)
Very nice

Reviewed on Dec 15, 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 ₩196,345 per night from Jan 6 to Jan 7
₩196,345
₩220,888 total
Jan 6 - Jan 7, 2026
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 ...
8.8/10 Excellent! (5,748 reviews)
Excellent

Reviewed on Dec 15, 2025

Universal's Cabana Bay Beach Resort
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 ₩91,987 per night from Dec 21 to Dec 22
₩91,987
₩133,381 total
Dec 21 - Dec 22
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! (3,896 reviews)
Check in was smooth! Lady at desk had a great sense of humor. Being from a different state, it was refreshing. Rooms clean

Reviewed on Dec 14, 2025

Wyndham I-Drive Avanti Resort & Conference Center
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
The price is ₩119,565 per night from Dec 21 to Dec 22
₩119,565
₩134,510 total
Dec 21 - Dec 22
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 ...
8.4/10 Very Good! (5,422 reviews)
Good hotel

Reviewed on Dec 16, 2025

Rosen Inn at Pointe 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
The price is ₩144,111 per night from Jan 11 to Jan 12
₩144,111
₩162,125 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (6,886 reviews)
Was there for a pre-cruise night/day for EPIC Universe. It was perfect!

Reviewed on Dec 13, 2025

DoubleTree by Hilton at the Entrance to Universal 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
Fully refundableReserve now, pay when you stay
The price is ₩164,162 per night from Jan 8 to Jan 9
₩164,162
₩184,682 total
Jan 8 - Jan 9, 2026
includes taxes & fees
Book a stay at this family-friendly 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! (4,114 reviews)
Next time I come to Florida I will come and stay at your resort. Very clean and comfortable. Loved having a kitchen with all the equipment.

Reviewed on Dec 17, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 39,770 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

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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
Love this tiny town, just 20 minutes from Walt Disney World. Inside #PlantStreetMarket you’ll find multiple vendors including local food, honey, coffee and desserts, and #crookedcanbrewing #wintergarden #lifeatexpedia

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