Oakland, FL

Winter Garden

Photo by Gregg Yutko

Popular places to visit


Oakland Hotel Deals

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 AED 489 per night from Dec 9 to Dec 10
AED 489
AED 550 total
9 Dec - 10 Dec
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! (5,682 reviews)
Great stay!

Reviewed on 1 December 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
Fully refundableReserve now, pay when you stay
The price is AED 365 per night from Jan 2 to Jan 3
AED 365
AED 411 total
2 Jan - 3 January 2026
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! (5,345 reviews)
Always a

Reviewed on 28 November 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 AED 387 per night from Dec 15 to Dec 16
AED 387
AED 436 total
15 Dec - 16 Dec
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! (4,003 reviews)
Room was spotless & staff was super courteous.

Reviewed on 27 November 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Avanti International Resort

Avanti International Resort

4 out of 5
8738 International Dr Orlando FL
The price is AED 209 per night from Dec 14 to Dec 15
AED 209
AED 309 total
14 Dec - 15 Dec
includes taxes & fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
7.8/10 Good! (4,250 reviews)
The location and price of the hotel is great. there was mold in the bathroom and we noticed they had painted over the mold to hide it. Our door was stuck and we had to use force to open it every time which sucked. the hidden "resort" fees at check in were a bit steep for it being in such need of ...

Reviewed on 27 November 2025

Avanti International 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 AED 255 per night from Dec 14 to Dec 15
AED 255
AED 390 total
14 Dec - 15 Dec
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! (6,301 reviews)
Staff was fantastic, Room was great , pools bar property in general was like a resort loved it !! Only issue I am sure will get resolved is I used credit card for everything and didn’t want any charges to room. Kinda shocked when $277.00 was charged to room for food yet credit card was charged. So ...

Reviewed on 27 November 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
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 AED 523 per night from Dec 7 to Dec 8
AED 523
AED 791 total
7 Dec - 8 Dec
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 ...
7.8/10 Good! (8,811 reviews)
Everything was great, only the last day of my stay i was unable to ge a hold of guest services.

Reviewed on 29 November 2025

The Grove Resort & Water Park Orlando
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

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