The Best Hotels in Oakland, Winter Garden - 2026 Updated Prices

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Where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.

Horizon West

While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club.

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Orange sunset over distant hills on Lake Apopka near Orlando, Florida.

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.

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Downtown Winter Garden

If you're spending some time in Downtown Winter Garden, Winter Garden Art Association and West Orange Trail are top sights worth seeing.

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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.

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Top Oakland Hotel Reviews

Universal's Cabana Bay Beach Resort

8/10 Good

"It is very convenient as volcano bay is of walking distance. The rooms and the hotel itself are pretty. But is is overpriced."

Kompose Boutique Resort at Theme Parks

8/10 Good

"The hotel is beautiful very clean. The only issue was that we didn’t have enough washcloths. The only other issue is that the rooms did not have drawers to put your clothes in. The only other issue I have is I wish Expedia would state all the other costs that come with the hotel that would just be very helpful in planning our vacations"

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"The property was excellent It is very close to Disney World and other venues The amenities are great The villas were lovely We had a 1 bedroom villa with a kitchen which made our stay enjoyable The staff was friendly and very attentive I would definitely recommend this property"

The Grove Resort & Water Park Orlando

8/10 Good

"The rooms were spacious and felt more like a condo than a hotel, which was perfect for our group. Having a full kitchen, living room, washer, and dryer made the stay so much more comfortable. The location was one of my favorite parts close enough to Disney, Universal, and other attractions without feeling like we were in the middle of all the traffic. On our downtime days, the water park, lazy river, and pools gave us plenty to do without leaving the resort. The resort was, family-friendly and had enough to do on property"

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"From the moment I arrived, everything went smoothly. The staff was friendly, welcoming, and very helpful throughout my stay. They answered all of my questions about the hotel, shuttle services, operating hours, and the surrounding area. They also took the time to explain the room options I had selected and made sure I was placed in the room that best fit my needs. The hotel was clean, well-maintained, and had a fresh atmosphere with no unpleasant odors. I was very impressed with the overall cleanliness and comfort. The on-site cafeteria was another highlight of our stay. The food was delicious, and there was a great variety of options to choose from. After long days at the theme parks, it was convenient and enjoyable to have good food available right at the hotel. Most importantly, my kids absolutely loved the location and our overall experience. We truly enjoyed every moment of our stay and will definitely return on our next visit. Highly recommended!"

Frequently asked questions

What's it like in Oakland?

Travellers will be sure to enjoy their time in Winter Garden's Oakland neighbourhood. Consider a visit to Oakland Nature Preserve as part of your Oakland travel plans.

How many hotels can I expect to find in Oakland?

When you want to put your feet up after a day of exploring the sights in Winter Garden, you can choose from 11 Expedia hotels and other accommodation options in Oakland.

If I need to cancel my hotel reservation in Oakland, will I receive a refund?

Yes, you'll find most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to review the best options available in Oakland.

What is there to do in this Winter Garden neighbourhood?

Oakland Nature Preserve is an attraction you might want to check out while you're in Oakland. While you're out sightseeing in Winter Garden, make sure that you visit other sights such as Plant Street Market or Garden Theatre.

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Our top choices for Oakland hotels

Oakland Manor House

Kompose Boutique Resort at Theme Parks

Universal's Terra Luna Resort

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

Home2 Suites by Hilton Orlando at Flamingo Crossings

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Embassy Suites by Hilton Orlando Lake Buena Vista South

Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

Candlewood Suites Orlando - Lake Buena Vista by IHG

EVEN Hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG

DoubleTree by Hilton at the Entrance to Universal Orlando

Wyndham Garden Orlando Airport

Hyatt House Orlando International Drive

Cambria Hotel Orlando Airport

Rosen Shingle Creek

Orlando Palms Hotel

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Hilton Orlando Buena Vista Palace - Disney Springs® Area

Courtyard by Marriott Orlando Downtown

Where to stay in Oakland

Horizon West

Vista del Lago

Downtown Winter Garden

Killarney

Top Oakland Hotel Reviews

Universal's Cabana Bay Beach Resort

Frequently asked questions

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