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 12 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.

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

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Our top choices for Oakland hotels

Hilton Orlando/Altamonte Springs

26.5 km from Oakland

Latoya

₹12,587 total

includes taxes & fees

2 Apr - 3 Apr

Comfort Suites Downtown

25.5 km from Oakland

DWIGHT

₹12,392 total

includes taxes & fees

5 Apr - 6 Apr

Wyndham Garden Lake Buena Vista – Disney Springs® Area

23.2 km from Oakland

Audrey Nou

₹14,043 total

includes taxes & fees

22 Mar - 23 Mar

Wyndham Lake Buena Vista – Disney Springs® Area

23.3 km from Oakland

Yukari

₹16,100 total

includes taxes & fees

22 Mar - 23 Mar

Drury Plaza Hotel Orlando - Disney Springs Area

23.1 km from Oakland

BARRY

₹16,774 total

includes taxes & fees

5 Apr - 6 Apr

Mini-fridge, microwave, coffee/tea maker

AC Hotel by Marriott Orlando Lake Buena Vista

23.2 km from Oakland

Michelle

₹12,776 total

includes taxes & fees

22 Mar - 23 Mar

Courtyard by Marriott Orlando Downtown

25 km from Oakland

John

₹14,957 total

includes taxes & fees

22 Mar - 23 Mar

Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Homewood Suites by Hilton Orlando at Flamingo Crossings

19.3 km from Oakland

ALTON

₹13,731 total

includes taxes & fees

5 Apr - 6 Apr

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

19.3 km from Oakland

Catalina

₹14,854 total

includes taxes & fees

24 Mar - 25 Mar

Home2 Suites by Hilton Orlando at Flamingo Crossings

19.3 km from Oakland

VIMAL

₹10,988 total

includes taxes & fees

25 Mar - 26 Mar

The Delaney Hotel

25.3 km from Oakland

Cate

Staybridge Suites Orlando at SeaWorld by IHG

22.8 km from Oakland

Dianne

₹12,153 total

includes taxes & fees

23 Mar - 24 Mar

Meliá Orlando Celebration

26.5 km from Oakland

Brad

₹12,995 total

includes taxes & fees

30 Mar - 31 Mar

2 outdoor pools, pool umbrellas, pool loungers

Hilton Vacation Club Aqua Sol Orlando West

22.8 km from Oakland

Eduardo

₹15,841 total

includes taxes & fees

24 Mar - 25 Mar

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

19.3 km from Oakland

Christian

₹12,984 total

includes taxes & fees

24 Mar - 25 Mar

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

23.1 km from Oakland

Terrence

₹13,016 total

includes taxes & fees

8 Apr - 9 Apr

Hilton Vacation Club Grand Beach Orlando

25.2 km from Oakland

Jeannette

₹17,074 total

includes taxes & fees

5 Apr - 6 Apr

Aloft Orlando Lake Buena Vista

22.5 km from Oakland

Terry

₹9,348 total

includes taxes & fees

22 Mar - 23 Mar

Outdoor pool, pool loungers, lifeguards on site

Spectrum Resort Villas Orlando and Waterparks

31.2 km from Oakland

Donna

₹41,132 total

includes taxes & fees

11 Mar - 12 Mar

Westgate Town Center Resort

25.3 km from Oakland

Omar

₹13,476 total

includes taxes & fees

11 Mar - 12 Mar

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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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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

If you're spending some time in Downtown Winter Garden, West Orange Trail and Central Florida Railroad Museum 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

Westgate Lakes Resort & Spa Universal Studios Area

8/10 Good

"We did not enjoy our pool and hot rub area. The hot tub was only about 65 degrees maybe 70, so we ended up just using the jacuzzi tub in the room 2 nights in a row. Building 1500 pool area. "