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?

Expedia has 7 Oakland hotels and other accommodation options, and one might make a good home base for venturing out into the greater Winter Garden area.

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 Resurrection Catholic Church.

Top 10 Oakland Hotels of 2025 | Expedia Singapore

Top 10 Hotels in Oakland

"Great stay"

includes taxes & fees

11 Aug - 12 Aug

Desk, laptop workspace, blackout curtains, iron/ironing board

"Excellent, great hospitality from the staff"

includes taxes & fees

21 Jul - 22 Jul

"The hotel staff, restaurants and accommodations are very nice."

"Excellent all around place and stay "

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

"Good hotel "

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

"Nice place to stay near airport "

4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)

"Great staff, great food, beautiful property"

includes taxes & fees

26 Jul - 27 Jul

"Great hotel."

includes taxes & fees

17 Aug - 18 Aug

Premium bedding, desk, laptop workspace, iron/ironing board

"Excelente hotel"

includes taxes & fees

10 Aug - 11 Aug

Daily full breakfast (USD 14.88 per person)

"Great place to stay"

includes taxes & fees

31 Jul - 1 Aug

"nice place to stay"

includes taxes & fees

2 Aug - 3 Aug

"Enjoyed our stay!"

includes taxes & fees

31 Jul - 1 Aug

Outdoor pool, open 10 AM to 10 PM, pool loungers

"Excellent stay!!!"

includes taxes & fees

10 Aug - 11 Aug

"Great place to stay"

includes taxes & fees

10 Aug - 11 Aug

"Amazing hotel great location.! "

includes taxes & fees

27 Jul - 28 Jul

"Very great spot for couples and families "

"Great place to stay, very clean and modern. The staff were super friendly, and also the breakfast is really good."

includes taxes & fees

28 Jul - 29 Jul

"Great stay loved breakfast by the pool kids stayed wet and on the playground the gardens were gorgeous to walk through every morning and it was enjoyably quiet felt safe and had plenty to do and all the shopping and eateries around the area"

includes taxes & fees

27 Jul - 28 Jul

Outdoor pool, open 6:00 AM to midnight, pool umbrellas, pool loungers

"Very nice pool and plenty of different dining options."

includes taxes & fees

9 Aug - 10 Aug

Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, pool loungers

"Place was clean , front desk and everyone in the hotel was very helpful and nice. "

includes taxes & fees

21 Jul - 22 Jul

Where to stay in Oakland

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

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, West Orange Trail and Central Florida Railroad Museum are top sights worth seeing.

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Killarney

Killarney might not have many top sights, but Resurrection Catholic Church and West Orange Trail are two attractions nearby that you can check out.

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Top Oakland Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent

"Enjoyed my stay at Home2Suites. The staff was amazing and the hotel was very clean. "

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"I enjoyed staying at this property. The staff was great, the rooms were clean, and they had multiple pools with bars. I didn’t try the resort water park, but I’m sure it was top notch as well. I also liked the price, especially with all of the amenities that were included. Only issue was the price of the items in the convenience store that is located on the resort. Luckily there is a Walmart.5 miles down the road."

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"We’ve been coming to this hotel for years. It always great. Never had an issue and I will continue to come. I will say though if you sign up for their timeshare presentation, it’s a lie that’s it’s only 90 minutes and they will continue to try and push you into purchasing one even when you’ve made it clear you don’t want to. I lost about 5 hours of my day, left with a headache and was so annoyed and upset that day because of it."

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

10/10 Excellent

"To start with i just want to say the Fairfield was an amazing place to stay. Super affordable! Had a covered parking garage, a nice pool, a splash pad, a self serve laundry room and an amazing breakfast!! Ethan at tge front desk was sooooo helpful!! From the first phone call for information to check in and in between he was super friendly, extremely helpful and just so professional. I will definitely return just because of how friendly the staff was. If i have one complaint it would be the pillows. They werent too comfortable as they would go flat. If there were half firm and half soft pillows it would give guests more of an option. Other than that this place was perfect!!"

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Hotels in Oakland

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Top 10 Hotels in Oakland

Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport

Sonesta Essential Orlando

Sonesta Essential Orlando

The Alfond Inn

The Alfond Inn

The Delaney Hotel

The Delaney Hotel

Orlando Palms Hotel

Orlando Palms Hotel

Garnet Inn & Suites, Orlando

Garnet Inn & Suites, Orlando

Rosen Shingle Creek

Rosen Shingle Creek

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

La Quinta Inn & Suites by Wyndham Orlando Universal area

La Quinta Inn & Suites by Wyndham Orlando Universal area

TRYP by Wyndham Orlando

TRYP by Wyndham Orlando

Club Sevilla

Club Sevilla

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

Hyatt House across from Universal Orlando Resort

Hyatt House across from Universal Orlando Resort

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

Wyndham Garden Orlando Universal / I Drive

Wyndham Garden Orlando Universal / I Drive

Seasons Florida Resort

Seasons Florida Resort

Spark by Hilton Orlando near SeaWorld

Spark by Hilton Orlando near SeaWorld

Orlando International Drive North Hotel

Orlando International Drive North Hotel

Rosen Centre Hotel

Rosen Centre Hotel

Best Western Orlando Gateway Hotel

Best Western Orlando Gateway Hotel

Where to stay in Oakland

Vista del Lago

Downtown Winter Garden

Killarney

Top Oakland Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings

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