Photo by Gregg Yutko

Hotels in Oakland, Winter Garden

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Filter by

Popular filters
Popular filters
Price per night
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top 10 Hotels in Oakland, Winter Garden

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
9.6 out of 10, Exceptional, (804)
"Very nice!!!"
The price is RM588
RM662 total
includes taxes & fees
23 May - 24 May
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers
Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
9.4 out of 10, Exceptional, (2798)
"It was a very nice place with friendly staff and great food "
The price is RM521
RM586 total
includes taxes & fees
5 Jun - 6 Jun
Home2 Suites by Hilton Orlando at Flamingo Crossings
Lobby
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
9.4 out of 10, Exceptional, (1713)
"The only thing I would change is shuttle service — to and from the airport, and to and from Disney, but I know those are expensive to maintain. We were a little disappointed in the availability of the shuttle service to Disney and ended up ubering most of the time, but otherwise our stay was pleasant. "
The price is RM504
RM567 total
includes taxes & fees
23 May - 24 May
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers
Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
9.4 out of 10, Exceptional, (1206)
"It was a good stay, definitely recommend."
The price is RM526
RM591 total
includes taxes & fees
9 Jun - 10 Jun
Homewood Suites by Hilton Orlando at Flamingo Crossings
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1412)
"It is like living in your own home. Fully equipped kitchen. King size beds comfortable but the twin beds were not. The vacation home is very nice though. Close to a lot of restaurants.20 mins to Disney"
The Berkley, Orlando
2 outdoor pools, open 8 AM to 10 PM, pool loungers
Holiday Inn Club Vacations Orlando Breeze Resort, an IHG Hotel
3.5 star property
9.4 out of 10, Exceptional, (328)
"Loved everything about it didn't want to leave."
The price is RM607
RM732 total
includes taxes & fees
19 May - 20 May
Holiday Inn Club Vacations Orlando Breeze Resort, an IHG Hotel
Aerial view
Margaritaville Cottages Orlando by VStays
4.0 star property
9.2 out of 10, Wonderful, (1000)
"Excellent property, a little expensive "
Margaritaville Cottages Orlando by VStays
Mediterranean cuisine
Walt Disney World Swan Reserve
4.0 star property
9.2 out of 10, Wonderful, (420)
"Spacious room. "
The price is RM1,181
RM1,541 total
includes taxes & fees
27 May - 28 May
Walt Disney World Swan Reserve
Outdoor pool, a heated pool
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
9.2 out of 10, Wonderful, (1134)
"This hotel was really good. Facilities are great and the staff were always nice and willing to help. My only complaint is about the bathtub, which was not clean enough and the drain was somehow clogged. "
The price is RM445
RM501 total
includes taxes & fees
23 May - 24 May
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
9.2 out of 10, Wonderful, (1609)
"Very clean and convenient, fine breakfast buffet, relaxing accommodations. Excellent pool and patio and close to stores and other eateries across the street, plus great access to 429, can get to all of the Disney World venues easily within 10-15 minutes. Our new favorite place to stay!"
The price is RM447
RM503 total
includes taxes & fees
20 May - 21 May
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Premium bedding, desk, laptop workspace, blackout curtains
Hampton Inn & Suites Clermont
2.5 star property
9.2 out of 10, Wonderful, (606)
"Fast easy check in. Clean and updated rooms. "
The price is RM669
RM743 total
includes taxes & fees
26 May - 27 May
Hampton Inn & Suites Clermont
Outdoor pool, open 7:00 AM to 10 PM, pool umbrellas, pool loungers
Fairfield Inn & Suites by Marriott Clermont
2.5 star property
9.0 out of 10, Wonderful, (1000)
"Love this property, we stay here whenever we come to central Florida. The only short coming was not having daily maid service, we have to ask."
The price is RM553
RM613 total
includes taxes & fees
28 May - 29 May
Fairfield Inn & Suites by Marriott Clermont
Lobby
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (2994)
"It's a great property and I loved the cottage we stayed in. My pool time at the two huge pools was excellent! My one complaint is the cost of the drinks. I had the Margaritaville Pina Colada which was base price $17. A $3 service fee was added and a $3 gratuity. That's a $23 drink, which is excessive. The other drinks were priced the same. Plus the pina colada tasted terrible. I will stay here again, but won't be ordering any drinks. "
The price is RM573
RM864 total
includes taxes & fees
21 May - 22 May
Margaritaville Resort Orlando
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (836)
"The property was very nice but we had no idea what layout we would be getting until we arrived which made it hard to plan. The villa did not come with the frozen drink machine it was supposed to have and had no extra blankets or pillows "
Margaritaville Resort Orlando Cottages by Rentyl
Property amenity
Disney's Animal Kingdom Lodge
4.5 star property
8.8 out of 10, Excellent, (1000)
"Love the lobby"
Disney's Animal Kingdom Lodge
Terrace/patio
Home2 Suites by Hilton Clermont
3.0 star property
8.8 out of 10, Excellent, (538)
"Excellent "
The price is RM515
RM571 total
includes taxes & fees
29 May - 30 May
Home2 Suites by Hilton Clermont
Exterior
Holiday Inn Express Clermont, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (789)
"A"
The price is RM516
RM573 total
includes taxes & fees
27 May - 28 May
Holiday Inn Express Clermont, an IHG Hotel
2 outdoor pools, pool umbrellas, pool loungers
Hilton Vacation Club Aqua Sol Orlando West
3.5 star property
8.6 out of 10, Excellent, (3529)
"The hotel staff was very nice. We enjoyed the water park "
The price is RM436
RM649 total
includes taxes & fees
27 May - 28 May
Hilton Vacation Club Aqua Sol Orlando West
Property grounds
Bahama Bay Resort
3.5 star property
8.6 out of 10, Excellent, (2024)
"We had a lower end 2 bedroom unit. Very spacious & updated nicely. We will definitely return to this resort. "
Bahama Bay Resort
2 outdoor pools, pool umbrellas, pool loungers
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1253)
"It was great besides no air conditioning upstairs where bedrooms are , even though they clean after you leave there should be a dust pan and mop to do cleaning while there "
The price is RM484
RM1,236 total
includes taxes & fees
16 Jun - 17 Jun
Encantada Resort Vacation Townhomes by IDILIQ
Don't see what you're looking for?
See all available 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.

Oakland hotels information

Number of reviews
38,930
Accommodation
38,318 hotels
Lowest Price
RM246
Highest Price
RM1,181

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?

Expedia has 5 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 Resurrection Catholic Church or Garden Theatre.

Recent Reviews in Oakland

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

5/5 Excellent
"This is a fun hotel with quite a few amenities. The cafeteria style restaurant was surprisingly good. We particularly enjoyed the salad bar because it has so many items to choose from to build a salad. We had a mini suite room with a seating area and little kitchenette. It was nice to have that extra space. The transportation to the parks is very good. We never had to wait for a bus on either side. The staff were friendly and accommodating. I would stay there again. "
A verified traveller stayed at Universal's Cabana Bay Beach Resort
Posted 9 hours ago
Universal's Cabana Bay Beach Resort