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Oakland Hotels, Winter Garden

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36929 Cheap Hotels in Oakland - Specials, Reviews, & Last Minute Deals

The Grove Resort & Water Park Orlando
3 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas

The Grove Resort & Water Park Orlando

4.0 star property
8.2 out of 10, Very good, (6671)
"Is amazing place"
The price is AU$302
includes taxes & fees
1 Dec - 2 Dec
The Grove Resort & Water Park Orlando
Walt Disney World Dolphin
3 outdoor pools, open 6:00 AM to 11:00 PM, pool cabanas (surcharge)

Walt Disney World Dolphin

4.0 star property
8.6 out of 10, Excellent, (3529)
"This is a gorgeous hotel!! The location is amazing and convenient. We would stay here again and again!"
The price is AU$425
includes taxes & fees
1 Dec - 2 Dec
Walt Disney World Dolphin
Margaritaville Resort Orlando
Lobby

Margaritaville Resort Orlando

4.0 star property
9.0 out of 10, Wonderful, (3173)
"Nothing else "
The price is AU$328
includes taxes & fees
16 Dec - 17 Dec
Margaritaville Resort Orlando
Home2 Suites by Hilton Orlando at Flamingo Crossings
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, (3639)
"Really enjoyed the free breakfast in the morning to start my day."
The price is AU$227
includes taxes & fees
16 Dec - 17 Dec
Home2 Suites by Hilton Orlando at Flamingo Crossings
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1084)
"Very pretty, and spacious- but a bit far from the resort "
Margaritaville Resort Orlando Cottages by Rentyl
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Lobby

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

2.5 star property
9.4 out of 10, Exceptional, (2432)
"Great customer service from front desk to breakfast crew. Only complaint was having some small ants in bathroom by shower and on dresser and floor under tv. We pretty much just slept and showered in the room. We ate a couple snacks and everything we drank had a cap, so I know we weren't the cause."
The price is AU$216
includes taxes & fees
9 Dec - 10 Dec
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Hilton Vacation Club Aqua Sol Orlando West
2 outdoor pools, pool umbrellas, pool loungers

Hilton Vacation Club Aqua Sol Orlando West

4.0 star property
8.8 out of 10, Excellent, (3747)
"Amazing hotel "
The price is AU$205
includes taxes & fees
26 Nov - 27 Nov
Hilton Vacation Club Aqua Sol Orlando West
Homewood Suites by Hilton Orlando at Flamingo Crossings
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, (1507)
"very nice hotel, breakfast is good if you like Mexican food. Shuttle to Disney World if you make a reservation 24 hours in advance on the app"
The price is AU$242
includes taxes & fees
16 Dec - 17 Dec
Homewood Suites by Hilton Orlando at Flamingo Crossings
Margaritaville Cottages Orlando by VStays
Aerial view

Margaritaville Cottages Orlando by VStays

4.0 star property
9.0 out of 10, Wonderful, (1002)
"Safe 4 walking"
Margaritaville Cottages Orlando by VStays
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
Exterior

Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel

4.0 star property
8.6 out of 10, Excellent, (1543)
"We loved our villa! The kitchen was fully stocked, the rooms were clean and comfortable, the backyard was nice for the kids to get their energy out. We went to the lazy river and arcade and those were fun. We appreciated the short drive to Epcot. Would stay again! "
The price is AU$240
includes taxes & fees
26 Nov - 27 Nov
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
SpringHill 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, (1874)
"Spacious and clean room. In room microwave very convenient when traveling with a toddler. Excellent complimentary breakfast. Short drive to Disney property, and shopping and dining across the street."
The price is AU$185
includes taxes & fees
1 Dec - 2 Dec
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Walt Disney World Swan Reserve
Mediterranean cuisine

Walt Disney World Swan Reserve

4.0 star property
9.2 out of 10, Wonderful, (594)
"Overall, great experience and place to stay for couples trip to Disney world. Quiet, clean as well as friendly and accommodating staff. One of the bus drivers could improve her communication during the passenger onboarding process. Otherwise we would definitely stay again. "
The price is AU$644
includes taxes & fees
30 Nov - 1 Dec
Walt Disney World Swan Reserve
Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5025)
"Our unit was clean but in definite need of an update. The carpet was threadbare and torn in some areas. We still had a great stay and appreciated the prompt attention from security when we needed access to our unit."
The price is AU$274
includes taxes & fees
15 Dec - 16 Dec
Summer Bay Orlando by Exploria Resorts
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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, (1275)
"Affordable, clean, close proximity to the parks. The free breakfast is amazing!"
The price is AU$216
includes taxes & fees
18 Dec - 19 Dec
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

3.5 star property
9.0 out of 10, Wonderful, (1345)
"Nice and clean. Given its proximity to Disney, it was much quieter than I expected. Staff was nice and the breakfast is great. "
The price is AU$185
includes taxes & fees
1 Dec - 2 Dec
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Destiny Palms Hotel Maingate West
Fridge, coffee/tea maker

Destiny Palms Hotel Maingate West

2.5 star property
8.2 out of 10, Very good, (1692)
"A privately owned hotel that is a short UBER ride to the parks. Stephanie at the front desk makes you feel welcome the moment you walk in the door. Plenty of food options a short distance away makes this hotel a perfect stay."
The price is AU$110
includes taxes & fees
27 Nov - 28 Nov
Destiny Palms Hotel Maingate West
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1599)
"Clean, relaxing, spacious, lots of amenities."
The Berkley, Orlando
Embassy Suites By Hilton Orlando Sunset Walk
Exterior

Embassy Suites By Hilton Orlando Sunset Walk

3.5 star property
8.8 out of 10, Excellent, (83)
"First time staying at this hotel. We really enjoyed our stay. Close to the Sunset Walk, the pool and pool amenities were great and the service was excellent! We will be back!"
The price is AU$314
includes taxes & fees
1 Dec - 2 Dec
Embassy Suites By Hilton Orlando Sunset Walk
Holiday Inn Express And Suites Clermont Se West Orlando, an IHG Hotel
Exterior

Holiday Inn Express And Suites Clermont Se West Orlando, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (205)
"It was overall a good experience. "
The price is AU$174
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express And Suites Clermont Se West Orlando, an IHG Hotel
Home2 Suites By Hilton Winter Garden
Exterior

Home2 Suites By Hilton Winter Garden

3.0 star property
9.4 out of 10, Exceptional, (140)
"Great location and beautiful place "
The price is AU$241
includes taxes & fees
4 Dec - 5 Dec
Home2 Suites By Hilton Winter Garden
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.
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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.

What's the best place to stay in Oakland?

For your stay in Oakland, The Oak View Place.. is one of the top choices based on our traveller data.

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.