Photo by Gregg Yutko

Find hotels in Oakland, Winter Garden from SAR 216

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Discover 37,305 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Walt Disney World Dolphin
Exterior
Walt Disney World Dolphin
4.0 star property
8.6 out of 10, Excellent, (3480)
"This is a gorgeous hotel!! The location is amazing and convenient. We would stay here again and again!"
The price is SAR 860
SAR 1,123 total
includes taxes & fees
22 Nov - 23 Nov
Walt Disney World Dolphin
Margaritaville Resort Orlando
Aerial view
Margaritaville Resort Orlando
4.0 star property
9.0 out of 10, Wonderful, (3153)
"Love the property Hate that pool closed so early At least have a jacuzzi open late"
The price is SAR 555
SAR 786 total
includes taxes & fees
16 Dec - 17 Dec
Margaritaville Resort Orlando
Home2 Suites by Hilton Orlando at Flamingo Crossings
Exterior
Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
9.4 out of 10, Exceptional, (3626)
"Our stay was very pleasant. The property was clean. The room was spotless. Breakdast was delicious. "
The price is SAR 492
SAR 547 total
includes taxes & fees
11 Dec - 12 Dec
Home2 Suites by Hilton Orlando at Flamingo Crossings
Margaritaville Resort Orlando Cottages by Rentyl
Front of property
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (1084)
"This is our third time staying at Margaritaville (cottage the first time, villas the second and third time); I must say this villa was the least taken care of. It wasn’t super clean and the slider had some damage regarding opening/closing the blinds and locking/unlocking the sliding glass door. The front door didn’t have a safety lock at all (it looked to have been removed) so that made us a little uneasy. Our bed (queen) was very bouncy and it seemed to cave a little in the middle. Overall, it...
Margaritaville Resort Orlando Cottages by Rentyl
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Exterior
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
9.4 out of 10, Exceptional, (2430)
"Very nice and close to shopping and dining. "
The price is SAR 436
SAR 483 total
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
Exterior
Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
8.8 out of 10, Excellent, (3702)
"I loved everything about this property except for THE NOISE!!!!!! Omg, what were you guys doing!!!?? We couldn’t sleep past 7am because of the loud noises made by the workers repairing I don’t know what. Also, says that breakfast was included, but it’s actually an apple and a juice. "
The price is SAR 325
SAR 464 total
includes taxes & fees
27 Nov - 28 Nov
Hilton Vacation Club Aqua Sol Orlando West
Homewood Suites by Hilton Orlando at Flamingo Crossings
Pool
Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
9.4 out of 10, Exceptional, (1496)
"Wonderful staff ! Great location ! Comfortable stay !"
The price is SAR 492
SAR 547 total
includes taxes & fees
12 Dec - 13 Dec
Homewood Suites by Hilton Orlando at Flamingo Crossings
Margaritaville Cottages Orlando by VStays
Outdoor pool
Margaritaville Cottages Orlando by VStays
4.0 star property
9.0 out of 10, Wonderful, (1001)
"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, (1534)
"NA"
The price is SAR 381
SAR 548 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Pool
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
9.2 out of 10, Wonderful, (1854)
"Food"
The price is SAR 402
SAR 446 total
includes taxes & fees
2 Dec - 3 Dec
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Walt Disney World Swan Reserve
Exterior
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 SAR 1,449
SAR 1,777 total
includes taxes & fees
4 Dec - 5 Dec
Walt Disney World Swan Reserve
Summer Bay Orlando by Exploria Resorts
Property amenity
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 SAR 490
SAR 654 total
includes taxes & fees
5 Dec - 6 Dec
Summer Bay Orlando by Exploria Resorts
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Pool
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 SAR 469
SAR 521 total
includes taxes & fees
16 Dec - 17 Dec
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Pool
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
9.0 out of 10, Wonderful, (1334)
"I stay here every time I come to Disney. I am an annual pass holder and Florida resident. This hotel is extremely close to the parks. We have always had a wonderful experience at both hotels. "
The price is SAR 402
SAR 446 total
includes taxes & fees
3 Dec - 4 Dec
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Destiny Palms Hotel Maingate West
Exterior
Destiny Palms Hotel Maingate West
2.5 star property
8.2 out of 10, Very Good, (1681)
"Rooms are clean. "
The price is SAR 216
SAR 258 total
includes taxes & fees
11 Dec - 12 Dec
Destiny Palms Hotel Maingate West
The Berkley, Orlando
Outdoor pool
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1599)
"The pool area was a great spot to relax! Lots of chairs, tables and loungers! We would definitely recommend this resort! "
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 SAR 526
SAR 757 total
includes taxes & fees
25 Nov - 26 Nov
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 SAR 315
SAR 420 total
includes taxes & fees
4 Dec - 5 Dec
Holiday Inn Express And Suites Clermont Se West Orlando, an IHG Hotel
Home2 Suites By Hilton Winter Garden
Room
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 SAR 523
SAR 578 total
includes taxes & fees
2 Dec - 3 Dec
Home2 Suites By Hilton Winter Garden
Disney's Coronado Springs Resort
Front of property - evening/night
Disney's Coronado Springs Resort
4.0 star property
9.0 out of 10, Wonderful, (1003)
"It was an awesome experience!"
Disney's Coronado Springs Resort
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?

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

How many hotels should I expect to find in the Oakland area?

Expedia has 5 Oakland hotels and other accommodations, 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, the majority of room reservations are refundable if you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to get the top deals on offer in Oakland.

Where can I learn more about changing or cancelling my trip to Oakland?

For more information about picking new dates or cancelling your trip to Oakland, go to https://www.expedia.com/service/.

What is there to do in this Winter Garden neighborhood?

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, be sure to visit other sights like Resurrection Catholic Church or Garden Theatre.