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Find hotels in Oakland, Winter Garden from AED91

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Discover 38,027 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Aerial view
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (3007)
"So welcoming and relaxing!"
The price is AED 592
AED 838 total
includes taxes & fees
27 May - 28 May
Margaritaville Resort Orlando
Front of property
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (843)
"Great place "
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
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Exterior
WoodSpring Suites Orlando West - Clermont
2.5 star property
5.0 out of 10, (622)
"Amenities for extended stay and/or prepare food. Microwave, cook top, sink and full refrigerator/freezer. Nothing fancy, but clean. Basic room- good if you’re looking for a safe budget friendly stay. Limited parking on occasion due to long stay business trucks w equipment "
The price is AED 356
AED 395 total
includes taxes & fees
26 May - 27 May
WoodSpring Suites Orlando West - Clermont
Exterior
Hampton Inn & Suites Clermont
2.5 star property
9.2 out of 10, Wonderful, (607)
"Clean, friendly staff and accessible to main road restaurants."
The price is AED 475
AED 517 total
includes taxes & fees
29 May - 30 May
Hampton Inn & Suites Clermont
Lobby lounge
Fairfield Inn & Suites Orlando Ocoee
2.5 star property
8.8 out of 10, Excellent, (579)
"Excellent stay and friendly staff. very comfortable beds."
The price is AED 485
AED 538 total
includes taxes & fees
23 Jun - 24 Jun
Fairfield Inn & Suites Orlando Ocoee
Outdoor pool
The Grove Resort by ACO
3.0 star property
7.6 out of 10, Good, (7)
"When we got there the cleaning lady was seating on the sofa on the phone and told us that she was not done , she finished on the phone and left the bathroom super dirty, no shampoo or conditioner, I was there for 3 nights and the beds were never made or did not receive clean towels I go to the groove every year and this year I was impressed about how dirty the apartment .. but the apartment it’s very cute and comfortable , they just need to work on the cleaning "
The Grove Resort by ACO
World's first billiard table pool (and lazy river)
Sleep Up To 54 At The Great Escape Parkside - 15 BR Game Themed Mansion!
Sleep Up To 54 At The Great Escape Parkside - 15 BR Game Themed Mansion!
Exterior
Edgewater Hotel
2.5 star property
9.6 out of 10, Exceptional, (274)
"Great area and unique property. Family suites are great value."
The price is AED 546
AED 602 total
includes taxes & fees
11 Jun - 12 Jun
Edgewater Hotel
Living Room
Shuttle to Disney World + On-Site Water Park
Shuttle to Disney World + On-Site Water Park
DISNEY House - 8 GUESTS!+ FREE Resort! -35
DISNEY House - 8 GUESTS!+ FREE Resort! -35
Kissimmee Vacation Rental | 1BR | 1BA | 750 Sq Ft | Stairs Only Access
Resort Condo w/ Balcony: 6 Mi to Magic Kingdom
9.2 out of 10, Wonderful, (53)
"Perfect stay. Roy was a great host. Excellent communication. Love this property. Tucked away but easy access to everything. Would definitely return."
Resort Condo w/ Balcony: 6 Mi to Magic Kingdom
Living Room
"At Sea" Condo 15 Minutes from Disney
9.4 out of 10, Exceptional, (167)
"Decided to take the plunge and travel to Florida by myself! Enjoyed the time by myself as I could come and go as I pleased!"
"At Sea" Condo 15 Minutes from Disney
Exterior
Holiday home winter / summer
9.8 out of 10, Exceptional, (97)
"The location of the property was perfect. It is very close to Disney and other attractions and restaurants. However the home is located in a quiet neighborhood with easy access. The owner and host were very helpful and available if needed. The home was comfortable and a great place to relax. We would enjoy staying here again."
Holiday home winter / summer
Living area
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
9.6 out of 10, Exceptional, (99)
"A wonderful place to stay."
The price is AED 239
AED 772 total
includes taxes & fees
28 May - 29 May
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
Pool
Orange Lake Resort - Holiday Inn Club Vacations
Orange Lake Resort - Holiday Inn Club Vacations
Pool
3 bedroom, 2 bathroom Bahama Bay Resort Villa near all of Orlando's magic!
9.8 out of 10, Exceptional, (55)
"Gets a thumbs up from us"
3 bedroom, 2 bathroom Bahama Bay Resort Villa near all of Orlando's magic!
Pool
Resort Open/Grill/Movie Room/15 Mins to Disney/flexible canx policy
9.6 out of 10, Exceptional, (29)
"We had a wonderful visit! Love the neighborhood and such a relaxing and beautiful home♥️"
Resort Open/Grill/Movie Room/15 Mins to Disney/flexible canx policy
Pool
PROMO 10% WEEKLY DISCOUNT! Fun-Filled Family Getaways Near the Magic of Disney
9.8 out of 10, Exceptional, (23)
"We were very impressed right from the first moment we walked in. The place was very nice. We did have issues with one of the tvs and internet, but they helped us get these issues addressed quickly. We stayed for 8 days and found this location to be very comfortable. The pool areas were kept clean and nicely maintained. Easy in and out even though it is a gated community. Everything you would need for dining shopping or gas are all very close and even some within walking distance. The only bummer...
PROMO 10% WEEKLY DISCOUNT! Fun-Filled Family Getaways Near the Magic of Disney
Room
Vacation Home Near Disney
3.0 star property
9.0 out of 10, Wonderful, (2)
"The property was perfect for my families needs, and the management was exception with fast responses and exemplary service."
Vacation Home Near Disney
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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.

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.

Recent reviews of Oakland hotels

Rosen Inn International

Rosen Inn International

5/5 Excellent
"Great stay for a few days. Close to everything. Great value, nice staff and clean property. I’ve stayed on their properties many times and this is my favorite location. "
A verified traveler stayed at Rosen Inn International
Posted 21 hours ago
Rosen Inn International