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Find hotels in Oakland, Winter Garden from $89

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May 12 - May 13
Tomorrow
May 13 - May 14
Next weekend
May 17 - May 19

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Discover 38,427 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Margaritaville Resort Orlando
Lobby
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (2998)
"We love the pool area. "
The price is $139
$203 total
includes taxes & fees
May 13 - May 14
Margaritaville Resort Orlando
Margaritaville Resort Orlando Cottages by Rentyl
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (829)
"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
Disney's Animal Kingdom Lodge
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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OYO Townhouse Orlando West
Lobby
OYO Townhouse Orlando West
2.0 star property
6.8 out of 10, (1002)
"The workers are so nice and wonderful and easy to talk to! place is super quiet and the beds are super soft!"
The price is $76
$93 total
includes taxes & fees
Jun 4 - Jun 5
OYO Townhouse Orlando West
WoodSpring Suites Orlando West - Clermont
Exterior
WoodSpring Suites Orlando West - Clermont
2.5 star property
5.0 out of 10, (618)
"I needed an inexpensive over night stay. This was pretty good for the price. It was clean and comfortable. Nothing fancy but I was only there to sleep. Fit the bill!"
The price is $89
$99 total
includes taxes & fees
May 17 - May 18
WoodSpring Suites Orlando West - Clermont
Hampton Inn & Suites Clermont
Suite, 1 King Bed, Non Smoking | Premium bedding, desk, laptop workspace, blackout drapes
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 $129
$143 total
includes taxes & fees
May 26 - May 27
Hampton Inn & Suites Clermont
Fairfield Inn & Suites Orlando Ocoee
Lobby lounge
Fairfield Inn & Suites Orlando Ocoee
2.5 star property
8.8 out of 10, Excellent, (576)
"I liked it. Felt safe for a single traveler. Accessible amenities which was great. Room was nice too. "
The price is $116
$131 total
includes taxes & fees
May 26 - May 27
Fairfield Inn & Suites Orlando Ocoee
The Grove Resort by ACO
Exterior
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
The Surf Shack - Three Bedroom House, Sleeps 8
Fridge, microwave, oven, dishwasher
The Surf Shack - Three Bedroom House, Sleeps 8
9.2 out of 10, Wonderful, (17)
"Clean, modern, new. Had an overall nice stay with family. Only minor irk is that the location they provide on the booking site is different from the actual place. The real address is actually about a 20 min drive to the Disney parks. The community is new and huge with a security guard entrance who were all friendly. There was a community pool right outside the balcony and the game rooms were a plus. "
The Surf Shack - Three Bedroom House, Sleeps 8
Sleep Up To 54 At The Great Escape Parkside - 15 BR Game Themed Mansion!
Dining
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!
Communal facilities/free shuttles to parks
Fridge, microwave, oven, stovetop
Communal facilities/free shuttles to parks
10.0 out of 10, Exceptional, (6)
"This was a lovely house. We had everything we needed, and the beds were very comfortable. Our family truly enjoyed our stay and would commend it highly."
Communal facilities/free shuttles to parks
Shuttle to Disney World + On-Site Water Park
A heated pool
Shuttle to Disney World + On-Site Water Park
Shuttle to Disney World + On-Site Water Park
SPACIOUS, LOVELY THEMED HOME NEAR DISNEY
Private kitchen
SPACIOUS, LOVELY THEMED HOME NEAR DISNEY
9.6 out of 10, Exceptional, (109)
"property was like the listing said. My great grandaughter really enjoyed the princes room. My great grandson also enjoyed his room. It had most everything we needed for our stay. we could not enjoy the pool due to the weather but it looked inviting. We will stay again."
SPACIOUS, LOVELY THEMED HOME NEAR DISNEY
Disney's Animal Kingdom Villas - Jambo House
Lobby
Disney's Animal Kingdom Villas - Jambo House
2.0 star property
Disney's Animal Kingdom Villas - Jambo House
DISNEY House - 8 GUESTS!+ FREE Resort! -35
Pool
DISNEY House - 8 GUESTS!+ FREE Resort! -35
DISNEY House - 8 GUESTS!+ FREE Resort! -35
Holiday home winter / summer
Property grounds
Holiday home winter / summer
9.8 out of 10, Exceptional, (96)
"We had a fabulous time. The house was so clean and convenient to attractions. Dan was so nice and accommodating. We tried to leave everything as we found it. The beds were very comfortable and we slept great!"
Holiday home winter / summer
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
Pool
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
9.6 out of 10, Exceptional, (99)
"If you have a family of 4 or 3 this is a good property to stay at. Fairly close to Disney."
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
Orange Lake Resort - Holiday Inn Club Vacations
Outdoor pool
Orange Lake Resort - Holiday Inn Club Vacations
Orange Lake Resort - Holiday Inn Club Vacations
3 bedroom, 2 bathroom Bahama Bay Resort Villa near all of Orlando's magic!
Pool | Outdoor pool, a heated 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!
Resort Open/Grill/Movie Room/15 Mins to Disney/flexible canx policy
Outdoor 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
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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.

Where is 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 traveler data.

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.