Photo by Gregg Yutko

Hotels in Oakland, Winter Garden from CA $125

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Oakland hotels and places to stay

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
Exterior
1-101 Legacy Dunes, Just steps from our beach style pool, minutes from Disney!
10.0 out of 10, Exceptional, (24)
"Great property everything. Was close by. The house was clean and had everything we needed :) thank you to the host! Highly recommend"
1-101 Legacy Dunes, Just steps from our beach style pool, minutes from Disney!
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
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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
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
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
Pool
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
9.6 out of 10, Exceptional, (99)
"A wonderful place to stay."
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
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
Outdoor pool, a heated pool
Perfect! 3 Bed 3 Bath Family Townhouse At Regal Palms-Disney/Universal/Golf!
9.6 out of 10, Exceptional, (157)
"We would stay here again!!"
The price is CA $184
CA $394 total
includes taxes & fees
May 19 - May 20
Perfect! 3 Bed 3 Bath Family Townhouse At Regal Palms-Disney/Universal/Golf!
Lobby
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
9.4 out of 10, Exceptional, (1711)
"Overall stay was nice.. the only suck part was the hot water wasn’t even hot, more lukewarm and it gets cold out of nowhere and than back to lukewarm again. After a long day at Disney all you want is a hot nice shower ( I don’t need it to be scalding hot) and unfortunately we didn’t get that. "
The price is CA $146
CA $164 total
includes taxes & fees
May 22 - May 23
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
City view from property
Edgewater Hotel
2.5 star property
9.4 out of 10, Exceptional, (272)
"Loved the breakfast area, the full breakfast, and the ability to sit and chat with others was great. Service from check-in to checkout was fantastic!"
The price is CA $187
CA $211 total
includes taxes & fees
May 27 - May 28
Edgewater Hotel
Outdoor pool, a heated pool
"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
Suite, 1 King Bed, Non Smoking
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 CA $176
CA $196 total
includes taxes & fees
May 27 - May 28
Hampton Inn & Suites Clermont
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
TV
Family Home w/ Private Pool ~ 9 Mi to Disney!
9.2 out of 10, Wonderful, (39)
"Lovely house, plenty of room for 6 with the added bonus of a pool. Good location with easy drive to Disney parks, Universal a bit further but reachable in 45 mins or so."
Family Home w/ Private Pool ~ 9 Mi to Disney!
Exclusive Condo
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
Lobby
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (2992)
"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 CA $166
CA $250 total
includes taxes & fees
May 19 - May 20
Margaritaville Resort Orlando
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (836)
"The food by the pool was delicious!"
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
Lobby lounge
Fairfield Inn & Suites Orlando Ocoee
2.5 star property
8.8 out of 10, Excellent, (577)
"I liked it. Felt safe for a single traveler. Accessible amenities which was great. Room was nice too. "
The price is CA $180
CA $202 total
includes taxes & fees
May 27 - May 28
Fairfield Inn & Suites Orlando Ocoee
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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.

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.

Recent Reviews in Oakland