Photo by Gregg Yutko

Find hotels in Oakland, Winter Garden

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Discover 38,664 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Rosen Shingle Creek
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (3994)
"Great stay!"
Rosen Shingle Creek
Hilton Garden Inn Orlando I-4 Millenia Blvd Mall
Lobby

Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

3.0 star property
9.0 out of 10, Wonderful, (366)
"Very nice place to stay totally recommended "
Hilton Garden Inn Orlando I-4 Millenia Blvd Mall
Wyndham Garden Orlando Airport
Outdoor pool, sun loungers

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3815)
"Great place to stay."
Wyndham Garden Orlando Airport
Magic Moment Resort and Kids Club
Royal Room, 2 Queen Beds, Pool View | Pool | Outdoor pool, a heated pool, open 9 AM to 9:00 PM, free cabanas

Magic Moment Resort and Kids Club

3.0 star property
8.4 out of 10, Very Good, (2485)
"We loved our stay. The best stay for the money. "
Magic Moment Resort and Kids Club
Holiday Inn Orlando International Dr-ICON by IHG
Lobby

Holiday Inn Orlando International Dr-ICON by IHG

3.0 star property
9.0 out of 10, Wonderful, (2177)
"Absolutely amazing and loved my stay"
Holiday Inn Orlando International Dr-ICON by IHG
Palazzo Lakeside Hotel
1 bedroom, in-room safe, laptop workspace, blackout drapes

Palazzo Lakeside Hotel

3.0 star property
8.2 out of 10, Very Good, (5184)
"Great hotel!"
Palazzo Lakeside Hotel
Seasons Florida Resort
Property grounds

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (3075)
"We love staying here "
Seasons Florida Resort
Sonesta Essential Orlando
Room, 2 Queen Beds | Desk, laptop workspace, blackout drapes, iron/ironing board

Sonesta Essential Orlando

3.0 star property
7.2 out of 10, Good, (1709)
"Nice place, very friendly staff and a nice breakfast"
Sonesta Essential Orlando
Pestana Orlando Suites - Lake Buena Vista
Hypo-allergenic bedding, minibar, in-room safe, individually decorated

Pestana Orlando Suites - Lake Buena Vista

4.0 star property
9.4 out of 10, Exceptional, (1749)
"Good place prefect for short stay"
Pestana Orlando Suites - Lake Buena Vista
The Eo Inn - Downtown
Front of property

The Eo Inn - Downtown

3.0 star property
8.0 out of 10, Very Good, (1003)
"Great find with a friendly and hospitable staff!"
The Eo Inn - Downtown
Margaritaville Resort Orlando with H2O Waterpark
Lobby

Margaritaville Resort Orlando with H2O Waterpark

4.0 star property
9.0 out of 10, Wonderful, (3581)
"Great place to stay."
Margaritaville Resort Orlando with H2O Waterpark
The Delaney Hotel
Terrace/patio

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1014)
"great restaurant and even better rooms!"
The Delaney Hotel
Drury Plaza Hotel Orlando - Disney Springs Area
Outdoor pool, sun loungers

Drury Plaza Hotel Orlando - Disney Springs Area

3.0 star property
9.8 out of 10, Exceptional, (4842)
"AMAZING place to stay "
Drury Plaza Hotel Orlando - Disney Springs Area
Rosen Centre Hotel
Outdoor pool, open 6:00 AM to midnight, pool umbrellas, sun loungers

Rosen Centre Hotel

4.0 star property
9.0 out of 10, Wonderful, (3935)
"Perfect stay close to the parks."
Rosen Centre Hotel
Orlando Palms Hotel
Outdoor pool, open 9 AM to 10 PM, sun loungers

Orlando Palms Hotel

2.5 star property
7.6 out of 10, Good, (2048)
"room was clean and staffs were friendly"
Orlando Palms Hotel
DoubleTree by Hilton at the Entrance to Universal Orlando
Outdoor pool

DoubleTree by Hilton at the Entrance to Universal Orlando

4.0 star property
8.4 out of 10, Very Good, (6610)
"Beautiful place to stay "
DoubleTree by Hilton at the Entrance to Universal Orlando
Hyatt House Orlando International Drive
Free daily buffet breakfast

Hyatt House Orlando International Drive

4.0 star property
9.2 out of 10, Wonderful, (915)
"We enjoyed our stay at "
Hyatt House Orlando International Drive
Red Lion Hotel Orlando Lake Buena Vista South
Water park

Red Lion Hotel Orlando Lake Buena Vista South

3.5 star property
8.8 out of 10, Excellent, (4061)
"Excellent hotel and staff."
Red Lion Hotel Orlando Lake Buena Vista South
Wyndham Lake Buena Vista – Disney Springs® Area
2 outdoor pools, a heated pool, cabanas (surcharge), pool umbrellas

Wyndham Lake Buena Vista – Disney Springs® Area

4.0 star property
8.8 out of 10, Excellent, (2728)
"Love this place, stay here often!"
Wyndham Lake Buena Vista – Disney Springs® Area
Meliá Orlando Celebration
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)

Meliá Orlando Celebration

4.0 star property
8.6 out of 10, Excellent, (1531)
"Excellent hotel, great location. Close to Disney"
Meliá Orlando Celebration
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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Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most.

Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Downtown Winter Garden

While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum.

Killarney

If you're looking for some top things to see and do in Killarney and surrounding area, you can visit Bella Collina Golf Club and West Orange Trail.

Top Oakland Hotel Reviews

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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?

When you want to kick up your feet after a day of exploring the sights in Winter Garden, you can choose from 12 Expedia hotels and other accommodations in Oakland.

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 Plant Street Market or Garden Theatre.