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Find hotels in Oakland, Winter Garden from ￥5,334

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Discover 39,130 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Our top choices for Oakland hotels

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, (1683)
"Nice place, very friendly staff and a nice breakfast"
The price is ￥11,254
￥13,105 total
includes taxes & fees
Sep 14 - Sep 15
Sonesta Essential Orlando
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, (3991)
"Great resort vibes while being close to the parks and other tourist places. "
The price is ￥12,154
￥13,673 total
includes taxes & fees
Oct 2 - Oct 3
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, (404)
"Great spot and very nice spacious rooms"
The price is ￥13,721
￥15,435 total
includes taxes & fees
Sep 21 - Sep 22
Hilton Garden Inn Orlando I-4 Millenia Blvd Mall
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, (3931)
"Perfect stay close to the parks."
The price is ￥11,112
￥12,626 total
includes taxes & fees
Sep 26 - Sep 27
Rosen Centre Hotel
Seasons Florida Resort
Property grounds

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (3113)
"Great place to stay "
The price is ￥7,513
￥8,527 total
includes taxes & fees
Sep 17 - Sep 18
Seasons Florida Resort
Lakeside Inn
Outdoor pool, sun loungers

Lakeside Inn

3.0 star property
8.8 out of 10, Excellent, (1198)
"Such a point place love the atmosphere restaurant was great"
Lakeside Inn
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, (2208)
"Good hotel good location great staff lots of activities within walking distance. "
The price is ￥12,366
￥16,121 total
includes taxes & fees
Sep 22 - Sep 23
Holiday Inn Orlando International Dr-ICON by IHG
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, (1769)
"Very easy to get to the parks from this hotel! Nice area with nearby places to eat and stuff, very clean; would stay here again! "
The price is ￥11,188
￥14,242 total
includes taxes & fees
Sep 21 - Sep 22
Pestana Orlando Suites - Lake Buena Vista
Wyndham Garden Orlando Airport
Outdoor pool, sun loungers

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3833)
"Great stay!"
The price is ￥11,224
￥12,627 total
includes taxes & fees
Sep 14 - Sep 15
Wyndham Garden Orlando Airport
The Eo Inn - Downtown
Front of property

The Eo Inn - Downtown

3.0 star property
8.0 out of 10, Very Good, (1002)
"Great find with a friendly and hospitable staff!"
The price is ￥12,486
￥14,046 total
includes taxes & fees
Sep 14 - Sep 15
The Eo Inn - Downtown
Palazzo Lakeside Hotel
In-room safe, laptop workspace, blackout drapes, iron/ironing board

Palazzo Lakeside Hotel

3.0 star property
8.2 out of 10, Very Good, (5169)
"Nice to stay with family and breakfast was perfect "
The price is ￥5,334
￥11,081 total
includes taxes & fees
Sep 14 - Sep 15
Palazzo Lakeside Hotel
Comfort Suites Maingate East
Outdoor pool, pool umbrellas, sun loungers

Comfort Suites Maingate East

3.0 star property
8.6 out of 10, Excellent, (2234)
"Great stay!"
The price is ￥13,013
￥14,770 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Suites Maingate East
Galleria Palms Hotel
Property entrance

Galleria Palms Hotel

2.5 star property
8.8 out of 10, Excellent, (3576)
"Great place to stay!! "
Galleria Palms Hotel
Candlewood Suites Orlando - Lake Buena Vista by IHG
1 bedroom, premium bedding, desk, laptop workspace

Candlewood Suites Orlando - Lake Buena Vista by IHG

2.5 star property
9.0 out of 10, Wonderful, (2075)
"Honestly a very nice place I loved staying there."
The price is ￥9,127
￥11,924 total
includes taxes & fees
Sep 16 - Sep 17
Candlewood Suites Orlando - Lake Buena Vista by IHG
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

3.5 star property
9.0 out of 10, Wonderful, (2185)
"Great and close to Disney "
The price is ￥12,807
￥14,407 total
includes taxes & fees
Oct 2 - Oct 3
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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, (2068)
"room was clean and staffs were friendly"
The price is ￥7,609
￥8,561 total
includes taxes & fees
Sep 21 - Sep 22
Orlando Palms Hotel
Rosen Plaza on International Drive
Meeting facility

Rosen Plaza on International Drive

4.0 star property
9.2 out of 10, Wonderful, (1607)
"Excellent location, great staff, good food."
The price is ￥11,670
￥13,454 total
includes taxes & fees
Sep 22 - Sep 23
Rosen Plaza on International Drive
Kompose Boutique Resort at Theme Parks
Suite, 1 King Bed with Sofa bed, Balcony | 1 bedroom, premium bedding, minibar, in-room safe

Kompose Boutique Resort at Theme Parks

3.0 star property
9.4 out of 10, Exceptional, (1276)
"Great place to stay"
The price is ￥8,334
￥11,232 total
includes taxes & fees
Sep 18 - Sep 19
Kompose Boutique Resort at Theme Parks
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, (4068)
"Excellent hotel and staff."
The price is ￥7,382
￥12,557 total
includes taxes & fees
Sep 21 - Sep 22
Red Lion Hotel Orlando Lake Buena Vista South
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
Front of property - evening/night

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

3.0 star property
8.6 out of 10, Excellent, (2196)
"Excelent hotel!! "
The price is ￥12,494
￥14,056 total
includes taxes & fees
Sep 28 - Sep 29
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
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.

Where to stay in Oakland

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

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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Wonderful suites! Clean and spacious. "
Brenda 2-night trip
Posted 2 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.