Photo by Gregg Yutko

Winter Garden Hotel Guide. Hotels in Oakland, Winter Garden, United States of America

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15 Aug - 16 Aug
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16 Aug - 17 Aug
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15 Aug - 17 Aug
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22 Aug - 24 Aug

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Top Trending Hotels Near Oakland, Winter Garden

The Delaney Hotel
Terrace/patio

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1000)
"Excelente, buen hotel"
The Delaney Hotel
Lakeside Inn
Outdoor pool, pool loungers

Lakeside Inn

3.0 star property
8.8 out of 10, Excellent, (1199)
"Lovely location and quiet peaceful stay"
Lakeside Inn
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Property amenity

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

2.5 star property
8.4 out of 10, Very good, (803)
"The hotel was amazing! "
The price is €72
includes taxes & fees
25 Aug - 26 Aug
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
The Grove Resort & Water Park Orlando
Aerial view

The Grove Resort & Water Park Orlando

4.0 star property
8.0 out of 10, Very good, (8334)
"Was an amazing stay definitely would recommend it"
The price is €172
includes taxes & fees
17 Aug - 18 Aug
The Grove Resort & Water Park Orlando
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, (6525)
"Nice, friendly, and comfortable place to stay "
The price is €89
includes taxes & fees
10 Sept - 11 Sept
DoubleTree by Hilton at the Entrance to Universal Orlando
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Front of property – evening/night

SPOT X Hotel Orlando/Intl Dr by The Red Collection

3.0 star property
8.6 out of 10, Excellent, (2663)
"It was a very pleasant stay"
The price is €73
includes taxes & fees
18 Aug - 19 Aug
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Avanti International Resort
View from property

Avanti International Resort

4.0 star property
7.8 out of 10, Good, (4055)
"great resort will stay there again"
Avanti International Resort
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Exterior

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 star property
7.0 out of 10, Good, (3975)
"Second time staying here and both times were great. "
The price is €127
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Hyatt Regency Orlando
2 outdoor pools, pool cabanas (surcharge), pool umbrellas

Hyatt Regency Orlando

4.5 star property
9.2 out of 10, Wonderful, (1712)
"Great stay! "
The price is €191
includes taxes & fees
18 Aug - 19 Aug
Hyatt Regency Orlando
Rosen Inn International
Front of property – evening/night

Rosen Inn International

3.0 star property
8.4 out of 10, Very good, (5728)
"Excellent hotel "
The price is €73
includes taxes & fees
18 Aug - 19 Aug
Rosen Inn International
Hyatt Regency Grand Cypress
3 outdoor pools, open 7 AM to 10:00 PM, pool cabanas (surcharge)

Hyatt Regency Grand Cypress

4.0 star property
9.2 out of 10, Wonderful, (2216)
"Amazing place to stay "
The price is €186
includes taxes & fees
24 Aug - 25 Aug
Hyatt Regency Grand Cypress
Wyndham Garden Orlando Airport
Outdoor pool, pool loungers

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3772)
"I enjoy really enjoyed the stay staff was friendly restaurant food was really good"
The price is €86
includes taxes & fees
17 Aug - 18 Aug
Wyndham Garden Orlando Airport
Rosen Inn Lake Buena Vista
View from room

Rosen Inn Lake Buena Vista

3.5 star property
8.6 out of 10, Excellent, (5361)
"Nice place to stay."
The price is €73
includes taxes & fees
1 Sept - 2 Sept
Rosen Inn Lake Buena Vista
Rosen Shingle Creek
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (3958)
"Great stay!"
The price is €100
includes taxes & fees
7 Sept - 8 Sept
Rosen Shingle Creek
Caribe Royale Orlando
Sports court

Caribe Royale Orlando

4.5 star property
9.2 out of 10, Wonderful, (4333)
"Great stay "
The price is €190
includes taxes & fees
31 Aug - 1 Sept
Caribe Royale Orlando
The Alfond Inn
Exterior

The Alfond Inn

4.0 star property
9.4 out of 10, Exceptional, (1002)
"Beautiful Rooms, Stay, just about Everything ❤️🙏"
The Alfond Inn
DoubleTree by Hilton Hotel Orlando at SeaWorld
Exterior

DoubleTree by Hilton Hotel Orlando at SeaWorld

4.0 star property
7.4 out of 10, Good, (6064)
"Love this place "
The price is €88
includes taxes & fees
20 Aug - 21 Aug
DoubleTree by Hilton Hotel Orlando at SeaWorld
Hotel SonoHotel IDrive District
Lobby

Hotel SonoHotel IDrive District

3.0 star property
7.2 out of 10, Good, (2881)
"I love the cleanliness of the rooms here…also the rooms are very well priced for what your getting here."
Hotel SonoHotel IDrive District
Holiday Inn Club Vacations at Orange Lake Resort by IHG
7 outdoor pools, pool cabanas (surcharge), pool umbrellas

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4.0 star property
8.8 out of 10, Excellent, (2322)
"Great place to stay can’t wait to go back"
The price is €135
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations at Orange Lake Resort by IHG
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, (2159)
"Excellent property for leisure or travel. "
The price is €90
includes taxes & fees
17 Aug - 18 Aug
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 for the activities you enjoy most.
Vista del Lago map

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 map

Downtown Winter Garden

If you're spending some time in Downtown Winter Garden, West Orange Trail and Central Florida Railroad Museum are top sights worth seeing.

Killarney map

Killarney

Killarney might not have many top sights, but Bella Collina Golf Club and West Orange Trail are two attractions nearby that you can check out.

Top Oakland Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"I highly recommend this property for families who are seeking a quiet and spacious place for vacation. 15 minutes from.Magic kingdom and 20 minutes from.Disney springs. The water park was amazing. They have also 4 other pools for the resident of the property. You can spend the day just chilling on the pool or the water park. Parking is extra around 25$ a day. But still a better deal than disney resorts. The rooms were big and spacious and each room came with a full bathroom and a full kitchen. My husband forgot his wedding ring in the room after we left we contacted them and they shipped it back to us! I would be back next year. "
RANA 5-night trip
Posted 15 hours ago
The Grove Resort & Water Park Orlando

Frequently asked questions

What's it like in Oakland?

Travellers will be sure to enjoy their time in Winter Garden's Oakland neighbourhood. Consider a visit to Oakland Nature Preserve as part of your Oakland travel plans.

What's 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 traveller data.

How many hotels can I expect to find in Oakland?

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

If I need to cancel my hotel reservation in Oakland, will I receive a refund?

Yes, you'll find most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to review the best options available in Oakland.

What is there to do in this Winter Garden neighbourhood?

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, make sure that you visit other sights such as Plant Street Market or Resurrection Catholic Church.