Photo by Gregg Yutko

Search Hotels in Oakland, Winter Garden

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
4 Jul - 5 Jul
Tomorrow
5 Jul - 6 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Filter by

Guest rating
Guest rating
Property class

Top Trending Hotels Near Oakland, Winter Garden

Lakeside Inn
Outdoor pool, pool loungers

Lakeside Inn

3.0 star property
8.8 out of 10, Excellent, (1190)
"Unique Building,fantastic location, friendly staff.. great if you want a more quiet stay"
Lakeside Inn
The Delaney Hotel
Terrace/patio

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1003)
"Great restaurant downstairs and clean quiet hotel in a great location!"
The Delaney Hotel
The Eo Inn - Downtown
Lake

The Eo Inn - Downtown

3.0 star property
8.0 out of 10, Very good, (1000)
"Very nice cozy little hotel, the room was clean and staff was friendly. "
The price is 2.986.914 ₫
3.360.277 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Eo Inn - Downtown
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, (8002)
"Great stay"
The price is 4.421.716 ₫
6.151.811 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Grove Resort & Water Park Orlando
Holiday Inn Express And Suites Clermont Se West Orlando by IHG
Property amenity

Holiday Inn Express And Suites Clermont Se West Orlando by IHG

2.5 star property
8.2 out of 10, Very good, (654)
"Very nice and friendly staff, clean good location "
The price is 2.043.678 ₫
2.661.497 ₫ total
includes taxes & fees
4 Aug - 5 Aug
Holiday Inn Express And Suites Clermont Se West Orlando by IHG
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, (6343)
"Nice place to stay "
The price is 2.204.814 ₫
2.480.416 ₫ total
includes taxes & fees
4 Aug - 5 Aug
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
8.8 out of 10, Excellent, (2584)
"Good place for stay"
The price is 1.979.084 ₫
2.226.470 ₫ total
includes taxes & fees
28 Jul - 29 Jul
SPOT X Hotel Orlando/Intl Dr by The Red Collection
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, (2163)
"Pool are is so fun, amenities and dining was wonderful "
The price is 4.683.356 ₫
6.740.631 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Hyatt Regency Grand Cypress
The Alfond Inn
Exterior

The Alfond Inn

4.0 star property
9.4 out of 10, Exceptional, (1002)
"Beautiful hotel and surrounding town "
The Alfond Inn
Hyatt Regency Orlando
2 outdoor pools, pool cabanas (surcharge), pool umbrellas

Hyatt Regency Orlando

4.5 star property
9.2 out of 10, Wonderful, (1656)
"Great place to stay!"
The price is 3.898.436 ₫
5.842.453 ₫ total
includes taxes & fees
7 Jul - 8 Jul
Hyatt Regency Orlando
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Exterior

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 star property
7.2 out of 10, Good, (3468)
"Great place for families, my son truly enjoyed it. "
The price is 1.726.824 ₫
3.856.050 ₫ total
includes taxes & fees
10 Jul - 11 Jul
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Avanti International Resort
View from property

Avanti International Resort

4.0 star property
7.8 out of 10, Good, (3913)
"I enjoyed my stay"
Avanti International Resort
Caribe Royale Orlando
Property entrance

Caribe Royale Orlando

4.5 star property
9.2 out of 10, Wonderful, (4201)
"Such a nice resort!"
The price is 4.427.969 ₫
6.101.689 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Caribe Royale Orlando
Rosen Inn Lake Buena Vista
View from room

Rosen Inn Lake Buena Vista

3.5 star property
8.6 out of 10, Excellent, (5207)
"The location cleaness of the rooms and price is great.."
The price is 1.991.014 ₫
2.239.924 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Rosen Inn Lake Buena Vista
Orlando Palms Hotel
Lobby sitting area

Orlando Palms Hotel

2.5 star property
7.6 out of 10, Good, (1881)
"Very nice place will stay again"
Orlando Palms Hotel
Rosen Inn International
Front of property – evening/night

Rosen Inn International

3.0 star property
8.4 out of 10, Very good, (5671)
"Always a great stay"
The price is 2.305.426 ₫
2.593.637 ₫ total
includes taxes & fees
1 Aug - 2 Aug
Rosen Inn International
Wyndham Garden Orlando Airport
Outdoor pool, pool loungers

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3738)
"Great stay "
The price is 2.627.960 ₫
2.956.521 ₫ total
includes taxes & fees
7 Jul - 8 Jul
Wyndham Garden Orlando Airport
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, (1905)
"Love this place we stay her frequently great for families too."
The price is 2.065.909 ₫
2.585.787 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Candlewood Suites Orlando - Lake Buena Vista by IHG
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, (3862)
"Nice large resort with plenty of restaurants and pools."
The price is 3.118.749 ₫
3.508.593 ₫ total
includes taxes & fees
11 Jul - 12 Jul
Rosen Shingle Creek
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Exterior

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4.0 star property
8.6 out of 10, Excellent, (2118)
"Excellent hotel "
The price is 3.091.277 ₫
4.628.935 ₫ total
includes taxes & fees
8 Jul - 9 Jul
Holiday Inn Club Vacations at Orange Lake Resort by IHG
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, Winter Garden Art Association and West Orange Trail 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.

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.

How many hotels can I expect to find in Oakland?

Expedia has 7 Oakland hotels and other accommodation options, 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, 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.