Search Hotels in Oakland, Winter Garden

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
10 Oct - 12 Oct
Next weekend
17 Oct - 19 Oct

Filter by

Guest rating
Guest rating
Star rating

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, (1014)
"great restaurant and even better rooms!"
The Delaney Hotel
Lakeside Inn
Outdoor pool, pool loungers

Lakeside Inn

3.0 star property
8.8 out of 10, Excellent, (1198)
"Historic Inn was charming. "
Lakeside Inn
The Eo Inn - Downtown
Front of property

The Eo Inn - Downtown

3.0 star property
8.0 out of 10, Very good, (1006)
"I loved this hotel. The staff was very down to earth "
The price is Rp1.474.997
Rp1.659.372 total
includes taxes & fees
12 Oct - 13 Oct
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, (8609)
"Great stay "
The price is Rp2.799.992
Rp3.895.552 total
includes taxes & fees
9 Nov - 10 Nov
The Grove Resort & Water Park 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, (2788)
"Great property to stay with family while visiting the parks"
The price is Rp993.086
Rp1.415.278 total
includes taxes & fees
26 Oct - 27 Oct
SPOT X Hotel Orlando/Intl Dr by The Red Collection
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, (6736)
"Very close to universal would stay again"
The price is Rp1.344.990
Rp1.513.115 total
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton at the Entrance to Universal Orlando
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, (970)
"Clean rooms and everything was nice. Good breakfast as well. "
The price is Rp1.354.843
Rp1.504.000 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Westgate Lakes Resort & Spa Universal Studios Area
7 outdoor pools, pool cabanas (surcharge), pool umbrellas

Westgate Lakes Resort & Spa Universal Studios Area

4.0 star property
8.2 out of 10, Very good, (5384)
"Would stay again great for families such a nice place "
The price is Rp1.618.362
Rp2.304.941 total
includes taxes & fees
15 Oct - 16 Oct
Westgate Lakes Resort & Spa Universal Studios Area
Hyatt Regency Orlando
2 outdoor pools, pool cabanas (surcharge), pool umbrellas

Hyatt Regency Orlando

4.5 star property
9.2 out of 10, Wonderful, (1753)
"Great place to stay "
The price is Rp2.236.680
Rp3.436.100 total
includes taxes & fees
12 Oct - 13 Oct
Hyatt Regency Orlando
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, (1497)
"Great resort ,highly recommend!!!"
The price is Rp1.020.565
Rp1.357.660 total
includes taxes & fees
28 Oct - 29 Oct
Kompose Boutique Resort at Theme Parks
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, (2261)
"Great stay!"
The price is Rp2.667.448
Rp3.932.829 total
includes taxes & fees
19 Oct - 20 Oct
Hyatt Regency Grand Cypress
Rosen Inn International
Front of property – evening/night

Rosen Inn International

3.0 star property
8.4 out of 10, Very good, (5837)
"Great value and convenient location. "
The price is Rp1.325.274
Rp1.490.954 total
includes taxes & fees
10 Nov - 11 Nov
Rosen Inn International
Rosen Inn Lake Buena Vista
View from room

Rosen Inn Lake Buena Vista

3.5 star property
8.6 out of 10, Excellent, (5464)
"We have stayed here several times, nice place friendly staff."
The price is Rp1.298.766
Rp1.460.966 total
includes taxes & fees
20 Oct - 21 Oct
Rosen Inn Lake Buena Vista
Avanti International Resort
View from property

Avanti International Resort

4.0 star property
7.8 out of 10, Good, (4147)
"Great pool area especially for children. Excellent location to explore International Drive, as its really close to restaurants, icon park etc. "
Avanti International Resort
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, (4053)
"Loved everything as always a wonderful stay !!!! "
The price is Rp1.709.818
Rp1.923.544 total
includes taxes & fees
8 Nov - 9 Nov
Rosen Shingle Creek
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, (6183)
"Good place to stay."
The price is Rp1.255.156
Rp1.878.249 total
includes taxes & fees
29 Oct - 30 Oct
DoubleTree by Hilton Hotel Orlando at SeaWorld
Caribe Royale Orlando
Sports court

Caribe Royale Orlando

4.5 star property
9.2 out of 10, Wonderful, (4436)
"Great place to stay"
The price is Rp2.966.567
Rp4.045.883 total
includes taxes & fees
11 Oct - 12 Oct
Caribe Royale Orlando
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, (2141)
"Excellent stay"
The price is Rp1.027.526
Rp1.342.413 total
includes taxes & fees
4 Nov - 5 Nov
Candlewood Suites Orlando - Lake Buena Vista by IHG
Wyndham Garden Orlando Airport
Outdoor pool, pool loungers

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3857)
"Clean rooms so peaceful and staff are very professional and friendly "
The price is Rp1.325.440
Rp1.491.120 total
includes taxes & fees
12 Oct - 13 Oct
Wyndham Garden Orlando Airport
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, (4252)
"Perfect for families. The water park inside the hotel was amazing! "
The price is Rp1.060.352
Rp2.404.514 total
includes taxes & fees
15 Oct - 16 Oct
Holiday Inn Resort Orlando Suites - Waterpark 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.
View all properties

Where to stay in Oakland

Find the best Oakland areas 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

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

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

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Nice place"
Jaliha 4-night trip
Posted 1 day ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?
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 Garden Theatre.