Search Hotels in Oakland, Winter Garden

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Oakland hotels

Orlando Palms Hotel

Orlando Palms Hotel
2.5 star property
25.8 km from Oakland
7.8 out of 10, Good, (2,415 reviews)
"Love this place "
United States
Lisa
The price is 1.790.013 ₫
2.324.799 ₫ total
includes taxes & fees
5 Mar - 6 Mar
Orlando Palms Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
28.9 km from Oakland
8.2 out of 10, Very good, (5,148 reviews)
"Great staff and excellent location "
United States
bruce
The price is 2.184.572 ₫
3.366.502 ₫ total
includes taxes & fees
6 Mar - 7 Mar
Palazzo Lakeside Hotel

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
3.0 star property
28.3 km from Oakland
8.4 out of 10, Very good, (2,956 reviews)
"Our family loved this hotel."
United States
Amanda
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Orlando International Drive North Hotel

Orlando International Drive North Hotel
3.0 star property
19.6 km from Oakland
7.2 out of 10, Good, (2,940 reviews)
"Hotel was great"
United States
Miguel A.
The price is 1.798.002 ₫
2.462.221 ₫ total
includes taxes & fees
2 Apr - 3 Apr
Orlando International Drive North Hotel

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
30.2 km from Oakland
9.0 out of 10, Wonderful, (3,454 reviews)
"Great stay for the price"
United States
David
The price is 1.641.654 ₫
1.863.277 ₫ total
includes taxes & fees
22 Mar - 23 Mar
Seasons Florida Resort

Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport
3.0 star property
29.4 km from Oakland
8.0 out of 10, Very good, (654 reviews)
"great stay"
United States
Ibrahim
The price is 2.840.322 ₫
3.195.493 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Sonesta Essential Orlando Airport

Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Express Orlando International Airport by IHG
2.5 star property
31.3 km from Oakland
9.0 out of 10, Wonderful, (1,955 reviews)
"Clean, nice rooms , easy shuttle… perfect for what was needed!"
United States
Veronika
The price is 3.300.246 ₫
3.712.778 ₫ total
includes taxes & fees
30 Mar - 31 Mar
Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG
3.5 star property
25.3 km from Oakland
7.2 out of 10, Good, (4,916 reviews)
"Excellent for a quick Stay!"
United States
Matthew
The price is 1.850.118 ₫
3.224.808 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Holiday Inn Resort Orlando Suites - Waterpark by IHG

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
19.2 km from Oakland
8.4 out of 10, Very good, (6,869 reviews)
"Very nice hotel"
Canada
XIAOLAN
The price is 2.756.415 ₫
3.100.968 ₫ total
includes taxes & fees
29 Mar - 30 Mar
DoubleTree by Hilton at the Entrance to Universal Orlando

Wyndham Garden Lake Buena Vista – Disney Springs® Area

Wyndham Garden Lake Buena Vista – Disney Springs® Area
3.5 star property
23.2 km from Oakland
8.2 out of 10, Very good, (4,011 reviews)
"Rooms were clean and staff was friendly. "
United States
Audrey Nou
The price is 2.459.875 ₫
3.822.448 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Wyndham Garden Lake Buena Vista – Disney Springs® Area

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
31.4 km from Oakland
8.8 out of 10, Excellent, (1,929 reviews)
"Great hotel amazing staff "
United States
Gloria
The price is 2.857.260 ₫
3.214.417 ₫ total
includes taxes & fees
30 Mar - 31 Mar
Cambria Hotel Orlando Airport

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
19.3 km from Oakland
9.4 out of 10, Exceptional, (4,571 reviews)
"Amazing room and great breakfasts for the price "
United States
Christian
The price is 3.100.902 ₫
3.488.516 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
22.9 km from Oakland
8.6 out of 10, Excellent, (5,658 reviews)
"Room was clean and beds were very comfortable."
United States
RONALD
The price is 2.281.117 ₫
2.566.192 ₫ total
includes taxes & fees
8 Mar - 9 Mar
Rosen Inn Lake Buena Vista

Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
28.4 km from Oakland
8.8 out of 10, Excellent, (4,347 reviews)
"The grounds were amazing, the staff helpful and just a great place to stay!!"
United States
Tami
The price is 1.336.300 ₫
2.629.378 ₫ total
includes taxes & fees
9 Mar - 10 Mar
Radisson Hotel Orlando Lake Buena Vista South

Days Inn by Wyndham Orlando Conv. Center/International Dr

Days Inn by Wyndham Orlando Conv. Center/International Dr
2.0 star property
22.3 km from Oakland
8.2 out of 10, Very good, (2,666 reviews)
"Great staff, clean room, and in a great place!"
United States
Eva
The price is 2.157.602 ₫
2.427.302 ₫ total
includes taxes & fees
29 Mar - 30 Mar
Days Inn by Wyndham Orlando Conv. Center/International Dr

Rosen Inn, closest to Universal

Rosen Inn, closest to Universal
3.0 star property
19.1 km from Oakland
8.4 out of 10, Very good, (3,535 reviews)
"Great location, not the newest hotel but well staffed with good security and clean rooms."
United States
Scott
The price is 1.899.368 ₫
2.136.496 ₫ total
includes taxes & fees
29 Mar - 30 Mar
Rosen Inn, closest to Universal

Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
29.9 km from Oakland
9.0 out of 10, Wonderful, (4,069 reviews)
"Very clean, friendly staff & close to the airport easy travel "
United States
Justin Paul
The price is 3.876.127 ₫
4.360.644 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Wyndham Garden Orlando Airport

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
24 km from Oakland
8.4 out of 10, Very good, (3,799 reviews)
"Very nice staff ,clean rooms"
United States
Luis
The price is 1.928.292 ₫
3.048.787 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway
3.0 star property
25.2 km from Oakland
8.0 out of 10, Very good, (3,917 reviews)
"Great location and friendly staff"
United States
Dana
The price is 1.678.135 ₫
2.437.048 ₫ total
includes taxes & fees
22 Mar - 23 Mar
Ramada by Wyndham Kissimmee Gateway

Club Sevilla

Club Sevilla
2.0 star property
31.2 km from Oakland
8.8 out of 10, Excellent, (1,000 reviews)
"Best resort in the area for quiet relaxing stay "
United States
Lizette
The price is 1.661.197 ₫
2.020.960 ₫ total
includes taxes & fees
5 Mar - 6 Mar
Club Sevilla
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.

Horizon West

While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club.

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

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.