Photo by Gregg Yutko

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
7 Jan - 8 Jan
Tomorrow
8 Jan - 9 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Oakland hotels

In-room safe, laptop workspace, blackout curtains, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
28.9 km from Oakland
8.2 out of 10, Very good, (5142)
"Awesome place to stay! Clean and staff incredible!"
United States
Jeffrey
The price is ₹2,373
₹5,766 total
includes taxes & fees
8 Jan - 9 Jan
Palazzo Lakeside Hotel
Courtyard
DoubleTree by Hilton at the Entrance to Universal Orlando

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, (6971)
"we enjoyed the stay here, it is having nice rooms and breakfast."
United States
suresh
The price is ₹8,799
₹9,899 total
includes taxes & fees
27 Jan - 28 Jan
DoubleTree by Hilton at the Entrance to Universal Orlando
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
19.2 km from Oakland
7.4 out of 10, Good, (4062)
"Love the property and staff"
United States
RONNIE
The price is ₹5,619
₹8,147 total
includes taxes & fees
11 Jan - 12 Jan
Wyndham I-Drive Avanti Resort & Conference Center
Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
3.5 star property
18.5 km from Oakland
9.0 out of 10, Wonderful, (6011)
"Great place to stay"
United States
Peggy
The price is ₹11,993
₹13,492 total
includes taxes & fees
13 Jan - 14 Jan
Universal's Cabana Bay Beach Resort
Reception
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

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, (2810)
"Our family loved this hotel."
United States
Amanda
The price is ₹3,829
₹7,419 total
includes taxes & fees
22 Jan - 23 Jan
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Reception
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
30.2 km from Oakland
8.8 out of 10, Excellent, (3349)
"A great place to stay for the price"
United States
Jennie
The price is ₹5,177
₹5,875 total
includes taxes & fees
11 Jan - 12 Jan
Seasons Florida Resort
View from room
Rosen Inn Lake Buena Vista

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, (5619)
"Great property to stay"
United States
Deepankar
The price is ₹6,636
₹7,466 total
includes taxes & fees
11 Jan - 12 Jan
Rosen Inn Lake Buena Vista
Property amenity
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
22.5 km from Oakland
8.6 out of 10, Excellent, (3512)
"Nice and clean, location was close to Disney, lot of dining options nearby, breakfast was good, staff was amazing, lot of stuffs for kids to enjoy."
United States
Ravi
The price is ₹7,845
₹8,826 total
includes taxes & fees
25 Jan - 26 Jan
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
View from room
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando
3.0 star property
20.7 km from Oakland
8.6 out of 10, Excellent, (5561)
"Great stay"
United States
Stephanie
The price is ₹6,919
₹7,783 total
includes taxes & fees
26 Jan - 27 Jan
Rosen Inn at Pointe Orlando
Suite, 2 Queen Beds | Laptop workspace, blackout curtains, iron/ironing board
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport
3.0 star property
29.4 km from Oakland
8.0 out of 10, Very good, (343)
"Very clean, super nice staff. Convenient location!"
United States
Nadjah
The price is ₹8,035
₹9,040 total
includes taxes & fees
26 Jan - 27 Jan
Sonesta Essential Orlando Airport
Exterior
Holiday Inn Express Orlando International Airport by IHG

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, (1878)
"Rooms were nice but staff was great"
United States
Prachi
The price is ₹11,037
₹12,417 total
includes taxes & fees
26 Jan - 27 Jan
Holiday Inn Express Orlando International Airport by IHG
Outdoor pool, a heated pool, pool umbrellas, pool loungers
Holiday Inn Resort Orlando - Lake Buena Vista by IHG

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, (3612)
"We have stayed at this hotel many times and enjoyed it. Friendly for families who travel with pets."
United States
Jennifer
The price is ₹6,320
₹10,157 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Outdoor banquet area
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
24.2 km from Oakland
9.4 out of 10, Exceptional, (4358)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is ₹9,890
₹11,126 total
includes taxes & fees
23 Jan - 24 Jan
Rosen Shingle Creek
Exterior
avid hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG
2.5 star property
31.5 km from Oakland
9.2 out of 10, Wonderful, (2071)
"Rooms were very clean and the staff was awesome and always available. "
United States
Gwendolyn
The price is ₹10,112
₹11,376 total
includes taxes & fees
26 Jan - 27 Jan
avid hotel Orlando International Airport by IHG
2 restaurants, breakfast, lunch, dinner served; Mexican cuisine
Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South
3.5 star property
28.4 km from Oakland
8.8 out of 10, Excellent, (4336)
"The breakfast was great for a hotel option, very clean room and facility. "
United States
Jacob
The price is ₹6,681
₹9,633 total
includes taxes & fees
11 Jan - 12 Jan
Red Lion Hotel Orlando Lake Buena Vista South
Exterior
Ramada by Wyndham Kissimmee Gateway

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, (3950)
"Phenomenal hotel for the price point as well as the children. "
United States
Destiny
The price is ₹4,861
₹7,360 total
includes taxes & fees
2 Feb - 3 Feb
Ramada by Wyndham Kissimmee Gateway
Lobby lounge
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
22.5 km from Oakland
8.8 out of 10, Excellent, (1946)
"Good place to stay "
United States
victor
The price is ₹7,394
₹8,318 total
includes taxes & fees
25 Jan - 26 Jan
Aloft Orlando Lake Buena Vista
Exterior
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG
3.5 star property
24.6 km from Oakland
8.4 out of 10, Very good, (1161)
"Excellent amenities including breakfast and comfortable stay. "
Canada
SAGAR
The price is ₹6,055
₹8,663 total
includes taxes & fees
8 Jan - 9 Jan
Holiday Inn Resort Kissimmee by the Parks by IHG
2 outdoor pools, pool umbrellas, pool loungers
Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites
3.0 star property
19.8 km from Oakland
9.2 out of 10, Wonderful, (5114)
"The entire resort was great"
United States
Elizabeth
The price is ₹13,075
₹14,709 total
includes taxes & fees
14 Jan - 15 Jan
Universal's Endless Summer Resort - Dockside Inn and Suites
Free daily buffet breakfast
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
19.3 km from Oakland
9.4 out of 10, Exceptional, (4425)
"Great breakfast options and coffee bar."
United States
Adam
The price is ₹10,473
₹11,782 total
includes taxes & fees
26 Jan - 27 Jan
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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.

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 Flamingo Crossings Town Center 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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"The room was great the staff was awesome transportation between Disney and universal isn’t far at all"
Kanise 3-night trip
Posted 10 hours ago
Westgate Lakes Resort & Spa Universal Studios Area

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.

Explore a world of travel with Expedia