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Find hotels in Oakland, Winter Garden

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Our top choices for Oakland hotels

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
24.2 km from Oakland
9.4 out of 10, Exceptional, (4376)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is ¥18,426
¥20,728 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Rosen Shingle Creek

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, (5844)
"Solid place for a vacation Will be staying again in the future "
United States
Jared G
The price is ¥20,740
¥23,333 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Universal's Cabana Bay Beach Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
30.2 km from Oakland
8.8 out of 10, Excellent, (3310)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is ¥8,549
¥9,704 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Seasons Florida Resort

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, (3929)
"Excellent room and the beds were very comfortable, also very clean "
United States
Daisy
The price is ¥9,729
¥14,108 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wyndham I-Drive Avanti Resort & Conference Center

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, (6870)
"Great hotel great food"
United States
Malika
The price is ¥13,938
¥15,681 total
includes taxes & fees
Jan 15 - Jan 16, 2026
DoubleTree by Hilton at the Entrance to Universal 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, (5438)
"Great stay"
United States
Stephanie
The price is ¥14,569
¥16,390 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Rosen Inn at Pointe Orlando

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, (3895)
"Phenomenal hotel for the price point as well as the children. "
United States
Destiny
The price is ¥7,859
¥12,106 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Ramada by Wyndham Kissimmee Gateway

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, (5643)
"Great property to stay"
United States
Deepankar
The price is ¥12,508
¥14,071 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Rosen Inn Lake Buena Vista

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
24.3 km from Oakland
9.4 out of 10, Exceptional, (4176)
"Great stay"
United States
Shawna
The price is ¥17,341
¥19,509 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
18.9 km from Oakland
9.0 out of 10, Wonderful, (479)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is ¥13,450
¥15,130 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Spark by Hilton Orlando near Universal

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
28.9 km from Oakland
8.2 out of 10, Very Good, (5143)
"Beautiful place to stay."
United States
Mohammad
The price is ¥6,085
¥12,221 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Palazzo Lakeside Hotel

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
26.5 km from Oakland
8.6 out of 10, Excellent, (1579)
"was a very nice stay"
United States
Taylor Elaine
The price is ¥14,502
¥22,123 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Meliá Orlando Celebration

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, (3584)
"Very convenient and liked the hotel"
United States
Melanie
The price is ¥10,292
¥16,842 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Holiday Inn Resort Orlando - Lake Buena Vista 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, (2029)
"Easy check in, great people service, clean room, great location. "
United States
Tiffany
The price is ¥16,686
¥18,772 total
includes taxes & fees
Jan 6 - Jan 7, 2026
avid hotel Orlando International Airport by IHG

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
3.0 star property
23.1 km from Oakland
9.8 out of 10, Exceptional, (5448)
"Great stay!"
United States
Kiran
The price is ¥25,183
¥28,331 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Drury Plaza Hotel Orlando - Disney Springs Area

Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL
3.5 star property
22 km from Oakland
9.0 out of 10, Wonderful, (3689)
"Friendly staff, great service, clean rooms, enjoyed the stay. "
United States
Katherine
The price is ¥13,956
¥15,700 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tru By Hilton Orlando Convention Center Area, FL

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
31.4 km from Oakland
8.8 out of 10, Excellent, (1937)
"Clean room and pleasant staff. "
United States
Mariama Velinique
The price is ¥14,061
¥15,818 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cambria Hotel 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, (1885)
" Nice hotel"
United States
Shalanda
The price is ¥16,997
¥19,122 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG
3.5 star property
24.7 km from Oakland
8.4 out of 10, Very Good, (1097)
"Great hotel"
United States
Steven
The price is ¥11,072
¥15,664 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Holiday Inn Resort Kissimmee by the Parks by IHG

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
20.6 km from Oakland
9.4 out of 10, Exceptional, (1395)
"Good location, good breakfast "
United States
Andrea
The price is ¥18,425
¥20,728 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hyatt House Orlando International Drive
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 and neighborhoods for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland

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

While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum.

Killarney

If you're looking for some top things to see and do in Killarney and surrounding area, you can visit Bella Collina Golf Club and West Orange Trail.

Top Oakland Hotel Reviews

Frequently asked questions

What's it like in Oakland?
Travelers will be sure to enjoy their time in Winter Garden's Oakland neighborhood. Consider a visit to Oakland Nature Preserve as part of your Oakland travel plans.
How many hotels should I expect to find in the Oakland area?
When you want to kick up your feet after a day of exploring the sights in Winter Garden, you can choose from 12 Expedia hotels and other accommodations in Oakland.
If I need to cancel my hotel reservation in Oakland, will I receive a refund?
Yes, the majority of room reservations are refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to get the top deals on offer in Oakland.
Where can I learn more about changing or cancelling my trip to Oakland?
For more information about picking new dates or cancelling your trip to Oakland, go to https://www.expedia.com/service/.
What is there to do in this Winter Garden neighborhood?
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, be sure to visit other sights like Plant Street Market or Garden Theatre.

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