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Our top choices for Oakland hotels

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
30.2 km from Oakland
8.8 out of 10, Excellent, (3299)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is ¥11,246
¥12,763 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Seasons Florida Resort

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, (1379)
"The staff was really friendly and the property was nice and cozy "
United States
curtis
The price is ¥18,615
¥20,941 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hyatt House Orlando International Drive

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
24.2 km from Oakland
9.4 out of 10, Exceptional, (4366)
"Room, facilities and staff were great. "
United States
Gary E
The price is ¥19,076
¥21,462 total
includes taxes & fees
Dec 21 - Dec 22
Rosen Shingle Creek

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
28.9 km from Oakland
8.2 out of 10, Very Good, (5160)
"Beautiful place to stay."
United States
Mohammad
The price is ¥4,657
¥10,657 total
includes taxes & fees
Dec 21 - Dec 22
Palazzo Lakeside Hotel

Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
26 km from Oakland
9.2 out of 10, Wonderful, (4509)
"Excellent hotel I will be booking again"
United States
Wilshaundra
The price is ¥25,082
¥34,960 total
includes taxes & fees
Dec 21 - Dec 22
Caribe Royale 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, (6890)
"Great hotel great food"
United States
Malika
The price is ¥15,183
¥17,081 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, (5399)
"Fantastic hotel"
United States
Gabe
The price is ¥12,602
¥14,177 total
includes taxes & fees
Dec 21 - Dec 22
Rosen Inn at Pointe Orlando

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
31.4 km from Oakland
8.8 out of 10, Excellent, (1933)
"Clean room and pleasant staff. "
United States
Mariama Velinique
The price is ¥15,475
¥17,410 total
includes taxes & fees
Dec 22 - Dec 23
Cambria Hotel Orlando Airport

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, (3899)
"Always great to stay there "
United States
Giandre
The price is ¥7,842
¥12,080 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Ramada by Wyndham Kissimmee Gateway

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, (3920)
"The bar and pool were great"
United States
Melissa
The price is ¥9,203
¥13,548 total
includes taxes & fees
Dec 21 - Dec 22
Wyndham I-Drive Avanti Resort & Conference Center

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, (3574)
"Love staying here friendly staff and well kept property. "
United States
Carlos
The price is ¥10,727
¥17,392 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Holiday Inn Resort Orlando - Lake Buena Vista by IHG

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 ¥13,308
¥14,970 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Rosen Inn Lake Buena Vista

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, (1065)
"Great hotel"
United States
Steven
The price is ¥11,048
¥15,630 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Holiday Inn Resort Kissimmee by the Parks by IHG

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
24.9 km from Oakland
9.4 out of 10, Exceptional, (2025)
"Very nice place to stay in, we love it!!"
United States
Basim
The price is ¥7,752
¥15,064 total
includes taxes & fees
Dec 21 - Dec 22
Kompose Boutique Resort at Theme Parks

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, (2018)
"Easy check in, great people service, clean room, great location. "
United States
Tiffany
The price is ¥17,116
¥19,255 total
includes taxes & fees
Jan 12 - Jan 13, 2026
avid hotel Orlando International Airport by IHG

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, (5788)
"Always love this resort!"
United States
Holly
The price is ¥20,695
¥23,281 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Universal's Cabana Bay Beach Resort

Galleria Palms Hotel

Galleria Palms Hotel
2.5 star property
24.8 km from Oakland
9.0 out of 10, Wonderful, (3631)
"Nice affordable place to stay "
United States
Jenny
Galleria Palms Hotel

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
26.5 km from Oakland
8.6 out of 10, Excellent, (1574)
"was a very nice stay"
United States
Taylor Elaine
The price is ¥14,471
¥22,075 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Meliá Orlando Celebration

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, (452)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is ¥13,655
¥15,362 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Spark by Hilton Orlando near Universal

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, (3475)
"Wonderful staff and great location and clean room"
United States
farrah a
The price is ¥13,724
¥15,439 total
includes taxes & fees
Jan 4 - Jan 5, 2026
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
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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