Find hotels in Oakland, Winter Garden from ₩115,839

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Discover 39,187 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Terrace/patio
The Delaney Hotel

The Delaney Hotel

3.5 star property
25.3 km from Oakland
9.6 out of 10, Exceptional, (1006)
"All around wonderful stay"
United States
Caleb
The Delaney Hotel
5 outdoor pools, free cabanas, pool umbrellas
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4.0 star property
24.1 km from Oakland
9.2 out of 10, Wonderful, (2656)
"Stayed here before always enjoyed it "
United States
Margaret
The price is ₩141,214
₩158,865 total
includes taxes & fees
Dec 14 - Dec 15
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
6 outdoor pools, free cabanas, pool umbrellas
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
9.2 out of 10, Wonderful, (3986)
"Nice place to stay for family. "
United States
Niketan Chhaganbhai
The price is ₩120,620
₩135,698 total
includes taxes & fees
Nov 30 - Dec 1
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
5 outdoor pools, pool umbrellas, sun loungers
Summer Bay Orlando by Exploria Resorts

Summer Bay Orlando by Exploria Resorts

3.5 star property
23.3 km from Oakland
8.8 out of 10, Excellent, (2067)
"The staff are very friendly and the resort is gorgeous! "
United States
Katherina
The price is ₩146,871
₩212,011 total
includes taxes & fees
Dec 4 - Dec 5
Summer Bay Orlando by Exploria Resorts
Property grounds
SPOT X Hotel Orlando/Intl Dr by The Red Collection

SPOT X Hotel Orlando/Intl Dr by The Red Collection

3.0 star property
23.3 km from Oakland
8.6 out of 10, Excellent, (2897)
"One of the best hotel!"
United States
Li
The price is ₩91,627
₩129,549 total
includes taxes & fees
Dec 9 - Dec 10
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Property amenity
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

2.5 star property
23.1 km from Oakland
8.4 out of 10, Very Good, (1038)
"Great room great breakfast"
United States
Kelly
The price is ₩140,037
₩155,441 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Aerial view
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4.0 star property
21.7 km from Oakland
8.0 out of 10, Very Good, (8782)
"Great stay"
United States
Breanna
The price is ₩161,449
₩262,718 total
includes taxes & fees
Dec 10 - Dec 11
The Grove Resort & Water Park Orlando
Outdoor pool
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, (6898)
"Great stay "
United States
Anthony
The price is ₩131,476
₩147,910 total
includes taxes & fees
Dec 15 - Dec 16
DoubleTree by Hilton at the Entrance to Universal Orlando
View from property
Avanti International Resort

Avanti International Resort

4.0 star property
20.4 km from Oakland
7.8 out of 10, Good, (4243)
"Great room, helpful cleaners, wonderful pool, great location"
United Kingdom
Gabrielle
The price is ₩83,508
₩123,739 total
includes taxes & fees
Dec 14 - Dec 15
Avanti International Resort
Meeting facility
Hampton Inn & Suites Orlando Intl Dr N

Hampton Inn & Suites Orlando Intl Dr N

2.5 star property
19.3 km from Oakland
9.2 out of 10, Wonderful, (1054)
"Second time staying at this hotel and loved it great hotel for family and close to the main attractions "
United States
Kadeisha
The price is ₩128,269
₩144,303 total
includes taxes & fees
Dec 14 - Dec 15
Hampton Inn & Suites Orlando Intl Dr N
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

4.5 star property
24.2 km from Oakland
9.4 out of 10, Exceptional, (4277)
"Great resort "
United States
Camille
The price is ₩163,573
₩184,020 total
includes taxes & fees
Dec 14 - Dec 15
Rosen Shingle Creek
Outdoor pool, pool umbrellas, sun loungers
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, (1825)
"Great stay."
United States
Jasmin
The price is ₩69,857
₩137,713 total
includes taxes & fees
Dec 1 - Dec 2
Kompose Boutique Resort at Theme Parks
Lobby lounge
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, (1877)
"Great stay"
United States
Ramprasad
The price is ₩102,969
₩115,839 total
includes taxes & fees
Nov 30 - Dec 1
Aloft Orlando Lake Buena Vista
Front of property - evening/night
Rosen Inn International

Rosen Inn International

3.0 star property
19.3 km from Oakland
8.4 out of 10, Very Good, (5899)
"Close to all attractions "
United States
JoAnn
The price is ₩117,664
₩132,374 total
includes taxes & fees
Nov 26 - Nov 27
Rosen Inn International
Property entrance
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

3.0 star property
22.6 km from Oakland
8.8 out of 10, Excellent, (2246)
"Every thing was good, it was an enjoyable stay ! "
United States
Cheyenne
The price is ₩116,207
₩130,734 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
Outdoor pool, free cabanas, pool umbrellas
Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG

Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG

3.0 star property
23.2 km from Oakland
9.0 out of 10, Wonderful, (1665)
"Good place to stay "
United States
Arturo
The price is ₩122,386
₩137,685 total
includes taxes & fees
Dec 2 - Dec 3
Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG
3 outdoor pools, open 7 AM to 10:00 PM, cabanas (surcharge)
Hyatt Regency Grand Cypress

Hyatt Regency Grand Cypress

4.0 star property
22.4 km from Oakland
9.2 out of 10, Wonderful, (2290)
"Rooms were a nice size and clean, we enjoyed the property grounds and overall atmosphere of the hotel."
United States
Casey
The price is ₩231,680
₩343,382 total
includes taxes & fees
Nov 29 - Nov 30
Hyatt Regency Grand Cypress
Business center
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, (336)
"A great hotel, comfy"
United States
Theresa
The price is ₩116,502
₩131,064 total
includes taxes & fees
Dec 1 - Dec 2
Spark by Hilton Orlando near Universal
View from room
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, (5600)
"Amazing stay "
United States
Elsy
The price is ₩115,310
₩129,711 total
includes taxes & fees
Dec 15 - Dec 16
Rosen Inn Lake Buena Vista
Exterior
Caribe Royale Orlando

Caribe Royale Orlando

4.5 star property
26 km from Oakland
9.2 out of 10, Wonderful, (4506)
"Hotel was very clean, staff was super friendly, a lot of food options!"
United States
Justin
The price is ₩263,305
₩359,102 total
includes taxes & fees
Nov 25 - Nov 26
Caribe Royale Orlando
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.
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Where to stay in Oakland

Find the best Oakland areas and neighborhoods 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

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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Have stayed here several times with the family. Super convenient to City Walk and the parks! "
Leila 4-night trip
Posted 15 hours ago
Universal's Cabana Bay Beach Resort

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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.