Oakland Hotels, Winter Garden

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20 Nov - 21 Nov
Tomorrow
21 Nov - 22 Nov
This weekend
21 Nov - 23 Nov
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28 Nov - 30 Nov

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39169 Cheap Hotels in Oakland - Specials, Reviews, & Last Minute Deals

Terrace/patio
The Delaney Hotel

The Delaney Hotel

3.5 star property
25.3 km from Oakland
9.6 out of 10, Exceptional, (1004)
"All around wonderful stay"
United States
Caleb
The Delaney Hotel
5 outdoor pools, pool umbrellas, pool 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, (2064)
"The staff are very friendly and the resort is gorgeous! "
United States
Katherina
The price is NZ$291
includes taxes & fees
29 Nov - 30 Nov
Summer Bay Orlando by Exploria Resorts
6 outdoor pools, free pool 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, (3951)
"Nice place to stay for family. "
United States
Niketan Chhaganbhai
The price is NZ$199
includes taxes & fees
11 Dec - 12 Dec
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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, (2890)
"One of the best hotel!"
United States
Li
The price is NZ$177
includes taxes & fees
8 Dec - 9 Dec
SPOT X Hotel Orlando/Intl Dr by The Red Collection
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, (8762)
"Great stay"
United States
Breanna
The price is NZ$397
includes taxes & fees
23 Nov - 24 Nov
The Grove Resort & Water Park Orlando
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, (1032)
"Great room great breakfast"
United States
Kelly
The price is NZ$172
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
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, (6868)
"Great stay "
United States
Anthony
The price is NZ$194
includes taxes & fees
18 Dec - 19 Dec
DoubleTree by Hilton at the Entrance to Universal Orlando
Outdoor pool, pool umbrellas, pool 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, (1807)
"Great stay."
United States
Jasmin
The price is NZ$167
includes taxes & fees
1 Dec - 2 Dec
Kompose Boutique Resort at Theme Parks
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, (1044)
"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 NZ$175
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Orlando Intl Dr N
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, (1871)
"Great stay"
United States
Ramprasad
The price is NZ$140
includes taxes & fees
24 Nov - 25 Nov
Aloft Orlando Lake Buena Vista
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

4.5 star property
24.2 km from Oakland
9.4 out of 10, Exceptional, (4245)
"Great resort "
United States
Camille
The price is NZ$188
includes taxes & fees
18 Dec - 19 Dec
Rosen Shingle Creek
View from property
Avanti International Resort

Avanti International Resort

4.0 star property
20.4 km from Oakland
7.8 out of 10, Good, (4232)
"Great room, helpful cleaners, wonderful pool, great location"
United Kingdom
Gabrielle
The price is NZ$175
includes taxes & fees
16 Dec - 17 Dec
Avanti International Resort
3 outdoor pools, open 7 AM to 10:00 PM, pool 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, (2285)
"Rooms were a nice size and clean, we enjoyed the property grounds and overall atmosphere of the hotel."
United States
Casey
The price is NZ$423
includes taxes & fees
15 Dec - 16 Dec
Hyatt Regency Grand Cypress
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, (2238)
"Every thing was good, it was an enjoyable stay ! "
United States
Cheyenne
The price is NZ$160
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
Outdoor pool, free pool 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, (1656)
"Good place to stay "
United States
Arturo
The price is NZ$175
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG
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, (5889)
"Close to all attractions "
United States
JoAnn
The price is NZ$160
includes taxes & fees
23 Nov - 24 Nov
Rosen Inn International
Hypo-allergenic bedding, minibar, in-room safe, individually decorated
Pestana Orlando Suites - Lake Buena Vista

Pestana Orlando Suites - Lake Buena Vista

4.0 star property
22.3 km from Oakland
9.4 out of 10, Exceptional, (1906)
"Staff was friendly, beds were comfortable, clean "
United States
Pauline
The price is NZ$180
includes taxes & fees
30 Nov - 1 Dec
Pestana Orlando Suites - Lake Buena Vista
Business centre
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, (320)
"A great hotel, comfy"
United States
Theresa
The price is NZ$157
includes taxes & fees
18 Dec - 19 Dec
Spark by Hilton Orlando near Universal
1 bedroom, premium bedding, desk, laptop workspace
Candlewood Suites Orlando - Lake Buena Vista by IHG

Candlewood Suites Orlando - Lake Buena Vista by IHG

2.5 star property
22.3 km from Oakland
9.0 out of 10, Wonderful, (2242)
"Best hotel"
United States
Viany
The price is NZ$154
includes taxes & fees
30 Nov - 1 Dec
Candlewood Suites Orlando - Lake Buena Vista by IHG
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, (5576)
"Amazing stay "
United States
Elsy
The price is NZ$145
includes taxes & fees
15 Dec - 16 Dec
Rosen Inn 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.
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Our guide on 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

Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"Very long lines at breakfast. Bathroom and rooms were small"
Janet 1-night trip
Posted 2 days ago
Walt Disney World Dolphin

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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.