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Top Trending Hotels Near Oakland, Winter Garden

Terrace/patio
The Delaney Hotel

The Delaney Hotel

3.5 star property
25.3 km from Oakland
9.6 out of 10, Exceptional, (1014)
"The Hotel is wonderful had a great restaurant and bar the staff was very friendly and the room looked like the photos "
United States
Michael
The Delaney Hotel
Exterior
Hilton Garden Inn Apopka City Center

Hilton Garden Inn Apopka City Center

3.0 star property
18.5 km from Oakland
9.4 out of 10, Exceptional, (930)
"We love this place! Staff is wonderful and the property is immaculate ! "
United States
don
The price is ₹10,017
₹11,269 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Apopka City Center
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, (2080)
"Enjoyed the friendly bartenders and staff. "
United States
Todd J
The price is ₹10,934
₹15,134 total
includes taxes & fees
10 Dec - 11 Dec
Summer Bay Orlando by Exploria Resorts
5 outdoor pools, free pool 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, (2712)
"Stayed here before always enjoyed it "
United States
Margaret
The price is ₹8,639
₹9,719 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Property amenity
Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown

3.0 star property
25 km from Oakland
9.6 out of 10, Exceptional, (1005)
"Good location helpful staff"
United States
Gary
The price is ₹9,269
₹10,428 total
includes taxes & fees
24 Dec - 25 Dec
Courtyard by Marriott Orlando Downtown
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, (1057)
"Great room great breakfast"
United States
Kelly
The price is ₹9,899
₹10,988 total
includes taxes & fees
8 Jan - 9 Jan 2026
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
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
9.4 out of 10, Exceptional, (4066)
"Very clean best resort "
United States
Shatira
The price is ₹10,007
₹11,258 total
includes taxes & fees
4 Jan - 5 Jan 2026
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, (2935)
"Clean room, close to Disney and good breakfast at a reasonable price"
United States
pamela
The price is ₹6,803
₹9,273 total
includes taxes & fees
17 Dec - 18 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, (8788)
"Everything about it was excellent The staff , the rooms , the resort , very convenient location .We were very very pleased with everything very beautiful area "
United States
Ruben
The price is ₹13,409
₹20,046 total
includes taxes & fees
10 Dec - 11 Dec
The Grove Resort & Water Park 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, (1940)
"Beautiful resort with very friendly staff. "
United States
kristie
The price is ₹3,263
₹7,280 total
includes taxes & fees
11 Dec - 12 Dec
Kompose Boutique Resort at Theme Parks
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, (6884)
"Wonderful stay. Great location!"
United States
Charmaine
The price is ₹8,051
₹9,058 total
includes taxes & fees
16 Dec - 17 Dec
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, (4289)
"Enjoyed our stay "
United States
Sheltra
The price is ₹6,242
₹8,844 total
includes taxes & fees
14 Dec - 15 Dec
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, (1072)
"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 ₹8,114
₹9,128 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Orlando Intl Dr N
7 outdoor pools, pool cabanas (surcharge), pool umbrellas
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4.0 star property
20.9 km from Oakland
8.2 out of 10, Very good, (5550)
"Nice i will stay again "
United States
Raquis
The price is ₹8,790
₹12,926 total
includes taxes & fees
17 Dec - 18 Dec
Westgate Lakes Resort & Spa Universal Studios Area
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, (1905)
"Great rooms, staff, and property!"
United States
Cindy
The price is ₹6,659
₹7,492 total
includes taxes & fees
17 Dec - 18 Dec
Aloft Orlando Lake Buena Vista
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, (2287)
"The staff was attentive and we really enjoyed the amenities! "
United States
Michelle
The price is ₹14,498
₹21,372 total
includes taxes & fees
13 Dec - 14 Dec
Hyatt Regency Grand Cypress
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, (4338)
"Great resort "
United States
Camille
The price is ₹9,416
₹10,594 total
includes taxes & fees
14 Dec - 15 Dec
Rosen Shingle Creek
Suite, Multiple Beds | In-room safe, desk, laptop workspace, blackout curtains
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, (2254)
"Nice hotel and room for the price"
United States
Justin
The price is ₹7,469
₹8,403 total
includes taxes & fees
17 Dec - 18 Dec
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, (1665)
"Good place to stay "
United States
Arturo
The price is ₹8,346
₹9,389 total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG
Exterior
Caribe Royale Orlando

Caribe Royale Orlando

4.5 star property
26 km from Oakland
9.2 out of 10, Wonderful, (4499)
"Clean and very friendly staff"
United States
Nafeeza
The price is ₹14,323
₹19,964 total
includes taxes & fees
14 Dec - 15 Dec
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.
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

Avanti International Resort

Avanti International Resort

10/10 Excellent
"Everything good "
Mayra 1-night trip
Posted 22 hours ago
Avanti International Resort

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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.