Oakland Hotels, Winter Garden

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Check prices for these dates

Tonight
5 Jan - 6 Jan
Tomorrow
6 Jan - 7 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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Our top choices for Oakland hotels

Outdoor pool
DoubleTree by Hilton at the Entrance to Universal 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, (6961)
"we enjoyed the stay here, it is having nice rooms and breakfast."
United States
suresh
The price is NZ$174
includes taxes & fees
15 Jan - 16 Jan
DoubleTree by Hilton at the Entrance to Universal Orlando
In-room safe, laptop workspace, blackout curtains, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
28.9 km from Oakland
8.2 out of 10, Very good, (5171)
"Awesome place to stay! Clean and staff incredible!"
United States
Jeffrey
The price is NZ$111
includes taxes & fees
6 Jan - 7 Jan
Palazzo Lakeside Hotel
Property grounds
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
30.2 km from Oakland
8.8 out of 10, Excellent, (3354)
"A great place to stay for the price"
United States
Jennie
The price is NZ$107
includes taxes & fees
6 Jan - 7 Jan
Seasons Florida Resort
Lobby lounge
Aloft Orlando Lake Buena Vista

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, (1939)
"Good place to stay "
United States
victor
The price is NZ$152
includes taxes & fees
7 Jan - 8 Jan
Aloft Orlando Lake Buena Vista
Exterior
Holiday Inn Express Orlando International Airport by IHG

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, (1877)
"Very clean and good breakfast. Friendly staff and very helpful"
United States
Connie
The price is NZ$238
includes taxes & fees
12 Jan - 13 Jan
Holiday Inn Express Orlando International Airport by IHG
2 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas
Universal's Cabana Bay Beach Resort

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, (5988)
"Great place to stay"
United States
Peggy
The price is NZ$259
includes taxes & fees
6 Jan - 7 Jan
Universal's Cabana Bay Beach Resort
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center

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, (4035)
"Great location "
United States
Mark
The price is NZ$165
includes taxes & fees
6 Jan - 7 Jan
Wyndham I-Drive Avanti Resort & Conference Center
View from room
Rosen Inn at Pointe 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, (5541)
"Great stay"
United States
Stephanie
The price is NZ$155
includes taxes & fees
26 Jan - 27 Jan
Rosen Inn at Pointe Orlando
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
24.2 km from Oakland
9.4 out of 10, Exceptional, (4392)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is NZ$200
includes taxes & fees
23 Jan - 24 Jan
Rosen Shingle Creek
Exterior
Holiday Inn Resort Kissimmee by the Parks 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, (1149)
"Excellent amenities including breakfast and comfortable stay. "
Canada
SAGAR
The price is NZ$182
includes taxes & fees
7 Jan - 8 Jan
Holiday Inn Resort Kissimmee by the Parks by IHG
Lobby
Holiday Inn Resort Orlando - Lake Buena Vista by IHG

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, (3615)
"Room was great, Staff was polite and hotel had many amenities. "
United States
Bridget
The price is NZ$187
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Exterior
Ramada by Wyndham Kissimmee Gateway

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, (3943)
"Phenomenal hotel for the price point as well as the children. "
United States
Destiny
The price is NZ$142
includes taxes & fees
1 Feb - 2 Feb
Ramada by Wyndham Kissimmee Gateway
Water park
Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South
3.5 star property
28.4 km from Oakland
8.8 out of 10, Excellent, (4330)
"The breakfast was great for a hotel option, very clean room and facility. "
United States
Jacob
The price is NZ$185
includes taxes & fees
6 Jan - 7 Jan
Red Lion Hotel Orlando Lake Buena Vista South
6 outdoor pools, free pool cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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, (4254)
"Great stay!"
Canada
Sylvie
The price is NZ$217
includes taxes & fees
25 Jan - 26 Jan
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Bar (on property)
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

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, (3518)
"Nice and clean, location was close to Disney, lot of dining options nearby, breakfast was good, staff was amazing, lot of stuffs for kids to enjoy."
United States
Ravi
The price is NZ$170
includes taxes & fees
25 Jan - 26 Jan
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
Exterior
avid hotel Orlando International Airport 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, (2063)
"Easy check in, great people service, clean room, great location. "
United States
Tiffany
The price is NZ$226
includes taxes & fees
12 Jan - 13 Jan
avid hotel Orlando International Airport by IHG
View from room
Rosen Inn Lake Buena Vista

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, (5655)
"Great property to stay"
United States
Deepankar
The price is NZ$123
includes taxes & fees
19 Jan - 20 Jan
Rosen Inn Lake Buena Vista
Room, 2 Queen Beds
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport
3.0 star property
29.4 km from Oakland
7.8 out of 10, Good, (333)
"Very clean, super nice staff. Convenient location!"
United States
Nadjah
The price is NZ$174
includes taxes & fees
26 Jan - 27 Jan
Sonesta Essential Orlando Airport
Exterior
Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
31.4 km from Oakland
8.8 out of 10, Excellent, (1954)
"Clean room and pleasant staff. "
United States
Mariama Velinique
The price is NZ$209
includes taxes & fees
6 Jan - 7 Jan
Cambria Hotel Orlando Airport
Outdoor pool, pool cabanas (surcharge), pool umbrellas
Hyatt Regency Orlando

Hyatt Regency Orlando

Hyatt Regency Orlando
4.5 star property
21.4 km from Oakland
9.2 out of 10, Wonderful, (1943)
"Great luxury stay"
United States
Darshan
The price is NZ$588
includes taxes & fees
24 Jan - 25 Jan
Hyatt Regency 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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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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Was there over Christmas break, which is the busiest time of year in Orlando, but the property is spread out enough that it didn’t feel overcrowded. "
Tracey 6-night trip
Posted 13 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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.

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