Search Hotels in Oakland, Winter Garden

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Oakland hotels

Holiday Inn Express Hotel & Suites Ocoee East by IHG

Holiday Inn Express Hotel & Suites Ocoee East by IHG
2.5 star property
14.6 km from Oakland
8.4 out of 10, Very good, (1,002 reviews)
"What a great place!!"
United States
Vince
The price is ₹10,903
₹12,266 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites Ocoee East by IHG

Wyndham Garden Lake Buena Vista – Disney Springs® Area

Wyndham Garden Lake Buena Vista – Disney Springs® Area
3.5 star property
23.2 km from Oakland
8.2 out of 10, Very good, (3,951 reviews)
"Great hotel"
United States
Jose Carlos
The price is ₹8,136
₹12,864 total
includes taxes & fees
25 Jan - 26 Jan
Wyndham Garden Lake Buena Vista – Disney Springs® Area

Wyndham Lake Buena Vista – Disney Springs® Area

Wyndham Lake Buena Vista – Disney Springs® Area
4.0 star property
23.3 km from Oakland
8.8 out of 10, Excellent, (2,804 reviews)
"Friendly, excellent staff, easy to access to Disney world!"
United States
Yukari
The price is ₹11,371
₹16,503 total
includes taxes & fees
25 Jan - 26 Jan
Wyndham Lake Buena Vista – Disney Springs® Area

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
3.0 star property
23.1 km from Oakland
9.8 out of 10, Exceptional, (5,575 reviews)
"Staff was reallyh nice and the hotel is awesome. great place to stayh. "
Singapore
Wei-Kai Victor
The price is ₹16,432
₹18,486 total
includes taxes & fees
4 Feb - 5 Feb
Drury Plaza Hotel Orlando - Disney Springs Area

AC Hotel by Marriott Orlando Lake Buena Vista

AC Hotel by Marriott Orlando Lake Buena Vista
3.5 star property
23.2 km from Oakland
9.2 out of 10, Wonderful, (1,755 reviews)
"Absolutely would stay here again!"
United States
Jasuntria
The price is ₹14,568
₹16,390 total
includes taxes & fees
25 Jan - 26 Jan
AC Hotel by Marriott Orlando Lake Buena Vista

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
19.2 km from Oakland
9.2 out of 10, Wonderful, (5,214 reviews)
"great place to stay nearest to all location ."
Canada
VIMAL
The price is ₹9,692
₹10,903 total
includes taxes & fees
2 Feb - 3 Feb
Home2 Suites by Hilton Orlando at Flamingo Crossings

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
19.3 km from Oakland
9.6 out of 10, Exceptional, (2,006 reviews)
"Great place, breakfast is good, and it's a safe area"
United States
Meenakshi
The price is ₹13,102
₹14,740 total
includes taxes & fees
10 Feb - 11 Feb
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
19.3 km from Oakland
9.4 out of 10, Exceptional, (2,216 reviews)
"Clean rooms, decent breakfast, and pleasant staff."
United States
Shaun
The price is ₹11,946
₹13,439 total
includes taxes & fees
22 Feb - 23 Feb
Homewood Suites by Hilton Orlando at Flamingo Crossings

The Delaney Hotel

The Delaney Hotel
3.5 star property
25.3 km from Oakland
9.6 out of 10, Exceptional, (1,050 reviews)
"Excellent hotel! Great location and the food and atmosphere was great"
United States
mario
The price is ₹17,258
₹19,415 total
includes taxes & fees
15 Feb - 16 Feb
The Delaney Hotel

Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
3.0 star property
25 km from Oakland
9.6 out of 10, Exceptional, (1,003 reviews)
"Hotel itself was very nice. Will definitely stay again."
United States
Erica
The price is ₹13,194
₹14,843 total
includes taxes & fees
1 Feb - 2 Feb
Courtyard by Marriott Orlando Downtown

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
26.5 km from Oakland
8.6 out of 10, Excellent, (1,570 reviews)
"Very nice property, clean, with a lot of amenities, we will be back for sure!!!!"
United States
Licet
The price is ₹8,521
₹12,999 total
includes taxes & fees
9 Feb - 10 Feb
Meliá Orlando Celebration

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
22.8 km from Oakland
8.8 out of 10, Excellent, (4,111 reviews)
"Just loved the hotel in general! "
United States
Noel
The price is ₹9,735
₹13,529 total
includes taxes & fees
3 Feb - 4 Feb
Hilton Vacation Club Aqua Sol Orlando West

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, (1,124 reviews)
"Staff were all very nice and helpful! "
United States
jamie
The price is ₹8,129
₹9,023 total
includes taxes & fees
26 Jan - 27 Jan
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
19.3 km from Oakland
9.4 out of 10, Exceptional, (4,462 reviews)
"Amazing room and great breakfasts for the price "
United States
Christian
The price is ₹10,262
₹11,545 total
includes taxes & fees
2 Feb - 3 Feb
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
25.2 km from Oakland
9.4 out of 10, Exceptional, (1,465 reviews)
"Loved everything about this hotel "
United States
Giselle
The price is ₹11,462
₹15,472 total
includes taxes & fees
4 Feb - 5 Feb
Hilton Vacation Club Grand Beach Orlando

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, (1,957 reviews)
"Super nice hotel at a great price."
United States
Terry
The price is ₹7,541
₹8,483 total
includes taxes & fees
26 Jan - 27 Jan
Aloft Orlando Lake Buena Vista

Spectrum Resort Villas Orlando and Waterparks

Spectrum Resort Villas Orlando and Waterparks
4.0 star property
31.2 km from Oakland
9.2 out of 10, Wonderful, (879 reviews)
"Great location for a family vacation"
United States
Deanne
The price is ₹20,171
₹43,901 total
includes taxes & fees
25 Jan - 26 Jan
Spectrum Resort Villas Orlando and Waterparks

Westgate Town Center Resort

Westgate Town Center Resort
4.0 star property
25.3 km from Oakland
8.0 out of 10, Very good, (1,415 reviews)
"Great place! Will definitely be back! "
United States
Amanda
The price is ₹8,290
₹12,528 total
includes taxes & fees
25 Jan - 26 Jan
Westgate Town Center Resort

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
21.6 km from Oakland
8.0 out of 10, Very good, (8,995 reviews)
"Great place to stay with the family. "
United States
Nabeel
The price is ₹12,736
₹19,378 total
includes taxes & fees
28 Jan - 29 Jan
The Grove Resort & Water Park Orlando

Summer Bay Orlando MOD Collection by Sonesta

Summer Bay Orlando MOD Collection by Sonesta
3.5 star property
23.3 km from Oakland
8.8 out of 10, Excellent, (2,094 reviews)
"Excellent stay."
United States
Octavio
The price is ₹10,079
₹14,238 total
includes taxes & fees
25 Jan - 26 Jan
Summer Bay Orlando MOD Collection by Sonesta
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 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 Island H2O Live! 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

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.

Explore a world of travel with Expedia