Photo by Gregg Yutko

Oakland Hotels near Winter Garden

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 6 - Aug 7
Tomorrow
Aug 7 - Aug 8
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Oakland, Winter Garden

Wyndham Garden Orlando Airport
Relax by the pool surrounded by lush greenery and comfortable lounge seating.

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3777)
"I enjoy really enjoyed the stay staff was friendly restaurant food was really good"
The price is P5,390
P6,064 total
includes taxes & fees
Sep 2 - Sep 3
Wyndham Garden Orlando Airport
Drury Plaza Hotel Orlando - Disney Springs Area
Relax by the pool surrounded by palm trees and lounge chairs.

Drury Plaza Hotel Orlando - Disney Springs Area

3.0 star property
9.8 out of 10, Exceptional, (4653)
"Great hotel! "
The price is P7,801
P8,776 total
includes taxes & fees
Aug 11 - Aug 12
Drury Plaza Hotel Orlando - Disney Springs Area
Lakeside Inn
Relax by the serene pool surrounded by lounge chairs and scenic views.

Lakeside Inn

3.0 star property
8.8 out of 10, Excellent, (1198)
"Lovely location and quiet peaceful stay"
Lakeside Inn
Hyatt House Orlando International Drive
Enjoy a delicious spread of scrambled eggs, casserole, and mixed vegetables at our buffet.

Hyatt House Orlando International Drive

4.0 star property
9.4 out of 10, Exceptional, (760)
"Nice place to stay"
The price is P5,938
P6,680 total
includes taxes & fees
Aug 14 - Aug 15
Hyatt House Orlando International Drive
Rosen Shingle Creek
Relax by the pool surrounded by lounge chairs and umbrellas, with a view of the resort's distinctive building in the background.

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (3947)
"Great place to stay "
The price is P6,872
P7,731 total
includes taxes & fees
Aug 31 - Sep 1
Rosen Shingle Creek
The Alfond Inn
Stunning hotel entrance with a central tower and beautifully landscaped surroundings.

The Alfond Inn

4.0 star property
9.4 out of 10, Exceptional, (1000)
"The hotel staff, restaurants and accommodations are very nice."
The Alfond Inn
Seasons Florida Resort
Relax in this serene outdoor seating area with a round table and comfortable chairs.

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (3031)
"Very nice clean accomodation with helpful and friendly staff."
The price is P3,502
P3,975 total
includes taxes & fees
Aug 17 - Aug 18
Seasons Florida Resort
Club Sevilla
Club Sevilla's elegant entrance features a distinctive red awning, palm trees, and a beautifully maintained garden.

Club Sevilla

2.0 star property
9.0 out of 10, Wonderful, (1004)
"Always a great stay. Quiet and secluded. Great value for location."
The price is P2,162
P2,753 total
includes taxes & fees
Aug 7 - Aug 8
Club Sevilla
Pestana Orlando Suites - Lake Buena Vista
Hypo-allergenic bedding, minibar, in-room safe, individually decorated

Pestana Orlando Suites - Lake Buena Vista

4.0 star property
9.4 out of 10, Exceptional, (1692)
"Excellent stay, friendly staff "
The price is P4,266
P5,448 total
includes taxes & fees
Sep 3 - Sep 4
Pestana Orlando Suites - Lake Buena Vista
Rosen Centre Hotel
Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas at your disposal.

Rosen Centre Hotel

4.0 star property
9.0 out of 10, Wonderful, (3879)
"It was an amazing stay"
The price is P5,354
P6,084 total
includes taxes & fees
Sep 1 - Sep 2
Rosen Centre Hotel
Galleria Palms Hotel
Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas at your disposal.

Galleria Palms Hotel

2.5 star property
8.8 out of 10, Excellent, (3568)
"This hotel is very good and affordable!"
Galleria Palms Hotel
Holiday Inn Orlando International Dr-ICON by IHG
Enjoy meals at the large dining table and stay productive at the computer desk, with a view of the outdoors through the large windows.

Holiday Inn Orlando International Dr-ICON by IHG

3.0 star property
9.0 out of 10, Wonderful, (2128)
"Excellent stay with family for the price."
The price is P4,843
P6,313 total
includes taxes & fees
Aug 13 - Aug 14
Holiday Inn Orlando International Dr-ICON by IHG
Palazzo Lakeside Hotel
Relax in comfort with a plush bed, tufted headboard, and cozy armchair.

Palazzo Lakeside Hotel

3.0 star property
8.2 out of 10, Very Good, (5144)
"Nice place will stay again "
The price is P2,106
P4,353 total
includes taxes & fees
Aug 7 - Aug 8
Palazzo Lakeside Hotel
Motel 6 Kissimmee, FL - Orlando
Welcome to our reception area, featuring a reception desk, a potted plant, and informative posters.

Motel 6 Kissimmee, FL - Orlando

2.0 star property
7.4 out of 10, Good, (1338)
"Wonderful stay."
The price is P3,458
P4,041 total
includes taxes & fees
Aug 7 - Aug 8
Motel 6 Kissimmee, FL - Orlando
Sonesta Essential Orlando
Two single beds with white bedding and a flat-screen TV are featured in this stylish room.

Sonesta Essential Orlando

3.0 star property
7.2 out of 10, Good, (1701)
"Excellent, great hospitality from the staff"
The price is P4,600
P5,405 total
includes taxes & fees
Aug 21 - Aug 22
Sonesta Essential Orlando
The Delaney Hotel
Relax in the outdoor seating area with a sofa, coffee table, and fire feature.

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1001)
"Excellent all around place and stay "
The Delaney Hotel
Kompose Boutique Resort at Theme Parks
Relax in style with a view of the outdoor pool from our spacious lobby, featuring a stunning chandelier and unique sculpture.

Kompose Boutique Resort at Theme Parks

3.0 star property
9.4 out of 10, Exceptional, (938)
"We had a great stay!"
The price is P3,325
P4,468 total
includes taxes & fees
Aug 10 - Aug 11
Kompose Boutique Resort at Theme Parks
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
La Quinta offers modern accommodations with city views from its rooms.

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

3.0 star property
8.6 out of 10, Excellent, (2155)
"The hotel was very clean and nice!!"
The price is P5,369
P6,041 total
includes taxes & fees
Aug 11 - Aug 12
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
Candlewood Suites Orlando - Lake Buena Vista by IHG
Cozy retreat with a kitchenette, comfortable seating area, and a bed with a headboard.

Candlewood Suites Orlando - Lake Buena Vista by IHG

2.5 star property
9.0 out of 10, Wonderful, (2016)
"Great place to stay if on vacation "
The price is P4,554
P5,772 total
includes taxes & fees
Aug 10 - Aug 11
Candlewood Suites Orlando - Lake Buena Vista by IHG
Holiday Inn Resort Kissimmee by the Parks by IHG
Relax in our spacious lobby with a view of the outdoor pool, featuring comfortable seating and lush greenery.

Holiday Inn Resort Kissimmee by the Parks by IHG

3.5 star property
8.6 out of 10, Excellent, (392)
"location, staff, and hotel great for adults and kids."
The price is P3,185
P4,761 total
includes taxes & fees
Aug 22 - Aug 23
Holiday Inn Resort Kissimmee by the Parks by IHG
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

DoubleTree by Hilton Hotel Orlando Downtown

DoubleTree by Hilton Hotel Orlando Downtown

10/10 Excellent
"Nice staff, clean room, good amenities "
Vivian 1-night trip
Posted 19 hours ago
DoubleTree by Hilton Hotel Orlando Downtown

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 Resurrection Catholic Church.