Photo by Gregg Yutko

Oakland Hotels, Winter Garden

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Filter by

Popular filters
Popular filters
Total price
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

37518 Cheap Hotels in Oakland - Specials, Reviews, & Last Minute Deals

Lobby
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (3034)
"Went here for a solo trip, was very safe, walkable, and overall a great place to vacation. I have been to all inclusive resorts out of the country and this definitely has that feel (except that you have to pay lol) "
The price is NZ$322
per night
10 Jun - 11 Jun
Margaritaville Resort Orlando
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (846)
"Nice, clean, and quiet. "
Margaritaville Resort Orlando Cottages by Rentyl
Lobby
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
9.4 out of 10, Exceptional, (1765)
"Great stay, room was perfect for my little family! "
The price is NZ$196
per night
13 Jun - 14 Jun
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property amenity
Disney's Animal Kingdom Lodge
4.5 star property
8.8 out of 10, Excellent, (1000)
"Love the lobby"
Disney's Animal Kingdom Lodge
2 outdoor pools, open 8 AM to 10 PM, pool loungers
Holiday Inn Club Vacations Orlando Breeze Resort, an IHG Hotel
3.5 star property
9.4 out of 10, Exceptional, (330)
"One of the best places I’ve ever stayed "
The price is NZ$237
per night
4 Jun - 5 Jun
Holiday Inn Club Vacations Orlando Breeze Resort, an IHG Hotel
Lobby
OYO Townhouse Orlando West
2.0 star property
6.8 out of 10, (1000)
"tks"
The price is NZ$149
per night
5 Jun - 6 Jun
OYO Townhouse Orlando West
Exterior
WoodSpring Suites Orlando West - Clermont
2.5 star property
5.2 out of 10, (627)
"nice place"
The price is NZ$175
per night
4 Jun - 5 Jun
WoodSpring Suites Orlando West - Clermont
Suite, 1 King Bed, Non Smoking
Hampton Inn & Suites Clermont
2.5 star property
9.2 out of 10, Wonderful, (611)
"It was quiet"
The price is NZ$233
per night
5 Jun - 6 Jun
Hampton Inn & Suites Clermont
Lobby lounge
Fairfield Inn & Suites Orlando Ocoee
2.5 star property
8.8 out of 10, Excellent, (580)
"It was everything I would expect from a hotel. "
The price is NZ$242
per night
2 Jun - 3 Jun
Fairfield Inn & Suites Orlando Ocoee
Exterior
The Grove Resort by ACO
3.0 star property
7.6 out of 10, Good, (7)
"When we got there the cleaning lady was seating on the sofa on the phone and told us that she was not done , she finished on the phone and left the bathroom super dirty, no shampoo or conditioner, I was there for 3 nights and the beds were never made or did not receive clean towels I go to the groove every year and this year I was impressed about how dirty the apartment .. but the apartment it’s very cute and comfortable , they just need to work on the cleaning "
The Grove Resort by ACO
Dining
Sleep Up To 54 At The Great Escape Parkside - 15 BR Game Themed Mansion!
Sleep Up To 54 At The Great Escape Parkside - 15 BR Game Themed Mansion!
City view from property
Edgewater Hotel
2.5 star property
9.6 out of 10, Exceptional, (274)
"Great area and unique property. Family suites are great value."
The price is NZ$249
per night
11 Jun - 12 Jun
Edgewater Hotel
A heated pool
Shuttle to Disney World + On-Site Water Park
Shuttle to Disney World + On-Site Water Park
Private kitchen
SPACIOUS, LOVELY THEMED HOME NEAR DISNEY
9.6 out of 10, Exceptional, (110)
"Thank you So much for making Eli’s day so special! See loved her Squishmallow! She said I had the Best Birthday ever!"
SPACIOUS, LOVELY THEMED HOME NEAR DISNEY
Lobby
Disney's Animal Kingdom Villas - Jambo House
2.0 star property
Disney's Animal Kingdom Villas - Jambo House
Pool
DISNEY House - 8 GUESTS!+ FREE Resort! -35
DISNEY House - 8 GUESTS!+ FREE Resort! -35
Pool
Resort Condo w/ Balcony: 6 Mi to Magic Kingdom
9.2 out of 10, Wonderful, (53)
"Perfect stay. Roy was a great host. Excellent communication. Love this property. Tucked away but easy access to everything. Would definitely return."
Resort Condo w/ Balcony: 6 Mi to Magic Kingdom
Property grounds
Holiday home winter / summer
9.8 out of 10, Exceptional, (97)
"The location of the property was perfect. It is very close to Disney and other attractions and restaurants. However the home is located in a quiet neighborhood with easy access. The owner and host were very helpful and available if needed. The home was comfortable and a great place to relax. We would enjoy staying here again."
Holiday home winter / summer
Pool
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
9.6 out of 10, Exceptional, (99)
"A wonderful place to stay."
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
Outdoor pool
Orange Lake Resort - Holiday Inn Club Vacations
Orange Lake Resort - Holiday Inn Club Vacations
Don't see what you're looking for?
See all available properties in Oakland
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.

Oakland hotels information

Number of reviews
10,368
Accommodation
37,518 hotels
Lowest Price
NZ$149
Highest Price
NZ$322

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.

What's the best place to stay in Oakland?

For your stay in Oakland, The Oak View Place.. is one of the top choices based on our traveller data.

How many hotels can I expect to find in Oakland?

Expedia has 5 Oakland hotels and other accommodation options, and one might make a good home base for venturing out into the greater Winter Garden area.

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 Resurrection Catholic Church or Garden Theatre.

Recent Reviews in Oakland

Caribe Royale Orlando

Caribe Royale Orlando

5/5 Excellent
"Great service "
A verified traveller stayed at Caribe Royale Orlando
Posted 3 hours ago
Caribe Royale Orlando