Photo by Gregg Yutko

Compare and book 5 Star hotels in Oakland, 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
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Oakland 5 Star Hotels

This weekend
Next weekend

Top Oakland 5 Star Hotels

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5.0 star property
9.2 out of 10, Wonderful, (291)
"Excellent service and food "
The price is 7.514.301 ₫
9.925.313 ₫ total
includes taxes & fees
25 Jul - 26 Jul
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Conrad Orlando at Evermore

5.0 star property
9.4 out of 10, Exceptional, (226)
"Beautiful resort.. The staff were all wonderful."
The price is 10.413.272 ₫
13.023.131 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Conrad Orlando at Evermore

The Ritz-Carlton Orlando, Grande Lakes

5.0 star property
9.2 out of 10, Wonderful, (1009)
"Top notch resort. All class!"
The price is 9.837.664 ₫
12.686.401 ₫ total
includes taxes & fees
1 Aug - 2 Aug
The Ritz-Carlton Orlando, Grande Lakes

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

5.0 star property
9.6 out of 10, Exceptional, (852)
"Great stay highly recommended "
The price is 26.033.180 ₫
30.759.052 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

ette hotel

5.0 star property
9.8 out of 10, Exceptional, (311)
"great hotel and very friendly staff very clean rooms and fast service "
ette hotel

Encore Resort and Water Park At Reunion by Rentyl

5.0 star property
8.4 out of 10, Very good, (1002)
"A luxurious and fun hotel for the whole family, the pool is excellent and so is the water park , the staff was helpful"
Encore Resort and Water Park At Reunion by Rentyl

Splendid 5Bd Close to Disney at Storey Lake 4251

5.0 star property
9.0 out of 10, Wonderful, (10)
"Amazing Stay...Home away from Home... Definitely recommend for families..."
Splendid 5Bd Close to Disney at Storey Lake 4251

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629

5.0 star property
8.8 out of 10, Excellent, (3)
"Nice "
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629

The Bear's Den Resort Orlando

5.0 star property
8.0 out of 10, Very good, (22)
"Great place , I recommend it to everyone."
The Bear's Den Resort Orlando

2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms

5.0 star property
8.0 out of 10, Very good, (13)
"The kids really enjoyed it and everyone was comfortable, no complaints."
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms

Family Vacation Home, Water Park+Endless Amenities

5.0 star property
8.2 out of 10, Very good, (20)
"Property is very well kept and close to attractions. Nick, the property manager is very attentive and responds immediately"
Family Vacation Home, Water Park+Endless Amenities

Family Friendly Four Bedroom w GameRoom @Disney 5145

5.0 star property
8.4 out of 10, Very good, (5)
"It was fantastic!"
Family Friendly Four Bedroom w GameRoom @Disney 5145

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

5.0 star property
8.8 out of 10, Excellent, (3)
"It was very clean and comfortable. "
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Stunning 4 Bd Close to Disney @ Storey Lake 2569

5.0 star property
10.0 out of 10, Exceptional, (2)
Stunning 4 Bd Close to Disney @ Storey Lake 2569

Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

5.0 star property
8.4 out of 10, Very good, (6)
"The property was a perfect get a way during Hurricane Milton. The kids loved the space and the amenities."
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

5.0 star property
9.4 out of 10, Exceptional, (10)
"Super clean and confortable. "
Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

Stunning 2 Bd Condo Close to Disney 304 3191

5.0 star property
6.6 out of 10, (4)
"The Place Awesome it was a family trip we had great time my 2 kids love the Pool, the Lazy river. they love the hold place. places are not far from Condo. Great communication they always was checking if we needed anything it was great. Thank You "
Stunning 2 Bd Condo Close to Disney 304 3191

Luxury 8Bd with Pool @ Sonoma Resort 2639

5.0 star property
2.0 out of 10, (1)
"The property had 8 bedrooms, only 2 were king size. All the beds are so low to the ground. The refrigerator was broken. The coffee table was broken. They charge a massive deposit. Then they send you an email after check out that they deducted money from your deposit and say that you have things damaged. I called the first day to tell them the defects and no one response. I wonder never recommend this place. "
Luxury 8Bd with Pool @ Sonoma Resort 2639

Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

5.0 star property
8.0 out of 10, Very good, (4)
"The house was huge we had enough room for everyone I loved the theme rooms and it was quiet "
Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

Marvelous 4Bd with Pool at Storey Lake Resort 2601

5.0 star property
10.0 out of 10, Exceptional, (2)
Marvelous 4Bd with Pool at Storey Lake Resort 2601
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oakland.
Still don't see what you're looking for?
See all properties in Oakland.
You can also use these popular filters to refine your search.
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.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Oakland?
You can find various pricing options for 5-star hotels in Oakland on Expedia. How much you'll pay will depend on when you plan to travel, length of stay and other factors. Compare available accommodation for your desired dates and use our pricing and other filters to score the perfect luxury stay.

  • Search for the lowest price per night from 2.201.701 ₫

What makes a hotel 5 stars in Oakland?
In Oakland, a hotel needs to offer a specific amount of upscale conveniences to earn 5 stars. These can include on-site gyms, saunas and spas, gourmet restaurants, premium bedding, luxury bathroom products and more. What also sets 5-star hotels apart is their superior service. You'll enjoy things like concierge services, in-room massages and nightly turn-down services. Some may also offer additional touches like a welcome gift.
Are there any 5-star all-inclusive resorts in Oakland?
Find an upscale stay that includes your room, meals, activities and entertainment in Oakland with the help of Expedia's filters. Search for resorts with a 5-star rating and select the "All inclusive" filter. Have a look at what's included in the purchase price. This way, you can take full advantage of the premium perks on offer from the moment you step into the lobby.