A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.

Oakland Hotel Guide - 5 Stars 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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Oakland 5 Star Hotels

Our top choices for Oakland 5-star hotels

A hotel with a swimming pool, lounge chairs, and palm trees.

1. Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
5.0 star property
Orlando
9.4 out of 10, Exceptional, (657 reviews)
"Great Hotel and Great Staff."
United States
Ray
The price is Rp5.721.003
Rp7.438.391 total
includes taxes & fees
27 Sept - 28 Sept
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
A resort with multiple swimming pools, lounge areas, and a modern building with balconies.

2. Conrad Orlando at Evermore

Conrad Orlando at Evermore
5.0 star property
Orlando
9.6 out of 10, Exceptional, (579 reviews)
"Great service, delicious food and tons to do!"
United States
Marlon
The price is Rp6.500.363
Rp8.203.810 total
includes taxes & fees
11 Oct - 12 Oct
Conrad Orlando at Evermore
A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.

3. Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5.0 star property
Golden Oak
9.6 out of 10, Exceptional, (957 reviews)
"Experience was amazing"
United States
Patrick
The price is Rp17.109.780
Rp20.356.965 total
includes taxes & fees
30 Sept - 1 Oct
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
A water park with multiple slides and a pool area surrounded by palm trees and a golf course.

4. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
5.0 star property
Orlando
9.2 out of 10, Wonderful, (1,003 reviews)
"Great hotel!"
United States
Teresa
The price is Rp8.356.642
Rp10.503.801 total
includes taxes & fees
26 Sept - 27 Sept
The Ritz-Carlton Orlando, Grande Lakes
A pool area with lounge chairs and umbrellas, surrounded by tropical plants.

5. ette hotel Orlando

ette hotel Orlando
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (498 reviews)
"Super quiet, beautiful linens, delicious restaurant."
United States
Lorie
The price is Rp4.135.147
Rp4.693.392 total
includes taxes & fees
30 Sept - 1 Oct
ette hotel Orlando

6. Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
5.0 star property
Kissimmee
8.4 out of 10, Very good, (1,000 reviews)
"This place was so awesome, had a free shuttle to parks, and a great pool area!"
United States
Tara
The price is Rp4.821.196
Rp15.029.553 total
includes taxes & fees
5 Oct - 6 Oct
Encore Resort and Water Park at Reunion by Rentyl
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.

7. Disney's Beach Club Resort

Disney's Beach Club Resort
5.0 star property
Bay Lake
8.8 out of 10, Excellent, (718 reviews)
"The best"
United States
Carl
The price is Rp12.704.234
Rp14.292.265 total
includes taxes & fees
27 Sept - 28 Sept
Disney's Beach Club Resort
A pool with inflatable rings, lounge chairs, and a wooden deck with stairs.

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

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
5.0 star property
Kissimmee
8.8 out of 10, Excellent, (5 reviews)
"Awesome pools. Family friendly."
United States
Nydia
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.

9. Disney's Beach Club Villas

Disney's Beach Club Villas
2.5 star property
Bay Lake
9.2 out of 10, Wonderful, (40 reviews)
"Clean and great location"
United States
Anonymous traveller
The price is Rp12.774.108
Rp14.370.872 total
includes taxes & fees
27 Sept - 28 Sept
Disney's Beach Club Villas
A swimming pool with lounge chairs, palm trees, and a golf course.

10. 5 Bedroom at Storey Lake Orlando FL close to Disney 4851

5 Bedroom at Storey Lake Orlando FL close to Disney 4851
5.0 star property
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"Pool heating cost additional. Property Lazy river and pool was heated in November, was awesome. great Spot for a vacation. Highly recomend."
United States
Nita
5 Bedroom at Storey Lake Orlando FL close to Disney 4851
A modern living room with a sofa, a TV mounted on the wall, and a balcony with glass doors.

11. Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
5.0 star property
Clermont
9.6 out of 10, Exceptional, (9 reviews)
"Wonderful stay!"
Canada
Angela
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
A modern kitchen with a granite countertop, stainless steel appliances, and wooden cabinets. There are three bar stools and a hanging light fixture above the counter.

12. Family Friendly 5 Bedrooms Home Close to Disney 4849

Family Friendly 5 Bedrooms Home Close to Disney 4849
5.0 star property
Kissimmee
9.0 out of 10, Wonderful, (4 reviews)
"Everything was well clean and very easy access"
United States
Raquel
Family Friendly 5 Bedrooms Home Close to Disney 4849
An aerial view of a resort with a large swimming pool, water slides, and a mini-golf area.

13. Stunning 2 Bd Condo Close to Disney 304 3191

Stunning 2 Bd Condo Close to Disney 304 3191
5.0 star property
Kissimmee
5.0 out of 10, (6 reviews)
"Pools were filthy. The washer dryer combo did not work. Like a previous "
United States
Stephanie
Stunning 2 Bd Condo Close to Disney 304 3191
A resort with multiple swimming pools, sun loungers, and palm trees.

14. Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (9 reviews)
"Overall wonderful home, great price, great property and amenities for families. Location is great near absolutely everything. "
United States
Lance
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
An aerial view of a resort with a large swimming pool, palm trees, and a water slide.

15. Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
5.0 star property
Kissimmee
8.6 out of 10, Excellent, (8 reviews)
"The accommodation not only has a good equipment and location, but is also absolutely top and highly recommended. I will be very happy to book here again."
Germany
Thomas
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
A swimming pool with a glass enclosure, surrounded by a patio area with a view of a residential building.

16. 5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759

5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
5.0 star property
Kissimmee
10.0 out of 10, Exceptional, (4 reviews)
"Looks just like photos, very nice and spacious. I would book again."
United States
Kimesha
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
An aerial view of a resort with a large water park, multiple swimming pools, and a variety of recreational facilities.

17. Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort

Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort
5.0 star property
Kissimmee
8.4 out of 10, Very good, (11 reviews)
"Very roomy, clean and equipped apartment, worth for the money paid."
United States
Prasad
Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort
An aerial view of a resort with multiple swimming pools, sun loungers, and palm trees.

18. Stunning 4 Bd Close to Disney @ Storey Lake 2569

Stunning 4 Bd Close to Disney @ Storey Lake 2569
5.0 star property
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"The unit was clean and full accommodations. The overall resort is friendly and safe. Great parking close to parks and restaurants, grocery etc. "
United States
Claudine
Stunning 4 Bd Close to Disney @ Storey Lake 2569
A rectangular swimming pool with a tiled edge, surrounded by a brick patio. There are lounge chairs and a small table near the pool.

19. Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
5.0 star property
Kissimmee
5.6 out of 10, (4 reviews)
"The coffee pot was broke, we emailed about it and received a new one within a a few hours. The listing says water park access but you don’t get water park access. The dryer was broken and unable to be fixed during our stay. The company is very attentive to needs. I brought up something’s in the house that probably need evaluated and they said things need to be addressed at the beginning on the stay. (Things like the fridge seal not being great, broken can opener, broken pool chairs ) make sure...
United States
Bronte
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
A modern indoor pool area with a dining setup and a view of the ocean.

20. The Ritz-Carlton Residences Orlando, Grande Lakes

The Ritz-Carlton Residences Orlando, Grande Lakes
5.0 star property
Orlando
The Ritz-Carlton Residences Orlando, Grande Lakes
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oakland.
Avanti International Resort

Avanti International Resort

8738 International Dr Orlando FL
The price is Rp1.275.619 per night from 27 Sept to 28 Sept
Rp1.275.619
Rp1.797.869 total
27 Sept - 28 Sept
includes taxes & fees
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.
PoolSpaHot tubBreakfast includedWaterpark
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.

Top Oakland Hotel Reviews

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 Rp1.797.869

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.

Explore a world of travel with Expedia