Historic Downtown Kissimmee 5 Stars Hotels

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Check prices for these dates

Tonight
Nov 11 - Nov 12
Tomorrow
Nov 12 - Nov 13
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Historic Downtown Kissimmee 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, (685 reviews)
"Very nice hotel in every way."
United States
John
The price is ₩388,390
₩512,534 total
includes taxes & fees
Nov 12 - Nov 13
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, (617 reviews)
"A uniquely beautiful resort staffed by uniquely beautiful people. Excellent service, amazing amenities, one of a kind lagoon pool, and delicious food."
United States
Kelly
The price is ₩546,658
₩690,543 total
includes taxes & fees
Nov 25 - Nov 26
Conrad Orlando at Evermore
A poolside area with a wooden gazebo, lounge chairs, and a table.

3. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
5.0 star property
Orlando
9.2 out of 10, Wonderful, (1,007 reviews)
"Great hotel!"
United States
Teresa
The price is ₩643,637
₩807,205 total
includes taxes & fees
Nov 25 - Nov 26
The Ritz-Carlton Orlando, Grande Lakes
A hotel with a central courtyard, a reflective pool, and a large building with a prominent entrance.

4. 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, (974 reviews)
"Amazing stay, beautiful property and grounds with an incredible water park complex."
United States
Benjamin
The price is ₩1,685,653
₩1,987,022 total
includes taxes & fees
Dec 11 - Dec 12
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
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, (518 reviews)
"Great Services. Great hotel. Great atmosphere!"
United States
Wigberto
The price is ₩417,048
₩473,353 total
includes taxes & fees
Nov 22 - Nov 23
ette hotel Orlando
A rectangular swimming pool with lounge chairs and palm trees.

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, (1,001 reviews)
"A+ definitely staying with my family again."
United States
Jose
The price is ₩290,285
₩1,122,650 total
includes taxes & fees
Dec 3 - Dec 4
Encore Resort and Water Park at Reunion by Rentyl
A pool area with a waterfall, palm trees, and a rocky backdrop.

7. Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,635 reviews)
"Huge property - not a golfer but still enjoyed the stay"
United States
Karen G
The price is ₩381,678
₩496,870 total
includes taxes & fees
Nov 12 - Nov 13
Reunion Resort & Golf Club
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.

8. Disney's Beach Club Resort

Disney's Beach Club Resort
5.0 star property
Bay Lake
8.8 out of 10, Excellent, (720 reviews)
"The best"
United States
Carl
The price is ₩978,366
₩1,100,662 total
includes taxes & fees
Nov 17 - Nov 18
Disney's Beach Club Resort
A pool area with a wooden deck, rope ladder, and palm trees.

9. 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 modern living room with a sofa, a TV mounted on the wall, and a balcony with glass doors.

10. 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, (10 reviews)
"Wonderful stay!"
Canada
Angela
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
A bedroom with a brick wall, a large bed with red bedding, two bedside lamps, a nightstand, a potted plant, and a red door.

11. Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
5.0 star property
Tuscan Hills
9.0 out of 10, Wonderful, (10 reviews)
"Great stay"
United States
Tiffany
Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
A residential area with a large swimming pool and a golf course.

12. 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
An aerial view of a resort with a central swimming pool, surrounded by lounge chairs and palm trees, with a body of water and buildings in the background.

13. Amazing 4Bd Screened Pool Close to Disney 4572

Amazing 4Bd Screened Pool Close to Disney 4572
5.0 star property
Bellavida
8.4 out of 10, Very good, (8 reviews)
" Great for our family, close to activities, parks, attractiins"
United States
Charlene
Amazing 4Bd Screened Pool Close to Disney 4572
A swimming pool with a glass enclosure, surrounded by a patio area with a view of a residential building.

14. 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
A row of modern two-story houses with attached garages, well-maintained lawns, and a street lamp.

15. 5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney

5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
5.0 star property
Kissimmee
8.0 out of 10, Very good, (10 reviews)
"My family and I truly enjoyed our stay. The team was friendly and communicated effectively the entire time. Will definitely stay again and recommend to others. "
United States
Ben-Jade
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

16. Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887

Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
5.0 star property
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"House was really good..but thermostat wasn't working at all..some part carpet was wet all time"
United States
Pareshkumar
Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
Pool

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
A rectangular swimming pool with a tiled edge, surrounded by a brick patio. There are lounge chairs and a small table near the pool.

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

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
5.0 star property
Kissimmee
6.4 out of 10, (5 reviews)
"The communication was exceptional, before, during and after the stay. Friendly. Everything was like in the pictures. You got everything you need to make your stay as comfortable as your own home."
United States
Denise
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

19. 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 resort with multiple swimming pools, palm trees, and lounge areas.

20. Gorgeous 5Bd Screened Pool at Champions Gate 1125

Gorgeous 5Bd Screened Pool at Champions Gate 1125
5.0 star property
Davenport
9.6 out of 10, Exceptional, (8 reviews)
"The house was exactly as the pictures posted. Very well maintained, cleaned, and well equipped with all essential equipment for cooking ext. My family and I loved it. It exceeded our expectations! We truly recommend this house, and will definitely rent this house again."
United States
Carmen
Gorgeous 5Bd Screened Pool at Champions Gate 1125

Top Historic Downtown Kissimmee Hotel Reviews

A hotel with a swimming pool, lounge chairs, and palm trees.
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

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

10/10 Excellent

Perfect
United States
samuel
Reviewed May 26, 2025
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Frequently Asked Questions

How much does it cost to stay in a 5-star hotel in Historic Downtown Kissimmee?

You can find a range of pricing options for a 5-star hotel in Historic Downtown Kissimmee on Expedia. How much you'll pay will depend on when you travel, length of your trip and other factors. Compare all of the available accommodations for your preferred dates and use our pricing and other filters to discover the perfect high-end stay.

  • Search for the lowest price per night from ₩290,285

What makes a hotel 5 stars in Historic Downtown Kissimmee?

From fine dining restaurants and 24-hour fitness centers to pools and superior bedding, the 5-star experience in Historic Downtown Kissimmee is all about luxury and relaxation. But it requires more than just upscale conveniences to get a 5-star rating. Hotels also have to provide superb guest services like in-room massages, laundry and dry cleaning and 24-hour concierge services.

Are there any 5-star all-inclusive resorts in Historic Downtown Kissimmee?

Find an upscale getaway that includes your room, meals, drinks and entertainment in Historic Downtown Kissimmee with Expedia's filters. Search for properties rated 5 stars and select the "All inclusive" filter. Be sure to check what's included in the price. That way, you can take full advantage of all the premium perks as soon as you arrive.

Are there any 5-star vacation rentals in Historic Downtown Kissimmee?

You won't find any 5-star vacation rentals in Historic Downtown Kissimmee on our site, but there are a few other highly rated properties worth looking into. Search through our vacation rentals in Historic Downtown Kissimmee to discover the best place for your stay.