Compare and book 5 Star hotels in Historic Downtown Kissimmee, Orlando

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Check availability on Historic Downtown Kissimmee 5 Star Hotels

Tonight
26 Jun - 27 Jun
Tomorrow
27 Jun - 28 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Historic Downtown Kissimmee 5 Star Hotels

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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5.0 star property
9.2 out of 10, Wonderful, (281)
"Excellent service and food "
The price is 7.509.993 ₫
9.919.624 ₫ total
includes taxes & fees
25 Jul - 26 Jul
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Conrad Orlando at Evermore
Outdoor pool, pool cabanas (surcharge), pool umbrellas

Conrad Orlando at Evermore

5.0 star property
9.4 out of 10, Exceptional, (221)
"The lagoon was perfect"
The price is 11.191.772 ₫
13.898.194 ₫ total
includes taxes & fees
14 Jul - 15 Jul
Conrad Orlando at Evermore
The Ritz-Carlton Orlando, Grande Lakes
Property amenity

The Ritz-Carlton Orlando, Grande Lakes

5.0 star property
9.2 out of 10, Wonderful, (1004)
"Well maintained, high-end property and friendly staff. "
The price is 10.694.941 ₫
13.649.909 ₫ total
includes taxes & fees
30 Jun - 1 Jul
The Ritz-Carlton Orlando, Grande Lakes
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
3 outdoor pools, pool cabanas (surcharge), pool umbrellas

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

5.0 star property
9.6 out of 10, Exceptional, (851)
"Great stay highly recommended "
The price is 26.026.215 ₫
30.750.823 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1313)
"We had a fantastic time, enjoyed our stay and will definitely go back again"
The price is 5.474.660 ₫
7.453.582 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Reunion Resort & Golf Club
ette hotel
Outdoor pool, open 9:00 AM to 6:00 PM, free pool cabanas, pool umbrellas

ette hotel

5.0 star property
9.8 out of 10, Exceptional, (310)
"great hotel and very friendly staff very clean rooms and fast service "
ette hotel
Encore Resort and Water Park At Reunion by Rentyl
Outdoor pool, a heated pool, pool cabanas (surcharge), pool umbrellas

Encore Resort and Water Park At Reunion by Rentyl

5.0 star property
8.4 out of 10, Very good, (1002)
"Can’t wait to come back, our family loved our stay, close enough to all the major parks, plazas and airport and then a touch of home when you get back and relax with the privacy of the yard "
Encore Resort and Water Park At Reunion by Rentyl
Splendid 5Bd Close to Disney at Storey Lake 4251
Water park

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
Exclusive House | Private pool

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
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
Water park

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

5.0 star property
10.0 out of 10, Exceptional, (4)
"Fantastic!"
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
The Bear's Den Resort Orlando
Front of property

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
Outdoor pool

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
WonderFull 4Bd with Pool at Champions Gate 1174
Resort view

WonderFull 4Bd with Pool at Champions Gate 1174

5.0 star property
9.0 out of 10, Wonderful, (4)
"This home was exactly as the pictures and more. It was beautiful and perfect size for my family. The pool was also perfect when we didn’t want to be in the crowds anymore at the resorts. Wonder vacation homes were amazing hosts and took great care of all of our questions "
WonderFull 4Bd with Pool at Champions Gate 1174
Charming 3Bd Close to Disney @ Festival 1026
In-room safe, individually decorated, individually furnished, desk

Charming 3Bd Close to Disney @ Festival 1026

5.0 star property
8.8 out of 10, Excellent, (3)
"Nice location "
Charming 3Bd Close to Disney @ Festival 1026
Gorgeous 5Bd Screened Pool at Champions Gate 1125
Water park

Gorgeous 5Bd Screened Pool at Champions Gate 1125

5.0 star property
9.4 out of 10, Exceptional, (3)
"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."
Gorgeous 5Bd Screened Pool at Champions Gate 1125
Family Vacation Home, Water Park+Endless Amenities
Water park

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
Reunion Resort & Golf Club
10 outdoor pools, pool umbrellas, pool loungers

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (12)
"Enjoy the accommodations view was wonderful and close to everything"
Reunion Resort & Golf Club
Family Friendly Four Bedroom w GameRoom @Disney 5145
Exclusive House | In-room safe, individually decorated, individually furnished, desk

Family Friendly Four Bedroom w GameRoom @Disney 5145

5.0 star property
8.4 out of 10, Very good, (5)
"Nice comfortable accomodation, only 2 minor complaints; a lot of parked cars in the streets makes it hard to get on and of the private driveways sometimes and our patio was not accessible due to renovations which we were not aware of."
Family Friendly Four Bedroom w GameRoom @Disney 5145
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
Exclusive House | Private kitchen | Full-sized fridge, microwave, oven, stovetop

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
Water park

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
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Historic Downtown Kissimmee.
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard, Orlando, FL
The price is 5.203.651 ₫ per night from 8 Jul to 9 Jul
5.203.651 ₫
5.854.238 ₫ total
8 Jul - 9 Jul
includes taxes & fees
9.4/10 Exceptional! (3,313 reviews)
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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 Historic Downtown Kissimmee?
The amount you pay for a 5-star hotel in Historic Downtown Kissimmee can vary depending on the time of year you travel and how long you plan to stay, among several factors. Use our price per night filter and other search tools to find the best rate on a luxurious getaway.
  • Search for the lowest price per night from 2.483.346 ₫

What makes a hotel 5 stars in Historic Downtown Kissimmee?
From high-end dining venues and all-day gyms to pools and dreamy bedding, the 5-star experience in Historic Downtown Kissimmee is all about comfort and luxury. But it requires more than just top-notch perks to get a 5-star rating. Accommodation must also deliver outstanding guest-focused services like beauty treatments, on-site dry cleaning and laundry and room service any time night or day.
Are there any 5-star all-inclusive resorts in Historic Downtown Kissimmee?
Our handy filters are the best way to narrow down what you're looking for. Select "All inclusive" and "5-star" to see the most upscale properties in Historic Downtown Kissimmee where your accommodation, meals, activities and entertainment are included in the price. At these stays, your trip is pure extravagance from the moment you enter the lobby.