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

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Historic Downtown Kissimmee 5 Star Hotels

Tonight
20 Jul - 21 Jul
Tomorrow
21 Jul - 22 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Top Historic Downtown Kissimmee 5 Star Hotels

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Guests can enjoy stunning views from the hotel's spacious balconies overlooking a well-maintained pool area surrounded by palm trees.

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5.0 star property
9.2 out of 10, Wonderful, (306)
"This hotel was amazing great rooms and staff."
The price is ₹24,745
₹32,684 total
includes taxes & fees
8 Aug - 9 Aug
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, (242)
"Amazing resort and would definitely go back again "
The price is ₹33,000
₹41,433 total
includes taxes & fees
4 Aug - 5 Aug
Conrad Orlando at Evermore
The Ritz-Carlton Orlando, Grande Lakes
View from property

The Ritz-Carlton Orlando, Grande Lakes

5.0 star property
9.2 out of 10, Wonderful, (1002)
"Excellent place to stay"
The price is ₹32,396
₹41,777 total
includes taxes & fees
3 Aug - 4 Aug
The Ritz-Carlton Orlando, Grande Lakes
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Relax by the pool surrounded by palm and cypress trees, with lounge chairs and umbrellas providing shade.

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

5.0 star property
9.6 out of 10, Exceptional, (859)
"Friendly staffs, awesome pools, great restaurant, will definitely visit again! "
The price is ₹77,974
₹92,567 total
includes taxes & fees
10 Aug - 11 Aug
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Reunion Resort & Golf Club
Surrounded by lush greenery and palm trees, this resort offers multiple pools and a lazy river.

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1346)
"Great Resort."
Reunion Resort & Golf Club
ette hotel
Relax by the pool surrounded by lush tropical plants and lounge chairs.

ette hotel

5.0 star property
9.8 out of 10, Exceptional, (317)
"Great place "
ette hotel
Encore Resort and Water Park At Reunion by Rentyl
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Encore Resort and Water Park At Reunion by Rentyl

5.0 star property
8.4 out of 10, Very good, (1007)
"Perfect home away from home!"
Encore Resort and Water Park At Reunion by Rentyl
WonderFull 4Bd with Pool at Champions Gate 1174
Relax by the resort's central pool, surrounded by palm trees and lounge areas.

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
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Relax by the pool with a clear view of the sky through the glass ceiling.

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
Enjoy a relaxing stay in this home with a spacious garage, balcony, and beautifully maintained yard.

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
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
Enjoy cooking in this fully equipped kitchen with a microwave, oven, and dishwasher.

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 w/ Pool Close to Disney at Champions Gate 1158
Relax by the resort's central pool surrounded by palm trees and lounge areas, offering multiple swimming options.

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
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
Relax by the resort's multiple pools and lounging areas, featuring sun loungers and shaded spots.

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653

5.0 star property
10.0 out of 10, Exceptional, (2)
"Everything was excellent. I like the property was really cozy and nice. The only thing I didn’t like was that more concerned about when you leaving?"
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
Family Friendly Four Bedroom w GameRoom @Disney 5145
Relax in this stylish living room with a sofa, coffee table, and dining area.

Family Friendly Four Bedroom w GameRoom @Disney 5145

5.0 star property
7.4 out of 10, Good, (6)
"It was fantastic!"
Family Friendly Four Bedroom w GameRoom @Disney 5145
Stunning 4Bd With Pool At Storey Lake Resort 4821
Golf

Stunning 4Bd With Pool At Storey Lake Resort 4821

5.0 star property
Stunning 4Bd With Pool At Storey Lake Resort 4821
Family Vacation Home, Water Park+Endless Amenities
Relax by the pool surrounded by lush greenery and palm trees.

Family Vacation Home, Water Park+Endless Amenities

5.0 star property
8.2 out of 10, Very good, (21)
"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
Relax by the pools surrounded by lush greenery and palm trees.

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
Amazing 4Bd Screened Pool Close to Disney 4572
Relax by the resort's central pool surrounded by lounge areas and palm trees.

Amazing 4Bd Screened Pool Close to Disney 4572

5.0 star property
9.4 out of 10, Exceptional, (3)
"The dryer didnt work and No Highchair , also never received my tickets to Water park with Lazy pool ticket. Other than that My Family enjoyed Everything. Pool is a Plus "
Amazing 4Bd Screened Pool Close to Disney 4572
Stunning 4 Bd Close to Disney @ Storey Lake 2569
Relax by the resort's multiple pools, surrounded by palm trees and lounge chairs.

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
Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
Relax by the resort's multiple pools, surrounded by lounge areas and lush vegetation.

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

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

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard, Orlando, FL
The price is ₹15,306 per night from 22 Jul to 23 Jul
₹15,306
₹17,219 total
22 Jul - 23 Jul
includes taxes & fees
9.4/10 Exceptional! (3,392 reviews)
Still don't see what you're looking for?
See all properties in Historic Downtown Kissimmee.
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 Historic Downtown Kissimmee Hotel Reviews

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 ₹7,208

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.