Find 5 Star Hotels in Historic Downtown Kissimmee, FL from $88

Compare Historic Downtown Kissimmee 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Waldorf Astoria Orlando
5.0 star property
9.0 out of 10, Wonderful, (19)
"Check in was smooth, our room was fantastic! Our evening at Bull & Bear was exceptional. We thoroughly enjoyed our stay! "
The price is $319
$415 total
includes taxes & fees
Jun 23 - Jun 24
Waldorf Astoria Orlando
Conrad Orlando
5.0 star property
9.8 out of 10, Exceptional, (36)
"Beautiful property. "
The price is $397
$503 total
includes taxes & fees
Jun 16 - Jun 17
Conrad Orlando
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5.0 star property
9.6 out of 10, Exceptional, (782)
"We stayed at the four seasons for our family getaway and we dont know where to start from phenomenal resort. The staff were amazing service was above and beyond. Restaurants amazing and great food! Very family friendly and a very safe resort. We would definitely recommend."
The price is $1,005
$1,131 total
includes taxes & fees
Jun 23 - Jun 24
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
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The Ritz-Carlton Orlando, Grande Lakes
5.0 star property
9.2 out of 10, Wonderful, (1001)
"Ester was an excellent host. "
The price is $399
$502 total
includes taxes & fees
Jun 15 - Jun 16
The Ritz-Carlton Orlando, Grande Lakes
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1126)
"Excellent service "
The price is $232
$304 total
includes taxes & fees
Jun 9 - Jun 10
Reunion Resort & Golf Club
Encore Resort at Reunion
5.0 star property
8.4 out of 10, Very Good, (736)
"Very private "
Encore Resort at Reunion
Splendid 5Bd Close to Disney at Storey Lake 4251
5.0 star property
9.4 out of 10, Exceptional, (3)
"Excellent property . Really clean and lots of space. Really close to Disney and plenty of restaurants a short drive away. My only complaint is the communication for check in. I got message and phone call 30 mins before check in saying if I don't fill out check in form my booking would be cancelled. This really wasn't ideal as I was driving. After I did it I received so many text and emails to help with my stay. I was getting them from several different numbers. Then 3 hrs after checking out. 4...
Splendid 5Bd Close to Disney at Storey Lake 4251
The Bear's Den Resort Orlando
5.0 star property
7.6 out of 10, Good, (16)
"Great experience "
The Bear's Den Resort Orlando
Waterpark Near Disney - Luxury Townhome
5.0 star property
8.2 out of 10, Very Good, (12)
"All the pool amenities and activities were great. The resort staff was great and stuck to the rules. I would say they could lighten up on the required tubes in the river and no jumping in the big pool. Place is for families and my kids got disappointed when they were asked to not jump in the pool at all, not even just a cannon ball. Im 41 and was told i needed a tube in the 3' lazy river. I was just walking around the river with my little kids"
Waterpark Near Disney - Luxury Townhome
7 Bedroom Villa, Private Pool, Resort Amenities
5.0 star property
8.0 out of 10, Very Good, (3)
"Everything was nice "
7 Bedroom Villa, Private Pool, Resort Amenities
Mickey's Terrace at Bahama Bay
5.0 star property
6.6 out of 10, (4)
"Pros: Kitchen and appliances sparkling upon arrival. Quiet section of the resort. Kitchen well appointed, although time to replace some of the cooking pans. Cons: Carpeting in poor shape. Needs to be replaced. Some plumbing issues (faucets dripping, guest bath shower control handle loose). "
Mickey's Terrace at Bahama Bay
Apartamento en Orlando Fl.
5.0 star property
2.0 out of 10, (1)
The price is $596
$671 total
includes taxes & fees
Jun 4 - Jun 5
Apartamento en Orlando Fl.
Family Vacation Home, Water Park, Endless Resort Amenities
5.0 star property
9.0 out of 10, Wonderful, (24)
"My entire family enjoyed our stay. The unit was spacious, comfortable, clean, and well equipped. The resort amenities kept the kids busy. The resort staff and security were friendly and helpful."
Family Vacation Home, Water Park, Endless Resort Amenities
Endless Summer at Margaritaville
5.0 star property
10.0 out of 10, Exceptional, (6)
"Property was clean and comfortable. Property manager was easy to communicate with answered any questions promptly."
Endless Summer at Margaritaville
House of Fun at Windsor Westside
5.0 star property
10.0 out of 10, Exceptional, (1)
"Very Nice. Great communication."
House of Fun at Windsor Westside
Chasing Adventures
5.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean and roomy. Great location to Disney and lots of restaurants and stores. "
Chasing Adventures
The Good Life at Legacy Park
5.0 star property
10.0 out of 10, Exceptional, (2)
"The host were quick to respond and friendly. The house is beautiful and clean. I felt like we were at a five star hotel. Our girls loved it so much they rathered stay at the house instead of going to explore Florida. We will definitely book this place again!"
The Good Life at Legacy Park
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
5.0 star property
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
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
Up to Scale at Margaritaville
5.0 star property
10.0 out of 10, Exceptional, (1)
"Otima experiência. Localização excelente. Facil acesso aos parques da Disney. Proxima a supermercados, restaurantes, e lojas. A casa é muito congortavel e o Check in e check out muito faceis de realizar. Retornaremos com certeza."
Up to Scale at Margaritaville

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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 depends on factors such as when you want to go and the length of your getaway. An insider tip for landing an awesome deal? Use our pricing filters to compare the available accommodations for your chosen dates.

  • Search for the lowest price per night from $88

What makes a hotel 5 stars in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, a hotel must provide a certain amount of upscale conveniences to be designated 5 stars. These can include on-site gyms, saunas and spas, gourmet restaurants, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their superior service. You’ll enjoy things like nightly turn-down services, concierge services and in-room massages. Some may even offer additional touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Historic Downtown Kissimmee?
Use our filter tool to find a high-end retreat in Historic Downtown Kissimmee where most of what you need is included in the price. After your initial search, narrow down your results for resorts that have a rating of 5 stars and are deemed “All inclusive.” The most important thing on the to-do list at these stays? Relaxation and indulgence.
Are there any 5-star vacation rentals in Historic Downtown Kissimmee?
There are no 5-star vacation rentals in Historic Downtown Kissimmee on our site, but there are a range of other highly rated properties worth checking out. Search through our vacation rentals in Historic Downtown Kissimmee to discover the perfect place for your stay.