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Featured Kissimmee 5 Star hotels

ette hotel

ette hotel

5 out of 5
3001 Sherberth Rd Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $405 per night from Jun 15 to Jun 16
CA $405
CA $460 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this luxury hotel in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (447 reviews)
"Amazing stay from start to departure. Helpful courteous staff, great decor. Overall, a true 5+_star experience"

Reviewed on May 5, 2026

Opens in a new windowette hotel
Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl

5 out of 5
7635 Fairfax Dr Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $378 per night from May 19 to May 20
CA $378
CA $1,022 total
May 19 - May 20
includes taxes & fees
Book a stay at this luxury resort in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. ...
Opens in a new windowEncore Resort and Water Park at Reunion by Rentyl
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
7593 Gathering Drive Kissimmee FL
Book a stay at this luxury aparthotel in Kissimmee. Enjoy 11 outdoor pools, 7 restaurants, and a golf course. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowReunion Resort & Golf Club
The Bear's Den Resort Orlando

The Bear's Den Resort Orlando

5 out of 5
7880 Nicklaus Clubhouse Lane Kissimmee FL
Book a stay at this luxury vacation home in Kissimmee. Enjoy free WiFi, free parking, and a golf course. Popular attractions ESPN Wide World of Sports Complex ...
7.8/10 Good! (24 reviews)
"Ivan at checkin was wonderful but the house had issues from the start. the entire pool deck wasn't cleaned, goggles floating in hot tub, crushed fruity pebbles, cigar and cigarettes butts on the ground and previous renters left heat on in spa/pool so pool was 103 degrees. Multiple calls to get resolution ..."

Reviewed on Apr 21, 2026

Opens in a new windowThe Bear's Den Resort Orlando
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 out of 5
2887 Stanza Ct Kissimmee FL
Book a stay at this luxury vacation home in Kissimmee. Enjoy free parking, private pools, and free water park access. Popular attractions Old Town and Disney ...
Opens in a new windowFantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

5 out of 5
4836 Dedication Street Kissimmee FL
Book a stay at this luxury vacation home in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Old Town and Disney Springs™ are ...
9.2/10 Wonderful! (16 reviews)
"The pool is screened in which was great! We got the pool heater (extra) it was working most of the time. When it wasn’t they got it checked out the next day. The hall bathroom upstairs shower was used by one person once and had some leaking in the kitchen. We reported right away and didn’t use that ..."

Reviewed on Mar 29, 2026

Opens in a new windowGorgeous 4 Bedroom w/ Pool Close to Disney 4836
Stunning 2 Bd Condo Close to Disney 304 3191

Stunning 2 Bd Condo Close to Disney 304 3191

5 out of 5
3191 Paradox Circle Kissimmee FL
Book a stay at this luxury condo in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Old Town and Disney Springs™ are located ...
5/10 (6 reviews)
"This property did not meet expectations based on the listing. The unit is advertised as sleeping seven guests and offering BBQ access, but neither was accurate during our stay. Communication was also very frustrating. It was not possible to reach an on-site property manager; instead, we were routed ..."

Reviewed on Mar 31, 2026

Opens in a new windowStunning 2 Bd Condo Close to Disney 304 3191
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms

2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms

5 out of 5
3191 Sea World Court Kissimmee FL
Book a stay at this luxury villa in Kissimmee. Enjoy free WiFi, free parking, and free water park access. Popular attractions Old Town and Disney Springs™ are ...
8.2/10 Very Good! (20 reviews)
"Pool was great kids loved it. Came with blender and coffe maker."

Reviewed on Apr 19, 2026

Opens in a new window2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191

Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191

5 out of 5
3191 Paradox Cir #404 Kissimmee FL
Book a stay at this luxury apartment in Kissimmee. Enjoy free parking, private pools, and free water park access. Popular attractions Old Town and Disney Springs™ ...
8.8/10 Excellent! (6 reviews)
"This place was great. We stayed here for 6 nights in Jan 2026. Family of 4. We were able to check in a couple hours early - thank you Wonder Vacations team. The place is spacious and airy and was prepared very well for our arrival: everything was clean and tidy. It is newly renovated condo with updated ..."

Reviewed on Jan 26, 2026

Opens in a new windowGorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

5 out of 5
461 Lasso Drive Kissimmee FL
Book a stay at this luxury villa in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions ESPN Wide World of Sports Complex and Disney's ...
5.6/10 (4 reviews)
"Problemas con la ducha del baño, se dañó y quedó encendida con agua caliente saliendo no cerraba, tardaron 4 días en atender la situación. Los números de teléfono para llamar no funcionan, nadie los atiende, la asistencia al cliente vía Email, es decepcionante, Expedia me ayudo a contactarlos pero ..."

Reviewed on Jul 22, 2025

Opens in a new windowWonderful 8Bd w/ Pool & GameRoom @ Encore 461
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Five Star Hotels in Kissimmee

Looking for your own little slice of heaven during your next trip? Check out all the best 5 star hotels in Kissimmee to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the five star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Kissimmee 5 star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5 star hotels in Kissimmee before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

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