Search Villas in Kissimmee

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Villas in Kissimmee and around

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (323)
"We enjoyed our stay here. We've rented houses in various cities and states, and I appreciated that this property was well-stocked. We didn't have to take time from our trip to get extra dish soap, paper towels, pool towels, etc. Especially for a shorter trip, this was wonderful! It was convenient enough to all the parks and our needs. The home was well-appointed and just as pictured. The kids enjoyed the themed rooms, video games and theater room. The community may not have been as charming as...
Lakeview Luxury Villa with Everything

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (373)
"The home was beautiful. The managers were responsive. There had been unexpected updates to the game room that were a wonderful surprise. Seems there is a leak in pool filter but this has a minimal affect on use of pool. We stayed for 5 days and had a great time! "
Modern Luxury Villa with Everything

Lakeview Luxury Villa with Everything

10.0 out of 10, Exceptional, (72)
"Love the property! Great hosts, house and location! "
Lakeview Luxury Villa with Everything

Ultimate Lakeview Villa with Everything!

9.4 out of 10, Exceptional, (98)
"The house was exactly what we needed. It was close for both our work commimments and also for our Disney time when work was over.The house exceeded our expectations it was clean, roomy but most of all FUN to stay in. There was something for everybody. from the "Frozen" theamed bedroom through to the Games room and Pool with Hot tub!"
Ultimate Lakeview Villa with Everything!

Heavenly 5 Bedroom, 6 Bathroom Private Pool Home with Beautiful Lakeview in Gated Resort!

9.2 out of 10, Wonderful, (9)
"The house is beautiful, biggest, confortable. We lover and our children too. So near to a walmart and to disney. Fully recomended"
Heavenly 5 Bedroom, 6 Bathroom Private Pool Home with Beautiful Lakeview in Gated Resort!

Large Margaritaville Villa w/ Private Pool + View

4.0 star property
8.4 out of 10, Very good, (5)
"Great property, comfortable beds, kitchen equipped with everything you need, washer and dryer, dinning table for 10 people, every room with tv, terrace tv, bathroom and small pool but very pleasant. No rooms on first floor. 3 rooms on second floor and 2 rooms on third floor. I will stay again."
Large Margaritaville Villa w/ Private Pool + View

*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney

9.2 out of 10, Wonderful, (62)
"Pretty good stay. We've always enjoyed the location of Windsor Hills; close to Disney, easy to get to, comfortable and safe. The house was roomy and more than adequate for our family of twelve. If there was anything negative it would be: only two cars can be parked in the driveway (if you have a 3rd car, it has to be parked at the main entrance area), the pool was murky and not useful for our stay. The pool maintenance guy came out twice to add chemicals, but didn't solve it. No kitchen towels....
*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney

Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View

8.6 out of 10, Excellent, (83)
"We have stayed at this property 3 times. The host is amazing, very responsive and kind. The location is great and the home is a great value. "
Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View

Ultimate Lakeview Villa with Everything!

9.8 out of 10, Exceptional, (334)
"We was very impressed with everything there. Worked out great for our needs. "
Ultimate Lakeview Villa with Everything!

Villa in Kissimmee next to Disney!

8.0 out of 10, Very good, (16)
"Nothing really to complain about, a little dusty and could use a deep cleaning for the carpets"
Villa in Kissimmee next to Disney!

Modern Luxury Villa with Everything

9.6 out of 10, Exceptional, (211)
"Our entire family from old to young enjoyed this vacation home. We weren’t far at all to all Disney parks. Lots of restaurants and shopping options near the home. Very quiet area to be able to rest and relax in between park visits. Communication was very simple and easy also. If we go back to Disney, we will be back to this property for sure!"
Modern Luxury Villa with Everything

Modern villa with patio, grill, central AC, WiFi, shared pool, tennis, & gym

9.6 out of 10, Exceptional, (7)
"We would return again"
Modern villa with patio, grill, central AC, WiFi, shared pool, tennis, & gym

Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community

8.6 out of 10, Excellent, (33)
"Lovely villa, excellent area to stay, we loved the club house and all the amenities. Would definitely stay again. Any problems we had were sorted quickly, excellent service. "
Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community

Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

10.0 out of 10, Exceptional, (169)
"The home and location were just as stated on line. We paid extra for the pool to heated during our stay and it was perfect. The home is within easy access to shopping, groceries, restaurants, and theme parks. The home had lots of glasses, dishes, and cutlery. The downside to our trip was it there was not enough essentials in the home. There was 6 adults and 3 children in our group and we stayed for 9 days. We only had the 1 roll of toilet paper that was on the dispenser in each bathroom,...
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

Experience Kissimmee living near vibrant Old Town

9.4 out of 10, Exceptional, (28)
"Basically nice and convenient property. Jump to the cons: dated, ceiling fan in living room absolutely filthy. Two story house with 1 thermostat, upstairs hot and lower level cold. Ordered pool heated and couldn't get water above 70⁰ ( note: it was unusually cold during our stay. Owner was very responsive and refunded heating fees in full.) Even with just a 2 night stay we ran out of toilet paper. There wasn't even half a roll in each bathroom.We were only there for 2 nights before a cruise so...
Experience Kissimmee living near vibrant Old Town

Private Heated Pool! Only 8 miles to Disney! Gated Community

10.0 out of 10, Exceptional, (51)
"Clean, quiet, close to Disney, great communication and easy check in and out procedures. Everything was perfect and smooth. Would definitely stay here again. "
Private Heated Pool! Only 8 miles to Disney! Gated Community

Beautiful 12 bedroom 11 Bathroom house Bella Vida Resort Villa

8.6 out of 10, Excellent, (4)
"The house was great and fit our needs very well. Large kitchen with 2 refrigerators and 2 dishwashers, as well as well-stocked cupboards with dishes. The dining and living room area was comfortable for all of us. The game room was wonderful for the kids and we all enjoyed the pool and hot tub. Located close to many parks and shopping areas. We enjoyed the house very much! "
Beautiful 12 bedroom 11 Bathroom house Bella Vida Resort Villa

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

10.0 out of 10, Exceptional, (272)
"The stay was really good. The host was fantastic and communicated well. The only problem we had was ants on the kitchen counter."
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

South facing pool & spa on water conservation area in gated community

10.0 out of 10, Exceptional, (12)
"Excellent property. Well-maintained house with plenty of space. Will definitely recommend this location to friends and family. "
South facing pool & spa on water conservation area in gated community

Luxury 7 bedroom Villa on the gated Bellavida Resort, close to everything Disney

2.0 star property
8.0 out of 10, Very good, (7)
"Overall good stay. Would recommend "
Luxury 7 bedroom Villa on the gated Bellavida Resort, close to everything Disney
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.
Don't see what you're looking for?
See all available properties in Kissimmee
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Kissimmee

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1529)
"Several pool and hot tub options. Nice area for walking. Family friendly. Shuttle around the village and to grocery store. Friendly staff While it is generally peaceful, we could hear moving of furniture and other sounds from the unit above us. "
The price is €113
includes taxes & fees
23 Mar - 24 Mar
Vacation Village at Parkway

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1209)
"Everything appeared to be new and clean. The cottages were near all the attractions and the staff was efficient and friendly. "
Margaritaville Resort Orlando Cottages by Rentyl

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1689)
"Easy checking in"
The price is €117
includes taxes & fees
3 Mar - 4 Mar
Barefoot Suites
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 do villas in Kissimmee cost?
Villas in Kissimmee range between and per night. These getaways provide the privacy to enjoy your own space at a price that fits your budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Kissimmee?
Choose from multiple villas in Kissimmee that have a total average guest review rating of 9.2. 4962 Windermere Ave is always a hit with travellers. This 4.5-star stay features a swimming pool and a terrace. Ultra Luxury 6 Bedroom Massimo With Pool By Disney 6 Bedroom Villa is another good option. It has a 3-star rating and conveniences such as a barbecue grill and a swimming pool.
How many villas are there in Kissimmee?
Kissimmee has 5868 villas to select from. Find your perfect stay quickly and easily by clicking the “Villa” checkbox under the “Property type” tab in our filter tool.
What are the best cheap villas in Kissimmee?
With villas starting from only per night, you may want to extend your trip to Kissimmee! One option that’s easy on your budget is Christine’s Villa - 3 Bedroom Villa By Redawning. It comes with the privacy and comfort you need as well as a swimming pool and a barbecue grill. Another cost-effective choice is Windsor At Westside 1780. A swimming pool and WiFi are just two of the many conveniences here. If you’d like to hold on to your hard-earned dollars and still experience the best of Kissimmee, add a few fabulous free attractions to your must-do list. Osceola Square Mall and 192 Flea Market are always popular among visitors. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly villas in Kissimmee?
Kick back at 4962 Windermere Ave, a 4.5-star option just a short drive from town. Conveniences here include a playground and an oven. Another family-friendly getaway is Ultra Luxury 6 Bedroom Massimo With Pool By Disney 6 Bedroom Villa. WiFi and an oven help make this 3-star retreat a hit with travellers. Once you’ve checked in and dropped off your bags, there’s no shortage of family-friendly attractions to explore around Kissimmee. Kissimmee Golf Club and 192 Flea Market are two of our top picks.
Are there any 5-star villas in Kissimmee?
Free Resort Access 4 Bedroom Near Disney With Themed Rooms is an excellent 5-star villa in Kissimmee. Around 6 kilometres from the downtown area, a swimming pool and a private entrance are among the amenities here. Waterpark Near Disney - Luxury Townhome is another luxurious stay around 10 kilometres from the city centre. Also rated 5 stars, this property includes a swimming pool and a private entrance.
Why book your villa in Kissimmee with Expedia?
We think that holidays shouldn’t be complicated, so if you’re on the lookout for villas at a competitive price, Expedia has you covered. Save those pennies and opt for an all-inclusive stay, or splurge on a luxe villa to treat your sweetheart. Our handy filters make it easy to secure a property in Kissimmee that meets your needs.
How can I find cheap villas in Kissimmee?
With Expedia’s filter tool, scoring cheap villas in Kissimmee is a breeze. To find accommodation that are gentle on your bank balance, refine your search by budget, star rating and amenities.
What is there to do near my villa in Kissimmee?
You’ll find plenty of superb things to fill your days in Kissimmee. Drop by big attractions like Fun Spot America, Medieval Times and Capone’s Dinner Show. Skate Reflections, AMF Bowling Centre and Wizardz Magic Theatre are also visited by many.