We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Kissimmee, FL

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 3,952 Rentals in Kissimmee
loading...
Sort by
From
$121
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
23 photos Details Reviews (8) Make Inquiry
From
$240
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 14
Bookings
24 photos Details Reviews (2) Make Inquiry
From
$90
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
21 photos Details Reviews (2) Make Inquiry
Also consider
Barley house
5 Bedrooms, sleeps 10
$137 / night
Disney - 4 Bed Villa + Private Pool+games Room
4 Bedrooms, sleeps 8
$105 - $127 / night
Westgate Vacation Villas--Orlando, FL
1 Bedroom, sleeps 4
$800 / week
The Great Escape
4 Bedrooms, sleeps 9
$116 - $127 / night
From
$120
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
20 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 5, 2013
The house was plenty spacious and a very good location to everything we needed. Having a private pool was terrific for our children to swim anytime they wanted. We had a wonderful...
See all reviews
From
$106
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
24 photos Details Reviews (11) Make Inquiry
5 of 5 stars Reviewed October 8, 2014
Our 2 night stay was perfect! We booked this trip at the last minute to celebrate my 40th birthday! The kids loved the pool and game room, there was plenty for everyone to do...
5 of 5 stars Reviewed August 3, 2014
We really enjoyed our stay in Paula's villa it has a real home from home feel. Paula contacted us to see if all was ok (which is a nice touch). I wanted to celebrate my 50th...
See all reviews
From
$100
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
22 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed June 23, 2014
We had a fabulous holiday at this villa. Everything was as described. The area was very quiet and peaceful. Supermarkets and restaurants are close by. It took a bit longer to get...
5 of 5 stars Reviewed May 1, 2014
Our first trip to Florida and Ventura Villa. This defiantly won't be my last. The house was super clean and spacious. Its located in a quiet neighborhood only minutes from all...
See all reviews
From
$63
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
15 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 27, 2014
The condo is in a great location, not far from Disney. It was clean & well kept, all facilities supplied, TVs in all rooms. Nice area, pool was great too.
4 of 5 stars Reviewed August 13, 2014
Nice, clean and great size condo Very close to Disney and close to a lot of restaurants and other facilities Quiet Have good fun at the pool
See all reviews
From
$97
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
23 photos Details Reviews (12) Make Inquiry
5 of 5 stars Reviewed July 13, 2014
Stayed at this accommodation with a 19 year old and 18 year old and it provided everything we could want or need. Great location, extremely clean and a lovely place to come back...
5 of 5 stars Reviewed May 19, 2014
My family had a great time in Kissimmee. Condo was nicely decorated and cozy. Had all the comforts of home. Quiet area and close to everything. Kitchen was well-equipped...
See all reviews
Get the List
From
$105
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
22 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed September 26, 2014
I stayed in this home for 3 weeks - it was amazing !! It had everything you needed and more, the living room is nicely decorated and the house was very clean. The house was an end...
5 of 5 stars Reviewed March 16, 2014
The quality of service from the owner of this property is more than enough to inspire us to return! The residence was far better than we could have expected. The place was clean...
See all reviews
From
$70
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
24 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed September 21, 2014
The House was very nicly decorated. 3 good sized bedrooms, with comfortable beds. Kitchen was fully equipped. Netflix was very good to have for the kids. Short drive to...
5 of 5 stars Reviewed August 25, 2014
We were there end of June 2014 for about 3 weeks. The owner Paul sent us an email with all the useful informations for the relevant stay, which is very kind and helpful. Perfect...
See all reviews
From
$1,110
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
24 photos Details Reviews (10) Make Inquiry
5 of 5 stars Reviewed September 22, 2014
We have today returned home from a holiday at this fantastic villa. From the moment we booked it, we had great communication with the owner (Steve) who supplied us with all the...
5 of 5 stars Reviewed January 13, 2014
Apologies Steve for the delay in reviewing! Real life has taken over - the holiday is but a distant but very fond memory! This is our second time in Orlando, and our first...
See all reviews
From
$32
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
20 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed August 24, 2013
Excellent accommodation. Very clean and very comfortable. Looks over a lake at back with lots of wildlife to watch from the lounge or conservatory. The club house is good and the...
See all reviews
From
$240
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 16
Booking
22 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 7, 2014
My family and I just returned from an excellent stay at Sri's property, Simba's Magic! The home is beautifully decorated and the pictures don't do it justice! It was the...
See all reviews
From
$64
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
24 photos Details Reviews (5) Make Inquiry
4 of 5 stars Reviewed August 23, 2014
A big thank you to Mary, the booking process was simple and I was in touch with her throughout the whole process, from general enquiry to booking and even questions via email...
5 of 5 stars Reviewed August 6, 2014
the complex was well maintained and looked after,the condo was clean and tidy with all the amenities that you needed . The pool was great after a long day at the parks to relax...
See all reviews
From
$105
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
12 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed January 24, 2014
This home was everything we needed for our stay in Florida, it was quiet and had all the amenities we required. There was plenty of space and the pool and hot tub were both much...
See all reviews
From
$240
Per Night
6 Bedrooms, 6 Bathrooms, Sleeps 14
Booking
24 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed August 24, 2014
The house and the resort it's on are lovely and very we'll cared for. The house it self is fabulous and can cater for the 9 of us easily and having the pool and spa is a wonderful...
See all reviews
From
$105
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
10 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed October 8, 2014
The villa is MASSIVE. A little outdated in places and not quite up to my standards cleanliness-wise. However, the layout of the villa is very well thought out and looks...
4 of 5 stars Reviewed May 11, 2014
We had a wonderful time in the house, was clean and had everything you needed, was a real home from home. The house was situated near to all the attractions and was convenient...
See all reviews
From
$100
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
24 photos Details Make Inquiry
From
$75
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
13 photos Details Make Inquiry
From
$676
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
19 photos Details Make Inquiry
From
$153
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
24 photos Details Make Inquiry
From
$140
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
20 photos Details Make Inquiry
From
$240
Per Night
7 Bedrooms, 4 Bathrooms, Sleeps 16
24 photos Details Make Inquiry
From
$140
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
19 photos Details Make Inquiry
From
$113
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
16 photos Details Make Inquiry
From
$240
Per Night
7 Bedrooms, 4 Bathrooms, Sleeps 16
Booking
23 photos Details Make Inquiry
From
$95
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
15 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed July 24, 2014
"Our stay has been outstanding .We couldn't fault the villa or its location in any way. Steve the owner was very friendly and helpfull...nothing was too much trouble. The photos...
5 of 5 stars Reviewed May 28, 2014
I stayed in this villa with my family at the end of April and the first week in May. It is a well equipped and maintained villa with a lovely pool area. The master bedroom and en...
See all reviews
From
$105
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
21 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed July 17, 2014
We stayed in this Villa for 2 weeks in June. 4 Adults and a small child and it was brilliant. The villa is in a great setting, very quiet and ideal for visiting Disney...
5 of 5 stars Reviewed February 3, 2014
My husband and I traveled to FL to visit the parks and have a leisurely time with our two children (ages 18 and 3). This home was the best choice we could've made. It was very...
See all reviews
From
$142
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
20 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed September 5, 2014
We chose this rental through Trip Advisor and from the moment we booked we had nothing but fantastic service from Maureen. Any questions we raised she answered and the whole...
5 of 5 stars Reviewed March 21, 2014
The house was simply perfect for our entire family and we had the most enjoyable time there. We could not have asked for anything more. There were 12 of us, eight adults and 4...
See all reviews
From
$72
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
24 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed August 24, 2014
We arrived during a summer downpour but it did not affect our very good impression of the place, a very nice condo, very quiet and extremely well located, close to all parks and...
5 of 5 stars Reviewed July 24, 2014
My son and I traveled to Disney for a short summer visit to celebrate his 13th birthday. This is a great condo - very comfortable, clean, well furnished/stocked and in a nice...
See all reviews
From
$981
Per Week
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
20 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed July 16, 2014
We have stayed in villas for the last 10 years and have enjoyed many great holidays, but this villa was just superb. We couldn't rate it anything other than magnificent...
5 of 5 stars Reviewed May 16, 2014
I have been fortunate to have stayed at this property for the last 4 years and every year the holiday just seems to get better and better. The owners and property management...
See all reviews
From
$124
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
14 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed June 17, 2014
After a lengthy search for a villa that ticked all the boxes, we chose to stay at Witcomb Villa for our fortnight holiday in Florida, and were certainly not disappointed! The...
See all reviews
From
$95
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
12 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed June 17, 2014
Now I have stayed in this Villa in Florida, i don't know how i will be able to go back to a shared pool and small room in a hotel as such on other holidays. The Villa is...
5 of 5 stars Reviewed May 22, 2014
The villa was very home from home, it had everything we needed and more for a perfect two week holiday. Our kids loved the pool and the games room so much they swapped a day at...
See all reviews
From
$48
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
20 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed September 8, 2014
This holiday home has it all under 1 roof, 4 bedrooms, 3.5 bathrooms a spacious kitchen, dinning room and lounge, it also boasts an impressive outdoor patio for relaxing and a...
5 of 5 stars Reviewed June 12, 2014
this rental was super nice my fam. and kids felt safe , like the house we stayed at it was clean and beautiful comfortable ,easy to get to ,close to the parks about 1/2 hour on...
See all reviews
From
$72
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
16 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 9, 2014
We had a great Stay at the Terra Verde Townhome. It has all your basic needs. The Kitchen was well equiped. The furnishings are low budget items. Townhome has a washer and...
5 of 5 stars Reviewed September 26, 2014
Rente la casa sin tener la opinión de nadie para orientarme, pero valió la pena el resort es hermoso tiene un lago, picina, espacios recreacionales y la casa en si es muy cómoda...
See all reviews
From
$137
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
24 photos Details Reviews (2) Make Inquiry
3 of 5 stars Reviewed April 8, 2012
Owner was helpful with questions before booking and returned security deposit very quickly. Emerald island is a great location for Disney and also the 192. The resort facilities...
4 of 5 stars Reviewed October 12, 2011
We stayed here for our very first trip to Disney World with our three teenaged daughters and our young grade-school daughter. We loved the home; it had everything we needed...
See all reviews
From
$97
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
14 photos Details Make Inquiry
From
$121
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details Make Inquiry
From
$161
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
24 photos Details Make Inquiry
From
$137
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
17 photos Details Make Inquiry
Go to map view
Book Online(2559)
Use filters to find the best results!

Suitability

  • Wheelchair access (590)
  • Elder access (1,524)
  • Suitable for children (2,052)
  • Pet friendly (183)
  • Smoking allowed (9)

Amenities

  • Air Conditioning (2,770)
  • Internet (2,694)
  • All pools (2,430)
  • Other outdoor space (1,796)
  • Washer/Dryer (1,779)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List

More Family destinations:

More Golf destinations:

Filter search results by:
Book Online(2559)

Suitability

  • Wheelchair access (590)
  • Elder access (1,524)
  • Suitable for children (2,052)
  • Pet friendly (183)
  • Smoking allowed (9)

Amenities

  • Air Conditioning (2,770)
  • Internet (2,694)
  • All pools (2,430)
  • Other outdoor space (1,796)
  • Washer/Dryer (1,779)
  • View all amenities
Kissimmee Vacation Rentals

Don’t automatically think you need to rent a vacation home in Orlando to be close to Walt Disney World. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate—as well as a very short commute to the parks.

Kissimmee Vacation Rentals for Families

More and more families are choosing to celebrate major events like birthdays and anniversaries with a multi-generational trip to Disney World. (It’s one of the few destinations where everyone from toddlers to seniors can have an equally great time.) And we can help you find a Kissimmee vacation rental that can handle any size family. Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, our helpful vacation rental reviews make your selection easy.

Advantages of renting a vacation home in Kissimmee

Let’s be honest—while it’s great fun to spend a week visiting the Magic Kingdom, Epcot, Disney’s MGM Studios, Universal Studios and Islands of Adventure, for most of us, it’s a significant strain on our bank accounts. Staying in a hotel and eating in Orlando-area restaurants also adds up. However, we can help you find a great deal on a villa rental in Kissimmee… and even if you just take a few meals in your vacation home instead of in restaurants, your budget will thank you. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.

Rent a vacation house with a pool in Kissimmee, Florida

How do you visit the Orlando theme parks and maintain your sanity? Escape the crowds in the mid-afternoon, when the heat peaks and everybody’s nerves are frazzled. By staying just a short distance away in Kissimmee, you can zip home for a refreshing dip in the pool. Little kids can nap in the comfortable A/C of your Kissimmee vacation rental. You’ll all return to WDW or Universal in a much better mood!

Rental deals in Kissimmee

Remember that Florida’s a year-round vacation destination—but it definitely has an off-season when you can snag a great deal on Kissimmee condo rentals. If you really want a bargain, plan to visit Kissimmee between Thanksgiving and Christmas. Your condo will be cheap, the parks will be less crowded, and if you’re coming from a northern climate, the weather in Kissimmee will still seem great compared to what you’d get at home.

Kissimmee and Orlando beyond Disney

Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Just over an hour away, on Florida’s Space Coast, you’ll find the Kennedy Space Center and fantastic sandy beaches like Cocoa Beach. Taking a Disney Cruise departing from Port Canaveral? A vacation rental in Kissimmee is the perfect pre-cruise accommodation.