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Vacation Rentals in Kissimmee, FL

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All 3,952 Rentals in Kissimmee
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From
$199
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 16
Bookings
25 photos Details Reviews (1) Make Inquiry
From
$129
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
9 photos Details Reviews (2) Make Inquiry
From
$225
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 16
Bookings
43 photos Details Reviews (1) Make Inquiry
Also consider
The Great Escape
4 Bedrooms, sleeps 9
$116 - $127 / night
Halcyon Daze
6 Bedrooms, sleeps 14
$151 - $208 / night
Our Disney Lodge - Vacation in the Florida Sun
6 Bedrooms, sleeps 14
$225 - $370 / night
Beautiful 6BR/4BA villa, Pool/Spa, 2miles2Disney
6 Bedrooms, sleeps 14
$175 - $255 / night
From
$160
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
31 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed January 15, 2014
We loved this house! In a quite neighborhood just off of us 192 and an easy drive to all of the theme parks, it is perfect for families getting together to visit all of the...
4 of 5 stars Reviewed October 9, 2014
Se está procurando economizar e não abrir mão do conforte é uma ótima opção. Fui com um grupo de amigos, então o valor da diária por pessoa saiu bem mais barato que um hotel. Para...
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From
$150
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
24 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed August 6, 2014
We are a family of two adults, a teenager and nine year old. Would recommend staying here, will do so again if we visit Cumbeian lakes again. The view is a dream, sat out having...
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From
$375
Per Night
8 Bedrooms, 5 Bathrooms, Sleeps 19
Booking
24 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed January 5, 2014
We rented this property at Emerald Island and was an incredible experience, the owner answered all our questions at the time of the rental, and when we arrive there, the house...
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From
$241
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
Bookings
23 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed April 29, 2014
The house was great very spacious and all 12 of us enjoyed it very much. The downside of getting to a property after being delayed for over 2 hours was it was late at night and...
5 of 5 stars Reviewed September 15, 2013
Had a fantastic stay in this home, away from home. A beautiful house equipped with everything a family needs while on holiday, we had a small toddler so this made our holiday so...
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From
$225
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 14
Booking
24 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed August 16, 2014
We stayed in this lovely, spacious villa for 2 weeks in August and it was absolutely perfect for a large family with 4 teenagers, who were all delighted to have their own...
5 of 5 stars Reviewed March 9, 2014
This holiday home was outstanding. It was comfy and luxurious and with 10 people staying there was still ample room around the house. Everything you could ask for in a holiday...
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From
$200
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 16
Bookings
14 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 28, 2010
We stayed in the villa for a week with extended family and friends which included little kids and teenagers. The whole family had enough room to relax by the pool or in...
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From
$142
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
16 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed November 1, 2013
We could not have picked a better place to stay for our lovely holiday in Florida. From the moment we booked to when we returned home, the service and attention to detail was...
5 of 5 stars Reviewed October 16, 2013
My family of 2 adults, 2 children aged 12 & 15 stayed in Brian's fabulous villa for 10 nights. We found it to be exactly as outlined in the listing details, and then some...
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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...
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From
$159
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
Bookings
17 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed April 25, 2014
Great location, 15-20 Mins to Disney World, 30 Mins to Universal / Airport. 5 Mins to Biggest Waltmart. Big house with plenty of room for a large family with kids. We had a great...
5 of 5 stars Reviewed February 16, 2014
I have stayed in this villa several times now and will do so in the future. It's clean, with a stylish interior and plenty of space for larger families. There's also ample space...
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From
$125
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
22 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 21, 2014
Had a lovely two weeks here. There were 6 adults and we never felt cramped. Nice pool area and a large games room. Close to many restaurants etc and easy to get to all parks etc...
5 of 5 stars Reviewed October 29, 2013
Excellent holiday home for all ages. Good location with many major attractions a few minutes drive away. Excellent facilities, including most major items for babies and young...
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From
$100
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
21 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed March 18, 2014
We have stayed at quite a few villas in and near Kissimmee, and this one was the best in the most important areas of being extremly clean, very comfortable, the furnishings were...
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From
$200
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
17 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 24, 2013
On arrival the place was nice and clean and well presented. Very large property, we were a group of 8 and everybody had their own space. There was excellent washing facilities...
5 of 5 stars Reviewed September 21, 2013
The property is very clean and spacious and fills with lots of light giving a very relaxed comfortable feel. Has all the necessary luxuries of a fully furnished property...
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From
$121
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
15 photos Details Reviews (3) Make Inquiry
3 of 5 stars Reviewed August 30, 2014
We enjoyed our stay here it's near the Disney Parks and Universal Studios, but it needs some looking at. There was nine of us staying but not enough knives,teaspoons or...
5 of 5 stars Reviewed July 2, 2014
I was there with my large family for a wedding and we were not crowded or felt on top of each other. The kids had a great time in the pool and game room and the adults had a great...
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From
$85
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
37 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed April 3, 2014
This is such a beautiful condo and extremely spacious for my family of 7. If we went the hotel route, we would have needed at least 2 rooms and not get any of the amenities as we...
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From
$150
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
24 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed October 1, 2014
This is my home away from home: spacious and comfortable. Near Disney parks and close to a Walmart. The owner is really a trustworthy person to do business with.
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From
$149
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
17 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed May 30, 2013
The house we rented was great! It had all the amenities we needed to make our stay, a home away from home. It was very clean and beautiful. The office staff was always very...
4 of 5 stars Reviewed December 5, 2012
We really enjoyed our stay at this lovely home. The home was nice and spacious. We had two minor problems a running toilet and a small problem with dryer. I must say the...
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From
$114
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 9
16 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed May 9, 2013
Very nice villa. Had family and parents along to get away from NH for a while. Plenty of room for all of us, great pool. I love the location. West of the parks so out of Traffic...
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From
$159
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 14
Bookings
18 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed April 25, 2014
Spacious, comfortable house even for big groups/extended families with a heated pool and all amenities needed. Nice, peaceful and safe environment within a short, easy drive to...
5 of 5 stars Reviewed October 28, 2011
Home from home - if home had all these mod cons and a heated pool outside the lounge and a games room in the garage. Great location for Disney assuming you have a car. Plenty of...
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From
$270
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 14
Booking
25 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 27, 2014
We thoroughly enjoyed our 2 week stay in your villa. We were extremely impressed with the layout, cleanliness and the fact that this is the first villa that did not leave our...
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From
$454
Per Night
9 Bedrooms, 5 Bathrooms, Sleeps 18
Booking
16 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 28, 2014
This house was great, but not the one I looked at on the computer. They gave us 1406 wexford way, but the address I got first was 1410 wexford way. Several of the TV's had a...
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From
$101
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
19 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed September 16, 2014
We had a fantastic holiday,made even better by staying in such a lovely villa. As soon as we walked in we felt right at home,it was so comfortable.We had everything we needed.In a...
5 of 5 stars Reviewed August 22, 2014
We were immensely happy when we finally arrived at the villa (got a bit lost trying to find it). The location was superb. It had a good supermarket a 2 minute drive away and was...
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From
$160
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
33 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed September 1, 2014
Lake Berkley is a beautiful secure gated estate just off the 192 & Poinceana. The Villa was a little tired. Carpets, blinds, settees, and pool all showing signs of age. Lovely...
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From
$250
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
26 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed January 27, 2012
It was wonderful to arrive at such a well put together rental house. It had everything we needed. We rented it, my husband and I and my 2 sons to be close to Disneyworld and the...
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From
$170
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
17 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 31, 2014
Amazing place, amazing location. Very welcoming home after a long day at the plentiful Orlando attractions
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From
$249
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 12
36 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed July 30, 2014
una casa muy comoda, espaciosa....nuestro grupo estaba conformado por cuatro familias y compartimos sobre todo en la cocina y la piscina. área muy tranquila, personas en el...
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From
$135
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
17 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed October 27, 2013
This home was not only brand new, but fully equipped and really next door to Disney. It's so close to Disney that we could hear the fireworks from our rooms. It's is bigger than...
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From
$230
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
Bookings
32 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed January 11, 2014
When we arrived the house was nice and clean, close to all attractions, kitchen stocked with all appliances and utensils. It was great having the private pool and hot tub, used it...
5 of 5 stars Reviewed September 27, 2013
My family had such a great time staying at Mickey's Garden Villa. The house is gorgeous and spacious, exactly what you see in the photos. The kitchen is very well stocked with...
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From
$210
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Booking
44 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed March 9, 2014
Hi Dawn, Just wanted to drop you a few lines to say how fabulous your villa is. A little bit of luxury in Paradise. Excellent location - on Disney's doorstep but only an hour...
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From
$161
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
49 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed September 1, 2014
This was my 7th trip to Orlando and The Retreat is the best place I have stopped in. The villa is huge, very clean, great pool area, lovely quiet gated community, very close to...
5 of 5 stars Reviewed July 8, 2014
This is an absolutely beautiful holiday home. It is in a perfect location, only a 10 minute drive to Disney, near to many restaurants and a large Target superstore. It is...
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From
$92
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
19 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed May 8, 2014
stayed here with 6 friends to play golf, the house was very spacious and clean. great location for disney, outlet stores and golf courses. very quiet and peaceful and just a 2...
5 of 5 stars Reviewed January 11, 2014
I stayed here for 10 nights with my family and friends. The house is like it is described. From the very beginning through emails I had a terrific contact with Alison, the owner...
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From
$121
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
Booking
17 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 29, 2013
We've just re-booked this wonderful villa again for next year. This will be our third visit to the same villa which speaks for itself how wonderful it is. Nothing is too much...
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From
$122
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
22 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed March 20, 2014
I stayed for 9nights and we loved the place. Everything was very clean. Pool was nice too and kids loved it. Very convenient location. Definitely coming back!
4 of 5 stars Reviewed July 24, 2014
Excelente lugar para vacacionar, en especial si vas a los parques de orlando. Todo muy bien, la casa, pileta, baños, camas. Impecable, super comodo. Personalmente opino que mucho...
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From
$153
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 12
24 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed September 14, 2014
this is a well appointed villa in a great location,very clean, has a great pool and hot tub it is at the end of a cul-de-sac ( very easy to find ) close to everything you may...
5 of 5 stars Reviewed September 12, 2014
This villa is fantastic. Extremely spacious and every appliance you could want. Immaculate inside and out. After a full day at the theme parks it was great to come back to the...
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From
$100
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
24 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 28, 2014
My family and I have just returned from 2 weeks at this villa. The villa is perfect , nicely decorated with everything you could need to keep everyone happy. The rooms are all...
4 of 5 stars Reviewed July 29, 2014
Really enjoyed our stay in this property. First time we have rented a property and this did what it said on the tin!! Lots of space, good sized rooms, great pool for kids and main...
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From
$125
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
Bookings
15 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed June 23, 2014
PROS- it has a lot of room for everyone. Really enjoyed the pool after a long day at theme parks. The owner (ms. Angela)is very responsive and promt - answers emails within a day...
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From
$127
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
19 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 25, 2014
The villa was well appointed with all the equipment we needed for our stay. There was superb access to all the major routes allowing easy travel to the Disney resorts and all...
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From
$135
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 11
Bookings
28 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed September 9, 2014
We were a little nervous booking a place that we had not seen in person. We ended up thrilled. There was considerable space, ample enough for 6 adults, including a big...
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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)
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  • Other outdoor space (1,796)
  • Washer/Dryer (1,779)
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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.