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Vacation Rentals in Kissimmee, FL

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From
$89
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
10 photos Details Reviews (1) Make Inquiry
From
$228
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
11 photos Details Reviews (1) Make Inquiry
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$275
Per Night
2 Bedrooms, 6 Bathrooms, Sleeps 8
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18 photos Details Reviews (1) Make Inquiry
Also consider
Legacy Vacation rental in Orlando, Florida
3 Bedrooms, sleeps 7
$100 / night
3BR 3BA WINDSOR HILLS POOL TOWNHOME 2 mi to DISNEY
3 Bedrooms, sleeps 8
$130 / night
Precious 4 Bed Townhome Private Pool Near Disney
4 Bedrooms, sleeps 9
$149 - $199 / night
Luxury 5 Bed Villa with own pool near Disney
5 Bedrooms, sleeps 10
$120 - $135 / night
From
$80
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
26 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed September 7, 2014
My family of 4 just stayed here for 8 nights while we visited Disney, Kennedy Space Centre, Gatorland and of course the shopping outlets. The house itself is massive, with a main...
5 of 5 stars Reviewed June 10, 2014
The home was just as it was described and the pictures definitely showed it well. From the moment we drove into the neighborhood and walked through the door, we knew this was a...
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From
$109
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
17 photos Details Reviews (1) Make Inquiry
From
$80
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
10 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 29, 2014
Owner are very nice. The house is clean and professionally setup for renter. If you have kids, the pool in the back will make your kids happy. Location is centrally located to...
5 of 5 stars Reviewed April 27, 2014
Location was awesome! Clean, spacious, the management company was on point & responsive. Owners were more than understanding & flexible when our plans changed last minute. Would...
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From
$88
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
14 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed June 17, 2010
The condo we stayed in was exactly what we needed for our family of five. It was spacious, quiet, close to amenities and Disney Parks and a good price. We had a great experience...
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From
$79
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
20 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed August 30, 2014
The 6 of us really enjoyed our stay here. It was clean and tidy, had enough space to chill out in the evenings and secure. The pool was nice but communal. The back garden was more...
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From
$100
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
10 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed September 13, 2014
We have stayed at Andy's Villa four different times and have really enjoyed his villa, and the area. The villa is close to all the amusement parks and many different restaurants...
5 of 5 stars Reviewed August 18, 2014
We couldn't have asked more from our two weeks at this beautiful villa. We especially loved the pool and the large decking area, which allowed us to have some more chilled days...
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From
$120
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
22 photos Details Reviews (4) Make Inquiry
4 of 5 stars Reviewed March 28, 2014
This home was amazing. What you see is what you get :). It is a beautiful home that was equipped with all my needs, primarily a big screen tv in the living area. However, there is...
5 of 5 stars Reviewed February 19, 2014
Loved the home, very convenient to all the attractions. My kids loved the gameroom, and the heated pool. Everytime we visit Disney I hope to stay here. The company and owner were...
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From
$103
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
36 photos Details Reviews (7) Make Inquiry
5 of 5 stars Reviewed April 3, 2014
thank you so much, it was the perfect rental, wish they could all be like yours.
5 of 5 stars Reviewed January 7, 2014
I just wanted to thank Paul for letting my family use his house in our vacation time in Orlando. Our stay at this house was a wonderful experience. The house is perfect, clean...
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From
$100
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
15 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 20, 2014
Beautiful home. Nice area, close to main drag [rte 192] for shopping and eating .Disney just a couple of minutes away. Clean and comfortable. Plenty big enough for 9 adults. All...
5 of 5 stars Reviewed October 27, 2013
We rent this beautiful house for 2 months. We can't say enough good things about it. It is so big and spacious it has everything you could possible need and more. The location it...
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From
$67
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
12 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed February 17, 2014
Hadn't stayed in a vacation house rental before. The house is comfortable, clean, secure and beautiful. House was furnished with TV and internet, but we had to fiddle with all of...
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From
$129
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 11
Bookings
48 photos Details Reviews (3) Make Inquiry
3 of 5 stars Reviewed March 18, 2014
My family and I recently took a trip to Orlando and chose to stay at this home. The home was very very spacial and very very clean. Looked exactly like the picture. The resort was...
5 of 5 stars Reviewed March 6, 2014
I had the pleasure of staying in Paradise Palms Resort three times. Each time I've been staying in the same house (Tronds apartment), but I can imagine the other compartments has...
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From
$120
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
20 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed June 17, 2014
We really enjoyed this home. Spacious one level, lovely community. The tiled floors made this home seem way cleaner than carpeted ones we have stayed in before, and as our...
5 of 5 stars Reviewed June 14, 2014
Would not hesitate to stay here again. Cumbrian Lakes is fantastic community, it's not all bundled together like other areas, and it's close to where you need to get to. House was...
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From
$139
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
24 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed May 14, 2014
Staying at Villa Sol Waterfront made our Florida trip the best yet. The home is beautifully decorated, spotlessly clean, has all the amenities you are looking for, and is very...
5 of 5 stars Reviewed March 26, 2013
Rent this property with confidence that it is clean, comfortable and everything that is promised. This house is beautiful! It has everything you would need. Just pack your...
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From
$106
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
42 photos Details Reviews (10) Make Inquiry
5 of 5 stars Reviewed March 30, 2014
We spent a week in this home. It was everything as advertised. Very clean and well located close to the attractions we were interested in. The neighborhood was very quiet and well...
5 of 5 stars Reviewed March 3, 2014
As a family of 4, 2 adults and 2 teenage boys, we have stayed in several holiday villas around Orlando. The Mouse House was the only one that felt like a "home" that was loved...
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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
$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
$88
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
26 photos Details Reviews (26) Make Inquiry
5 of 5 stars Reviewed June 8, 2014
Everything you need for a relaxing holiday especially after touring all the nice parks and other places to see including Daytona beach. Plenty of shopping oppurtunities. old town...
5 of 5 stars Reviewed March 4, 2014
We hade a great 10 day stay att this villa. We were a big party of 7 and there were plenty of space for us all. Four bedrooms and several restrooms and big dining and sofa areas...
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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
$95
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
13 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 31, 2014
We really loved the property. Everything was very clean and neat from inside and the pool was really clean. Our kids really enjoyed the pool. The owner is really helpful in...
5 of 5 stars Reviewed June 10, 2014
I would stay in this home again.The pool is great and the patio is very relaxing My daughter loved the pool table. and the neighborhood was so quite that she did most of her...
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From
$116
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed October 3, 2013
We stayed here September 2012. Had an amazing time. Not only as while on holiday but also in the villa. It was luxurious and really well maintained and really close to 192. One...
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From
$95
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
45 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed May 5, 2014
Foram 10 pessoas (3 delas abaixo de 4 anos) hospedadas no imóvel que além de bonito e muito bem localizado, estava impecavelmente limpo. Tudo o que nos foi prometido foi cumprido...
5 of 5 stars Reviewed March 23, 2014
Viajei com minha esposa mais, mais dois casais de amigos para o Lucaya Village Resort. Desde o princípio achamos tudo maravilhoso. Parecia que estávamos em nossa casa. Casa bem...
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From
$130
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
41 photos Details Reviews (2) Make Inquiry
3 of 5 stars Reviewed August 12, 2014
Home is very spacious and open concept. The house and pool is well maintained with free wi-fi. Very quite community
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From
$99
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
22 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed June 10, 2014
The Town house was very Clean and up to date. Enjoyed our long weekend. I would have placed an excellent review, except for the problem with the neighbors dog.
5 of 5 stars Reviewed June 8, 2014
The rental was just as it was in the pictures. It was clean, spacious, and comfortable. It was definitely a great value. I recommend this place! I will definitely book this place...
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From
$109
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
16 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed April 26, 2014
This home was everything I was looking for! I traveled to Florida for Spring Break with my family and it was just right for us. Before finding Paradise Palms, I had multiple...
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From
$120
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
34 photos Details Reviews (20) Make Inquiry
5 of 5 stars Reviewed July 30, 2014
Our holiday to Kissimmee was the long time coming so we did a lot of research. We weren't disappointed in any way. Dorothy's condo is an absolute gem. Part of a gated community...
4 of 5 stars Reviewed July 28, 2014
Good The condo is very nice! It is clean, nicely decorated, and spacious. It has all the amenities of home right down to scotch tape, needle and thread and scissors. The tenant...
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From
$95
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
26 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed June 29, 2014
Really enjoyed our stay.it was a beautiful and peaceful place.my granddaughter enjoyed the pool and the community park directly across from the house.The only down fall was you...
5 of 5 stars Reviewed April 28, 2014
well we were there for 17 days and I couldn't beat the price we paid and also you have a privet pool. it was very nice to come home from the parks and go swimming.. parks were...
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From
$95
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
14 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed April 10, 2014
Very nice & well decorated. The beds slept fine. The master bathroom shower was great (it is HUGE!!).
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From
$115
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
13 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed February 26, 2011
My wife and I stayed here for two winters. The condo is extremely well kept and very comfortable. The kitchen was well stocked and linens were abundant. The view of the...
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From
$68
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
20 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed July 1, 2014
This house was beautiful! It looked exactly like the picture and was super clean. Our children loved that the house had wifi and TV in each bedrooms. It was relaxing and we felt...
4 of 5 stars Reviewed January 17, 2014
The condo is very clean, spacious and well equipped. The WiFi did not work at all - we tried everything but gave up as we did not have time to fool around with it. We were...
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From
$72
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
24 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 11, 2014
Great place to stay. I travelled with my husband and 2 teenage sons. The apartment was clean, spacious, very well equiped, yet affordable. It is close to Disney and the shops, but...
5 of 5 stars Reviewed April 27, 2014
Las vacaciones han sido excelente durante estos días en orlando , la casa muy buena , espaciosa y muy acogedora la verdad ideal se las recomiendo ....
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From
$129
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
9 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed January 10, 2014
Well appointed and immaculately maintained house situated on a lake. Located in well planned community with great recreational facilities including its own movie theater. Easy...
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From
$180
Per Night
7 Bedrooms, 6 Bathrooms, Sleeps 16
Bookings
38 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed March 17, 2014
This house was everything it promised it would be. My family had a very relaxing vacation with only miles away from Disney World. After a long hectic day at the park we were...
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From
$65
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
12 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed September 7, 2014
This place was the perfect place for my family,my kids loved the private pool ,we loved that we had a huge master bed with our own bath , the kitchen came very handy :we had a...
5 of 5 stars Reviewed July 13, 2014
This is a very nice place to rent. We had plenty of room for 2 adults and two children. Very convenient location close to the attractions, restaurants and shopping. Very clean and...
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From
$85
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
14 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 14, 2014
My wife and I decided to take our adult children on a vacation this summer. We had decided, as a family, to come to the Orlando area to see Universal Studios. After searching...
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From
$121
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
23 photos Details Reviews (8) Make Inquiry
4 of 5 stars Reviewed September 10, 2014
Having been to Orlando before (this our 4th stay) and having stayed in condos previously, we decided to try the villa experience. We were not disappointed!! Firstly...
5 of 5 stars Reviewed July 29, 2014
Even before the holiday started when we were trying to decide just which of the very many villa's to choose from. Jan Staines responded to all my questions promptly and clearly...
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From
$45
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
23 photos Details Reviews (5) Make Inquiry
4 of 5 stars Reviewed September 29, 2014
Our family with 4 kids and my in laws recently stayed at this rental. It was a short distance from Disney, and plenty of room for all 8 of us. The owner was very prompt to help in...
4 of 5 stars Reviewed May 5, 2014
I would rate it 4 1/2 stars. Our family had a fantastic time in Orlando at the parks and this rental was a peaceful oasis to come "home" to and have some downtime. Sue was great...
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From
$120
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
13 photos Details Reviews (1) Make Inquiry
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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)
  • All pools (2,430)
  • 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.