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Vacation homes in Kissimmee, FL

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All 4,064 Rentals in Kissimmee
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From
$125
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
13 photos Details Reviews (1) Make Enquiry
From
$271
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details Reviews (2) Make Enquiry
From
$99
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
24 photos Details Reviews (11) Make Enquiry
Also consider inquiring on or booking these rentals
Fresh poolvilla with free WI-FI and BBQ
4 Bedrooms, sleeps 8
$107 - $128 / night
4 bed/3 bath private pool villa
4 Bedrooms, sleeps 8
$111 / night
1006 BELVOIR
5 Bedrooms, sleeps 12
$198 / night
Luxury Florida Villa
4 Bedrooms, sleeps 8
$108 - $126 / night
From
$193
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 17
26 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 31 July 2014
My family and I enjoyed staying here. We all enjoyed the game room and pool. We would rent this home again. Beautiful is all I can say about it.
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From
$308
Per Night
2 Bedrooms, 6 Bathrooms, Sleeps 8
Booking
18 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 July 2014
At the time of our check in our wonderful vacation began. The villa was classically appointed. Everything was spotless and functional. The lush landscape was a fitting...
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From
$1,462
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 12
Booking
30 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 19 November 2012
I urge anyone traveling to the Kissimmee--Orlando area looking for a rental,to look up the Blue Horizon Villa. Very close to everything from Disney to shopping Malls...Plenty of...
5 of 5 stars Reviewed 18 November 2012
We first rented the Blue Horizon in October 2010. My family loved the house and the kids especially liked the pool. When we decided to go back to Florida for Spring Break in...
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From
$506
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 12
20 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 12 December 2012
We had a wonderful time at Whispering Palms and think it is an excellent choice of villa both for the quality of accommodation and its location. It is large, comfortable and well...
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From
$1,068
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details Reviews (4) Make Enquiry
4 of 5 stars Reviewed 27 October 2013
Owner at this resort for 16yrs. The recent change of property to a Diamond Resort has seen an improvement of activities also they have just started to completely refurbish all...
5 of 5 stars Reviewed 11 July 2013
After traveling with a small child and friends, it was refreshing to stay at such a great resort. I was confident after speaking with Lillian Vasquez (Mystic Dunes employee) that...
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From
$160
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
9 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 2 April 2014
Melhor opção para família. 5 quartos muito confortáveis. Todo luxo e conforto que uma família precisa. O Sr. Thomaz, responsável pela locação, esteve presente e deu apoio total a...
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From
$88
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
17 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 14 October 2014
The house was exactly what we expected. It was clean and there was no surprises when we arrived. The property management company company was a pleasure to deal with and was very...
4 of 5 stars Reviewed 5 October 2014
Hai Pamela, We had a wonderful stay at 1069 Tourmaline drive. Everything was smooth and the small issues we had where promptly taken care off... It was really hard for us, my...
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From
$135
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 10 January 2014
Estuvimos diciembre 2013 y la ubicación es excelente, una vista con muchos arboles. La casa estaba en perfectas condiciones, muy limpia y nos impresionó lo bien equipada que se...
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From
$236
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
23 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 10 October 2014
De viaje con la familia completa de Disney nos alojamos en esta hermosa villa con piscina privada y jacuzzi. Eramos 8 adultos y 3 niños. Los adultos teníamos cada uno su pieza...
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From
$116
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
11 photos Details Reviews (3) Make Enquiry
4 of 5 stars Reviewed 29 October 2013
We stayed for 7 days at Violet Cove, and found it to be appropriate for the price. A nice home, in a quiet neighborhood at the end of a cul-de-sac, my husband and I loved it as...
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From
$191
Per Night
6 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
19 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 20 February 2014
El servicio recibido fue excelente. La casa estaba en impecables condiciones para alojar. Resultó ser muy cómoda para la cantidad de personas que alojamos. Todo exclelente.
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From
$84
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 19 August 2014
The townhome was great spacious and well kept. The community had so much to do that we would not have had to go anywhere if we didn't want to. It is right off of the main street...
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From
$225
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 14
24 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 23 May 2013
We stayed here for a week after a tiring but fun road trip and as a base station for the theme parks! It was exactly what we needed for a group of 7 friends! Good location for the...
4 of 5 stars Reviewed 9 April 2012
Very large and comfortable villa could easily accommodate two families. Helpful owner and location is very good for all attractions. Wildlife around the lake was a...
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From
$129
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
13 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 26 February 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
$101
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
15 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 27 March 2014
We enjoyed the condo so very much. It provided comfort; it was very clean; it had all the kitchen facilities we needed to cook at home. we love the heated pool - the kids had a...
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From
$101
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
9 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 21 March 2014
Amazing property....very clean and beautifully decorated. Very convenient location to all venues. We called maintenance for the pool light that went out during our stay and they...
5 of 5 stars Reviewed 4 October 2013
Both my wife and I were more than pleased with the property, as soon as you opened the door it felt like you were on holiday. bright and airy with plenty of space to relax. The...
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From
$96
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
19 photos Details Reviews (1) Make Enquiry
From
$172
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
40 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 26 September 2014
Best villa i have ever rented very spacious very clean top quality appliances large tvs with full channel packages awesome high quality beds remote control lights and fans very...
5 of 5 stars Reviewed 7 May 2014
Very fancy house, everything new, good quality, good beds. Sad that we only stayed 4 nights, we would gave liked a light at the pool, so we could have taken a dip after the warm...
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From
$134
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
24 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 21 February 2014
We really enjoyed our stay at your lovely vacation home.We were very impressed with how spacious and clean the home was. We liked the gated community because it gave us a greater...
5 of 5 stars Reviewed 8 January 2014
If I had a vacation home in the Disney area, this would be it. Your in a secure development that is well maintained. The condition of the house was what we expected and it was as...
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From
$134
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
29 photos Details Reviews (2) Make Enquiry
From
$511
Per Night
9 Bedrooms, 5 Bathrooms, Sleeps 18
Booking
16 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 28 July 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
$225
Per Night
7 Bedrooms, 4 Bathrooms, Sleeps 14
20 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 2 September 2014
We have stayed at several vacation rentals and time sharing condominiums, but this is by the far the best. My family usually takes a cruise and then spend a week in Orlando. This...
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From
$5,409
Per Week
8 Bedrooms, 8 Bathrooms, Sleeps 18
23 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 17 August 2013
From start to finish, this has been a dream! Firstly, Christine and her family were fabulous with quick responses to emails making booking the villa very easy! This fantastic...
5 of 5 stars Reviewed 22 April 2013
Outstanding house with lovely owners. They are very professional and welcoming. The house is luxurious with marble floors, a movie theater, heated pool and a huge kitchen...
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From
$1,094
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details Reviews (1) Make Enquiry
From
$193
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
24 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 3 April 2014
Our extended family of 8 loved this rental. Everyone had plenty of room to play and rest. The pool and rec room had lots of use. The on site property management was courteous and...
5 of 5 stars Reviewed 4 September 2013
First time staying at emerald island, and really enjoyed our holiday. The villa was excellent, would of stayed here again this year but its booked up. The owner Justin was...
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From
$160
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
32 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 2 June 2010
After stayning in hotels in a small room, what a difference staying in a villa. A huge amount of space with a standard well above most hotels we have stayed in and all this for...
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From
$101
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
4 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 30 April 2014
We have owned for 29 years at Orange Lake, we have gone through many expansions. Each time we go to Orange Lake we are pleasantly surprised with the improvements to the property
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From
$193
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
Bookings
23 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 11 May 2014
If you want to stay in the Disney area in total comfort then this is the place for you. Right from the entry gate on the Westside Road, you get the sense that this estate is well...
5 of 5 stars Reviewed 6 February 2014
The management company was very courteous and quick to respond to our questions or concerns. The house was beautiful and well maintained. It accommodated all our needs. Exactly...
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From
$135
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
34 photos Details Reviews (20) Make Enquiry
5 of 5 stars Reviewed 30 July 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 28 July 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
$902
Per Week
5 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
13 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 23 April 2013
Having used other villas around Orlando I came across this one as our normal one was booked, I contacted the owner who could not of been more helpfull and booked up our stay...
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From
$100
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
18 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 August 2013
Easy access to the sites! Clean and comfortable with all the amenities of home. Would recommend to family and friends.
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From
$225
Per Night
6 Bedrooms, 6 Bathrooms, Sleeps 12
21 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 29 April 2011
This lovely rental home is one of the best that we have found. It is wonderfully decorated, furnished and maintained. It is conveniently located to many of Orlando's...
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From
$121
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
17 photos Details Reviews (1) Make Enquiry
From
$143
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
19 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 25 August 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, 2 Bathrooms, Sleeps 10
Booking
13 photos Details Reviews (1) Make Enquiry
From
$812
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
24 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 22 July 2014
We stayed here for a week while visiting the usual Orlando attractions, travelled with wife and 2 young kids (8 & 11). Great location (20 min drive to Disney) and 5 mins from...
5 of 5 stars Reviewed 6 November 2012
About to take our 8th Florida villa holiday we approached Dot who was helpful and prompt to reply. Knowing what a superb,convenient and safe location Cumbrian Lakes is we booked...
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From
$119
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
42 photos Details Reviews (10) Make Enquiry
5 of 5 stars Reviewed 30 March 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 3 March 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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Suitability

  • Wheelchair access (597)
  • Elder access (1,582)
  • Suitable for children (2,122)
  • Pet friendly (185)
  • Smoking allowed (9)

Amenities

  • Air Conditioning (2,899)
  • Internet (2,823)
  • All pools (2,245)
  • Washer/Dryer (1,909)
  • Other outdoor space (1,902)
  • View all amenities
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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.