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Holiday Rentals in Kissimmee, FL

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From
$140
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Private Outdoor Pool (Heated), Wi-Fi & more
22 photos Details Reviews (1) Make Enquiry
From
$181
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Private Pool, Dishwasher, Air Conditioning & more
37 photos Details Reviews (5) Make Enquiry
From
$97
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Private Pool, Internet Access, Grill & more
17 photos Details Reviews (14) Make Enquiry
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4 Bedrooms, sleeps 8
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4 Bedrooms, sleeps 8
$785 / week
Beautiful, luxurious vacation home in Orlando!
4 Bedrooms, sleeps 10
$170 / night
Sheraton Vistana Fountains II - Timeshare
2 Bedrooms, sleeps 8
$170 / night
From
$124
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Private Pool, Dishwasher, Satellite TV & more
11 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 11 July 2013
Renting from Loyalty was very easy. The office staff and maintenance staff were very helpful. The house was beautifully furnished and the exterior was very neat. The...
2 of 5 stars Reviewed 5 July 2013
The lay-out of the home was great, however it really needs updating. The TV remote did not work in the 2nd. bedroom,and we were promised a replacement which never happened. The CD...
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From
$148
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Private Outdoor Pool (Heated), Wi-Fi, Gym & more
24 photos Details Reviews (12) Make Enquiry
5 of 5 stars Reviewed 10 September 2014
We booked this villa in 2013 for our 4 week holiday in July 2014. The owner Richard and Carol have been fantastic to deal with. From start to finish nothing is too much trouble...
5 of 5 stars Reviewed 7 August 2014
This is the second time we've stayed at this villa and wouldn't stay anywhere else, it has everything you need, the pool and spa are fantastic my hubby and son loved the pool...
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From
$159
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
Private Outdoor Pool (Heated), Housekeeping Optional & more
18 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 29 January 2014
Our vacation home was the best! we loved it! the place was absolutely perfect! It was as clean and neat and beautiful as it can be! The spaces were perfect for each member of the...
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From
$153
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
Outdoor Pool, Air Conditioning, Grill & more
30 photos Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 10 August 2014
The house was beautiful. Everything was top notch! The backyard is stunning and a very warming appeal to the whole house. I would definitely return. The price to rent is such a...
4 of 5 stars Reviewed 14 July 2014
A wonderful home with lots of room for 6 adults and 2 kids. Almost everything, from the kitchen appliances and nice dishes and cutlery, to the screened-in pool and deck, was just...
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From
$101
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Private Pool, Internet Access, Satellite TV & more
21 photos Details Reviews (14) Make Enquiry
3 of 5 stars Reviewed 10 August 2013
It was a lovely lovely home. The beds need to be updated with more comfortable mattresses and there were sugar ants that I was unaware of. My daughter ended up eating cereal that...
5 of 5 stars Reviewed 24 July 2013
really enjoyed how beautiful the house was. the management was great thank you for a wonderful stay look forward to doing buisness with you soon. the downstairs bathroom was...
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From
$110
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
Booking
Private Outdoor Pool (Heated), Wi-Fi & more
20 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 6 September 2014
We had a fantastic holiday in Florida at this villa. We travelled as a group of 4 with two children 8-10. The villa is 25 minutes from the airport and the directions from the...
5 of 5 stars Reviewed 21 July 2014
We stayed in this villa as a family of 5 adults and 2 children. There was lots of room for everyone to relax and have their own space. It is a very well equipped villa with plenty...
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From
$91
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
Pool, Wi-Fi, Balcony & more
13 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 17 March 2014
Thank you once again for another great condo! We just completed our second annual rental week at Kissimmee Regal Oaks. The condo was as always in the best location for as and...
5 of 5 stars Reviewed 7 August 2013
My wife and kids really happy with the house!!! Clean, comfortable, etc, etc, etc!!! 100% recommended!!!
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From
$114
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Private Pool, Wi-Fi, Air Conditioning & more
23 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 23 January 2014
This vacation home was a perfect choice for our family. Blue Ribbon Management was great. Easy to work with, very accessable. I loved the keyless entry so we didnt have to check...
4 of 5 stars Reviewed 22 November 2013
The townhouse was very nicely decorated and well kept. It had all facilities we needed during our one week stay and since we had been traveling for a week before we reached...
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From
$158
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
Private Outdoor Pool (Heated), Wi-Fi, Pool Table & more
24 photos Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 14 May 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 27 March 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
$135
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Internet Access, Dishwasher, Air Conditioning & more
14 photos Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 18 April 2012
This house was really nice. The place was clean. The pool was lovely. The only problem we had was that the houses were literally right on top of each other and we heard noises...
3 of 5 stars Reviewed 15 July 2011
Great house close to the parks in a great neighborhood. We loved the pool. The mattresses, dishwasher, and washer could use an update (appliances were very loud) and the kitchen...
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From
$226
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 16
Pool, Grill, Internet Access & more
28 photos Details Reviews (6) Make Enquiry
4 of 5 stars Reviewed 10 October 2013
We stayed here for two weeks at the end of September beginning of October. There were 12 in our party all together and this was a comfortable number for the accommodation with...
5 of 5 stars Reviewed 7 March 2013
Spencer and Thompson Family of 16 we had an awesome time the kids loved the pool so did the adults..Close to disney.. We went to Daytona beach and to the race track it was so much...
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From
$148
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Private Pool, Internet Access, Air Conditioning & more
13 photos Details Reviews (1) Make Enquiry
From
$124
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
Heated Pool, Internet Access, Air Conditioning & more
20 photos Details Reviews (1) Make Enquiry
From
$306
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 14
Private Pool, Air Conditioning, Dryer & more
21 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 24 June 2012
The home was magnificent... Almost better than my staying at mom own home. The home is beautiful beautiful beautiful! Mari from Dvro recommended this home and words can not...
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From
$110
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Private Outdoor Pool (Unheated), Wi-Fi, Dishwasher & more
18 photos Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 23 July 2014
Location: perfect, perfect, perfect House: perfect Pool: perfect Cleanliness: perfect Wifi: perfect We have stayed in several villas in the Kissimmee area (Terra Verde, Lake...
5 of 5 stars Reviewed 25 May 2014
We have stayed in this villa three times now and are going back for our forth stay in two weeks, it's just lovely and ideal for us with its space and facilities, the pool is ideal...
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From
$124
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Private Pool, Air Conditioning, Satellite TV & more
11 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 4 January 2012
Nice vacation
4 of 5 stars Reviewed 28 July 2011
This was a lovely villa with plenty of utilities and a private pool, which was cleaned regularly; Although it was not up to the standard of the Terra Verdi complex that we last...
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From
$219
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
18 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 26 July 2014
Je recommande cette villa. Très bonne prestation . Propreté impeccable . Les enfants ont adoré la piscine privée ..villa dans un quartier calme et sécurisé . Merci encore.
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From
$165
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Dishwasher, Air Conditioning, Hot Tub & more
27 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 11 March 2014
We loved the spaciousness & since I booked very last minute, we didn't have high expectations. We were very pleased. My 3 boys loved each having their own room & a flat screen tv...
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From
$165
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Air Conditioning, Dishwasher, Satellite TV & more
21 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 3 May 2014
The villa was exactly as shown on the internet, in terms of location and environment as well as everything inside the villa (mostly everything was new and good quality). Before we...
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From
$909
Per Week
4 Bedrooms, 5 Bathrooms, Sleeps 10
Private Outdoor Pool (Heated), Wi-Fi & more
23 photos Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 29 July 2014
Could not fault this place at all and would definitely return. Stayed at Tuscany 2 years ago at a bigger villa but this actually felt much more comfortable and homely. We chose...
5 of 5 stars Reviewed 4 May 2014
I vacated with my husband and children at this villa and found it to be a very enjoyable, relaxing and comfortable place to stay. The villa has everything you need from space...
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From
$148
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Private Pool, Air Conditioning, Satellite TV & more
17 photos Details Reviews (3) Make Enquiry
From
$197
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
Bookings
Private Outdoor Pool (Heated), Dryer, Garden & more
23 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 12 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 7 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
$167
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Heated Pool, Grill
15 photos Details Reviews (18) Make Enquiry
4 of 5 stars Reviewed 23 January 2012
Couldn't have asked for better place to spend our Christmas vacation. Customer service was great. Getting our keys after hours was no problem at all. House was spacious and clean...
4 of 5 stars Reviewed 24 March 2011
I thought the place was a dream come true when we put the key in the door and opened it up it was amazing. We couldint have asked for more. The only thing that went a little...
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From
$199
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Pool, Hot Tub
18 photos Details Reviews (16) Make Enquiry
5 of 5 stars Reviewed 27 December 2013
I was very hesitant to book online but the staff made me feel comfortable. The property was fabulous! Ready to do it again and again.
5 of 5 stars Reviewed 1 November 2013
The house was well maintained and clean and everything we needed for our stay. Although it would be nice if there was an umbrella or something next to the pool so that you could...
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From
$156
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Private Outdoor Pool (Heated), Wi-Fi & more
24 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 28 August 2014
The villa is in an excellent location for all of the theme parks, close to shops and restaurants. The villa is lovely and of a very high standard. It was clean and all...
5 of 5 stars Reviewed 16 July 2014
My partner and two teenage girls spent just over a week in this lovely villa. It's modern, very clean and has everything you need, with some lovely finishing touches that add to...
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From
$266
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
Heated Pool, Grill
15 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 4 February 2013
We had a great time. The house is beautifully decorated and kitted out with everything we needed. We were two families and our Nana and had the most wonderful time. We just...
4 of 5 stars Reviewed 29 August 2011
The house and the neighborhood were excellent. We enjoyed having the enclosed lenai and pool. The one concern that we had was that a service employee entered the home on the day...
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From
$114
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Washer, Dishwasher, Dryer & more
20 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 19 March 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
$199
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
Bookings
Private Indoor Pool, Garden, Dryer & more
41 photos Details Reviews (8) Make Enquiry
5 of 5 stars Reviewed 13 March 2014
It was a Disneyland vacation which will not be forgotten anytime soon. Three generations of our family enjoyed every moment. Lovely home, huge pool, comfortable surroundings...
5 of 5 stars Reviewed 3 March 2014
This lovely home is the perfect complement to the Disney experience! We had our 4 & 6 yrs old granddaughters, their parents, 10 month old twin granddaughters & their parents with...
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From
$236
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
Private Outdoor Pool (Heated), Wi-Fi, Pool Table & more
22 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 23 March 2014
Overall, the house was clean, beds were comfortable and the resort was lovely. Only two complaints really. Although, we paid for pool heat, the type of heat exchanger for the pool...
5 of 5 stars Reviewed 8 May 2013
We spent a week in February, 2 adults, 2 teenagers, 2 children. We are from France. One of the best vacation we had, if not the best. Owner was easy to get in touch with, very...
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From
$125
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Heated Pool, Satellite TV, Air Conditioning & more
66 photos Details Reviews (22) Make Enquiry
5 of 5 stars Reviewed 25 March 2013
The experience was very good. We had a problem with the password of the house, which was quickly resolved.
5 of 5 stars Reviewed 11 December 2012
The condo was neat and clean. Property was safe and beautiful. Very nice option instead of a hotel. Would do it again.
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From
$494
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 15
Private Pool, Hot Tub, Dishwasher & more
20 photos Details Reviews (5) Make Enquiry
2 of 5 stars Reviewed 4 July 2014
Beautiful house... Gorgeous view... Not worth the hassle... Management is terrible and completely non responsive
4 of 5 stars Reviewed 23 April 2013
Our stay in the vacation home was awesome. The house was very roomy and a great atmosphere. The kids really enjoyed the pool. The representative Jessica was a joy to work with...
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From
$256
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 12
Hot Tub
14 photos Details Reviews (3) Make Enquiry
4 of 5 stars Reviewed 12 April 2014
This was a great house to bring our U14 Volleyball team. Rooms were a good size and there were enough beds for everyone. Everything seemed to be in good working order. Our only...
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From
$313
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
Private Outdoor Pool (Heated), Hot Tub, Dishwasher & more
46 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 27 May 2014
MiMi and PaPa had ten children and grandchildren in this spacious home. Pool, spa, and optional grill made our down time a delight. Six bedrooms allowed us to stretch out and even...
4 of 5 stars Reviewed 18 July 2013
Sherri you have a lovely home. The house was just like the pictures. The home was clean and the pool was clean also. We had a lot of room to move around. The kids enjoyed the...
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From
$108
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Private Outdoor Pool (Heated), Internet Access, Safe & more
13 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 1 September 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 10 June 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
$872
Per Week
4 Bedrooms, 2 Bathrooms, Sleeps 8
Private Outdoor Pool (Unheated), Wi-Fi, Grill & more
17 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 3 July 2013
Very spacious ,kids loved the gameroom and pool.Multiple tv's kept everyone satisfied.Very nice owners ,very helpful.Well maintained property.Felt like home.
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From
$94
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Sauna, Dishwasher, Air Conditioning & more
6 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 20 August 2014
Caribe Cove Resort was a great place, plenty of room for us all. The kids enjoyed the big spacious pool. The Apartment was well stocked with everything that we needed...all in...
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From
$138
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Private Outdoor Pool (Heated), Wi-Fi, Washer & more
19 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 24 January 2014
We lived in the Chart House for the week over New Years Eve. We had a great time and only experienced the best service from the owners. They were very fast during the booking...
5 of 5 stars Reviewed 6 September 2012
This house is excellent and very well maintained. It had all the amenities / facilities we needed and in good working order. Very comfortable and easy to relax after long days at...
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Suitability

  • Wheelchair access (597)
  • Elder access (1,594)
  • Suitable for children (2,139)
  • Pet friendly (184)
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Amenities

  • Air Conditioning (2,913)
  • Internet (2,834)
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  • Washer/Dryer (1,913)
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Villas in Kissimmee

Kissimmee, near Orlando in Florida, is a great family friendly destination, as it is so near so many of Florida's most famous tourist attractions and theme parks, including Walt Disney World. In addition to these attractions and a glorious sub-tropical climate, the area presents unique opportunities to spot exotic and endangered wildlife. Whether your family are, roller-coaster fanatics or naturalists, or a mixture of both, you will have a packed time in the area, and you can cut down on the expenses by investigating the wide range of villas and holiday rentals on offer.

Things to do in Kissimmee

Kissimmee is within easy reach of Disney World, Sea World Orlando and Universal Studios, but you can also go for lesser known attractions such as Forever Florida, where you can go on safari on horseback or on a coach to spot alligators, black bears and even the incredibly rare Florida panther. Florida is of course also famous for its swamps, so a trip to Boggy Creek is also a perfect day out, you can take a ride in a swamp buggy out to explore the wetlands and see turtles and various exotic birds. These kinds of attractions provide memories which will last a lifetime, and are great for kids. And for a bit of fun, make sure you go to Medieval Times for a dinner show with a difference, as knights joust on horseback. This is an expensive venue, but could be a highpoint of an unforgettable family holiday, and of course you'll be saving a considerable amount of money by renting a villa rather than forking out for a hotel room.

Kissimmee Holiday Rentals

A holiday full of theme parks can be an expensive business with even a small family. But you can make your budget go further by opting to rent a villa, as prices start around £500 a week for villas for up to six people. With air conditioning, pools, broadband and TVs included as standard, you can make yourself completely at home during your stay, and maybe even spend a day in the villa between theme park trips - with the extra space of self-catered accommodation this becomes a real option, whereas in a hotel kids are generally climbing up the walls within twenty minutes! By renting a villa, you can enjoy a low cost holiday in Kissimmee, and probably get to relax a whole lot more!