Our 10 best holiday houses in Kissimmee

Check out our best holiday houses in Kissimmee.

Holiday houses in Kissimmee with private pools

Enjoy the space and privacy of a holiday house with a private pool.

Cheap holiday houses in Kissimmee

Rent one of our cheapest holiday houses in Kissimmee for a low cost holiday.

Reviews of our holiday houses in Kissimmee

We have 68 reviews of our holiday houses in Kissimmee.

3 bedroom Windsor Hills holiday home rental with private pool
July 2019

Fantastic communication from owner booking and leading up to the stay. Lovely town house owners have thought of everything that you could need to make your holiday enjoyable and stress free. We would totally recommend and would defiantly stay here again if we have another holiday in Orlando.

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Renter: Victoria
Victoria Family from Crawley, United Kingdom
3 bedroom holiday home in Kissimmee, Florida, with private pool
May 2019

My partner and I stayed at this property and we had a fantastic time. The property was clean, had loads of space, lots of amenities and was only 20 minutes from the airport maximum. Lots of clear directions and we felt lovely and safe in the property. The owners/management company were very friendly and able to answer any questions we had. I/we would happily stay again and use this company again for our vacations.

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Renter: Aaron
Aaron Couple from Gravesend, United Kingdom
3 bedroom holiday home in Kissimmee, Florida, with private pool
February 2019

We really enjoyed our stay at this villa. It was very clean, comfortable and well equipped - and the pool was excellent, with nice views over the lake. The service company looking after the property were very helpful during are stay. The villa is in a great location on a quite estate in a nice area - not too far from Orlando/ Kissimmee shopping and attractions, but also convenient for Kennedy Space Centre and some of the east coast beaches. There are some shops, a grill/ bar, supermarkets and takeaways reasonably close. Would definitely look at booking again if staying in Kissimmee – great value for money.

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Renter: Steven
Steven Couple from Hockley, Essex, United Kingdom
3 bedroom holiday home in Kissimmee, Florida
September 2018

We stayed at Hamish's place for our recent trip to Orlando and couldn't have asked for more. The property was absolutely stunning and was set in a beautiful complex which was completely secure and was staffed by really nice and knowledgable locals. It was also located in a great area and only took us about 15 minutes to get to all the disney parks and was close to all the outlets. The facilities in the property were fantastic as well and had everything you could need and more. Hamish was an amazing host as well and responded to emails so quickly and regularly answered questions which made us feel really at ease. He is a true credit to his property - absolutely fantastic! We are already looking at planning our next orlando holiday and we will definitely be staying in Hamish's place again.

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Renter: Oliver
Oliver Couple from Leeds, United Kingdom
3 bedroom holiday home in Kissimmee, Florida, with private pool
August 2018

Was a bit cautious at first after reading a few previous reviews but Villa was exactly as described. Has everything you would need as a home from home. In a great location with easy access to the parks, shops and motorways. The villa is Well looked after with great property managers who are there for your every need and Tony the owner very helpful and quick to answer any questions we had. Fantastic pool, newly furnished rooms, cable, internet and a great kitchen with everything utensil you could think of. Another plus side was the patio door alarm for the pool, as we was traveling with a 4yr old put my mind at ease. Would definitely stay here again as it has everything you need and more. We have stay in premium villas in Florida before which have not been as good as this one. Would definitely recommend it and hope to come back in the future. Had a fantastic 3 weeks here.

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Renter: Katherine
Katherine Family from Liverpool , United Kingdom
3 bedroom holiday home in Kissimmee, Florida, with private pool
July 2018

This was our 8th visit to orlando, previously always staying in clermont/davenport. The location of this villa was far superior. So close to all the parks, with very little traffic. Lovely area with all the expected shops and restaurants. The villa itself was beautifully decorated and had every home comfort you could possibly need. My children adored the pool and spent several happy hours in it watching the wildlife on the lake. I cannot recommend this villa highly enough and hope to stay here again for our future trips to Orlando.

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Renter: Louise
Louise Family from Newport, United Kingdom