Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Cabins
Condos
Cottages
Estates
Homes
Lodges
Townhomes
Villas
Barns
Boats
Castles
Chalets
Farmhouses
Hotels
Studios
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Kissimmee Area Long Term Vacation Rentals(1,178)

1,178 Results
Book it Now!
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
    (174)
    Book it Now!
    4 night minimum stay
    • 3 BR,
    • 3 BA,
    • Sleeps 8
      (81)
      Book it Now!
      6 night minimum stay
      • 3 BR,
      • 2 BA,
      • Sleeps 8
        (39)
        Book it Now!
        5 - 7 night minimum stay
        • 5 BR,
        • 5 BA,
        • Sleeps 12
          (54)
          Book it Now!
          4 night minimum stay
          • 4 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 8
            (26)
            Book it Now!
            5 - 7 night minimum stay
            • 4 BR,
            • 3 BA,
            • Sleeps 8
              (62)
              Book it Now!
              2 - 3 night minimum stay
              • 4 BR,
              • 3 BA,
              • Sleeps 10
                (27)
                Book it Now!
                3 - 5 night minimum stay
                • 6 BR,
                • 4 BA,
                • Sleeps 14
                  (57)
                  Book it Now!
                  3 - 6 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 8
                    (30)
                    Book it Now!
                    2 - 6 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • Sleeps 10
                      (58)
                      Book it Now!
                      3 - 7 night minimum stay
                      • 7 BR,
                      • 4 BA,
                      • 2 HF BA,
                      • Sleeps 16
                        (11)
                        Book it Now!
                        5 night minimum stay
                        • 5 BR,
                        • 4 BA,
                        • Sleeps 12
                          (26)
                          Book it Now!
                          4 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 8
                            (35)
                            Book it Now!
                            3 - 4 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • 1 HF BA,
                            • Sleeps 8
                              (30)
                              Book it Now!
                              3 - 5 night minimum stay
                              • 5 BR,
                              • 4 BA,
                              • Sleeps 10
                                (26)
                                Book it Now!
                                3 - 7 night minimum stay
                                • 8 BR,
                                • 4 BA,
                                • 2 HF BA,
                                • Sleeps 19
                                  (25)
                                  Book it Now!
                                  3 - 7 night minimum stay
                                  • 6 BR,
                                  • 5 BA,
                                  • 1 HF BA,
                                  • Sleeps 16
                                    (32)
                                    Book it Now!
                                    3 night minimum stay
                                    • 5 BR,
                                    • 4 BA,
                                    • Sleeps 12
                                      (29)
                                      Book it Now!
                                      2 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 8
                                        (28)
                                        Book it Now!
                                        2 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          (49)
                                          Book it Now!
                                          3 - 5 night minimum stay
                                          • 4 BR,
                                          • 2 BA,
                                          • Sleeps 8
                                            (50)
                                            Book it Now!
                                            4 - 5 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 9
                                              (34)
                                              Book it Now!
                                              4 - 7 night minimum stay
                                              • 6 BR,
                                              • 4 BA,
                                              • Sleeps 15
                                                (21)
                                                Book it Now!
                                                5 - 7 night minimum stay
                                                • 6 BR,
                                                • 3 BA,
                                                • 1 HF BA,
                                                • Sleeps 12
                                                  (33)
                                                  Book it Now!
                                                  2 - 7 night minimum stay
                                                  • 4 BR,
                                                  • 3 BA,
                                                  • Sleeps 8
                                                    (20)
                                                    Book it Now!
                                                    4 night minimum stay
                                                    • 5 BR,
                                                    • 3 BA,
                                                    • Sleeps 12
                                                      (22)
                                                      Book it Now!
                                                      2 - 7 night minimum stay
                                                      • 7 BR,
                                                      • 4 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 15
                                                        (18)
                                                        Book it Now!
                                                        4 - 30 night minimum stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 6
                                                          (28)
                                                          Book it Now!
                                                          4 - 7 night minimum stay
                                                          • 6 BR,
                                                          • 4 BA,
                                                          • Sleeps 11
                                                            (23)
                                                            Advertisement

                                                            Kissimmee Area

                                                             

                                                            Recent Kissimmee Area Reviews

                                                            Our Home Away From Home

                                                            5 of 5
                                                            I said I would write a review shortly after our trip and totally forgot. We are a family of seven, with two young grandchildren. We were so happy with Nana and Pop's home for our first Disney vacation. The house was very comfortable and the living space was great. Even though the bedrooms are off the living room, you would think there would be a lot of travel noise into the bedrooms. That was not the case at all. I found the bedrooms to be so quiet which was great for the little ones. The ride to the parks was so fast and convenient. One thing I did wish that the pool was a bit warmer since it was chilly, especially on cooler days, but I understand you keep it at a certain thermostat. Thank you Jim and Char for renting your home to us. We were very happy and comfortable in your home. We would definitely rent again should we make another trip to Disney.
                                                            • Submitted: Sep 14, 2014
                                                            • Stayed: Mar 2014

                                                            Great property,great service

                                                            5 of 5
                                                            This is definitely one of the nicest property's we have stayed in, decorated and furnished very nicely and more importantly well maintained and very clean. There was a problem with one of the services to the property while we were there, so unfortunately we had to move out for a couple of days, which obviously was a slight inconvenience, however both Phil and Judy the owners and Paul and Julie from the management company could not have been better, going above and beyond to make things right. We would highly recommend the property for a vacation rental as it is so nice and well equipped, coupled with the knowing that if anything does happen to go wrong (unlikely I know) it is dealt with straight away by someone who cares. Many thanks to Phil,Judy,Paul and Julie for helping make our holiday (sorry, vacation) so special. We will be back to stay again. Kind regards Darren, Tanya, Louis and Samuel.
                                                            • Submitted: Sep 14, 2014
                                                            • Stayed: Aug 2014

                                                            Very comfortable, but needs some updates

                                                            4 of 5
                                                            We travelled to Florida for my wedding. The house was very large and spacious. There were about 11 adults and 6 children and there was more than enough room to fit all of us. The unit was very clean upon arrival, but you can see some signs of wear. The owner Ben was very prompt with responses to emails we sent during our stay. We were very close to everything. Walmart was right around the corner, Wawa (we up north swear by their coffee lol), and bunches of restaurants. My family and I travel to Florida and rent houses at least twice a year and I know we would rent from Ben for sure in the future. Just a few recommendations: ALL of the pots and pans need to be replaced. Some were burned beyond recognition. You should also get some serving bowls for as most families will be preparing large meals. You could also use some new bed linens and towel sets. Other than that, the property is well maintained.
                                                            • Submitted: Sep 11, 2014
                                                            • Stayed: Jul 2014