A Kissimmee vacation rental makes the perfect home away from home

Kissimmee vacation homes & villas are located just south of Orlando and make a great home base for visiting major theme parks such as Walt Disney World, Universal Studios, Disney-MGM Studios, SeaWorld Orlando, and Disney’s Animal Kingdom. Guests of Kissimmee vacation rentals can also enjoy numerous other theme parks, arcades, and entertainment complexes.

Cultural attractions for guests of Kissimmee villas and vacation rentals include theatre, art, and concerts at the Osceola Center for the Arts and nearby opera, ballet, and symphony performances. Dinner shows in Kissimmee include the Medieval Times Dinner & Tournament, the Arabian Nights Dinner Attraction, and Capone's Dinner & Show.

Guests of Kissimmee vacation rentals can visit a variety of local museums, including the Flying Tigers Warbird Restoration Air Museum and the USSSA Sports Museum and Hall of Fame. Visitors can also learn about life as a Florida Cracker in the late 19th century at the Osceola County Historical Society and Pioneer Museum.

Other attractions for guests of Kissimmee vacation rentals and villas include live rodeo on Friday nights, parasailing, power boating, water skiing, airboating, and spectator sports such as Lacrosse, NCAA soccer, and Houston Astros spring training games. Shoppers will enjoy Kissimmee's historic downtown, as well as the numerous specialty shops, galleries, outlet malls, and regional malls in the area.

With Kissimmee accommodations ranging from luxury villas to condos to family-friendly vacation homes, you’re sure to find the perfect Kissimmee vacation rental for a memorable Orlando area vacation.

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While you're here, check out HomeAway's guide to Kissimmee.

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Kissimmee Area: Houses, Villas & More(3,824)

VRBO STAYED HERE!! 2.5 Miles to Disney! 6BR/4BA- 3100 Sf, Mickey Pool Private!!
    6 Bedrooms,
  • 4 Bathrooms
  • , Sleeps 16
Book it Now!
7 night Minimum Stay
  • 6 BR,
  • 4 BA,
  • Sleeps 16
#12630vb
    (25)
    Luxury 5BR/5BA Villa 2 miles to Disney with Games Room, Wifi + Free Pool Heating
      5 Bedrooms,
    • 5 Bathrooms
    • , Sleeps 12
    Book it Now!
    5 - 7 night Minimum Stay
    • 5 BR,
    • 5 BA,
    • Sleeps 12
    #320925
      (51)
      Windsor Hills is 1.5 Miles from Disney
        3 Bedrooms,
      • 2 Bathrooms
      • , Sleeps 8
      Book it Now!
      2 night Minimum Stay
      • 3 BR,
      • 2 BA,
      • Sleeps 8
      #83238vb
        (24)
        Fabulous 5 Bed, 5 Bath, Villa on 5 Star windsorhills
          5 Bedrooms,
        • 5 Bathrooms
        • , Sleeps 12
        Book it Now!
        5 - 7 night Minimum Stay
        • 5 BR,
        • 5 BA,
        • Sleeps 12
        #175219
          (24)
          Luxury Home, 4 miles from Disney, Large Pool & Spa
            6 Bedrooms,
          • 4 Bathrooms
          • , Sleeps 14
          Book it Now!
          4 night Minimum Stay
          • 6 BR,
          • 4 BA,
          • Sleeps 14
          #188987
            (17)
            FABULOUS 4 BED/3 BATH HOME WITH HDTV/AIR CON/WiFi/ POOL AND GAMES ROOM
              4 Bedrooms,
            • 3 Bathrooms
            • , Sleeps 8
            Book it Now!
            3 night Minimum Stay
            • 4 BR,
            • 3 BA,
            • Sleeps 8
            #227068
              (78)
              Luxury 5 min. from Disney w/princess room,private pool,spa,pool table,Wii,Xbox
                6 Bedrooms,
              • 4 Bathrooms
              • , Sleeps 14
              Book it Now!
              5 - 7 night Minimum Stay
              • 6 BR,
              • 4 BA,
              • Sleeps 14
              #270267
                (29)
                TOP VILLA - 5 Bedroom Reunion Golf Villa, Games Room, Cinema, Pool
                  5 Bedrooms,
                • 6 Bathrooms
                • 1 Half Bath
                • , Sleeps 10
                Book it Now!
                5 - 7 night Minimum Stay
                • 5 BR,
                • 6 BA,
                • 1 HF BA,
                • Sleeps 10
                #324844
                  (28)
                  TOP VILLA - 6BR, 4.5BA Reunion Rental, Games Room, Pool, Hot Tub
                    7 Bedrooms,
                  • 8 Bathrooms
                  • , Sleeps 16
                  Book it Now!
                  5 night Minimum Stay
                  • 7 BR,
                  • 8 BA,
                  • Sleeps 16
                  #325929
                    (24)
                    TOP VILLA - 8 Bedroom Reunion Resort Mansion, Games Room, Cinema, Gym
                      8 Bedrooms,
                    • 9 Bathrooms
                    • 2 Half Baths
                    • , Sleeps 18
                    Book it Now!
                    5 - 7 night Minimum Stay
                    • 8 BR,
                    • 9 BA,
                    • 2 HF BA,
                    • Sleeps 18
                    #325932
                      (37)
                      TOP VILLA - Luxury Reunion Resort 6 bed 6.5 Bath Villa, Amazing Pool
                        6 Bedrooms,
                      • 6 Bathrooms
                      • 1 Half Bath
                      • , Sleeps 12
                      Book it Now!
                      5 - 7 night Minimum Stay
                      • 6 BR,
                      • 6 BA,
                      • 1 HF BA,
                      • Sleeps 12
                      #356218
                        (25)
                        TOP VILLA - 6 Bedroom Luxury Villa with Cinema, Games Room & Pool
                          6 Bedrooms,
                        • 5 Bathrooms
                        • 1 Half Bath
                        • , Sleeps 12
                        Book it Now!
                        2 - 7 night Minimum Stay
                        • 6 BR,
                        • 5 BA,
                        • 1 HF BA,
                        • Sleeps 12
                        #356217
                          (21)
                          5 STAR...Ahead of the Ordinary, and beyond Compare...LUXURY DEFINED...
                            6 Bedrooms,
                          • 4 Bathrooms
                          • , Sleeps 12
                          Book it Now!
                          4 - 5 night Minimum Stay
                          • 6 BR,
                          • 4 BA,
                          • Sleeps 12
                          #368800
                            (19)
                            Summer Specials!!! Luxury 5BR/7BA on the Palmer Golf Course
                              5 Bedrooms,
                            • 7 Bathrooms
                            • , Sleeps 12
                            Book it Now!
                            3 night Minimum Stay
                            • 5 BR,
                            • 7 BA,
                            • Sleeps 12
                            #344050vb
                              (28)
                              From $69 night Free Wi-Fi 3bd 2 Bath Sleeps 8 15 minutes to Disney World HDDVR
                                3 Bedrooms,
                              • 2 Bathrooms
                              • , Sleeps 8
                              Book it Now!
                              3 - 7 night Minimum Stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 8
                              #186572
                                (12)
                                Beaut.Villa private S/W pool, spa, conservation view near Disney
                                  5 Bedrooms,
                                • 4 Bathrooms
                                • , Sleeps 10
                                Book it Now!
                                2 - 5 night Minimum Stay
                                • 5 BR,
                                • 4 BA,
                                • Sleeps 10
                                #285497
                                  (19)
                                  TOP VILLA - 6 beds, golf course views, pool, hot tub, games/cinema
                                    6 Bedrooms,
                                  • 6 Bathrooms
                                  • , Sleeps 12
                                  Book it Now!
                                  5 - 7 night Minimum Stay
                                  • 6 BR,
                                  • 6 BA,
                                  • Sleeps 12
                                  #393463
                                    (27)
                                    Fantastic Villa! Minutes to Disney ! Sparkling pool!
                                      3 Bedrooms,
                                    • 2 Bathrooms
                                    • , Sleeps 9
                                    Book it Now!
                                    4 night Minimum Stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 9
                                    #915319
                                      (40)
                                      Top VILLA - luxury Reunion Resort 5 Bedroom Home And Private Pool
                                        5 Bedrooms,
                                      • 5 Bathrooms
                                      • 1 Half Bath
                                      • , Sleeps 10
                                      Book it Now!
                                      5 - 7 night Minimum Stay
                                      • 5 BR,
                                      • 5 BA,
                                      • 1 HF BA,
                                      • Sleeps 10
                                      #916426
                                        (28)
                                        Near Disney 3/2 Decorated/Remodel Villa Free Wifi/Long Distance calls!
                                          3 Bedrooms,
                                        • 2 Bathrooms
                                        • , Sleeps 8
                                        Book it Now!
                                        4 night Minimum Stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 8
                                        #994975
                                          (16)
                                          Lindfields Luxury Holiday Villa, Kissimme, Florida. Minutes from Disney
                                            4 Bedrooms,
                                          • 4 Bathrooms
                                          • , Sleeps 10
                                          Book it Now!
                                          • 4 BR,
                                          • 4 BA,
                                          • Sleeps 10
                                          #835586
                                            (12)
                                            Luxury Home Free Pool/Spa Heat - Pinball, XBox 360, PS3 only 3 miles to Disney
                                              4 Bedrooms, Sleeps 8
                                            Book it Now!
                                            5 - 7 night Minimum Stay
                                            • 4 BR,
                                            • Sleeps 8
                                            #915075
                                              (19)
                                              TOP VILLA - Amazing 5 bed, 5 bath villa rental with the best golf view
                                                5 Bedrooms,
                                              • 5 Bathrooms
                                              • , Sleeps 10
                                              Book it Now!
                                              5 - 7 night Minimum Stay
                                              • 5 BR,
                                              • 5 BA,
                                              • Sleeps 10
                                              #916427
                                                (17)
                                                Sun! Sun! -Southwest Facing- Private Conservation View! No Chlorine Pool!
                                                  4 Bedrooms,
                                                • 3 Bathrooms
                                                • , Sleeps 8
                                                Book it Now!
                                                4 night Minimum Stay
                                                • 4 BR,
                                                • 3 BA,
                                                • Sleeps 8
                                                #930398
                                                  (27)
                                                  TOP VILLA - Reunion Resort vacation rental, golf course views
                                                    5 Bedrooms,
                                                  • 5 Bathrooms
                                                  • , Sleeps 10
                                                  Book it Now!
                                                  5 - 7 night Minimum Stay
                                                  • 5 BR,
                                                  • 5 BA,
                                                  • Sleeps 10
                                                  #393464
                                                    (17)
                                                    Your 5 Star 4/3 Disney Pool Home, 3D TV, Games Room +++
                                                      4 Bedrooms,
                                                    • 3 Bathrooms
                                                    • , Sleeps 8
                                                    Book it Now!
                                                    4 - 12 night Minimum Stay
                                                    • 4 BR,
                                                    • 3 BA,
                                                    • Sleeps 8
                                                    #911085
                                                      (28)
                                                      6 bedroom luxury vacation home with pool
                                                        6 Bedrooms,
                                                      • 4 Bathrooms
                                                      • 1 Half Bath
                                                      • , Sleeps 13
                                                      Book it Now!
                                                      2 - 5 night Minimum Stay
                                                      • 6 BR,
                                                      • 4 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 13
                                                      #292842
                                                        (14)
                                                        Luxury Home - 4 King Beds, WIFI, Pool/Spa, Game Room, Video Arcade, Near Disney!
                                                          7 Bedrooms,
                                                        • 4 Bathrooms
                                                        • 1 Half Bath
                                                        • , Sleeps 16
                                                        Book it Now!
                                                        4 - 6 night Minimum Stay
                                                        • 7 BR,
                                                        • 4 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 16
                                                        #169159
                                                          (19)
                                                          Fabulous Disney Area Home with Private Pool in the Gated Cumbrian Lakes Resort !
                                                            5 Bedrooms,
                                                          • 3 Bathrooms
                                                          • 2 Half Baths
                                                          • , Sleeps 12
                                                          Book it Now!
                                                          3 - 6 night Minimum Stay
                                                          • 5 BR,
                                                          • 3 BA,
                                                          • 2 HF BA,
                                                          • Sleeps 12
                                                          #941037
                                                            (12)
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                                                            Kissimmee Area