Kissimmee Vacation Rentals

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Kissimmee vacation rentals >>
These Kissimmee vacation homes, condos, villas, cabins, cottages, chalets, and bed & breakfasts are presented by their owners or agents. Please contact them directly with your inquiries. Click on the underlined descriptions below for more details and property photos.
Click Here to review listings ordered by city and # of bedrooms.
 
Premium Listings
Immaculate 4 Bedroom, 3 Bathroom Villa with Pool, less than 8 minutes from Disney World!
  • Kissimmee
  • Villa
  • 4 bedrooms, sleeps 10
  • 3 bathrooms
  • Weekly rates
    From 1015 to 1155 USD
 

The Luxurious Waterfront Bellagio
  • Kissimmee
  • Villa
  • 6 bedrooms, sleeps 14
  • 4 bathrooms
     

    Beautiful Executive Villa with Private Pool & Spa at Twin Palms, 4beds/4baths, Closest to Magic ! 1.5 miles to Disney!
    • Kissimmee
    • Villa
    • 4 bedrooms, sleeps 10
    • 4 bathrooms
       

      Sweetwater Club Condo in Kissimmee, Florida
      • Kissimmee
      • Condo
      • 3 bedrooms, sleeps 7
      • 2 bathrooms
      • Weekly rates
        From 525 to 775 USD
       

      Brand New Townhouse "Venetian Bay Villages" 15 min. to DisneyWorld, Universal Studios
      • Kissimmee
      • Townhouse
      • 3 - 4 bedrooms, sleeps 8 - 10
      • 2 - 3 bathrooms
         

        Fireworks View of Disney-Wonderful Home with Private Heated Pool- Free Calls & "High Speed" Internet
        • Kissimmee
        • House (single)
        • 4 bedrooms, sleeps 8
        • 3 bathrooms
           

          Windsor Hills - Luxurious 4 Bedroom Orlando Executive Vacation Pool Home
          • Kissimmee
          • Villa
          • 4 bedrooms
          • 4 bathrooms
             

            Luxury lakeview Florida holiday home. Our 5 bedroom 3 bath Orlando villa with private pool & spa is in the beautiful Crescent Lakes community.
            • Kissimmee
            • House (single)
            • 5 bedrooms, sleeps 12
            • 3 bathrooms
               

              A SLICE OF PARADISE
              • Kissimmee
              • House (single)
              • 3 bedrooms, sleeps 6
              • 2 bathrooms
              • Weekly rates
                From 695 to 895 USD
               

              Exclusive Sunridge Community with Private Pool - Close to Disney
              • Kissimmee
              • Villa
              • 4 bedrooms, sleeps 8-10
              • 2 bathrooms
                 

                Elegant Executive-Style Florida Vacation Rental Townhouse - Windsor Hills
                • Kissimmee
                • Townhouse
                • 3 bedrooms, sleeps 8
                • 3 bathrooms
                   

                  Brand New, 4 Bedroom Kissimmee Townhome, 3 Miles from Theme Park!
                  • Kissimmee
                  • Villa
                  • 4 bedrooms, sleeps 8-12
                  • 2 bathrooms
                  • Weekly rates
                    From 500 to 1000 USD
                   

                  Spectacular is the only word to describe Emerald Sunshine, nestled in a fabulous enclave at the prestigious Emerald Island Resort
                  • Kissimmee
                  • Villa
                  • 7 bedrooms, sleeps 14-16
                  • 5.5 bathrooms
                     

                    Disney Vacation Rental at Windsor Hills
                    • Kissimmee
                    • Townhouse
                    • 3 bedrooms, sleeps 8
                    • 3 bathrooms
                       

                      Stay At This Luxurious Vacation Home And Enjoy All Of The On Site Amenities, Plus It Is Less Than 5 Minutes Away From Disney !!
                      • Kissimmee
                      • Villa
                      • 4 bedrooms, sleeps 10
                      • 3 bathrooms
                         

                        Florida 4 Bedroom Vacation Home with Lake Views
                        • Kissimmee
                        • House (single)
                        • 4 bedrooms
                        • 3 bathrooms
                        • Weekly rates
                          From 750 to 1350 USD
                         

                        Orlando Pool Homes
                        • Kissimmee
                        • Home
                        • 3-7 bedrooms, sleeps 6-16
                        • 2-4 bathrooms
                           

                          Disney Area Vacation Homes is proud to offer you this 3 bedroom/2 bath condo.
                          • Kissimmee
                          • Condo
                          • 3 bedrooms
                          • 2 bathrooms
                             

                            Beautiful Luxury Villa Just Minutes Away From Parks
                            • Kissimmee
                            • Villa
                            • 4 bedrooms, sleeps 8
                            • 3 bathrooms
                               

                              Windsor Palms! Great Rates 3.5 miles to Disney
                              • Kissimmee
                              • House (single)
                              • 4 bedrooms
                              • 3 bathrooms
                                 

                                Awesome 2-Bedroom Condo in Orlando/Kissimmee, FL
                                • Kissimmee
                                • Condo
                                • 2 bedrooms, sleeps 6
                                • 2 bathrooms
                                   

                                  Fairytale Holiday Pool Villa near Disney, Universal
                                  • Kissimmee
                                  • Villa
                                  • 3 bedrooms, sleeps 8
                                  • 2 bathrooms
                                     

                                    7 Bed 3.5 Bath Villa With Pool, Games Room, Internet, and Free International calls
                                    • Kissimmee
                                    • Villa
                                    • 7 bedrooms
                                    • 3.5 bathrooms
                                    • Weekly rates
                                      From 205 to 2065 USD
                                     

                                    Amenity Filled Luxury Home - 5 Minutes to Disney!!!
                                    • Kissimmee
                                    • Villa
                                    • 6 bedrooms, sleeps 14
                                    • 4 bathrooms
                                       

                                      Windsor Palms!! Pet Friendly!
                                      • Kissimmee
                                      • Townhouse
                                      • 3 bedrooms
                                      • 3 bathrooms
                                         

                                        Location, location, location: Windsor Hills is the closest resort to the Disney parks! Prices start at $69 per night!!!
                                        • Kissimmee
                                        • Condo
                                        • 3 bedrooms, sleeps 8
                                        • 2 bathrooms
                                           

                                          4 Bed 3 Bath Townhouse located in Kissimmee
                                          • Kissimmee
                                          • House (single)
                                          • 4 bedrooms
                                          • 3 bathrooms
                                          • Weekly rates
                                            From 70 to 665 USD
                                           

                                          We Have A Lagoon Style Pool At The Clubhouse With A 2 Story Water Slide
                                          • Kissimmee
                                          • Villa
                                          • 6 bedrooms, sleeps 12-14
                                          • 4 bathrooms
                                             

                                            Orlando Pool Homes Happy Guests
                                            • Kissimmee
                                            • Home
                                            • 3-7 bedrooms, sleeps 8-14
                                            • 2-4 bathrooms
                                               

                                              5 Bedroom Kissimmee Vacation Rental with the Largest South-Facing Pool in Highly Sought After Indian Creek
                                              • Kissimmee
                                              • Executive
                                              • 5 bedrooms, sleeps 10-12
                                              • 4 bathrooms
                                              • Weekly rates
                                                From 1100 to 1300 USD
                                               

                                              Windsor Hills Luxury 6 Bed Home with Private Pool, Hydro Spa
                                              • Kissimmee
                                              • House (single)
                                              • 6 bedrooms, sleeps 2 King, 2 Q
                                              • 4 bathrooms
                                                 

                                                Model Home - Amenities Galore! - 5 Minutes to Disney!!!
                                                • Kissimmee
                                                • Villa
                                                • 4 bedrooms, sleeps 10
                                                • 3 bathrooms
                                                   

                                                  Beautiful 5 Bedroom/ 5 Bath Home enjoy the sights & sounds of Disney’s FIREWORKS!
                                                  • Kissimmee
                                                  • House (single)
                                                  • 5 bedrooms
                                                  • 5 bathrooms
                                                     

                                                    Emerald Island Community - Hula Heaven Villa
                                                    • Kissimmee
                                                    • Townhouse
                                                    • 3 bedrooms, sleeps 8
                                                    • 2 bathrooms
                                                       

                                                      6 Bed 3.5 Bath Villa With Pool, Spa, Internet Access, Games Room, and Free International Phone Calls
                                                      • Kissimmee
                                                      • Villa
                                                      • 6 bedrooms
                                                      • 3.5 bathrooms
                                                         

                                                        End Unit Grand Palms Retreat Condo Just Three Miles To New Disney Entrance!!
                                                        • Kissimmee
                                                        • Condo
                                                        • 3 bedrooms, sleeps 8
                                                        • 2 bathrooms
                                                        • Weekly rates
                                                          From 529 to 695 USD
                                                         

                                                        Beautiful Luxury Home with Private Pool & Spa
                                                        • Kissimmee
                                                        • House (single)
                                                        • 3 bedrooms, sleeps 8
                                                        • 3.5 bathrooms
                                                           

                                                          Luxury Villa on the Superb Terra Verde Resort - 6 Bedrooms - Florida
                                                          • Kissimmee
                                                          • Villa
                                                          • 6 bedrooms, sleeps 12
                                                          • 5.5 bathrooms
                                                          • Weekly rates
                                                            From 1050 to 1960 USD
                                                           

                                                          Eagle Pointe 4/3 Pool Home! $79 night Stay 3 get 4th free in Nov except Holida
                                                          • Kissimmee
                                                          • House (single)
                                                          • 4 bedrooms, sleeps 10
                                                          • 3 bathrooms
                                                          • Weekly rates
                                                            From 79 to 95 USD
                                                           

                                                          4 Bed 3 Bath Townhouse with Pool on The Excellent Terra Verde Resort
                                                          • Kissimmee
                                                          • Townhouse
                                                          • 4 bedrooms
                                                          • 3 bathrooms
                                                          • Weekly rates
                                                            From 70 to 665 USD
                                                           

                                                          Wyndham Orlando at Cypress Palms
                                                          • Kissimmee
                                                          • Condo
                                                          • 1-2 bedrooms
                                                             

                                                            Sunshine Property Rentals, Close to Disney World and other Theme parks
                                                            • Kissimmee
                                                            • House (single)
                                                            • 5 bedrooms, sleeps 10
                                                            • 3.5 bathrooms
                                                               

                                                              ** BEST AT DISNEY ** NOTHING TO COMPARE!
                                                              • Kissimmee
                                                              • Townhouse
                                                              • 3 bedrooms, sleeps 6
                                                              • 3 bathrooms
                                                              • Weekly rates
                                                                From 69 to 89 USD
                                                               

                                                              3 Bedroom/3 Bath Home Air Conditioned Game Room, Private Pool & Automatic Hydro Spa
                                                              • Kissimmee
                                                              • House (single)
                                                              • 3-6 bedrooms, sleeps 1-12
                                                              • 3-4 bathrooms
                                                                 

                                                                Disney Golfing VIlla
                                                                • Kissimmee
                                                                • Villa
                                                                • 5 bedrooms, sleeps 10
                                                                • 3 bathrooms
                                                                   

                                                                  Mary and Ed's Condo only 1 and 1/2 miles from Disney's Gates
                                                                  • Kissimmee
                                                                  • Condo
                                                                  • 3 bedrooms, sleeps 8
                                                                  • 2 bathrooms
                                                                  • Weekly rates
                                                                    From 630 to 985 USD
                                                                   

                                                                  Florida Vacation Rental, Kissimmee, Florida at Windsor Hills
                                                                  • Kissimmee
                                                                  • Townhouse
                                                                  • 3 bedrooms, sleeps 8
                                                                  • 3 bathrooms
                                                                     

                                                                    $59/nt LUXURY CONDO 3BD/2BTH 3 MILES TO DISNEY $59*$59*$59*$59*$59*$59*$59
                                                                    • Kissimmee
                                                                    • Condo
                                                                    • 3 bedrooms, sleeps 8
                                                                    • 2 bathrooms
                                                                       

                                                                      Beautiful Orlando Vacation Home with Pool - Close to Disney
                                                                      • Kissimmee
                                                                      • House (single)
                                                                      • 4 bedrooms, sleeps 8
                                                                      • 2 bathrooms
                                                                         

                                                                        4 Bed 3 Bath Villa With Pool and Spa Free International calls
                                                                        • Kissimmee
                                                                        • Villa
                                                                        • 4 bedrooms
                                                                        • 3 bathrooms
                                                                        • Weekly rates
                                                                          From 125 to 1015 USD
                                                                         

                                                                        Look No Further 3/3 Gem 2 miles from the Magic Kingdom - Disney
                                                                        • Kissimmee
                                                                        • Townhouse
                                                                        • 3 bedrooms, sleeps 6-8
                                                                        • 3 bathrooms
                                                                           

                                                                          7 Bed 4.5 Bath Villa With Pool, Spa, and Games Room
                                                                          • Kissimmee
                                                                          • Villa
                                                                          • 7 bedrooms
                                                                          • 4.5 bathrooms
                                                                          • Weekly rates
                                                                            From 205 to 2065 USD
                                                                           

                                                                          Windsor Palms 3 Bed 3 Bath! Splash Pool! Near the Parks
                                                                          • Kissimmee
                                                                          • Townhouse
                                                                          • 3 bedrooms, sleeps 8
                                                                          • 3 bathrooms
                                                                             

                                                                            Executive Orlando Vacation Villa - Terre Verde Resort Community
                                                                            • Kissimmee
                                                                            • Villa
                                                                            • 6 bedrooms, sleeps 14
                                                                            • 5.5 bathrooms
                                                                               

                                                                              VILLA DEL SOL CONDO - MINUTES FROM DISNEY
                                                                              • Kissimmee
                                                                              • Condo
                                                                              • 2 bedrooms, sleeps 6
                                                                              • 2 bathrooms
                                                                                 

                                                                                Luxury 4BR/3BA Home with Pool in Rolling Hills, Kissimmee
                                                                                • Kissimmee
                                                                                • House (single)
                                                                                • 4 bedrooms, sleeps 9
                                                                                • 3 bathrooms
                                                                                   

                                                                                   
                                                                                   
                                                                                  Rental Locations
                                                                                   
                                                                                   
                                                                                    City BR(s) BA(s) Sleeps Description
                                                                                   
                                                                                  Kissimmee BR BAInformation Coming soon!!!
                                                                                   
                                                                                  Kissimmee BR BA
                                                                                   
                                                                                  Kissimmee1-2 BR BAWyndham Orlando at Cypress Palms
                                                                                   
                                                                                  Kissimmee2 BR2 BA6VILLA DEL SOL CONDO - MINUTES FROM DISNEY
                                                                                   
                                                                                  Kissimmee2 BR2 BAWindsor Palms! Great Rates!! Close to Disney!!
                                                                                   
                                                                                  Kissimmee2 BR2 BAThe Carolina
                                                                                   
                                                                                  Kissimmee2 BR2 BATequila Sunrise - The Condo is completely furnished and is beautifully decorated.
                                                                                   
                                                                                  Kissimmee2 BR2 BA6Beautiful 2BR Condo - Just 7 Miles from Disney - Villa del Sol
                                                                                   
                                                                                  Kissimmee2 BR2 BA6Palm Villa Beutiful 2/2 Villa 1.5 miles from Disney
                                                                                   
                                                                                  Kissimmee2 BR2 BA6Awesome 2-Bedroom Condo in Orlando/Kissimmee, FL
                                                                                   
                                                                                  Kissimmee2 BR2 BA6FantasyWorld Club Villas
                                                                                   
                                                                                  Kissimmee3-7 BR2-4 BA6-16Orlando Pool Homes
                                                                                   
                                                                                  Kissimmee3-7 BR2-4 BA8-14Orlando Pool Homes Happy Guests
                                                                                   
                                                                                  Kissimmee3 BR3 BA8Florida Vacation Rental, Kissimmee, Florida at Windsor Hills
                                                                                   
                                                                                  Kissimmee3 BR2 BA8Close to Disney World - Kissimmee Vacation Rental
                                                                                   
                                                                                  Kissimmee3 BR2 BA8$59/nt. LUXURY 3 BD/ 2 BTH CONDO/ 3 MILES TO DISNEY $59*$59*$59*$59
                                                                                   
                                                                                  Kissimmee3 BR2 BA8$59/nt LUXURY CONDO 3BD/2BTH 3 MILES TO DISNEY $59*$59*$59*$59*$59*$59*$59
                                                                                   
                                                                                  Kissimmee3 BR2 BA"Southern Palms" 3 Bedroom Disney Villa - GOLF & LAKE VIEW
                                                                                   
                                                                                  Kissimmee3 BR2 BA8Fairytale Holiday Pool Villa near Disney, Universal
                                                                                   
                                                                                  Kissimmee3 BR2 BA8End Unit Grand Palms Retreat Condo Just Three Miles To New Disney Entrance!!
                                                                                   
                                                                                  Kissimmee3 BR3 BA8 Disney Vacation Rental at Windsor Hills
                                                                                   
                                                                                  Kissimmee3 BR3 BA8Windsor Hills Community with Olympic Pool & 58 seat theatre on resort
                                                                                   
                                                                                  Kissimmee3 BR2.5 BA8Beautiful 3 BR 2.5 BA Florida Vacation Rental Townhomein a Gated Community - Terra Verde
                                                                                   
                                                                                  Kissimmee3 BR3 BA8Elegant Executive-Style Florida Vacation Rental Townhouse - Windsor Hills
                                                                                   
                                                                                  Kissimmee3 BR2 BA6A SLICE OF PARADISE
                                                                                   
                                                                                  Kissimmee3 BR2 BA8Emerald Island Community - Hula Heaven Villa
                                                                                   
                                                                                  Kissimmee3 BR3.5 BA8Beautiful Luxury Home with Private Pool & Spa
                                                                                   
                                                                                  Kissimmee3 - 4 BR2 - 3 BA8 - 10Brand New Townhouse "Venetian Bay Villages" 15 min. to DisneyWorld, Universal Studios
                                                                                   
                                                                                  Kissimmee3-6 BR3-4 BA1-123 Bedroom/3 Bath Home Air Conditioned Game Room, Private Pool & Automatic Hydro Spa
                                                                                   
                                                                                  Kissimmee3 BR3 BA8Windsor Palms 3 Bed 3 Bath! Splash Pool! Near the Parks
                                                                                   
                                                                                  Kissimmee3 BR3 BAWindsor Palms!! Pet Friendly!
                                                                                   
                                                                                  Kissimmee3 BR2 BADisney Area Vacation Homes is proud to offer you this 3 bedroom/2 bath condo.
                                                                                   
                                                                                  Kissimmee3 BR3 BATropical Palm - Windsor Palms Resort
                                                                                   
                                                                                  Kissimmee3 BR3 BA8Windsor Hills! 3 Bed 3 Bath Close to Disney!!
                                                                                   
                                                                                  Kissimmee3 BR2 BA6Ground Floor! Near Pool!
                                                                                   
                                                                                  Kissimmee3 BR2 BA8Windsor Hills! Near Pool! Ground Floor!
                                                                                   
                                                                                  Kissimmee3 BR2 BA8Happiest Place On Earth With A Disney Themed Children's Room
                                                                                   
                                                                                  Kissimmee3 BR2 BA8Krissy's Place
                                                                                   
                                                                                  Kissimmee3 BR2 BA8Mickey's Oasis
                                                                                   
                                                                                  Kissimmee3 BR2 BA7-8Sumptuous Holiday Cottage Villa 5 Minutes from Disney World!
                                                                                   
                                                                                  Kissimmee3 BR2 BA8Location, location, location: Windsor Hills is the closest resort to the Disney parks! Prices start at $69 per night!!!
                                                                                   
                                                                                  Kissimmee3 BR3 BA6-8Look No Further 3/3 Gem 2 miles from the Magic Kingdom - Disney
                                                                                   
                                                                                  Kissimmee3 BR3 BA6** BEST AT DISNEY ** NOTHING TO COMPARE!
                                                                                   
                                                                                  Kissimmee3 BR