Vacation Rentals with Pool in Kissimmee

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Filtering by: Swimming pool

20,609 vacation rentals

(45) Excellent 

Certificate of Excellence

    35

    Fantasy Pool Home

    Central Florida / Kissimmee

    Kissimmee villa

    4 8 min stay varies

    • 4 bedrooms
    • sleeps 8
    • min stay varies
    • Nearest beach 125 mi
    • Swimming pool
    • Child Friendly

    Certificate of Excellence

    Price per night from

    $138

    Responds fast!
    avg. 2 hours 15 minutes

    Price per night from

    $138

    (22) Very Good 

      21

      Furnished apartment - weekly & monthly Orlando rental.

      Central Florida / Kissimmee

      Kissimmee hotel apartment

      3 6 min stay varies

      • 3 bedrooms
      • sleeps 6
      • min stay varies
      • Nearest beach 64 mi
      • Swimming pool
      • Child Friendly
      “Wonderful Place to stay” I stayed at the Island Club for a period of 3 months and was very happy with my stay. It was quiet, and comfortable. I liked the layout of my condo which was on one floor. My family of 5 had plenty of room to enjoy. I also
      …see more

      Price per night from

      $89

      Price per night from

      $89

      (10) Excellent 

      Certificate of Excellence

        49

        FIVE STAR 3 BR Home - Private Pool, Games Room, WiFi, BBQ - Orlando/Disney

        Central Florida / Kissimmee

        Kissimmee house

        3 7 min stay varies

        • 3 bedrooms
        • sleeps 7
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Air conditioning
        “Great Home, Safe & quiet neighborhood” I will be "Renting this Vacation Home Again" Home was clean. My RATING for this Home and Customer servive is *** A+*****. Beutiful Home. Thank you again Tonya.
        …see more

        Certificate of Excellence

        Price per night from

        $132

        Price per night from

        $132

          49

          NEW! 4/3 Private Town Home at Storey Lake Resort-Near Disney Theme Parks

          Central Florida / Kissimmee

          Kissimmee townhouse

          4 8 min stay varies

          • 4 bedrooms
          • sleeps 8
          • min stay varies
          • Swimming pool
          • Child Friendly
          • Air conditioning

          Price per night from

          $182

          Responds fast!
          avg. 14 minutes

          Price per night from

          $182

          (13) Very Good 

            27

            New Opening 5Br/3Ba Hot Tub/Lake View,Close Disney,Seaworld,Convention Center

            Central Florida / Kissimmee

            Kissimmee townhouse

            5 12 min stay varies

            • 5 bedrooms
            • sleeps 12
            • min stay varies
            • Beach / lakeside relaxation
            • Swimming pool
            • Child Friendly
            “Ok” Overall it was fine..checkout was at 11 and at 10 cleaners knocked on door and then preceded to sit in driveway waiting for us to leave. There was no dish soap or soap in bathrooms which would have been nice.
            …see more

            Price per night from

            $90

            Responds fast!
            avg. 3 hours 23 minutes

            Price per night from

            $90

            (6) Very Good 

              25

              From $80/nt,Close to Disney,Seaworld,Convention Center,4br Townhome with Hot Tub

              Central Florida / Kissimmee

              Kissimmee townhouse

              4 10 min stay varies

              • 4 bedrooms
              • sleeps 10
              • min stay varies
              • Nearest beach 97 mi
              • Swimming pool
              • Child Friendly
              “Great Family Friendly Home” We had a blast. It felt safe and secure. It was clean and spacious. I have a large family of 9 and everyone had plenty of space. Quiet but friendly neighbors. Amenities were awesome. Hot tub was so relaxing. We had a great
              …see more

              Price per night from

              $80

              Responds fast!
              avg. 3 hours 23 minutes

              Price per night from

              $80

              (16) Excellent 

                28

                Any Week in (FEBRUARY-SPECIAL) $999 (includes TAXES & Final Cleaning)

                Central Florida / Kissimmee

                Kissimmee house

                4 10 min stay varies

                • 4 bedrooms
                • sleeps 10
                • min stay varies
                • Swimming pool
                • Child Friendly
                • Air conditioning
                “Awesome Stay!” Can't say enough great things about this property. It was everything as described and pictured. The location was perfect being only about 20 minutes from the Disney parks. The pool, which is beautiful, was a welcome addition after s
                …see more

                Price per night from

                $132

                Price per night from

                $132

                (33) Very Good 

                  27

                  1.5 M to Disney,From $70/nt,3BR 1600 sqft Townhome

                  Central Florida / Kissimmee

                  Kissimmee apartment

                  3 8 min stay varies

                  • 3 bedrooms
                  • sleeps 8
                  • min stay varies
                  • Nearest beach 97 mi
                  • Swimming pool
                  • Child Friendly
                  “Spacious family friendly condo close to Disney.” Perfect location to visit Disney. Very spacious with a full kitchen . A great family friendly condo.
                  …see more

                  Price per night from

                  $70

                  Responds fast!
                  avg. 3 hours 22 minutes

                  Price per night from

                  $70

                  (17) Very Good 

                    36

                    Spacious 4-bed lakeside pool villa near Disney

                    Central Florida / Kissimmee

                    Kissimmee villa

                    4 10 min stay varies

                    • 4 bedrooms
                    • sleeps 10
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Nearest beach 97 mi
                    • Swimming pool
                    “Peaceful location with stunning views” We had a wonderful holiday in this lovely villa. It is spacious and well appointed everything was beautifully clean. The estate is quiet and peaceful considering how close it is to the 192 and all it has to offer
                    …see more

                    Price per night from

                    $114

                    Responds fast!
                    avg. 2 hours 19 minutes

                    Price per night from

                    $114

                    (14) Excellent 

                      33

                      Terra Verde 5 Bedroom with Conservation View

                      Central Florida / Kissimmee

                      Kissimmee villa

                      5 10 5 nights min

                      • 5 bedrooms
                      • sleeps 10
                      • 5 nights min
                      • Beach / lakeside relaxation
                      • Nearest beach 56 mi
                      • Swimming pool
                      “Very nice” The home was just as promised. It was clean and well kept. The location was a straight shot to disney. We didn't have to go on the toll road. Terra verde was great also. I liked the idea of a safe and secure place to stay in a home away fro
                      …see more

                      Price per night from

                      $180

                      Responds fast!
                      avg. 1 hour 0 minutes

                      Price per night from

                      $180

                      (32) Very Good 

                        49

                        Pat and Ron's Holiday Home, Relaxing Retreat

                        Central Florida / Kissimmee

                        Kissimmee villa

                        3 6 4 nights min

                        • 3 bedrooms
                        • sleeps 6
                        • 4 nights min
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning
                        “Good” I was a little disappointed this time. I have been going there since 2015. In the past when I had minor problems with the home, the response was quick. This time I called on Saturday to ask about no input message on the tv screen, I was told
                        …see more

                        Price per night from

                        $101

                        Price per night from

                        $101

                        (2) Excellent 

                          37

                          2636TW- Veranda Palms

                          Central Florida / Kissimmee

                          Kissimmee house

                          6 13 min stay varies

                          • 6 bedrooms
                          • sleeps 13
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $195

                          Price per night from

                          $195

                          (16) Excellent 

                            26

                            Kissimmee Townhouse 4 bedrooms

                            Central Florida / Kissimmee

                            Kissimmee townhouse

                            4 8 3 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 3 nights min
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning
                            “Great Place” This vacation home is absolutely beautiful and convenient to everything. Still here and having a great time.
                            …see more

                            Price per night from

                            $137

                            Price per night from

                            $137

                            (3) Very Good 

                              47

                              Kissimmee Windsor at Westside's "The Second Star to the Right" vacation home

                              Central Florida / Kissimmee

                              Kissimmee villa

                              7 17 min stay varies

                              • 7 bedrooms
                              • sleeps 17
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $286

                              Responds fast!
                              avg. 3 hours 11 minutes

                              Price per night from

                              $286

                              (4) Excellent 

                                41

                                Feb 23-March 2 special-Windsor Hills Luxury pool house/2 miles to Disney

                                Kissimmee / Windsor Hills Resort

                                Kissimmee house

                                6 13 min stay varies

                                • 6 bedrooms
                                • sleeps 13
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $199

                                Responds fast!
                                avg. 1 hour 21 minutes

                                Price per night from

                                $199

                                (3) Very Good 

                                  43

                                  Close2theMagic 3br/3ba Townhouse Windsor Hills

                                  Central Florida / Kissimmee

                                  Kissimmee house

                                  3 7 2 nights min

                                  • 3 bedrooms
                                  • sleeps 7
                                  • 2 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning
                                  “Vacation comfort at its Best!” This was a family vacation to bring my 5 yr old granddaughter to Disney for her first time. It was spectacular! The condo was so close to Disney that we could be there in a few minutes. The heated splash pool was so a
                                  …see more

                                  Price per night from

                                  $136

                                  Price per night from

                                  $136

                                  (7) Very Good 

                                    16

                                    The Charming Mickey's Tree House,

                                    Central Florida / Kissimmee

                                    Kissimmee villa

                                    4 9 min stay varies

                                    • 4 bedrooms
                                    • sleeps 9
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Air conditioning
                                    “Awesome vacation!!” My husband and I took our 3 year old daughter and had a wonderful time. The house had everything we needed and more. We felt right at home from the time we got there until the time we went home. The pool and hot tub were perfect
                                    …see more

                                    Price per night from

                                    $103

                                    Price per night from

                                    $103

                                    (34) Excellent 

                                      40

                                      Stunning Lake View 7 bdrms 5.5 baths(4 king bed suites)

                                      Central Florida / Kissimmee

                                      Kissimmee villa

                                      7 16 min stay varies

                                      • 7 bedrooms
                                      • sleeps 16
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Nearest beach 61 mi
                                      • Swimming pool
                                      “We enjoyed our stay” It was a nice house. Me and my family enjoyed ourselves. It was clean and the owners were nice and communicative.
                                      …see more

                                      Price per night from

                                      $183

                                      Responds fast!
                                      avg. 3 hours 26 minutes

                                      Price per night from

                                      $183

                                      (3) Excellent 

                                        62

                                        New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney

                                        Central Florida / Kissimmee

                                        Kissimmee house

                                        9 20 min stay varies

                                        • 9 bedrooms
                                        • sleeps 20
                                        • min stay varies
                                        • Swimming pool
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $320

                                        Responds fast!
                                        avg. 3 hours 23 minutes

                                        Price per night from

                                        $320

                                          17

                                          Christine’s Villa

                                          Central Florida / Kissimmee

                                          Kissimmee villa

                                          3 6 7 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 7 nights min
                                          • Swimming pool
                                          • Ask about children
                                          • Air conditioning

                                          Price per night from

                                          $180

                                          Price per night from

                                          $180

                                          (36) Very Good 

                                            21

                                            Luxurious 3 Bedroom Townhome-1.5 miles from Disney

                                            Central Florida / Kissimmee

                                            Kissimmee villa

                                            3 7 min stay varies

                                            • 3 bedrooms
                                            • sleeps 7
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning
                                            “Great Experience” The villa did not disappoint and was a great place for my family and I to stay during our world wind visit to Disney. I would recommend this place to anyone who is going to Orlando with a large group :-)
                                            …see more

                                            Price per night from

                                            $79

                                            Responds fast!
                                            avg. 1 hour 21 minutes

                                            Price per night from

                                            $79

                                            (17) Excellent 

                                              53

                                              'Casa Linda' Beautiful Lakeside Home with Gym and Hot Tub

                                              Central Florida / Kissimmee

                                              Kissimmee house

                                              3 8 4 nights min

                                              • 3 bedrooms
                                              • sleeps 8
                                              • 4 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 121 mi
                                              • Swimming pool
                                              “Amazing” Beautiful :) This was definitely a great place to stay My daughter and I had a nice relaxing vacation while staying here Definitely would recommend this to anyone looking for a nice place to stay Thank you :)
                                              …see more

                                              Price per night from

                                              $103

                                              Price per night from

                                              $103

                                              (12) Very Good 

                                                29

                                                From $90/nt,5br/3ba townhome with hot tub,Near Disney,Seaworld,Convention center

                                                Central Florida / Kissimmee

                                                Kissimmee apartment

                                                5 12 min stay varies

                                                • 5 bedrooms
                                                • sleeps 12
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Nearest beach 97 mi
                                                • Swimming pool
                                                “Vacation rental” The overall experience was nice. The hot was only hot for one day and wouldn't get hot again there after. The cookware needs to be updated but overall we had a great time. I wouldn't definitely rent this rental again.
                                                …see more

                                                Price per night from

                                                $90

                                                Responds fast!
                                                avg. 3 hours 23 minutes

                                                Price per night from

                                                $90

                                                (27) Excellent 

                                                  15

                                                  Luxury 4 Bedroom Villa w/pool, 2 Miles from Disney

                                                  Central Florida / Kissimmee

                                                  Kissimmee house

                                                  4 8 4 nights min

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • 4 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning
                                                  “Beautiful Home, It was so relaxing and comfortable!!” Our family had a wonderful time on our Vacation. The location was very convenient. The pool and hot tub was great. The house was amazing, and my children loved it, I like the entrance to the pool a
                                                  …see more

                                                  Price per night from

                                                  $106

                                                  Price per night from

                                                  $106

                                                    4

                                                    Furnished 4 Bedroom Villa for Rent

                                                    Central Florida / Kissimmee

                                                    Kissimmee villa

                                                    4 10 2 nights min

                                                    • 4 bedrooms
                                                    • sleeps 10
                                                    • 2 nights min
                                                    • Swimming pool
                                                    • Air conditioning

                                                    Price per night from

                                                    $235

                                                    Price per night from

                                                    $235

                                                    (8) Very Good 

                                                      18

                                                      Luxury 2 miles from Disney w/Princess Rm, Pool/Spa

                                                      Central Florida / Kissimmee

                                                      Kissimmee house

                                                      6 12 min stay varies

                                                      • 6 bedrooms
                                                      • sleeps 12
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning
                                                      “Great place” The location is perfect. The owners were easy to work with. I feel they red to find a better. Leaning company. Not as clean as I would have liked. Overall it was a great place to stay.
                                                      …see more

                                                      Price per night from

                                                      $185

                                                      Responds fast!
                                                      avg. 3 hours 37 minutes

                                                      Price per night from

                                                      $185

                                                      (37) Very Good 

                                                        34

                                                        7 Bedroom Home and only 10 minutes to Disney, Newly Renovated, Forest View,

                                                        Central Florida / Kissimmee

                                                        Kissimmee villa

                                                        7 17 3 nights min

                                                        • 7 bedrooms
                                                        • sleeps 17
                                                        • 3 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 97 mi
                                                        • Swimming pool
                                                        “Best time ever” This was our second time staying in that dame house, we loved it and plan on staying there more in the future. The house was more then enough on space. Everything very clean and comfortable. The pool was a amazing time on a hit day. E
                                                        …see more

                                                        Price per night from

                                                        $247

                                                        Responds fast!
                                                        avg. 1 hour 29 minutes

                                                        Price per night from

                                                        $247

                                                        (7) Very Good 

                                                          40

                                                          Lakefront, gated 4Br/3Ba, 6mile to Disney, Private Jacuzzi, Free WiFi/Cable TV

                                                          Central Florida / Kissimmee

                                                          Kissimmee villa

                                                          4 10 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 10
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 72 mi
                                                          • Swimming pool
                                                          “Very pleased” We were very pleased with the house and the attention given by the owner, I emailed a concern and 1 hour later it was resolved. House is good for parents with kids.
                                                          …see more

                                                          Price per night from

                                                          $89

                                                          Responds fast!
                                                          avg. 28 minutes

                                                          Price per night from

                                                          $89

                                                          (1) Very Good 

                                                            35

                                                            7778BC. 6 Bedroom Pool Home, Windsor Hills Resort In KISSIMMEE FL

                                                            Central Florida / Kissimmee

                                                            Kissimmee house

                                                            6 12 min stay varies

                                                            • 6 bedrooms
                                                            • sleeps 12
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Ask about children
                                                            • Air conditioning

                                                            Price per night from

                                                            $234

                                                            Price per night from

                                                            $234

                                                            (7) Very Good 

                                                              66

                                                              New Opening 8br/6ba pool villa from $260/nt ,Close to Disney

                                                              Central Florida / Kissimmee

                                                              Kissimmee house

                                                              8 18 min stay varies

                                                              • 8 bedrooms
                                                              • sleeps 18
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning
                                                              “Family vacation” This by far was the best we went to. There is something for everyone to do down to the kids, the house was beautiful.
                                                              …see more

                                                              Price per night from

                                                              $250

                                                              Responds fast!
                                                              avg. 3 hours 22 minutes

                                                              Price per night from

                                                              $250

                                                              (20) Excellent 

                                                                27

                                                                From $80/nt,4br/3ba townhome with hot tub/lake view,Near Disney,Seaworld

                                                                Central Florida / Kissimmee

                                                                Kissimmee apartment

                                                                4 8 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $80

                                                                Responds fast!
                                                                avg. 3 hours 23 minutes

                                                                Price per night from

                                                                $80

                                                                (47) Excellent 

                                                                Certificate of Excellence

                                                                  25

                                                                  Goofys Getaway Townhome @ Emerald Island Resort

                                                                  Central Florida / Kissimmee

                                                                  Kissimmee apartment

                                                                  3 6 4 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • 4 nights min
                                                                  • Nearest beach 116 mi
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  “Awesome, definitely would rent again!” I'm definitely going to recommend. Great price & location is so close to everything. I looked at hotel prices compared to this and it's much more reasonable and it's an entire house! As far as the townhouse, I ha
                                                                  …see more

                                                                  Certificate of Excellence

                                                                  Price per night from

                                                                  $109

                                                                  Responds fast!
                                                                  avg. 56 minutes

                                                                  Price per night from

                                                                  $109

                                                                  (20) Very Good 

                                                                    73

                                                                    Luxury Lakeside House with private solar heated pool & spa

                                                                    Central Florida / Kissimmee

                                                                    Kissimmee villa

                                                                    5 13 3 nights min

                                                                    • 5 bedrooms
                                                                    • sleeps 13
                                                                    • 3 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    “Wonderful vacation home” I rented this house for 6 days for our family’s Disney vacation. The house was wonderful. Great location, very clean. Everything we needed was provided. Would definitely book again.
                                                                    …see more

                                                                    Price per night from

                                                                    $100

                                                                    Price per night from

                                                                    $100

                                                                    (3) Average 

                                                                      50

                                                                      ☀ One Time Offer ☀ perfect for families! Spacious pool villa with spa near parks

                                                                      Kissimmee / Paradise Palms

                                                                      Kissimmee townhouse

                                                                      6 14 min stay varies

                                                                      • 6 bedrooms
                                                                      • sleeps 14
                                                                      • min stay varies
                                                                      • Nearest beach 97 mi
                                                                      • Swimming pool
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $210

                                                                      Price per night from

                                                                      $210

                                                                      (12) Very Good 

                                                                        64

                                                                        Brand New 8br/6ba pool villa from $260/nt ,Close to Disney

                                                                        Central Florida / Kissimmee

                                                                        Kissimmee house

                                                                        8 18 min stay varies

                                                                        • 8 bedrooms
                                                                        • sleeps 18
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        “Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.
                                                                        …see more

                                                                        Price per night from

                                                                        $250

                                                                        Responds fast!
                                                                        avg. 3 hours 22 minutes

                                                                        Price per night from

                                                                        $250

                                                                          11

                                                                          Beautiful 3bedroom/ 2 bath villa on Veranda Palms Resort with own pool & spa

                                                                          Central Florida / Kissimmee

                                                                          Kissimmee villa

                                                                          3 6 3 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 3 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $92

                                                                          Price per night from

                                                                          $92

                                                                            31

                                                                            DISNEY AREA 5 BEDROOM PRIVATE POOL VILLA

                                                                            Central Florida / Kissimmee

                                                                            Kissimmee villa

                                                                            5 10 7 nights min

                                                                            • 5 bedrooms
                                                                            • sleeps 10
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Ask about children
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $114

                                                                            Responds fast!
                                                                            avg. 3 hours 58 minutes

                                                                            Price per night from

                                                                            $114

                                                                            (4) Excellent 

                                                                              46

                                                                              Caribe Cove Resort - 2 BR * Unit Top floor * New Mattress - WiFi/Parking free

                                                                              Central Florida / Kissimmee

                                                                              Kissimmee apartment

                                                                              2 6 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $184

                                                                              Price per night from

                                                                              $184