Windsor Hills Rentals

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/ Vacation Rentals
/ United States
/ Florida
/ Central Florida
/ Orlando
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23,871 Houses

(7) Very Good 

    61

    Sweet Escape

    Orlando / Windsor Hills

    Orlando townhouse

    3 7 3 nights min

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

    Map

    Price per night from

    $121

    Responds fast!
    avg. 1 hour 41 minutes

    Price per night from

    $121

    Details

    Great rentals within 20 miles that match your search

    Distance approx 4.4 km from Windsor Hills Show on Map

    (7) Excellent 

      15

      Oleander Villa - Luxury 4 Bedroom Villa, 2.5 miles from Champions Gate.

      Central Florida / Davenport

      Davenport villa

      4 8 7 nights min

      • 4 bedrooms
      • sleeps 8
      • 7 nights min
      • Swimming pool
      • Child Friendly
      • Air conditioning

      Map

      Price per night from

      $149

      Responds fast!
      avg. 1 hour 13 minutes

      Price per night from

      $149

      Details

      Distance approx 1.83 km from Windsor Hills Show on Map

      (2) Very Good 

        16

        Emerald Island 7 bedroom villa 4 miles from Disney

        Central Florida / Kissimmee

        Kissimmee house

        7 16 6 nights min

        • 7 bedrooms
        • sleeps 16
        • 6 nights min
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Map

        Price per night from

        $573

        Price per night from

        $573

        Details

        Distance approx 7.56 km from Windsor Hills Show on Map

        (2) Excellent 

          30

          Sapphire Skies Vacation Villa

          Lake County / Clermont

          Clermont house

          4 8 4 nights min

          • 4 bedrooms
          • sleeps 8
          • 4 nights min
          • Swimming pool
          • Child Friendly
          • Car not necessary
          “Family Time” This house was great. We truely enjoyed our time. Everything was pretty close as far as attractions and stores. We didn't want to leave this house was perfect for our family gathering. We will be returning.
          …see more

          Map

          Price per night from

          $171

          Responds fast!
          avg. 3 hours 56 minutes

          Price per night from

          $171

          Details

          Distance approx 11.85 km from Windsor Hills

          (31) Excellent 

          Certificate of Excellence

            16

            Fabulous Beautiful Townhome Vista Cay Orlando

            Central Florida / Orlando

            Orlando villa

            3 6 3 nights min

            • 3 bedrooms
            • sleeps 6
            • 3 nights min
            • Swimming pool
            • Child Friendly
            • Air conditioning
            “Beautiful condo great location.” Thank you for a wonderful stay. The condo was beautiful (exactly what you see in the pictures) and super convenient. We are a family of 6 and had plenty of room. When looking for a place to stay online it can be overw
            …see more

            Certificate of Excellence

            Price per night from

            $194

            Responds fast!
            avg. 2 hours 16 minutes

            Price per night from

            $194

            Details

            Distance approx 4.53 km from Windsor Hills Show on Map

            (36) Excellent 

              23

              Woodville - in a beautiful location near Disney

              Central Florida / Davenport

              Davenport house

              4 8 min stay varies

              • 4 bedrooms
              • sleeps 8
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Air conditioning
              “Perfect everything you need!!'” This house is amazing had everything and more super clean and very well maintained great for the kids the game room was a plus and the pool is nice after long days at the parks . We have rented many houses and this is
              …see more

              Map

              Price per night from

              $149

              Responds fast!
              avg. 1 hour 41 minutes

              Price per night from

              $149

              Details

              Distance approx 4.74 km from Windsor Hills Show on Map

              (1) Excellent 

                19

                Exclusive Home Within High Grove Gated Community

                Clermont / High Grove

                Clermont house

                5 10 min stay varies

                • 5 bedrooms
                • sleeps 10
                • min stay varies
                • Beach / lakeside relaxation
                • Swimming pool
                • Child Friendly

                Map

                Price per night from

                $172

                Price per night from

                $172

                Details

                Distance approx 0.1 km from Windsor Hills Show on Map

                  23

                  Tinks Movie Castle

                  Central Florida / Four Corners

                  Four Corners villa

                  5 12 min stay varies

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

                  Map

                  Price per night from

                  $158

                  Responds fast!
                  avg. 41 minutes

                  Price per night from

                  $158

                  Details

                  Distance approx 7.5 km from Windsor Hills Show on Map

                    21

                    Stunning 5 bed property with private south facing extended deck and spa overlook

                    Central Florida / Davenport

                    Davenport house

                    5 12 min stay varies

                    • 5 bedrooms
                    • sleeps 12
                    • min stay varies
                    • Ask about children

                    Map

                    Price per night from

                    $155

                    Price per night from

                    $155

                    Details

                    Distance approx 4.73 km from Windsor Hills Show on Map

                    (1) Very Good 

                      4

                      Wyndham Bonnet Creek Resort - Close to Disney 2 BD - 2 BA Deluxe Suite

                      Central Florida / Orlando

                      Orlando condo

                      2 8 7 nights min

                      • 2 bedrooms
                      • sleeps 8
                      • 7 nights min
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning

                      Map

                      Price per night from

                      $328

                      Responds fast!
                      avg. 35 minutes

                      Price per night from

                      $328

                      Details

                      Distance approx 3.55 km from Windsor Hills Show on Map

                        24

                        Reunion Resort Condo Overlooking Golf Course!

                        Central Florida / Kissimmee

                        Kissimmee apartment

                        3 10 min stay varies

                        • 3 bedrooms
                        • sleeps 10
                        • min stay varies
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Map

                        Price per night from

                        $166

                        Responds fast!
                        avg. 19 minutes

                        Price per night from

                        $166

                        Details

                        Distance approx 4.15 km from Windsor Hills Show on Map

                          8

                          Fabulous 4 bed villa with south facing private pool and spa

                          Central Florida / Davenport

                          Davenport house

                          4 8 min stay varies

                          • 4 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Ask about children

                          Map

                          Price per night from

                          $138

                          Price per night from

                          $138

                          Details

                          Distance approx 8.82 km from Windsor Hills

                            14

                            NO LONGER AVAILABLE WOULD NOT LET ME CANCLE IT SORRY!!

                            Central Florida / Orlando

                            Orlando villa

                            2 6 5 nights min

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

                            Price per night from

                            $344

                            Price per night from

                            $344

                            Details

                            Distance approx 3.94 km from Windsor Hills Show on Map

                              49

                              Downing Florida House 402

                              Central Florida / Davenport

                              Davenport house

                              5 11 min stay varies

                              • 5 bedrooms
                              • sleeps 11
                              • min stay varies
                              • Swimming pool
                              • Car not necessary
                              • Air conditioning

                              Map

                              Price per night from

                              $196

                              Responds fast!
                              avg. 3 hours 35 minutes

                              Price per night from

                              $196

                              Details

                              Distance approx 3.99 km from Windsor Hills Show on Map

                                21

                                Enjoy the Sun! the Fun! the Location of Liki Tiki Phase II!!

                                Central Florida / Kissimmee

                                Kissimmee condo

                                2 6 5 nights min

                                • 2 bedrooms
                                • sleeps 6
                                • 5 nights min
                                • Child Friendly

                                Map

                                Price per night from

                                $224

                                Price per night from

                                $224

                                Details

                                Distance approx 13.14 km from Windsor Hills

                                  30

                                  South Beach Villa

                                  Central Florida / Haines City

                                  Haines City villa

                                  4 8 min stay varies

                                  • 4 bedrooms
                                  • sleeps 8
                                  • min stay varies
                                  • Swimming pool
                                  • Ask about children
                                  • Air conditioning

                                  Price per night from

                                  $162

                                  Price per night from

                                  $162

                                  Details

                                  Distance approx 4.03 km from Windsor Hills Show on Map

                                    26

                                    My Disney Dream Home

                                    Central Florida / Four Corners

                                    Four Corners house

                                    5 12 3 nights min

                                    • 5 bedrooms
                                    • sleeps 12
                                    • 3 nights min
                                    • Child Friendly

                                    Map

                                    Price per night from

                                    $144

                                    Price per night from

                                    $144

                                    Details

                                    Distance approx 13.12 km from Windsor Hills

                                      18

                                      Martin's Southern Dunes House

                                      Central Florida / Haines City

                                      Haines City villa

                                      4 8 min stay varies

                                      • 4 bedrooms
                                      • sleeps 8
                                      • min stay varies
                                      • Swimming pool
                                      • Ask about children
                                      • Air conditioning

                                      Price per night from

                                      $123

                                      Price per night from

                                      $123

                                      Details

                                      Distance approx 4.74 km from Windsor Hills Show on Map

                                        22

                                        2 bedroom for share in townhouse

                                        Central Florida / Loughman

                                        Loughman house

                                        2 4 1 night min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 1 night min
                                        • Nearest beach 50 mi
                                        • Swimming pool
                                        • Child Friendly

                                        Map

                                        Price per night from

                                        $58

                                        Price per night from

                                        $58

                                        Details

                                        Distance approx 3.07 km from Windsor Hills Show on Map

                                          57

                                          3217PP

                                          Central Florida / Four Corners

                                          Four Corners townhouse

                                          5 12 min stay varies

                                          • 5 bedrooms
                                          • sleeps 12
                                          • min stay varies
                                          • Swimming pool
                                          • Ask about children

                                          Map

                                          Price per night from

                                          $189

                                          Price per night from

                                          $189

                                          Details

                                          Distance approx 4.16 km from Windsor Hills Show on Map

                                            28

                                            South facing pool and spa with conservation view close to Disney

                                            Central Florida / Davenport

                                            Davenport house

                                            4 8 min stay varies

                                            • 4 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Ask about children

                                            Map

                                            Price per night from

                                            $138

                                            Price per night from

                                            $138

                                            Details

                                            Distance approx 6.07 km from Windsor Hills Show on Map

                                              44

                                              1625 Morning Star Drive Villa #52106

                                              Central Florida / Four Corners

                                              Four Corners villa

                                              5 10 3 nights min

                                              • 5 bedrooms
                                              • sleeps 10
                                              • 3 nights min
                                              • Swimming pool
                                              • Car not necessary
                                              • Air conditioning

                                              Map

                                              Price per night from

                                              $174

                                              Responds fast!
                                              avg. 3 hours 35 minutes

                                              Price per night from

                                              $174

                                              Details

                                              Distance approx 6.96 km from Windsor Hills Show on Map

                                                31

                                                Big house, Located Minutes from Disney-World 55

                                                Central Florida / Kissimmee

                                                Kissimmee house

                                                4 8 3 nights min

                                                • 4 bedrooms
                                                • sleeps 8
                                                • 3 nights min
                                                • Swimming pool
                                                • Ask about children
                                                • Air conditioning

                                                Map

                                                Price per night from

                                                $149

                                                Price per night from

                                                $149

                                                Details

                                                Distance approx 1.31 km from Windsor Hills Show on Map

                                                  50

                                                  9015 Sunshine Ridge Loop

                                                  Central Florida / Reunion

                                                  Reunion house

                                                  9 21 min stay varies

                                                  • 9 bedrooms
                                                  • sleeps 21
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Car not necessary

                                                  Map

                                                  Price per night from

                                                  $425

                                                  Responds fast!
                                                  avg. 3 hours 35 minutes

                                                  Price per night from

                                                  $425

                                                  Details

                                                  Distance approx 4.89 km from Windsor Hills Show on Map

                                                    8

                                                    Luxurious Four Bedroom Villa on the Prestigious Highgate Park Development, Sleep

                                                    Central Florida / Davenport

                                                    Davenport house

                                                    4 8 min stay varies

                                                    • 4 bedrooms
                                                    • sleeps 8
                                                    • min stay varies
                                                    • Ask about children

                                                    Map

                                                    Price per night from

                                                    $138

                                                    Price per night from

                                                    $138

                                                    Details

                                                    Distance approx 0.1 km from Windsor Hills Show on Map

                                                      11

                                                      Westgate Town Center-3BR 3BA 7 Ngt Max Lux Resort

                                                      Central Florida / Kissimmee

                                                      Kissimmee condo

                                                      3 12 7 nights min

                                                      • 3 bedrooms
                                                      • sleeps 12
                                                      • 7 nights min
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Map

                                                      Price per night from

                                                      $315

                                                      Price per night from

                                                      $315

                                                      Details

                                                      Distance approx 7.25 km from Windsor Hills Show on Map

                                                      (34) Very Good 

                                                      Certificate of Excellence

                                                        18

                                                        Magical Memories, Pet-Friendly Home with WiFi

                                                        Central Florida / Kissimmee

                                                        Kissimmee villa

                                                        3 6 min stay varies

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

                                                        Certificate of Excellence

                                                        Map

                                                        Price per night from

                                                        $126

                                                        Responds fast!
                                                        avg. 1 hour 37 minutes

                                                        Price per night from

                                                        $126

                                                        Details

                                                        Distance approx 12.5 km from Windsor Hills

                                                          45

                                                          Beautiful 4BR 3bth Champions Gate Townhouse with Private Splash Pool

                                                          Central Florida / Orlando

                                                          Orlando townhouse

                                                          4 10 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 10
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $147

                                                          Responds fast!
                                                          avg. 2 hours 12 minutes

                                                          Price per night from

                                                          $147

                                                          Details

                                                          Distance approx 3.41 km from Windsor Hills Show on Map

                                                          (15) Excellent 

                                                            24

                                                            My Disney Villa

                                                            Kissimmee / Calabria, Orlando

                                                            Kissimmee villa

                                                            5 10 min stay varies

                                                            • 5 bedrooms
                                                            • sleeps 10
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Map

                                                            Price per night from

                                                            $275

                                                            Responds fast!
                                                            avg. 3 hours 30 minutes

                                                            Price per night from

                                                            $275

                                                            Details

                                                            Distance approx 0.1 km from Windsor Hills Show on Map

                                                              20

                                                              Superb 6 bedroom home, private pool and spa, free pool heat for certain dates

                                                              Central Florida / Four Corners

                                                              Four Corners house

                                                              6 12 min stay varies

                                                              • 6 bedrooms
                                                              • sleeps 12
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Map

                                                              Price per night from

                                                              $111

                                                              Price per night from

                                                              $111

                                                              Details

                                                              Distance approx 11.87 km from Windsor Hills

                                                              (32) Excellent 

                                                              Certificate of Excellence

                                                                58

                                                                Fantastic Kissimmee Home and only 20 min

                                                                Kissimmee / Trafalgar Village

                                                                Kissimmee townhouse

                                                                3 6 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 80 mi
                                                                • Swimming pool
                                                                “Wonderful Townhouse” My husband and I stayed for 3 weeks in June/July. Townhouse is gorgeous and very comfortable. The community clubhouse was great. We loved using the pool almost daily. We were happily surprised to find added amenities in case you h
                                                                …see more

                                                                Certificate of Excellence

                                                                Price per night from

                                                                $97

                                                                Responds fast!
                                                                avg. 1 hour 46 minutes

                                                                Price per night from

                                                                $97

                                                                Details

                                                                Distance approx 4.5 km from Windsor Hills Show on Map

                                                                (76) Very Good 

                                                                  27

                                                                  Villa Tropico near Disney - FREE cancellation

                                                                  Central Florida / Davenport

                                                                  Davenport villa

                                                                  3 7 4 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 7
                                                                  • 4 nights min
                                                                  • Ask about children
                                                                  • Air conditioning

                                                                  Map

                                                                  Price per night from

                                                                  $137

                                                                  Price per night from

                                                                  $137

                                                                  Details

                                                                  Distance approx 12.51 km from Windsor Hills

                                                                    49

                                                                    New 8BR 6bth Luxury Resort home w/private south facing pool and spa

                                                                    Central Florida / Orlando

                                                                    Orlando house

                                                                    8 16 min stay varies

                                                                    • 8 bedrooms
                                                                    • sleeps 16
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $336

                                                                    Responds fast!
                                                                    avg. 2 hours 12 minutes

                                                                    Price per night from

                                                                    $336

                                                                    Details

                                                                    Distance approx 12.51 km from Windsor Hills

                                                                      21

                                                                      Lovely 5BR 3Bth Home with Private Pool, Spa and Pool Table, 15 Minutes to Disney

                                                                      Central Florida / Orlando

                                                                      Orlando house

                                                                      5 10 5 nights min

                                                                      • 5 bedrooms
                                                                      • sleeps 10
                                                                      • 5 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $176

                                                                      Responds fast!
                                                                      avg. 2 hours 12 minutes

                                                                      Price per night from

                                                                      $176

                                                                      Details

                                                                      Distance approx 5.83 km from Windsor Hills Show on Map

                                                                        11

                                                                        Sunrise Orlando Villa

                                                                        Lake County / Clermont

                                                                        Clermont villa

                                                                        4 9 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 9
                                                                        • min stay varies
                                                                        • Child Friendly

                                                                        Map

                                                                        Price per night from

                                                                        $105

                                                                        Price per night from

                                                                        $105

                                                                        Details

                                                                        Distance approx 12.5 km from Windsor Hills

                                                                          38

                                                                          Lovely 7BR 6Bth Veranda Palms home with 5 Ensuites, Private Pool and Spa

                                                                          Central Florida / Orlando

                                                                          Orlando house

                                                                          7 14 min stay varies

                                                                          • 7 bedrooms
                                                                          • sleeps 14
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $239

                                                                          Responds fast!
                                                                          avg. 2 hours 12 minutes

                                                                          Price per night from

                                                                          $239

                                                                          Details

                                                                          Distance approx 12.5 km from Windsor Hills

                                                                            27

                                                                            Chic 6 bedroom 5.5 bath Watersong Resort home from $135nt

                                                                            Central Florida / Orlando

                                                                            Orlando house

                                                                            6 12 min stay varies

                                                                            • 6 bedrooms
                                                                            • sleeps 12
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $178

                                                                            Responds fast!
                                                                            avg. 2 hours 12 minutes

                                                                            Price per night from

                                                                            $178

                                                                            Details

                                                                            Distance approx 5.24 km from Windsor Hills Show on Map

                                                                            (8) Excellent 

                                                                              25

                                                                              Beautiful Orlando Villa "Mags Den" Calabay Parc

                                                                              Central Florida / Davenport

                                                                              Davenport villa

                                                                              4 8 5 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • 5 nights min
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Map

                                                                              Price per night from

                                                                              $148

                                                                              Price per night from

                                                                              $148

                                                                              Details