Windermere Rentals

Close

/ Home
/ Vacation Rentals
/ United States
/ Florida
/ Central Florida
Book with confidence. Pay on FlipKey to get Payment Protection for this rental. Never pay by bank or wire transfer.
✕

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

23,042 Houses

    25

    PARADISE

    Central Florida / Windermere

    Windermere house

    4 10 min stay varies

    • 4 bedrooms
    • sleeps 10
    • min stay varies
    • Swimming pool
    • Ask about children

    Map

    Price per night from

    $1,000

    Price per night from

    $1,000

    Details
      31

      2901EW

      Central Florida / Windermere

      Windermere townhouse

      4 8 5 nights min

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

      Map

      Price per night from

      $129

      Responds fast!
      avg. 3 hours 58 minutes

      Price per night from

      $129

      Details
        49

        Private Home in the Heart of Orlando!

        Central Florida / Windermere

        Windermere guest house

        2 4 1 night min

        • 2 bedrooms
        • sleeps 4
        • 1 night min

        Map

        Price per night from

        $115

        Price per night from

        $115

        Details
          31

          2901EW

          Central Florida / Windermere

          Windermere townhouse

          4 8 5 nights min

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

          Map

          Price per night from

          $128

          Responds fast!
          avg. 1 hour 29 minutes

          Price per night from

          $128

          Details
            18

            Lucaya Village 17 - Modern townhouse with covered porch near Disney

            Central Florida / Windermere

            Windermere house

            4 8 5 nights min

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

            Map

            Price per night from

            $107

            Price per night from

            $107

            Details
              16

              Cozy Suite | Shuttle to Disney World + SeaWorld + Universal

              Central Florida / Windermere

              Windermere condo

              1 4 2 nights min

              • 1 bedroom
              • sleeps 4
              • 2 nights min
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Map

              Price per night from

              $100

              Responds fast!
              avg. 1 hour 38 minutes

              Price per night from

              $100

              Details
                13

                Family-Friendly Villa w/ WiFi Available, Free Theme Park Shuttle & Resort Pool

                Central Florida / Windermere

                Windermere house

                2 4 1 night min

                • 2 bedrooms
                • sleeps 4
                • 1 night min
                • Child Friendly

                Map

                Price per night from

                $236

                Price per night from

                $236

                Details
                  7

                  Deluxe Family-Friendly Villa w/ WiFi, Resort Pool & Free Theme Park Shuttle

                  Central Florida / Windermere

                  Windermere house

                  2 6 1 night min

                  • 2 bedrooms
                  • sleeps 6
                  • 1 night min
                  • Child Friendly

                  Map

                  Price per night from

                  $249

                  Price per night from

                  $249

                  Details
                    10

                    Disney Home

                    Central Florida / Windermere

                    Windermere house

                    3 6 min stay varies

                    • 3 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Child Friendly

                    Map

                    Price per night from

                    $165

                    Price per night from

                    $165

                    Details
                      31

                      Lucaya Village Resort 4 Bedroom TownHome

                      Central Florida / Windermere

                      Windermere townhouse

                      4 8 5 nights min

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

                      Map

                      Price per night from

                      $133

                      Responds fast!
                      avg. 1 hour 59 minutes

                      Price per night from

                      $133

                      Details
                        13

                        Cinderella's other Castle

                        Central Florida / Windermere

                        Windermere house

                        3 6 2 nights min

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

                        Map

                        Price per night from

                        $400

                        Price per night from

                        $400

                        Details
                          24

                          NEW! Orlando Resort Condo w/Pool, 2Mi to Universal

                          Central Florida / Windermere

                          Windermere condo

                          1 4 2 nights min

                          • 1 bedroom
                          • sleeps 4
                          • 2 nights min
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning

                          Map

                          Price per night from

                          $81

                          Responds fast!
                          avg. 33 minutes

                          Price per night from

                          $81

                          Details
                            16

                            Cheerful Suite | Shuttle to Disney World + Sea World + More!

                            Central Florida / Windermere

                            Windermere condo

                            1 6 2 nights min

                            • 1 bedroom
                            • sleeps 6
                            • 2 nights min
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Map

                            Price per night from

                            $125

                            Responds fast!
                            avg. 1 hour 38 minutes

                            Price per night from

                            $125

                            Details
                              7

                              Amazing House! - Lucaya Village - 2901EWUNIT14

                              Central Florida / Windermere

                              Windermere townhouse

                              4 8 5 nights min

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

                              Map

                              Price per night from

                              $193

                              Responds fast!
                              avg. 2 hours 16 minutes

                              Price per night from

                              $193

                              Details
                                52

                                Ultimate 6 Bedroom 5 Bathroom On Bay Hill

                                Central Florida / Windermere

                                Windermere villa

                                6 14 5 nights min

                                • 6 bedrooms
                                • sleeps 14
                                • 5 nights min
                                • Swimming pool
                                • Ask about children
                                • Air conditioning

                                Map

                                Price per night from

                                $698

                                Responds fast!
                                avg. 3 hours 58 minutes

                                Price per night from

                                $698

                                Details
                                  15

                                  Modern + Elegant Suite in a Great Location | Private Furnished Balcony

                                  Central Florida / Windermere

                                  Windermere condo

                                  1 4 2 nights min

                                  • 1 bedroom
                                  • sleeps 4
                                  • 2 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Map

                                  Price per night from

                                  $153

                                  Responds fast!
                                  avg. 1 hour 38 minutes

                                  Price per night from

                                  $153

                                  Details
                                    15

                                    Shuttle Access to Disney World + Universal Studios | Modest Suite!

                                    Central Florida / Windermere

                                    Windermere condo

                                    1 4 min stay varies

                                    • 1 bedroom
                                    • sleeps 4
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Air conditioning

                                    Map

                                    Price per night from

                                    $91

                                    Responds fast!
                                    avg. 1 hour 38 minutes

                                    Price per night from

                                    $91

                                    Details
                                      13

                                      Shuttle to Popular Orlando Theme Parks | Cozy + Equipped Suite

                                      Central Florida / Windermere

                                      Windermere condo

                                      1 4 2 nights min

                                      • 1 bedroom
                                      • sleeps 4
                                      • 2 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Map

                                      Price per night from

                                      $118

                                      Responds fast!
                                      avg. 1 hour 38 minutes

                                      Price per night from

                                      $118

                                      Details
                                        16

                                        Comfy Suite Close to Universal Orlando | Shuttle to Disney World

                                        Central Florida / Windermere

                                        Windermere condo

                                        2 6 2 nights min

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

                                        Map

                                        Price per night from

                                        $152

                                        Responds fast!
                                        avg. 1 hour 38 minutes

                                        Price per night from

                                        $152

                                        Details

                                        Great rentals within 20 miles that match your search

                                        Distance approx 5.39 km from Windermere Show on Map

                                          28

                                          Enjoyable 5BR 4Bath home with private pool & game room from $188/night

                                          Central Florida / Orlando

                                          Orlando house

                                          5 10 min stay varies

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

                                          Map

                                          Price per night from

                                          $215

                                          Responds fast!
                                          avg. 1 hour 47 minutes

                                          Price per night from

                                          $215

                                          Details

                                          Distance approx 11.28 km from Windermere

                                            4

                                            Orange Lake Resort, Orlando

                                            Central Florida / Kissimmee

                                            Kissimmee villa

                                            3 12 7 nights min

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

                                            Price per night from

                                            $263

                                            Price per night from

                                            $263

                                            Details

                                            Distance approx 10.66 km from Windermere

                                            (9) Excellent 

                                              12

                                              Bargain Vacation Home near Disney

                                              Central Florida / Kissimmee

                                              Kissimmee house

                                              2 6 min stay varies

                                              • 2 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Child Friendly
                                              • Air conditioning
                                              • Pet Friendly

                                              Price per night from

                                              $97

                                              Responds fast!
                                              avg. 2 hours 20 minutes

                                              Price per night from

                                              $97

                                              Details

                                              Distance approx 14.31 km from Windermere

                                                24

                                                NEW! Magnificent 3BR Kissimmee Townhome w/Wifi!

                                                Central Florida / Kissimmee

                                                Kissimmee house

                                                3 6 2 nights min

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

                                                Price per night from

                                                $171

                                                Responds fast!
                                                avg. 1 hour 2 minutes

                                                Price per night from

                                                $171

                                                Details

                                                Distance approx 11.12 km from Windermere

                                                  12

                                                  Orlando Vacation Condo

                                                  Central Florida / Kissimmee

                                                  Kissimmee house

                                                  2 8 7 nights min

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

                                                  Price per night from

                                                  $131

                                                  Price per night from

                                                  $131

                                                  Details

                                                  Distance approx 18.19 km from Windermere

                                                    16

                                                    Davenport Holiday Villa 27882

                                                    Central Florida / Loughman

                                                    Loughman villa

                                                    6 12 7 nights min

                                                    • 6 bedrooms
                                                    • sleeps 12
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Air conditioning

                                                    Price per night from

                                                    $330

                                                    Price per night from

                                                    $330

                                                    Details

                                                    Distance approx 16.34 km from Windermere

                                                    (20) Very Good 

                                                      18

                                                      Beautiful and Spacious Orlando Vacation Pool Home

                                                      Central Florida / Davenport

                                                      Davenport house

                                                      4 10 90 nights min

                                                      • 4 bedrooms
                                                      • sleeps 10
                                                      • 90 nights min
                                                      • Nearest beach 137 mi
                                                      • Swimming pool
                                                      • Child Friendly
                                                      “Awesome Place to Stay!” Stayed there for a week and had an absolute ball. Villa is extremely clean and exactly as pictured on the website. We had so much fun in the pool we forgot the Villa had a pool table! Definitely booking this one again next vaca
                                                      …

                                                      Price per night from

                                                      $103

                                                      Price per night from

                                                      $103

                                                      Details

                                                      Distance approx 12.74 km from Windermere

                                                      (52) Excellent 

                                                        26

                                                        Fabulous Large 4 bedrooms Regal Villa With Fantastic Pool & Internet & 3D TV

                                                        Central Florida / Four Corners

                                                        Four Corners villa

                                                        4 10 5 nights min

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • 5 nights min
                                                        • Nearest beach 90 mi
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “Third stay in this home and, hopefully, not the last!” We love this home. We enjoyed it the first time we stayed and notice that every time we go back there are more and more conveniences provided for renters. Plenty of linens, dishes, washer, dryer
                                                        …

                                                        Price per night from

                                                        $160

                                                        Price per night from

                                                        $160

                                                        Details

                                                        Distance approx 15.83 km from Windermere

                                                          33

                                                          Gleneagles Villa # 231002

                                                          Central Florida / Four Corners

                                                          Four Corners villa

                                                          5 10 min stay varies

                                                          • 5 bedrooms
                                                          • sleeps 10
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $261

                                                          Price per night from

                                                          $261

                                                          Details

                                                          Distance approx 5.44 km from Windermere Show on Map

                                                            4

                                                            Orlando's Sunshine Resort, May 26, 2018-June 2, 2018 only, sleeps 8, 2 bedroom

                                                            Central Florida / Orlando

                                                            Orlando condo

                                                            2 8 7 nights min

                                                            • 2 bedrooms
                                                            • sleeps 8
                                                            • 7 nights min
                                                            • Child Friendly

                                                            Map

                                                            Price per night from

                                                            $245

                                                            Price per night from

                                                            $245

                                                            Details

                                                            Distance approx 11.75 km from Windermere

                                                              23

                                                              Regal Resort 4 Bedroom 3 Bathroom Townhouse

                                                              Florida / Old Town

                                                              Old Town house

                                                              4 8 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Child Friendly

                                                              Price per night from

                                                              $122

                                                              Responds fast!
                                                              avg. 1 hour 21 minutes

                                                              Price per night from

                                                              $122

                                                              Details

                                                              Distance approx 11.11 km from Windermere

                                                                26

                                                                Great Furnished Resort aval in Orlando

                                                                Central Florida / Kissimmee

                                                                Kissimmee condo

                                                                1 4 7 nights min

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • 7 nights min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $229

                                                                Price per night from

                                                                $229

                                                                Details

                                                                Distance approx 14.5 km from Windermere

                                                                (9) Excellent 

                                                                  33

                                                                  The View Lake Berkley Resort Kissimmee 10 mins to Disney 4 bed 3 bath sleeps 10

                                                                  Kissimmee / Lake Berkley

                                                                  Kissimmee house

                                                                  4 10 min stay varies

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

                                                                  Price per night from

                                                                  $202

                                                                  Responds fast!
                                                                  avg. 2 hours 13 minutes

                                                                  Price per night from

                                                                  $202

                                                                  Details

                                                                  Distance approx 12.48 km from Windermere

                                                                    29

                                                                    2 BR WINDSOR HILLS 202C

                                                                    Central Florida / Kissimmee

                                                                    Kissimmee apartment

                                                                    2 6 min stay varies

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

                                                                    Price per night from

                                                                    $91

                                                                    Price per night from

                                                                    $91

                                                                    Details

                                                                    Distance approx 15.3 km from Windermere

                                                                      36

                                                                      904 N. Hampton, 3 Bed: Convenient Highlands Reserve Golf Community, near Disney

                                                                      Central Florida / Davenport

                                                                      Davenport house

                                                                      3 6 3 nights min

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

                                                                      Price per night from

                                                                      $102

                                                                      Responds fast!
                                                                      avg. 3 hours 29 minutes

                                                                      Price per night from

                                                                      $102

                                                                      Details

                                                                      Distance approx 13.28 km from Windermere

                                                                      (1) Excellent 

                                                                        26

                                                                        Steps to Disney in Top Rated Gated Resort, Beautiful 3BR Luxury Condo, Free Wifi

                                                                        Central Florida / Four Corners

                                                                        Four Corners condo

                                                                        3 7 min stay varies

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

                                                                        Price per night from

                                                                        $114

                                                                        Responds fast!
                                                                        avg. 1 hour 10 minutes

                                                                        Price per night from

                                                                        $114

                                                                        Details

                                                                        Distance approx 18.86 km from Windermere

                                                                          20

                                                                          UCF - European Art Gallery

                                                                          Florida / Alafaya

                                                                          Alafaya house

                                                                          2 4 1 night min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 1 night min
                                                                          • Nearest beach 60 mi
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $143

                                                                          Price per night from

                                                                          $143

                                                                          Details

                                                                          Distance approx 5.39 km from Windermere Show on Map

                                                                            20

                                                                            Lovely 5BR 3Bth Home with Private Pool, 8 Miles 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

                                                                            Map

                                                                            Price per night from

                                                                            $120

                                                                            Responds fast!
                                                                            avg. 1 hour 7 minutes

                                                                            Price per night from

                                                                            $120

                                                                            Details

                                                                            Distance approx 17.52 km from Windermere

                                                                              40

                                                                              NEW! Davenport Townhome - 20 Mins to Disney World!

                                                                              Central Florida / ChampionsGate

                                                                              ChampionsGate townhouse

                                                                              5 11 min stay varies

                                                                              • 5 bedrooms
                                                                              • sleeps 11
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $206

                                                                              Responds fast!
                                                                              avg. 17 minutes

                                                                              Price per night from

                                                                              $206

                                                                              Details