Vacation Rentals & Villas in Winter Park

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3,940 villas

    27

    Surfs Up Theme - Winter Park/Orlando

    Central Florida / Winter Park

    Winter Park house

    1 2 2 nights min

    • 1 bedroom
    • sleeps 2
    • 2 nights min
    • Nearest beach 100 mi
    • Child Friendly
    • Air conditioning

    Price per night from

    $86

    Responds fast!
    avg. 2 hours 33 minutes

    Price per night from

    $86

    (2) Excellent 

      27

      Winter Park-College Park-Orlando-1

      Central Florida / Winter Park

      Winter Park house

      1 2 3 nights min

      • 1 bedroom
      • sleeps 2
      • 3 nights min
      • Nearest beach 100 mi
      • Suitable for children age 5+
      • Air conditioning

      Price per night from

      $92

      Responds fast!
      avg. 2 hours 33 minutes

      Price per night from

      $92

        37

        Travel Themed Getaway Orlando / Winter Park

        Central Florida / Winter Park

        Winter Park house

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min
        • Nearest beach 60 mi
        • Child Friendly
        • Air conditioning

        Price per night from

        $86

        Responds fast!
        avg. 2 hours 33 minutes

        Price per night from

        $86

        (3) Very Good 

          22

          Botanical Gardens - Orlando / Winter Park

          Central Florida / Winter Park

          Winter Park house

          1 2 2 nights min

          • 1 bedroom
          • sleeps 2
          • 2 nights min
          • Nearest beach 100 mi
          • Child Friendly
          • Air conditioning

          Price per night from

          $92

          Responds fast!
          avg. 2 hours 33 minutes

          Price per night from

          $92

          (2) Excellent 

            13

            2br - 1000ft2 - Winter Park House

            Central Florida / Winter Park

            Winter Park house

            2 5 7 nights min

            • 2 bedrooms
            • sleeps 5
            • 7 nights min
            • Nearest beach 88 mi
            • Child Friendly
            • Air conditioning

            Price per night from

            $165

            Responds fast!
            avg. 1 hour 25 minutes

            Price per night from

            $165

              35

              The Cottage on Lake Fairview, Orlando.

              Central Florida / Winter Park

              Winter Park house

              3 6 3 nights min

              • 3 bedrooms
              • sleeps 6
              • 3 nights min
              • Beach / lakeside relaxation
              • Nearest beach 81 mi
              • Child Friendly

              Price per night from

              $516

              Price per night from

              $516

                10

                Live like a Local, 2/1 in the Heart of Orlando!

                Central Florida / Winter Park

                Winter Park townhouse

                2 6 2 nights min

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

                Price per night from

                $149

                Price per night from

                $149

                  11

                  The Ritz

                  Central Florida / Winter Park

                  Winter Park house

                  3 5 1 night min

                  • 3 bedrooms
                  • sleeps 5
                  • 1 night min
                  • Nearest beach 30 mi
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $121

                  Price per night from

                  $121

                  (2) Average 

                    20

                    Winter Park-College Park-Orlando -2

                    Central Florida / Winter Park

                    Winter Park house

                    1 2 3 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 3 nights min
                    • Nearest beach 100 mi
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $92

                    Responds fast!
                    avg. 2 hours 33 minutes

                    Price per night from

                    $92

                      29

                      Walkable, Peaceful, Garden District

                      Central Florida / Winter Park

                      Winter Park studio

                      Studio 4 2 nights min

                      • Studio
                      • sleeps 4
                      • 2 nights min
                      • Child Friendly
                      • Pet Friendly

                      Price per night from

                      $100

                      Price per night from

                      $100

                        7

                        Liki Tiki Village 1 BR, Sleeps 4, FRIDAY Check-In

                        Central Florida / Winter Park

                        Winter Park hotel apartment

                        1 4 7 nights min

                        • 1 bedroom
                        • sleeps 4
                        • 7 nights min
                        • Child Friendly

                        Price per night from

                        $70

                        Price per night from

                        $70

                          35

                          "Lakeside" in old Winter Park (exclusive 32789zip)

                          Central Florida / Winter Park

                          Winter Park villa

                          4 8 min stay varies

                          • 4 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Child Friendly
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $682

                          Price per night from

                          $682

                            14

                            Ritz’s Tiny House

                            Central Florida / Winter Park

                            Winter Park house

                            1 5 1 night min

                            • 1 bedroom
                            • sleeps 5
                            • 1 night min
                            • Nearest beach 80 mi
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $102

                            Responds fast!
                            avg. 3 hours 44 minutes

                            Price per night from

                            $102

                            Great rentals within 20 miles that match your search

                            Distance approx 12.87 km from Winter Park Show on Map

                            (15) Excellent 

                              28

                              Vista Cay Townhome..Luxury Resort..Great Location!

                              Central Florida / Orlando

                              Orlando hotel apartment

                              3 8 4 nights min

                              • 3 bedrooms
                              • sleeps 8
                              • 4 nights min
                              • Beach / lakeside relaxation
                              • Nearest beach 103 mi
                              • Swimming pool
                              “Great Place!” We stayed at this property at the end of February for the Disney Princess 1/2 marathon. We were 3 person, and the place was roomy enough to give us all privacy, while giving a great living/dining/kitchen area for us to gather. It was cle
                              …see more

                              Price per night from

                              $161

                              Price per night from

                              $161

                              Distance approx 16.22 km from Winter Park Show on Map

                                14

                                The Fountains Resort in Sunny Orlando Florida

                                Central Florida / Orlando

                                Orlando condo

                                2 6 2 nights min

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

                                Price per night from

                                $196

                                Price per night from

                                $196

                                Distance approx 18.36 km from Winter Park Show on Map

                                  32

                                  Beautiful 1 Bedroom Condo To Rent

                                  Central Florida / Orlando

                                  Orlando 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

                                  Distance approx 15.09 km from Winter Park Show on Map

                                    24

                                    Elegant Sanford Studio w/ Courtyard Near Downtown!

                                    Central Florida / Sanford

                                    Sanford studio

                                    Studio 2 3 nights min

                                    • Studio
                                    • sleeps 2
                                    • 3 nights min
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $138

                                    Responds fast!
                                    avg. 9 minutes

                                    Price per night from

                                    $138

                                    Distance approx 3.75 km from Winter Park Show on Map

                                      12

                                      The Vue at Downtown Orlando

                                      Central Florida / Orlando

                                      Orlando condo

                                      1 4 30 nights min

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

                                      Price per night from

                                      $138

                                      Price per night from

                                      $138

                                      Distance approx 18.24 km from Winter Park Show on Map

                                        12

                                        Sheraton Vistana Fountains 2 2 Bedroom Villa. 7 nights avalible. I'm and out on

                                        Central Florida / Orlando

                                        Orlando villa

                                        2 8 7 nights min

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

                                        Price per night from

                                        $178

                                        Price per night from

                                        $178

                                        Distance approx 16.11 km from Winter Park Show on Map

                                          11

                                          NEW YEARS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

                                          Central Florida / Orlando

                                          Orlando hotel apartment

                                          2 8 3 nights min

                                          • 2 bedrooms
                                          • sleeps 8
                                          • 3 nights min
                                          • Nearest beach 64 mi
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $246

                                          Price per night from

                                          $246

                                          Distance approx 19.84 km from Winter Park Show on Map

                                          (2) Very Good 

                                            23

                                            Wyndham Bonnet Creek Resort. Closest to Disney

                                            Central Florida / Celebration

                                            Celebration condo

                                            2 8 7 nights min

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

                                            Price per night from

                                            $278

                                            Responds fast!
                                            avg. 2 hours 36 minutes

                                            Price per night from

                                            $278

                                            Distance approx 19.84 km from Winter Park Show on Map

                                              7

                                              Disney Wyndham Bonnet Creek Presidential Suite

                                              Central Florida / Orlando

                                              Orlando villa

                                              2 8 min stay varies

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

                                              Price per night from

                                              $288

                                              Price per night from

                                              $288

                                              Distance approx 5.18 km from Winter Park Show on Map

                                              (1)  

                                                12

                                                Free delivery and pick to Disney ft wilderness campground,2018 model sleeps 8

                                                Central Florida / Orlando

                                                Orlando camper van

                                                1 7 1 night min

                                                • 1 bedroom
                                                • sleeps 7
                                                • 1 night min
                                                • Child Friendly
                                                • Air conditioning
                                                • Pet Friendly

                                                Price per night from

                                                $127

                                                Responds fast!
                                                avg. 44 minutes

                                                Price per night from

                                                $127

                                                Distance approx 16.95 km from Winter Park Show on Map

                                                  32

                                                  3 COZY 2BR/2BA APTs, 4 POOLS, 2 HOT TUBS, FREE SHUTTLE TO THE PARKS

                                                  Central Florida / Celebration

                                                  Celebration apartment

                                                  6 18 min stay varies

                                                  • 6 bedrooms
                                                  • sleeps 18
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Car not necessary

                                                  Price per night from

                                                  $404

                                                  Price per night from

                                                  $404

                                                  Distance approx 19.42 km from Winter Park Show on Map

                                                  (1) Average 

                                                    10

                                                    Calypso Cay Vacation Villas 1 BR Suite, Saturday Check-In

                                                    Central Florida / Kissimmee

                                                    Kissimmee hotel apartment

                                                    1 4 7 nights min

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • 7 nights min
                                                    • Child Friendly

                                                    Price per night from

                                                    $71

                                                    Price per night from

                                                    $71

                                                    Distance approx 13.78 km from Winter Park Show on Map

                                                      23

                                                      1 Week Rental in Orlando, FL 2 Bdm Deluxe Villa Close to Theme Parks

                                                      Central Florida / Orlando

                                                      Orlando villa

                                                      2 8 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 8
                                                      • 7 nights min
                                                      • Beach / lakeside relaxation
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $157

                                                      Price per night from

                                                      $157

                                                      Distance approx 16.86 km from Winter Park Show on Map

                                                        18

                                                        Orlando 2X2BR close to Universal -sleeps 12 Resort Amenities CPV

                                                        Central Florida / Orlando

                                                        Orlando villa

                                                        4 12 2 nights min

                                                        • 4 bedrooms
                                                        • sleeps 12
                                                        • 2 nights min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $1,004

                                                        Price per night from

                                                        $1,004

                                                        Distance approx 11.84 km from Winter Park Show on Map

                                                          19

                                                          Cozy 3BR 2Bth Home with Private Pool, Spa and Gameroom 20 Minutes to Legoland

                                                          Central Florida / Orlando

                                                          Orlando house

                                                          3 6 5 nights min

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

                                                          Price per night from

                                                          $138

                                                          Responds fast!
                                                          avg. 1 hour 30 minutes

                                                          Price per night from

                                                          $138

                                                          Distance approx 11.84 km from Winter Park Show on Map

                                                            24

                                                            Luxury 6 bedroom 5.5 bath Watersong Resort home from $155nt

                                                            Central Florida / Orlando

                                                            Orlando house

                                                            6 12 min stay varies

                                                            • 6 bedrooms
                                                            • sleeps 12
                                                            • min stay varies
                                                            • Child Friendly

                                                            Price per night from

                                                            $178

                                                            Responds fast!
                                                            avg. 1 hour 30 minutes

                                                            Price per night from

                                                            $178

                                                            Distance approx 11.83 km from Winter Park Show on Map

                                                            (1) Excellent 

                                                              52

                                                              New 5BR 4bath Champions Gate Townhouse w/private splash pool from $138 a night!

                                                              Central Florida / Orlando

                                                              Orlando townhouse

                                                              5 10 min stay varies

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

                                                              Price per night from

                                                              $159

                                                              Responds fast!
                                                              avg. 1 hour 30 minutes

                                                              Price per night from

                                                              $159

                                                              Distance approx 11.83 km from Winter Park Show on Map

                                                              (1) Excellent 

                                                                41

                                                                Luxury 5BR 4bath Champions Gate townhouse w/private splash pool from $138/nt

                                                                Central Florida / Orlando

                                                                Orlando townhouse

                                                                5 10 min stay varies

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

                                                                Price per night from

                                                                $159

                                                                Responds fast!
                                                                avg. 1 hour 30 minutes

                                                                Price per night from

                                                                $159

                                                                Distance approx 5.18 km from Winter Park Show on Map

                                                                (3) Excellent 

                                                                  25

                                                                  Villa 6 BR/4BA South Pool/Spa Near Disney

                                                                  Central Florida / Orlando

                                                                  Orlando villa

                                                                  6 12 3 nights min

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

                                                                  Price per night from

                                                                  $148

                                                                  Price per night from

                                                                  $148

                                                                  Distance approx 11.83 km from Winter Park Show on Map

                                                                    48

                                                                    Breathtaking 8BR 5bth Champions Gate home w/pool, spa & gameroom

                                                                    Central Florida / Orlando

                                                                    Orlando house

                                                                    9 16 min stay varies

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

                                                                    Price per night from

                                                                    $301

                                                                    Responds fast!
                                                                    avg. 1 hour 30 minutes

                                                                    Price per night from

                                                                    $301

                                                                    Distance approx 19.53 km from Winter Park Show on Map

                                                                      12

                                                                      Runaway Beach Resort Apartments 3

                                                                      Central Florida / Celebration

                                                                      Celebration apartment

                                                                      3 8 2 nights min

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

                                                                      Price per night from

                                                                      $285

                                                                      Responds fast!
                                                                      avg. 2 hours 8 minutes

                                                                      Price per night from

                                                                      $285

                                                                      Distance approx 11.84 km from Winter Park Show on Map

                                                                        18

                                                                        Comfortable 5 bedroom 3 beth Highlands Reserve home from $188nt

                                                                        Central Florida / Orlando

                                                                        Orlando house

                                                                        5 10 min stay varies

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

                                                                        Price per night from

                                                                        $215

                                                                        Responds fast!
                                                                        avg. 1 hour 30 minutes

                                                                        Price per night from

                                                                        $215

                                                                        Distance approx 13.85 km from Winter Park Show on Map

                                                                          4

                                                                          The best place to Orlando

                                                                          Central Florida / Orlando

                                                                          Orlando apartment

                                                                          1 4 7 nights min

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

                                                                          Price per night from

                                                                          $183

                                                                          Price per night from

                                                                          $183

                                                                          Distance approx 19.6 km from Winter Park Show on Map

                                                                            11

                                                                            Poinciana

                                                                            Central Florida / Celebration

                                                                            Celebration apartment

                                                                            2 6 2 nights min

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

                                                                            Price per night from

                                                                            $233

                                                                            Responds fast!
                                                                            avg. 2 hours 5 minutes

                                                                            Price per night from

                                                                            $233

                                                                            Distance approx 11.84 km from Winter Park Show on Map

                                                                              39

                                                                              Stunning 8 bedroom 5 bath Champions Gate home w/ Private South Facing Pool & 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

                                                                              $303

                                                                              Responds fast!
                                                                              avg. 1 hour 30 minutes

                                                                              Price per night from

                                                                              $303