Vacation Rentals with Pool in Winter Park

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Filtering by: Swimming pool

380 vacation rentals
    29

    Winter Park Home w/Ski Hill Views, Sauna & Hot Tub

    Grand County / Winter Park

    Winter Park house

    5 12 min stay varies

    • 5 bedrooms
    • sleeps 12
    • min stay varies
    • Swimming pool
    • Ski
    • Child Friendly

    Price per night from

    $456

    Responds fast!
    avg. 36 minutes

    Price per night from

    $456

      20

      Snowblaze Condominiums B22

      Grand County / Winter Park

      Winter Park apartment

      2 6 min stay varies

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

      Price per night from

      $152

      Price per night from

      $152

        24

        Winter Park Condo w/ Amenities - Mins to Slopes!

        Grand County / Winter Park

        Winter Park apartment

        1 4 min stay varies

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

        Price per night from

        $109

        Responds fast!
        avg. 9 minutes

        Price per night from

        $109

        (1) Excellent 

          18

          Bright, Updated Top Floor Unit With Great Views

          Grand County / Winter Park

          Winter Park condo

          2 6 min stay varies

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

          Price per night from

          $201

          Price per night from

          $201

            24

            Winter Park Condo w/Views & Ski-In/Ski-Out Access!

            Grand County / Winter Park

            Winter Park apartment

            1 5 min stay varies

            • 1 bedroom
            • sleeps 5
            • min stay varies
            • Swimming pool
            • Ski
            • Child Friendly

            Price per night from

            $98

            Responds fast!
            avg. 38 minutes

            Price per night from

            $98

              24

              Winter Park Condo w/Amenities - 4 Mi. to Ski Lifts

              Grand County / Winter Park

              Winter Park apartment

              1 4 min stay varies

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

              Price per night from

              $109

              Responds fast!
              avg. 30 minutes

              Price per night from

              $109

                31

                Winter Park Condo Only 2 Miles from Ski Lifts!

                Grand County / Winter Park

                Winter Park apartment

                1 4 min stay varies

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

                Price per night from

                $114

                Responds fast!
                avg. 9 minutes

                Price per night from

                $114

                (1) Excellent 

                  38

                  Snowblaze C24

                  Grand County / Winter Park

                  Winter Park house

                  2 7 min stay varies

                  • 2 bedrooms
                  • sleeps 7
                  • min stay varies
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $174

                  Price per night from

                  $174

                  (4) Very Good 

                    14

                    Winter Park CO from $65.00 per Ski Season night !!

                    Grand County / Winter Park

                    Winter Park villa

                    4 2 nights min

                    • sleeps 4
                    • 2 nights min
                    • Swimming pool
                    • Child Friendly
                    • Car not necessary

                    Price per night from

                    $57

                    Responds fast!
                    avg. 2 hours 21 minutes

                    Price per night from

                    $57

                      24

                      Inviting Winter Park Condo w/ Shuttle & Mtn Views!

                      Grand County / Winter Park

                      Winter Park apartment

                      3 8 min stay varies

                      • 3 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Swimming pool
                      • Ski
                      • Child Friendly

                      Price per night from

                      $188

                      Responds fast!
                      avg. 9 minutes

                      Price per night from

                      $188

                        36

                        Trailhead Lodges 822

                        Grand County / Winter Park

                        Winter Park condo

                        2 8 min stay varies

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

                        Price per night from

                        $211

                        Price per night from

                        $211

                          0

                          NEW LISTING! Cozy condo w/ shared hot tubs, pool, sauna, gym, and game room

                          Grand County / Winter Park

                          Winter Park house

                          2 7 min stay varies

                          • 2 bedrooms
                          • sleeps 7
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Car not necessary

                          Price per night from

                          $113

                          Responds fast!
                          avg. 2 hours 6 minutes

                          Price per night from

                          $113

                          (1) Very Good 

                            25

                            Winter Park Condo w/ Hot Tubs, 3 Mi to Ski Resort!

                            Grand County / Winter Park

                            Winter Park apartment

                            2 7 min stay varies

                            • 2 bedrooms
                            • sleeps 7
                            • min stay varies
                            • Swimming pool
                            • Ski
                            • Child Friendly

                            Price per night from

                            $144

                            Responds fast!
                            avg. 9 minutes

                            Price per night from

                            $144

                            (5) Very Good 

                              39

                              Hi Country House 21-15

                              Grand County / Winter Park

                              Winter Park apartment

                              3 8 min stay varies

                              • 3 bedrooms
                              • sleeps 8
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              “Spacey and cozy” This newly remodeled and newly furnished condo was very comfortable for my family with kids. New furniture made a lot of difference.
                              …see more

                              Price per night from

                              $126

                              Price per night from

                              $126

                              (1) Very Good 

                                32

                                Iron Horse Resort 3094

                                Grand County / Winter Park

                                Winter Park apartment

                                2 8 min stay varies

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

                                Price per night from

                                $260

                                Price per night from

                                $260

                                (1) Excellent 

                                  37

                                  Trailhead Lodges 323

                                  Grand County / Winter Park

                                  Winter Park house

                                  3 10 min stay varies

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

                                  Price per night from

                                  $235

                                  Price per night from

                                  $235

                                  (2) Excellent 

                                    35

                                    Trailhead Lodges 432

                                    Grand County / Winter Park

                                    Winter Park house

                                    2 8 min stay varies

                                    • 2 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    “Summertime in Winter Park” Outstanding from the first phone call to Winter Park Lodging till the day we left our unit, Trailhead Lodge 432. Crystal & Meg were fantastic in answering all questions and taking care of any concerns that we had.
                                    …see more

                                    Price per night from

                                    $211

                                    Price per night from

                                    $211

                                      29

                                      Iron Horse Resort 3084

                                      Grand County / Winter Park

                                      Winter Park studio

                                      Studio 4 min stay varies

                                      • Studio
                                      • sleeps 4
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $131

                                      Price per night from

                                      $131

                                        26

                                        New! 2BR Winter Park Condo - 4 Mins to Ski Area!

                                        Grand County / Winter Park

                                        Winter Park apartment

                                        2 4 min stay varies

                                        • 2 bedrooms
                                        • sleeps 4
                                        • min stay varies
                                        • Swimming pool
                                        • Ski
                                        • Child Friendly

                                        Price per night from

                                        $115

                                        Responds fast!
                                        avg. 9 minutes

                                        Price per night from

                                        $115

                                          34

                                          Trailhead Lodges 322

                                          Grand County / Winter Park

                                          Winter Park condo

                                          2 8 min stay varies

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

                                          Price per night from

                                          $222

                                          Price per night from

                                          $222

                                          (3) Very Good 

                                            20

                                            2 Bedroom End Unit at Beaver Village-Views, Pool, Hot Tubs

                                            Grand County / Winter Park

                                            Winter Park condo

                                            2 7 2 nights min

                                            • 2 bedrooms
                                            • sleeps 7
                                            • 2 nights min
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $171

                                            Price per night from

                                            $171

                                              25

                                              Winter Park Condo w/Sauna Near Skiing & Hiking!

                                              Grand County / Winter Park

                                              Winter Park apartment

                                              2 8 min stay varies

                                              • 2 bedrooms
                                              • sleeps 8
                                              • min stay varies
                                              • Swimming pool
                                              • Ski
                                              • Child Friendly

                                              Price per night from

                                              $201

                                              Responds fast!
                                              avg. 9 minutes

                                              Price per night from

                                              $201

                                                18

                                                Beaver Village Unit #2011

                                                Grand County / Winter Park

                                                Winter Park condo

                                                2 4 min stay varies

                                                • 2 bedrooms
                                                • sleeps 4
                                                • min stay varies
                                                • Swimming pool
                                                • Ski
                                                • Child Friendly

                                                Price per night from

                                                $173

                                                Price per night from

                                                $173

                                                (2) Excellent 

                                                  18

                                                  Winter Wonderland in WP!!!

                                                  Grand County / Winter Park

                                                  Winter Park condo

                                                  2 6 1 night min

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

                                                  Price per night from

                                                  $161

                                                  Responds fast!
                                                  avg. 18 minutes

                                                  Price per night from

                                                  $161

                                                  (1) Very Good 

                                                    24

                                                    2BR Ground-Floor w/ Granite Kitchen, Pool, & Hot Tub - Shuttle to Slopes

                                                    Grand County / Winter Park

                                                    Winter Park condo

                                                    2 7 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 7
                                                    • min stay varies
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $156

                                                    Price per night from

                                                    $156

                                                      29

                                                      Trailhead Lodges 424

                                                      Grand County / Winter Park

                                                      Winter Park house

                                                      2 7 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 7
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $208

                                                      Price per night from

                                                      $208

                                                      (47) Very Good 

                                                        35

                                                        Trailhead Lodges 512

                                                        Grand County / Winter Park

                                                        Winter Park house

                                                        1 4 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “happy” everything we needed, comfy and content! Great location, loved the area, we had one problem with the cable and they came right over, I would stay again
                                                        …see more

                                                        Price per night from

                                                        $152

                                                        Price per night from

                                                        $152

                                                        (2) Very Good 

                                                          39

                                                          Snowblaze Condominiums C14

                                                          Grand County / Winter Park

                                                          Winter Park apartment

                                                          2 7 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 7
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly

                                                          Price per night from

                                                          $152

                                                          Price per night from

                                                          $152

                                                          (3) Excellent 

                                                            19

                                                            Newly Remodeled Studio/Think Snow!

                                                            Grand County / Winter Park

                                                            Winter Park studio

                                                            Studio 3 2 nights min

                                                            • Studio
                                                            • sleeps 3
                                                            • 2 nights min
                                                            • Swimming pool
                                                            • Ski
                                                            • Child Friendly

                                                            Price per night from

                                                            $144

                                                            Price per night from

                                                            $144

                                                            (24) Excellent 

                                                              31

                                                              Trailhead Lodges 723

                                                              Grand County / Winter Park

                                                              Winter Park house

                                                              3 8 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              “Comfortable and great location.” Checking in late was easy and a great convenience for us. The condo was clean and great decor. It was quite roomy. We had eight people including six teenagers. There was plenty of room to relax after skiing all day. Th
                                                              …see more

                                                              Price per night from

                                                              $235

                                                              Price per night from

                                                              $235

                                                                28

                                                                Winter Park Condo w/Ski Bus - 2 Blocks to Downtown

                                                                Grand County / Winter Park

                                                                Winter Park apartment

                                                                2 8 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Ski
                                                                • Child Friendly

                                                                Price per night from

                                                                $126

                                                                Responds fast!
                                                                avg. 9 minutes

                                                                Price per night from

                                                                $126

                                                                  50

                                                                  Trailhead Lodges 524

                                                                  Grand County / Winter Park

                                                                  Winter Park townhouse

                                                                  3 10 min stay varies

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

                                                                  Price per night from

                                                                  $248

                                                                  Responds fast!
                                                                  avg. 2 hours 9 minutes

                                                                  Price per night from

                                                                  $248

                                                                    16

                                                                    Timber Lake 341 (************)

                                                                    Grand County / Winter Park

                                                                    Winter Park house

                                                                    3 8 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 8
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $234

                                                                    Price per night from

                                                                    $234

                                                                      25

                                                                      Ski-In/Ski-Out Winter Park Studio w/Hot Tub Access

                                                                      Grand County / Winter Park

                                                                      Winter Park studio

                                                                      Studio 4 min stay varies

                                                                      • Studio
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Ski
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $103

                                                                      Responds fast!
                                                                      avg. 9 minutes

                                                                      Price per night from

                                                                      $103

                                                                        37

                                                                        Trailhead Lodges 514

                                                                        Grand County / Winter Park

                                                                        Winter Park condo

                                                                        3 10 min stay varies

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

                                                                        Price per night from

                                                                        $253

                                                                        Price per night from

                                                                        $253

                                                                        (19) Excellent 

                                                                          34

                                                                          Trailhead Lodges 734

                                                                          Grand County / Winter Park

                                                                          Winter Park house

                                                                          2 8 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          “Spring Ski” It was a beautiful condo with everything you need for a relaxing vacation stay! It would be great for entertaining! The location had easy access to restaurants and shops.
                                                                          …see more

                                                                          Price per night from

                                                                          $222

                                                                          Price per night from

                                                                          $222

                                                                          (2) Very Good 

                                                                            22

                                                                            Iron Horse Resort 5064

                                                                            Grand County / Winter Park

                                                                            Winter Park studio

                                                                            Studio 4 min stay varies

                                                                            • Studio
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $131

                                                                            Price per night from

                                                                            $131

                                                                              24

                                                                              3BR Upscale Penthouse with Largest Deck at Base with Amazing View

                                                                              Grand County / Winter Park

                                                                              Winter Park condo

                                                                              3 8 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Car not necessary

                                                                              Price per night from

                                                                              $573

                                                                              Price per night from

                                                                              $573