Dog Friendly Vacation Rentals in Winter Park - FlipKey

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Filtering by: Pets allowed

98 pet friendly villas in Winter Park

    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. 30 minutes

    Price per night from

    $109

      28

      Riverside Winter Park Condo w/ Hot Tub Access!

      Grand County / Winter Park

      Winter Park apartment

      2 7 min stay varies

      • 2 bedrooms
      • sleeps 7
      • min stay varies
      • Ski
      • Child Friendly
      • Pet Friendly

      Price per night from

      $132

      Responds fast!
      avg. 1 hour 47 minutes

      Price per night from

      $132

        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

        (3) Average 

          29

          Mary Jane Chalet

          Grand County / Winter Park

          Winter Park house

          6 10 min stay varies

          • 6 bedrooms
          • sleeps 10
          • min stay varies
          • Ask about children
          • Pet Friendly
          “Perfect place for my group” Location in town was perfect for us close to restaurants and distance to mountain was just what i look for.

          Price per night from

          $331

          Price per night from

          $331

          (1) Very Good 

            26

            Custom High-End Mountain Home: Wooded Area, Close to Town Sleeps 16-20

            Grand County / Winter Park

            Winter Park house

            6 20 min stay varies

            • 6 bedrooms
            • sleeps 20
            • min stay varies
            • Child Friendly
            • Pet Friendly

            Price per night from

            $682

            Responds fast!
            avg. 3 hours 4 minutes

            Price per night from

            $682

              24

              Large Luxurious Home,Wooded,Close town Slps16-24

              Grand County / Winter Park

              Winter Park house

              6 24 min stay varies

              • 6 bedrooms
              • sleeps 24
              • min stay varies
              • Child Friendly
              • Car not necessary
              • Pet Friendly

              Price per night from

              $506

              Responds fast!
              avg. 3 hours 4 minutes

              Price per night from

              $506

              (1) Excellent 

                27

                Beautiful Mountain House - Luxury in a Rustic Mountain Setting

                Grand County / Winter Park

                Winter Park house

                4 14 min stay varies

                • 4 bedrooms
                • sleeps 14
                • min stay varies
                • Child Friendly
                • Pet Friendly
                “Reunion Weekend Getaway” We loved staying in this beautiful mountain home for a Law School Reunion Weekend Getaway with many friends! The location is picturesque and the house well-stocked, clean, comfortable, luxurious, and now home to a great memory

                Price per night from

                $444

                Responds fast!
                avg. 3 hours 4 minutes

                Price per night from

                $444

                (1) Excellent 

                  38

                  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

                  $22

                  Price per night from

                  $22

                    28

                    NEW LISTING! Charming dog-friendly cabin with private hot tub and mountain views

                    Grand County / Winter Park

                    Winter Park house

                    3 8 min stay varies

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

                    Price per night from

                    $252

                    Responds fast!
                    avg. 2 hours 52 minutes

                    Price per night from

                    $252

                      21

                      Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

                      Grand County / Winter Park

                      Winter Park townhouse

                      3 8 min stay varies

                      • 3 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Ski
                      • Child Friendly
                      • Pet Friendly

                      Price per night from

                      $256

                      Price per night from

                      $256

                        48

                        Selah Vista Lodge

                        Grand County / Winter Park

                        Winter Park house

                        6 16 min stay varies

                        • 6 bedrooms
                        • sleeps 16
                        • min stay varies
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $791

                        Price per night from

                        $791

                          43

                          Lakota Antlers 300

                          Grand County / Winter Park

                          Winter Park condo

                          4 12 min stay varies

                          • 4 bedrooms
                          • sleeps 12
                          • min stay varies
                          • Child Friendly
                          • Pet Friendly

                          Price per night from

                          $34

                          Price per night from

                          $34

                            32

                            NEW LISTING! Family-friendly condo w/private hot tub & fireplace - near skiing

                            Grand County / Winter Park

                            Winter Park house

                            3 8 min stay varies

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

                            Price per night from

                            $155

                            Responds fast!
                            avg. 2 hours 52 minutes

                            Price per night from

                            $155

                              24

                              Cozy Winter Park Cabin - Walk to Main Street & DT!

                              Grand County / Winter Park

                              Winter Park log cabin

                              2 8 min stay varies

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

                              Price per night from

                              $160

                              Responds fast!
                              avg. 30 minutes

                              Price per night from

                              $160

                              (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

                                $165

                                Price per night from

                                $165

                                (11) Very Good 

                                  30

                                  Charming Log Cabin w/Hot Tub, Deck, Ping Pong,Wifi

                                  Grand County / Winter Park

                                  Winter Park log cabin

                                  2 6 2 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 2 nights min
                                  • Ask about children
                                  • Car not necessary
                                  • Air conditioning
                                  “"Perfect in every way"” The cabin far exceeded our expectations, from the minute we walked in the door. "Perfect" location, decor & ammenities. My favorite was the huge back deck. Unfortunately we could only stay two nights, we will for sure be return

                                  Price per night from

                                  $238

                                  Price per night from

                                  $238

                                  (10) Excellent 

                                    33

                                    Bear Crossing 1390

                                    Grand County / Winter Park

                                    Winter Park house

                                    3 10 min stay varies

                                    • 3 bedrooms
                                    • sleeps 10
                                    • min stay varies
                                    • Child Friendly
                                    • Pet Friendly
                                    “Spring Break” A great place for two families (2 adults and 6 kids) to spend Spring Break. The beds were comfortable, plenty of bathrooms and the kitchen was well equipped. What more could you ask for? How about relaxing in the private hot tub après

                                    Price per night from

                                    $29

                                    Price per night from

                                    $29

                                    (1) Excellent 

                                      31

                                      Bear Crossing 745

                                      Grand County / Winter Park

                                      Winter Park house

                                      3 11 min stay varies

                                      • 3 bedrooms
                                      • sleeps 11
                                      • min stay varies
                                      • Child Friendly
                                      • Pet Friendly
                                      “Great place for families!” Property is centrally located between Fraser and Winter Park resort. Clean, modern, pet-friendly, with plenty of room to relax between hitting the slopes. Fabulous open kitchen area large enough for everyone to lend a hand i

                                      Price per night from

                                      $29

                                      Price per night from

                                      $29

                                      (2) Very Good 

                                        21

                                        Luxurious Cabin: Two Master Suites, Hot tub, Views

                                        Grand County / Winter Park

                                        Winter Park house

                                        4 14 min stay varies

                                        • 4 bedrooms
                                        • sleeps 14
                                        • min stay varies
                                        • Child Friendly
                                        • Pet Friendly
                                        “Beautiful, spacious home” This beautiful home was perfect for our extended family! We had a baby with us, so the baby gates, high chair and portable crib were great! Wonderful space to gather and play games and be together, plus room to spread out a

                                        Price per night from

                                        $408

                                        Responds fast!
                                        avg. 3 hours 4 minutes

                                        Price per night from

                                        $408

                                          39

                                          Trailhead Lodges 134

                                          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

                                          $27

                                          Price per night from

                                          $27

                                            33

                                            Sawmill Station 217

                                            Grand County / Winter Park

                                            Winter Park condo

                                            4 10 min stay varies

                                            • 4 bedrooms
                                            • sleeps 10
                                            • min stay varies
                                            • Child Friendly
                                            • Pet Friendly

                                            Price per night from

                                            $34

                                            Price per night from

                                            $34

                                              28

                                              Lakota Antlers 507

                                              Grand County / Winter Park

                                              Winter Park condo

                                              3 10 min stay varies

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

                                              Price per night from

                                              $29

                                              Price per night from

                                              $29

                                                34

                                                Rosie's Way

                                                Grand County / Winter Park

                                                Winter Park condo

                                                3 9 min stay varies

                                                • 3 bedrooms
                                                • sleeps 9
                                                • min stay varies
                                                • Child Friendly
                                                • Pet Friendly

                                                Price per night from

                                                $29

                                                Price per night from

                                                $29

                                                  34

                                                  Trailhead Lodges 133

                                                  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

                                                  $229

                                                  Price per night from

                                                  $229

                                                    25

                                                    Condo w/Comm. Amenities 2 Mi to Winter Park Resort

                                                    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

                                                    $115

                                                    Responds fast!
                                                    avg. 30 minutes

                                                    Price per night from

                                                    $115

                                                      24

                                                      New Listing! Remodeled Riverside Getaway w/ Hot Tubs, Pool & Shuttle to Slope

                                                      Grand County / Winter Park

                                                      Winter Park condo

                                                      1 4 min stay varies

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

                                                      Price per night from

                                                      $120

                                                      Price per night from

                                                      $120

                                                        30

                                                        New Listing! Mountain-View 3-Story Townhome in the Heart of Winter Park

                                                        Grand County / Winter Park

                                                        Winter Park townhouse

                                                        3 8 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 8
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Pet Friendly

                                                        Price per night from

                                                        $158

                                                        Price per night from

                                                        $158

                                                          28

                                                          NEW! Winter Park Home w/Hot Tub - Walk to Resort!

                                                          Grand County / Winter Park

                                                          Winter Park house

                                                          3 8 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 8
                                                          • min stay varies
                                                          • Ski
                                                          • Child Friendly
                                                          • Pet Friendly

                                                          Price per night from

                                                          $195

                                                          Responds fast!
                                                          avg. 11 minutes

                                                          Price per night from

                                                          $195

                                                            24

                                                            New Listing! Upscale Mountain Gem w/ Pool & Hot Tubs - Next to Ski Shuttle

                                                            Grand County / Winter Park

                                                            Winter Park condo

                                                            1 4 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Child Friendly
                                                            • Pet Friendly

                                                            Price per night from

                                                            $126

                                                            Price per night from

                                                            $126

                                                              35

                                                              Trailhead Lodges 812

                                                              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

                                                              $211

                                                              Responds fast!
                                                              avg. 2 hours 9 minutes

                                                              Price per night from

                                                              $211

                                                                24

                                                                New Listing! Riverside Mountain Condo Near Ski Shuttle w/ Hot Tubs & Pool

                                                                Grand County / Winter Park

                                                                Winter Park condo

                                                                1 4 min stay varies

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Pet Friendly

                                                                Price per night from

                                                                $122

                                                                Price per night from

                                                                $122

                                                                  24

                                                                  New Listing! 2 Separate Units: Pool, Hot Tubs, Next to Free City Shuttle

                                                                  Grand County / Winter Park

                                                                  Winter Park condo

                                                                  2 8 min stay varies

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

                                                                  Price per night from

                                                                  $134

                                                                  Price per night from

                                                                  $134

                                                                    26

                                                                    Updated Winter Park Family Condo - 4 Mi. to Resort

                                                                    Grand County / Winter Park

                                                                    Winter Park condo

                                                                    3 8 min stay varies

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

                                                                    Price per night from

                                                                    $172

                                                                    Responds fast!
                                                                    avg. 11 minutes

                                                                    Price per night from

                                                                    $172

                                                                      4

                                                                      Riverfront Upscale remodel in great location

                                                                      Grand County / Winter Park

                                                                      Winter Park condo

                                                                      1 4 4 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 4
                                                                      • 4 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $217

                                                                      Price per night from

                                                                      $217

                                                                        24

                                                                        Updated 2BR - Steps to Arapaho National Forest & Free Bus, Near Downtown

                                                                        Grand County / Winter Park

                                                                        Winter Park townhouse

                                                                        2 5 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $147

                                                                        Price per night from

                                                                        $147

                                                                        (3) Very Good 

                                                                          23

                                                                          Beautiful Mountain Lodge-Ski, Hike, Bike, Relax..

                                                                          Grand County / Winter Park

                                                                          Winter Park house

                                                                          5 19 3 nights min

                                                                          • 5 bedrooms
                                                                          • sleeps 19
                                                                          • 3 nights min
                                                                          • Ask about children
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $540

                                                                          Responds fast!
                                                                          avg. 1 hour 52 minutes

                                                                          Price per night from

                                                                          $540

                                                                          Great rentals within 20 miles that match your search

                                                                          Distance approx 2.58 km from Winter Park Show on Map

                                                                            34

                                                                            Historic Cabin w/ Hot Tub - 5 Mi. to Winter Park!

                                                                            Grand County / Fraser

                                                                            Fraser cottage

                                                                            5 15 min stay varies

                                                                            • 5 bedrooms
                                                                            • sleeps 15
                                                                            • min stay varies
                                                                            • Ski
                                                                            • Child Friendly
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $370

                                                                            Responds fast!
                                                                            avg. 39 minutes

                                                                            Price per night from

                                                                            $370

                                                                            Distance approx 17.42 km from Winter Park

                                                                            (2) Very Good 

                                                                              20

                                                                              Charming Log Cabin for Peaceful Mountain Getaway!

                                                                              Colorado / Black Hawk

                                                                              Black Hawk log cabin

                                                                              3 10 min stay varies

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

                                                                              Price per night from

                                                                              $216

                                                                              Price per night from

                                                                              $216