Vacation Rentals & Apartment Rentals in Winter Haven

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8,391 apartment rentals

    31

    Lake house #10

    Central Florida / Winter Haven

    Winter Haven villa

    2 7 min stay varies

    • 2 bedrooms
    • sleeps 7
    • min stay varies
    • Child Friendly
    • Air conditioning

    Price per night from

    $138

    Price per night from

    $138

      24

      Lake house #18

      Central Florida / Winter Haven

      Winter Haven villa

      1 4 min stay varies

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

      Price per night from

      $121

      Price per night from

      $121

      (3) Very Good 

        22

        Saltwater Pool Villa Next to Legoland and Near All Disney Attractions

        Central Florida / Winter Haven

        Winter Haven villa

        3 6 4 nights min

        • 3 bedrooms
        • sleeps 6
        • 4 nights min
        • Nearest beach 126 mi
        • Swimming pool
        • Child Friendly

        Price per night from

        $142

        Responds fast!
        avg. 3 hours 27 minutes

        Price per night from

        $142

        (3) Excellent 

          20

          45 Min to Disney 15 Min to Legoland on chain of la

          Central Florida / Winter Haven

          Winter Haven house

          3 10 3 nights min

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

          Price per night from

          $258

          Price per night from

          $258

          (6) Excellent 

            28

            Vacation home 3 Bedroom Next to LEGOLAND

            Central Florida / Winter Haven

            Winter Haven house

            3 6 1 night min

            • 3 bedrooms
            • sleeps 6
            • 1 night min
            • Child Friendly
            • Air conditioning
            • Private garden

            Price per night from

            $91

            Price per night from

            $91

              29

              Lake house #13

              Central Florida / Winter Haven

              Winter Haven villa

              1 4 min stay varies

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

              Price per night from

              $121

              Price per night from

              $121

              (2) Average 

                12

                Lakeview Tiny Home by Legoland/Disney w/ boats!

                Central Florida / Winter Haven

                Winter Haven house

                1 3 1 night min

                • 1 bedroom
                • sleeps 3
                • 1 night min
                • Child Friendly
                • Air conditioning
                • Ask about pets

                Price per night from

                $75

                Responds fast!
                avg. 3 hours 54 minutes

                Price per night from

                $75

                  28

                  Lake house #15

                  Central Florida / Winter Haven

                  Winter Haven villa

                  1 4 min stay varies

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

                  Price per night from

                  $121

                  Price per night from

                  $121

                    10

                    Snowbird - Central Florida - Waterfront / Bord de lac

                    Central Florida / Winter Haven

                    Winter Haven house

                    2 5 120 nights min

                    • 2 bedrooms
                    • sleeps 5
                    • 120 nights min
                    • Air conditioning
                    • Pet Friendly
                    • Private garden

                    Price per night from

                    $71

                    Price per night from

                    $71

                      33

                      Lake house #17

                      Central Florida / Winter Haven

                      Winter Haven villa

                      2 7 min stay varies

                      • 2 bedrooms
                      • sleeps 7
                      • min stay varies
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $138

                      Price per night from

                      $138

                        34

                        Lake house #9

                        Central Florida / Winter Haven

                        Winter Haven villa

                        2 6 min stay varies

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

                        Price per night from

                        $138

                        Price per night from

                        $138

                          6

                          NEW! Lakefront Vacation Home with Pool & Boatdock!

                          Central Florida / Winter Haven

                          Winter Haven house

                          3 6 3 nights min

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

                          Price per night from

                          $144

                          Responds fast!
                          avg. 3 hours 59 minutes

                          Price per night from

                          $144

                            4

                            Livin the Dream

                            Central Florida / Winter Haven

                            Winter Haven condo

                            3 6 min stay varies

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

                            Price per night from

                            $125

                            Price per night from

                            $125

                            Great rentals within 20 miles that match your search

                            Distance approx 18.5 km from Winter Haven

                            (11) Excellent 

                            Certificate of Excellence

                              90

                              Disney Area Villa with Pool

                              Central Florida / Davenport

                              Davenport villa

                              4 9 min stay varies

                              • 4 bedrooms
                              • sleeps 9
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Nearest beach 75 mi
                              • Swimming pool
                              “Wonderful home” My family and I had an awesome trip and this wonderful home was certainly a highlight. Very clean, spacious and a great location. We would love to stay again!

                              Certificate of Excellence

                              Price per night from

                              $106

                              Responds fast!
                              avg. 3 hours 7 minutes

                              Price per night from

                              $106

                              Distance approx 19.23 km from Winter Haven

                                16

                                Davenport Holiday Villa 27724

                                Central Florida / Loughman

                                Loughman villa

                                5 10 7 nights min

                                • 5 bedrooms
                                • sleeps 10
                                • 7 nights min
                                • Swimming pool
                                • Air conditioning

                                Price per night from

                                $302

                                Price per night from

                                $302

                                Distance approx 16.77 km from Winter Haven

                                  20

                                  Watersong Resort-406AOCJGI

                                  Central Florida / Davenport

                                  Davenport house

                                  6 12 6 nights min

                                  • 6 bedrooms
                                  • sleeps 12
                                  • 6 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Car not necessary

                                  Price per night from

                                  $446

                                  Price per night from

                                  $446

                                  Distance approx 13.19 km from Winter Haven

                                    24

                                    Golf Lovers Paradise

                                    Central Florida / Davenport

                                    Davenport house

                                    5 12 min stay varies

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

                                    Price per night from

                                    $160

                                    Responds fast!
                                    avg. 1 hour 42 minutes

                                    Price per night from

                                    $160

                                    Distance approx 17.02 km from Winter Haven

                                      60

                                      ★ SUMMER VACATION AT DISNEY 5BEDRM/4BATH AT SOLTERRA RESORT

                                      Central Florida / Loughman

                                      Loughman house

                                      5 16 min stay varies

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

                                      Price per night from

                                      $265

                                      Price per night from

                                      $265

                                      Distance approx 19.41 km from Winter Haven

                                      (2) Very Good 

                                        28

                                        Calusa Villa is a 6 bedroom 4 bathroom detached Villa.

                                        Davenport / Hampton Lakes

                                        Davenport villa

                                        6 14 5 nights min

                                        • 6 bedrooms
                                        • sleeps 14
                                        • 5 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 100 mi
                                        • Swimming pool

                                        Price per night from

                                        $228

                                        Price per night from

                                        $228

                                        Distance approx 17.07 km from Winter Haven

                                          28

                                          The Sanctuary at West Haven Luxury

                                          Central Florida / Davenport

                                          Davenport villa

                                          4 8 7 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 7 nights min
                                          • Nearest beach 97 mi
                                          • Swimming pool
                                          • Air conditioning

                                          Price per night from

                                          $171

                                          Price per night from

                                          $171

                                          Distance approx 17.95 km from Winter Haven

                                            101

                                            **Cinema Room***Elegant Champion Gates Cozy Escape Sleep 17 FREE Water Park

                                            Central Florida / ChampionsGate

                                            ChampionsGate house

                                            8 17 min stay varies

                                            • 8 bedrooms
                                            • sleeps 17
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $388

                                            Responds fast!
                                            avg. 2 hours 10 minutes

                                            Price per night from

                                            $388

                                            Distance approx 19.11 km from Winter Haven

                                            (27) Excellent 

                                              33

                                              KYLEMORE

                                              Davenport / The Manors North at Westridge

                                              Davenport villa

                                              5 11 7 nights min

                                              • 5 bedrooms
                                              • sleeps 11
                                              • 7 nights min
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $142

                                              Responds fast!
                                              avg. 3 hours 3 minutes

                                              Price per night from

                                              $142

                                              Distance approx 18 km from Winter Haven

                                              (4) Excellent 

                                                11

                                                Private one bedroom apartment at a great price

                                                Central Florida / Lakeland

                                                Lakeland apartment

                                                1 4 2 nights min

                                                • 1 bedroom
                                                • sleeps 4
                                                • 2 nights min
                                                • Child Friendly
                                                • Car not necessary
                                                • Air conditioning

                                                Price per night from

                                                $89

                                                Responds fast!
                                                avg. 3 hours 31 minutes

                                                Price per night from

                                                $89

                                                Distance approx 17 km from Winter Haven

                                                (10) Excellent 

                                                  21

                                                  5 star luxury Florida home - close to Disney

                                                  Central Florida / Davenport

                                                  Davenport house

                                                  4 8 min stay varies

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning
                                                  “Fantastisk” Det var f?rste gang, min familie og jeg var i usa, s? vi var rigitg sp?ndte p? hvad vi skulle bo i, og hvad vi kom over til. Huset er som beskrevet, Super. Et rigitg l?kket hus, og vi kommer helt sikkert igen, hvis turen g?r forbi orlando

                                                  Price per night from

                                                  $171

                                                  Price per night from

                                                  $171

                                                  Distance approx 18.24 km from Winter Haven

                                                  (3) Very Good 

                                                    93

                                                    Lake facing five bedroom property in Davenport, Florida

                                                    Central Florida / Davenport

                                                    Davenport house

                                                    5 8 3 nights min

                                                    • 5 bedrooms
                                                    • sleeps 8
                                                    • 3 nights min
                                                    • Child Friendly
                                                    “Outstanding Place and Communication” From start to end, the interaction with owner was superb and prompt. Arrival went seamless, the information provided prior and inside the hope left no room for extra questions. Accommodations were as expected and s

                                                    Price per night from

                                                    $149

                                                    Price per night from

                                                    $149

                                                    Distance approx 18.07 km from Winter Haven

                                                    (1) Excellent 

                                                      17

                                                      Your Villa in Florida

                                                      Central Florida / Davenport

                                                      Davenport house

                                                      4 10 3 nights min

                                                      • 4 bedrooms
                                                      • sleeps 10
                                                      • 3 nights min
                                                      • Child Friendly
                                                      “Awesome value” Great value, kids enjoyed pool and game room. Couldn't have asked for a better place. Laundry and fully stocked kitchen live saver for me. Really impressed with the ease of checking and out. Loved the place. Would stay again.

                                                      Price per night from

                                                      $129

                                                      Responds fast!
                                                      avg. 1 hour 25 minutes

                                                      Price per night from

                                                      $129

                                                      Distance approx 16.97 km from Winter Haven

                                                        38

                                                        Solterra Resort 6 Bedroom 4 Bath Villa 5340OA

                                                        Central Florida / Davenport

                                                        Davenport villa

                                                        6 12 min stay varies

                                                        • 6 bedrooms
                                                        • sleeps 12
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Car not necessary

                                                        Price per night from

                                                        $255

                                                        Price per night from

                                                        $255

                                                        Distance approx 18.29 km from Winter Haven

                                                        (2) Excellent 

                                                          29

                                                          StaySmooth Retreat- Near Disney!!!

                                                          Central Florida / Four Corners

                                                          Four Corners house

                                                          3 7 min stay varies

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

                                                          Price per night from

                                                          $125

                                                          Price per night from

                                                          $125

                                                          Distance approx 17.26 km from Winter Haven

                                                            78

                                                            At Last You can Rent the Perfect Luxury Villa on Champions Gate Resort, minutes

                                                            Central Florida / ChampionsGate

                                                            ChampionsGate villa

                                                            9 18 min stay varies

                                                            • 9 bedrooms
                                                            • sleeps 18
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $382

                                                            Price per night from

                                                            $382

                                                            Distance approx 17.39 km from Winter Haven

                                                            (2) Average 

                                                              14

                                                              4 bedroom pool homes near Disney

                                                              Central Florida / Davenport

                                                              Davenport house

                                                              4 8 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Nearest beach 80 mi
                                                              • Swimming pool
                                                              • Child Friendly

                                                              Price per night from

                                                              $143

                                                              Price per night from

                                                              $143

                                                              Distance approx 12.26 km from Winter Haven

                                                                26

                                                                Lakeside Villa

                                                                Central Florida / Davenport

                                                                Davenport villa

                                                                6 12 7 nights min

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

                                                                Price per night from

                                                                $224

                                                                Price per night from

                                                                $224

                                                                Distance approx 16.91 km from Winter Haven

                                                                  38

                                                                  Luxury 5 Star Villa on Solterra Resort,Minutes from Disney World, Orlando Villa

                                                                  Central Florida / Loughman

                                                                  Loughman villa

                                                                  15 26 min stay varies

                                                                  • 15 bedrooms
                                                                  • sleeps 26
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $679

                                                                  Price per night from

                                                                  $679

                                                                  Distance approx 19.27 km from Winter Haven

                                                                  (1)  

                                                                    27

                                                                    'Lake View Dream Villa' 5BR Davenport Home w/Pool!

                                                                    Central Florida / Davenport

                                                                    Davenport house

                                                                    5 10 5 nights min

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

                                                                    Price per night from

                                                                    $125

                                                                    Responds fast!
                                                                    avg. 40 minutes

                                                                    Price per night from

                                                                    $125

                                                                    Distance approx 16.52 km from Winter Haven

                                                                      77

                                                                      H6112 Beautiful 14 Bedroom 11 Bathroom Resoret

                                                                      Central Florida / Loughman

                                                                      Loughman villa

                                                                      14 28 min stay varies

                                                                      • 14 bedrooms
                                                                      • sleeps 28
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $834

                                                                      Price per night from

                                                                      $834

                                                                      Distance approx 17.26 km from Winter Haven

                                                                        26

                                                                        Beautiful 5 Star Villa with Private Pool on the Prestigious Champions Gate

                                                                        Central Florida / ChampionsGate

                                                                        ChampionsGate villa

                                                                        5 16 min stay varies

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

                                                                        Price per night from

                                                                        $314

                                                                        Price per night from

                                                                        $314

                                                                        Distance approx 18.74 km from Winter Haven

                                                                          27

                                                                          3BR Reunion Condo w/10 Pools - 4 Miles from Disney

                                                                          Central Florida / Reunion

                                                                          Reunion apartment

                                                                          3 8 3 nights min

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

                                                                          Price per night from

                                                                          $143

                                                                          Responds fast!
                                                                          avg. 14 minutes

                                                                          Price per night from

                                                                          $143

                                                                          Distance approx 17.25 km from Winter Haven

                                                                            48

                                                                            The Secret to Enjoying Your Luxury Home Holiday on Champions Gate Resort

                                                                            Central Florida / ChampionsGate

                                                                            ChampionsGate villa

                                                                            4 8 min stay varies

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

                                                                            Price per night from

                                                                            $162

                                                                            Price per night from

                                                                            $162

                                                                            Distance approx 17.71 km from Winter Haven

                                                                            (11) Excellent 

                                                                              33

                                                                              Luxury 6 bed new villa ,pool , hot tub , games rooms , home cinema

                                                                              Central Florida / Davenport

                                                                              Davenport house

                                                                              6 13 7 nights min

                                                                              • 6 bedrooms
                                                                              • sleeps 13
                                                                              • 7 nights min
                                                                              • Nearest beach 80 mi
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              “THIS HOME IS AMAZING!!!!!” This home is amazing there were 8 of us 6 adults and 2 children. It was spacious never once did we feel that we were on top of each other. Perfectly located 15 minuets to disney 20 minuets to universal and so easy to get the

                                                                              Price per night from

                                                                              $224

                                                                              Responds fast!
                                                                              avg. 42 minutes

                                                                              Price per night from

                                                                              $224

                                                                              About Winter Haven

                                                                              Whether you're in Winter Haven because of the kids (hello, Legoland!) or flying solo, there is something for everyone in this city! Why not visit FlipKey for the perfect Winter Haven vacation rental that you can relax in when you're done exploring?

                                                                              About Winter Haven

                                                                              The earliest people known to what is now Winter Haven were the Timucua and the Calusa. In the 1860s, the first settlers came to Winter Haven and it wasn't named Winter Haven until 1885 by P.D. Eycleshimer.

                                                                              Winter Haven has a myriad of interconnected lakes. Started in 1915 and completed by the early 1920s, be sure to check out the Chain of Lakes!

                                                                              Winter Haven has a long history which you can find out about at the Museum of Winter Haven.

                                                                              The second largest city in Polk County, Winter Haven is home to a variety of cultural experiences. Located between Tampa and Orlando, there is plenty to do in this fabulous city!

                                                                              Whether you want to discover your inner water baby by checking out the watersports Winter Haven has to offer, or you'd rather just relax and enjoy the eclectic food scene, Winter Haven is for everybody!

                                                                              What to do

                                                                              Why not start your day off by exploring Downtown Winter Haven? Full of great shops and restaurants, you will really get a feel of Winter Haven here!

                                                                              When you're done exploring, head on over to The Chain of Lakes so you can take part in a spot of fishing. Too boring? Then there are many watersports you can enjoy, such as jet skiing, water tubing, and boating.

                                                                              Make sure to check out the fountain in Central Park, which changes its colors during holidays!

                                                                              Winter Haven holds many events throughout the year. Enjoy local musicians at Pickin in the Park held the first Friday of the month.

                                                                              Check out the local produce at the Farmer's Market, which is held every Thursday 8 am - 5 pm.

                                                                              Last but not least, be sure to check out Legoland which is the second-largest Legoland in the world. The kids will be sure to enjoy it!

                                                                              Top Winter Haven travel tips

                                                                              Winter Haven enjoys a mild climate throughout most of the year, so you can mostly get away with a light sweater. Be aware of the occasional shower during the summer months, though!

                                                                              You'll be able to get to Winter Haven quite easily from Orlando. Orlando International Airport is only 45 minutes away. You can also access Winter Haven via Tampa International Airport. However, this is slightly further away.

                                                                              You can easily get around Winter Haven by bus using the two bus services on offer: Winter Haven Area Transit and Citrus connection.

                                                                              Winter Haven is the perfect vacation spot as there are so many things to do! Whether you're an art lover or a watersports enthusiast, Winter Haven doesn't turn anybody away. Find the perfect Winter Haven vacation rental FlipKey!