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Make a holiday villa in Winter Haven your home away from home

About as central as it's possible to get in Florida, Winter Haven holiday villas and apartments put you bang in the middle of the Sunshine State. As an absolute mecca for waterskiing enthusiasts, the area is riddled with over 50 lakes, interconnected by man-made canals; it's a positive nirvana for water sports. Holiday accommodation in Winter Haven are all fully air-conditioned, with all the modern appliances to keep your stay free of hassle. Nearly all Winter Haven rentals have access to a pool and welcome children, though only a few are accessible via wheelchair.

Things to do

-Theme parks: Opening just a couple of years ago on the site that was formerly Cypress Gardens, one of the world's first theme parks, Legoland Florida is a great family attraction. Legoland's 145 acres of park host over 50 Lego-themed rides, shows and attractions, as well as the preserved botanical garden area built by the former resident.

-Lakes: Winter Haven calls itself 'The Chain of Lakes City', and it's easy to see why. By far the most prominent features surrounding your Winter Haven holiday accommodation are the lakes and interconnecting waterways; teeming with wildlife, this is one of the world's premier bass fishing destinations, too.

-Watersports: With so many lakes, watersports are Winter Haven's raison d'etre. Cypress Gardens was instrumental in the invention of the sport of waterskiing, so the facilities for getting wet, and the variety of ways of doing so, are myriad. Rentals at Winter Haven are never far from the opportunity.

-Nightlife: There are far more bars and restaurants than needed to cater to a town of 26,000, which tells you all you need to know about Winter Haven's popularity as a holiday resort. From fast food to fine dining, laid-back pubs to energetic dance halls, there's something for everyone.

-Beaches: There's not much in the way of sandy beaches in this lake-strewn area, but either coast is only an hour away by car. From the amazing beaches at Tampa Bay in the west, to the equally pristine sand and surf of the Atlantic Space Coast, you're spoiled for choice.

Weather in Winter Haven

You could expect Florida's subtropical climate to be the hottest here, which is about as far from the sea as you can get in Florida. Fortunately, the extensive wetlands have a similar moderating influence, so temperatures in the summer rarely get intolerable. Typical highs don't exceed the mid-30°C mark, and this is further tempered by the summer thunderstorms which tend to cool things down a little. Winters are on a par with the British summer, so temperatures top 20°C and rainfall is infrequent at best.

Travel to Winter Haven

As close as Winter Haven is to Orlando and Tampa, it would be silly to fly into anywhere else, at only 48 and 59 miles away respectively. Public transport tends to be a bit of a joke in the US, and the automobile reigns supreme, so flying and driving a hire car is really the most effective, and cheapest, option. There is an Amtrak station in Winter Haven, however, which gives you the chance to experience an authentic American train trip, but they're somewhat unreliable when it comes to timetables. Nearby Lakeland has the only Greyhound station.

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  • Showing 1-50 of 300+
Additional service fee may apply.
    Wonderful! 4.8/5
    (48 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Separate Toilet
    • Sleeps 6
    Townhome #330133vb
    48
    Viewed 35 times in the last 48 hours
      Very Good! 4.2/5
      (27 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 6
      House #292488vb
      27
      Viewed 12 times in the last 48 hours
        Excellent! 4.3/5
        (14 reviews)
        • 1 BR
        • 1 BA
        • Sleeps 6
        Condo #4105218
        14
        Viewed 8 times in the last 48 hours
          Wonderful! 4.9/5
          (27 reviews)
          avg/night
          • 5 BR
          • 5 BA
          • Sleeps 18
          House #452437vb
          27
          Viewed 37 times in the last 48 hours
            Excellent! 4.6/5
            (8 reviews)
            avg/night
            • 4 BR
            • 2 BA
            • Sleeps 8
            House #784388vb
            8
            Viewed 21 times in the last 48 hours
              Wonderful! 4.9/5
              (23 reviews)
              avg/night
              • 4 BR
              • 2 BA
              • Separate Toilets
              • Sleeps 10
              House #786284vb
              23
              Viewed 87 times in the last 48 hours
                Wonderful! 4.9/5
                (12 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                Villa #817624vb
                12
                Viewed 54 times in the last 48 hours
                  Excellent! 4.5/5
                  (10 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  Villa #792155vb
                  10
                  Viewed 27 times in the last 48 hours
                    Excellent! 4.7/5
                    (13 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Villa #8012726
                    13
                    Viewed 19 times in the last 48 hours
                      Wonderful! 4.9/5
                      (13 reviews)
                      avg/night
                      • 5 BR
                      • 4 BA
                      • Separate Toilet
                      • Sleeps 10
                      Villa #790723vb
                      13
                      Viewed 56 times in the last 48 hours
                        Wonderful! 4.8/5
                        (12 reviews)
                        avg/night
                        • 4 BR
                        • 2 BA
                        • Sleeps 8
                        Villa #647001vb
                        12
                        Viewed 23 times in the last 48 hours
                          Exceptional! 5.0/5
                          (25 reviews)
                          avg/night
                          • 5 BR
                          • 4 BA
                          • Separate Toilet
                          • Sleeps 12
                          Villa #1605033
                          25
                          Viewed 69 times in the last 48 hours
                            Wonderful! 4.8/5
                            (23 reviews)
                            avg/night
                            • 5 BR
                            • 4 BA
                            • Separate Toilet
                            • Sleeps 10
                            House #1670963
                            23
                            Viewed 32 times in the last 48 hours
                              Excellent! 4.6/5
                              (38 reviews)
                              avg/night
                              • 6 BR
                              • 4 BA
                              • Sleeps 14
                              Villa #318549vb
                              38
                              Viewed 21 times in the last 48 hours
                                Wonderful! 4.9/5
                                (19 reviews)
                                avg/night
                                • 4 BR
                                • 3 BA
                                • Sleeps 10
                                House #4084338
                                19
                                Viewed 12 times in the last 48 hours
                                  Excellent! 4.7/5
                                  (13 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Condo #1636389
                                  13
                                  Viewed 62 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (10 reviews)
                                    avg/night
                                    • 5 BR
                                    • 3 BA
                                    • Separate Toilet
                                    • Sleeps 10
                                    Villa #8172417
                                    10
                                    Viewed 11 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (5 reviews)
                                      avg/night
                                      • 6 BR
                                      • 5 BA
                                      • Sleeps 12
                                      Villa #887138vb
                                      5
                                      Viewed 73 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (28 reviews)
                                        avg/night
                                        • 5 BR
                                        • 4 BA
                                        • Separate Toilet
                                        • Sleeps 12
                                        Villa #1034900
                                        28
                                        Viewed 28 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (27 reviews)
                                          avg/night
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 10
                                          House #764845vb
                                          27
                                          Viewed 33 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (15 reviews)
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 10
                                            Villa #783837vb
                                            15
                                            Viewed 41 times in the last 48 hours
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Villa #8017261
                                              3
                                              Viewed 22 times in the last 48 hours
                                                Excellent! 4.6/5
                                                (12 reviews)
                                                avg/night
                                                • 4 BR
                                                • 3 BA
                                                • Sleeps 10
                                                Villa #1623139
                                                12
                                                Viewed 5 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (36 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 3 BA
                                                  • Sleeps 8
                                                  Villa #52814
                                                  36
                                                  Viewed 33 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (26 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Condo #614671vb
                                                    26
                                                    Viewed 23 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (18 reviews)
                                                      avg/night
                                                      • 9 BR
                                                      • 5 BA
                                                      • Sleeps 29
                                                      House #779965vb
                                                      18
                                                      Viewed 64 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (44 reviews)
                                                        avg/night
                                                        • 5 BR
                                                        • 4 BA
                                                        • Sleeps 10
                                                        Villa #1052432
                                                        44
                                                        Viewed 55 times in the last 48 hours
                                                          Excellent! 4.6/5
                                                          (19 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 3 BA
                                                          • Sleeps 10
                                                          House #689551vb
                                                          19
                                                          Viewed 45 times in the last 48 hours
                                                            Wonderful! 4.8/5
                                                            (12 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 3 BA
                                                            • Sleeps 8
                                                            Villa #1894882
                                                            12
                                                            Viewed 7 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (16 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Separate Toilets
                                                              • Sleeps 6
                                                              Townhome #3471004
                                                              16
                                                              Viewed 53 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (8 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 3 BA
                                                                • Separate Toilet
                                                                • Sleeps 8
                                                                House #6479824
                                                                8
                                                                Viewed 36 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (19 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 10
                                                                  House #8035794
                                                                  19
                                                                  Viewed 26 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (38 reviews)
                                                                    avg/night
                                                                    • 5 BR
                                                                    • 3 BA
                                                                    • Sleeps 12
                                                                    Villa #287443
                                                                    38
                                                                    Viewed 28 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (105 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      Condo #321447vb
                                                                      105
                                                                      Viewed 77 times in the last 48 hours
                                                                        Excellent! 4.6/5
                                                                        (38 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 10
                                                                        House #930518
                                                                        38
                                                                        Viewed 17 times in the last 48 hours
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          Condo #809541vb
                                                                          1
                                                                          Viewed 9 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (26 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            House #886495
                                                                            26
                                                                            Viewed 16 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (44 reviews)
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 9
                                                                              Townhome #503537vb
                                                                              44
                                                                              Viewed 29 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (23 reviews)
                                                                                avg/night
                                                                                • 5 BR
                                                                                • 5 BA
                                                                                • Sleeps 14
                                                                                House #730480
                                                                                23
                                                                                Viewed 23 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (91 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 8
                                                                                  Townhome #332416
                                                                                  91
                                                                                  Viewed 26 times in the last 48 hours
                                                                                    Excellent! 4.6/5
                                                                                    (16 reviews)
                                                                                    avg/night
                                                                                    • 6 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 12
                                                                                    House #3876839
                                                                                    16
                                                                                    Viewed 73 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (52 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Villa #17887
                                                                                      52
                                                                                      Viewed 41 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (10 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 10
                                                                                        House #891925vb
                                                                                        10
                                                                                        Viewed 71 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (15 reviews)
                                                                                          avg/night
                                                                                          • 5 BR
                                                                                          • 3 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 12
                                                                                          House #87461
                                                                                          15
                                                                                          Viewed 50 times in the last 48 hours
                                                                                            Excellent! 4.6/5
                                                                                            (14 reviews)
                                                                                            avg/night
                                                                                            • 5 BR
                                                                                            • 4 BA
                                                                                            • Separate Toilets
                                                                                            • Sleeps 12
                                                                                            House #347979
                                                                                            14
                                                                                            Viewed 49 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (25 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 8
                                                                                              Villa #412776
                                                                                              25
                                                                                              Viewed 7 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (7 reviews)
                                                                                                avg/night
                                                                                                • 6 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 12
                                                                                                House #874387vb
                                                                                                7
                                                                                                Viewed 51 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (23 reviews)
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 4 BA
                                                                                                  • Sleeps 10
                                                                                                  Villa #1101043
                                                                                                  23
                                                                                                  Viewed 25 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (32 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    Villa #1186901
                                                                                                    32
                                                                                                    Viewed 26 times in the last 48 hours
                                                                                                      Excellent! 4.7/5
                                                                                                      (14 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      Villa #628627vb
                                                                                                      14
                                                                                                      Viewed 20 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      superb Southern Dunes Condo

                                                                                                      5 of 5
                                                                                                      Superb condo, just spent 2 amazing weeks here, would defiantly recommend (especially for golfers, as clubhouse and course are excellent. Great food served by lovely people). Condo well set out with 2 bedroom 2 bathroom suites. Everything you need for a relaxing holiday, well equipped and nicely decorated and furnished. Would definitely stay again.
                                                                                                      • Review Submitted: 28-Nov-2016
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      Lovely holiday villa

                                                                                                      5 of 5
                                                                                                      Lovely spacious villa in nice safe and quiet neighbourhood. Clean and well equipped. Good sized pool which is nice and private. Kids loved the games room. Close to restaurants, shops and the parks. Would highly recommend.
                                                                                                      • Review Submitted: 11-Nov-2016
                                                                                                      • Date of Stay: Jul 2016

                                                                                                      Fab

                                                                                                      5 of 5
                                                                                                      Had a fantastic time saying at this resort what a beautiful stunning location. House very clean and everything you need was there. Wouldn't hesitate to go again just a shame my dates were already booked for next year.
                                                                                                      • Review Submitted: 11-Nov-2016
                                                                                                      • Date of Stay: Oct 2016