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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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    Excellent! 4.3/5
    (32 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    House #292488vb
    32
    Viewed 43 times in the last 48 hours
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      • 3 BR
      • 2 BA
      • Sleeps 6
      House #915394vb
      3
      Viewed 24 times in the last 48 hours
        Wonderful! 4.9/5
        (28 reviews)
        avg/night
        • 5 BR
        • 5 BA
        • Sleeps 18
        House #452437vb
        28
        Viewed 70 times in the last 48 hours
          Excellent! 4.4/5
          (9 reviews)
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          • 2 BR
          • 2 BA
          • Separate Toilet
          • Sleeps 4
          Townhome #688860vb
          9
          Viewed 37 times in the last 48 hours
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            • 2 BR
            • 2 BA
            • Sleeps 4
            Mobile Home #908185vb
            Viewed 7 times in the last 48 hours
              Excellent! 4.4/5
              (15 reviews)
              avg/night
              • 4 BR
              • 4 BA
              • Sleeps 12
              House #239029vb
              15
              Viewed 56 times in the last 48 hours
                Very Good! 4.2/5
                (10 reviews)
                avg/night
                • 4 BR
                • 2 BA
                • Sleeps 8
                House #784388vb
                10
                Viewed 9 times in the last 48 hours
                  Wonderful! 4.8/5
                  (9 reviews)
                  avg/night
                  • 4 BR
                  • 3 BA
                  • Sleeps 8
                  House #980140vb
                  9
                  Viewed 36 times in the last 48 hours
                    Exceptional! 5/5
                    (6 reviews)
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                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    Cottage #614884vb
                    6
                    Viewed 18 times in the last 48 hours
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                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      House #4010682
                      Viewed 27 times in the last 48 hours
                        Exceptional! 5/5
                        (4 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        House #7020516
                        4
                        Viewed 22 times in the last 48 hours
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                          • 3 BR
                          • 4 BA
                          • Sleeps 6
                          House #4178419
                          2
                          Viewed 28 times in the last 48 hours
                            Exceptional! 5/5
                            (5 reviews)
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                            • 3 BR
                            • 3 BA
                            • Sleeps 10
                            House #833008vb
                            5
                            Viewed 20 times in the last 48 hours
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                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              Condo #280128vb
                              Viewed 28 times in the last 48 hours
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                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                House #3836505
                                1
                                Viewed 17 times in the last 48 hours
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Recreational Vehicle #956770vb
                                  1
                                  Viewed 34 times in the last 48 hours
                                    Exceptional! 5/5
                                    (6 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 7
                                    House #513036vb
                                    6
                                    Viewed 7 times in the last 48 hours
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                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      Cabin #868244vb
                                      2
                                      Viewed 32 times in the last 48 hours
                                        Exceptional! 5/5
                                        (5 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 8
                                        House #3598724
                                        5
                                        Viewed 28 times in the last 48 hours
                                          Exceptional! 5/5
                                          (5 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Cabin #843594vb
                                          5
                                          Viewed 58 times in the last 48 hours
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                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 6
                                            House #441073vb
                                            2
                                            Viewed 15 times in the last 48 hours
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                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 6
                                              House #4241926
                                              2
                                              Viewed 10 times in the last 48 hours
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 6
                                                House #967877vb
                                                2
                                                Viewed 13 times in the last 48 hours
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  House #4325842
                                                  1
                                                  Viewed 19 times in the last 48 hours
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 3
                                                    Mobile Home #920257vb
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                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Bungalow #4028926
                                                      Viewed 21 times in the last 48 hours
                                                        • 5 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        House #714148vb
                                                        Viewed 28 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (21 reviews)
                                                          avg/night
                                                          • 9 BR
                                                          • 5 BA
                                                          • Sleeps 28
                                                          House #4172017
                                                          21
                                                          Viewed 291 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (122 reviews)
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                                                            • 5 BR
                                                            • 5 BA
                                                            • Sleeps 12
                                                            Villa #93899
                                                            122
                                                            Viewed 157 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (16 reviews)
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                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Villa #817624vb
                                                              16
                                                              Viewed 90 times in the last 48 hours
                                                                • 6 BR
                                                                • 6 BA
                                                                • Sleeps 14
                                                                House #758691vb
                                                                1
                                                                Viewed 73 times in the last 48 hours
                                                                  Excellent! 4.7/5
                                                                  (13 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  Condo #1636389
                                                                  13
                                                                  Viewed 47 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (13 reviews)
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                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    House #4167364
                                                                    13
                                                                    Viewed 69 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 9
                                                                      #8118888
                                                                      1
                                                                      Viewed 56 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (39 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        Villa #1186901
                                                                        39
                                                                        Viewed 60 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (18 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 7
                                                                          House #268194
                                                                          18
                                                                          Viewed 50 times in the last 48 hours
                                                                            Exceptional! 5/5
                                                                            (6 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            Villa #1873690
                                                                            6
                                                                            Viewed 55 times in the last 48 hours
                                                                              Exceptional! 5/5
                                                                              (9 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 5 BA
                                                                              • Sleeps 12
                                                                              Villa #6577162
                                                                              9
                                                                              Viewed 82 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (30 reviews)
                                                                                avg/night
                                                                                • 6 BR
                                                                                • 4 BA
                                                                                • Separate Toilets
                                                                                • Sleeps 14
                                                                                Villa #3561059
                                                                                30
                                                                                Viewed 292 times in the last 48 hours
                                                                                  Exceptional! 5/5
                                                                                  (11 reviews)
                                                                                  avg/night
                                                                                  • 5 BR
                                                                                  • 5 BA
                                                                                  • Sleeps 12
                                                                                  House #25712vb
                                                                                  11
                                                                                  Viewed 85 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (31 reviews)
                                                                                    avg/night
                                                                                    • 5 BR
                                                                                    • 4 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 12
                                                                                    Villa #1034900
                                                                                    31
                                                                                    Viewed 61 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (12 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      Villa #8007005
                                                                                      12
                                                                                      Viewed 56 times in the last 48 hours
                                                                                        Excellent! 4.5/5
                                                                                        (24 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        House #603330vb
                                                                                        24
                                                                                        Viewed 96 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (20 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          Villa #8110519
                                                                                          20
                                                                                          Viewed 42 times in the last 48 hours
                                                                                            Exceptional! 5/5
                                                                                            (11 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                            Condo #445097vb
                                                                                            11
                                                                                            Viewed 30 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (39 reviews)
                                                                                              avg/night
                                                                                              • 6 BR
                                                                                              • 4 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 12
                                                                                              House #586096vb
                                                                                              39
                                                                                              Viewed 56 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (27 reviews)
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 10
                                                                                                Villa #1101043
                                                                                                27
                                                                                                Viewed 45 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (15 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Condo #74574
                                                                                                  15
                                                                                                  Viewed 53 times in the last 48 hours
                                                                                                    Exceptional! 5/5
                                                                                                    (18 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    Townhome #845652vb
                                                                                                    18
                                                                                                    Viewed 408 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (4 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #626324vb
                                                                                                      4
                                                                                                      Viewed 91 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Winter Haven Holiday Homes & Villas (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

                                                                                                      Brilliant Base

                                                                                                      5 of 5
                                                                                                      The location was great, close enough to all the attractions and amenities but secluded enough to be quiet and safe. The house was a perfect size for the 4 of us, and the pool was a safe size and depth for the kids. The house was really well equipped with everything you'd need for the stay, apart from food etc we didn't need to purchase anything extra as we have had to with other properties. The house was immaculate on arrival. I would heartily recommend a stay at this house for families visiting orlando, we will certainly book here if we come to Florida again.
                                                                                                      • Review Submitted: 14-Nov-2016
                                                                                                      • Date of Stay: Oct 2016

                                                                                                      Great Family Villa

                                                                                                      5 of 5
                                                                                                      We holidayed at this villa for just shy of three weeks - the villa was fantastic with everything that you would need (three out of the four bedrooms had double beds!) and a great pool area. The location of the villa made for easy access to the I-4, the Disney parks and a range of shops and eateries. Booking the villa was an easy and smooth process with Shelly available at all stages. We would love to come back and stay here if we were lucky enough to visit Florida again. Thanks Shelly.
                                                                                                      • Review Submitted: 19-Jul-2016
                                                                                                      • Date of Stay: Jun 2016