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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 18 times in the last 48 hours
      Excellent! 4.6/5
      (8 reviews)
      avg/night
      • 4 BR
      • 2 BA
      • Sleeps 8
      House #784388vb
      8
      Viewed 9 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 7 times in the last 48 hours
          Wonderful! 4.9/5
          (27 reviews)
          avg/night
          • 5 BR
          • 5 BA
          • Sleeps 18
          House #452437vb
          27
          Viewed 21 times in the last 48 hours
            Exceptional! 5.0/5
            (5 reviews)
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 2
            Cottage #614884vb
            5
            Viewed 7 times in the last 48 hours
              • 3 BR
              • 3 BA
              • Sleeps 10
              House #833008vb
              4
              Viewed 5 times in the last 48 hours
                Excellent! 4.6/5
                (18 reviews)
                avg/night
                • 4 BR
                • 4 BA
                • Sleeps 12
                House #239029vb
                18
                Viewed 8 times in the last 48 hours
                  • 2 BR
                  • 2 BA
                  • Sleeps 8
                  House #3598724
                  3
                    avg/night
                    • 3 BR
                    • 3 BA
                    • Sleeps 6
                    House #4241926
                    1
                    Viewed 10 times in the last 48 hours
                      • 2 BR
                      • 1 BA
                      • Sleeps 4
                      Recreational Vehicle #956770vb
                      Viewed 22 times in the last 48 hours
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        House #915394vb
                        Viewed 6 times in the last 48 hours
                          Exceptional! 5.0/5
                          (8 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          House #3842641
                          8
                          Viewed 22 times in the last 48 hours
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            House #7020516
                            3
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 3
                              Cabin #868244vb
                              2
                              Viewed 28 times in the last 48 hours
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                House #4325842
                                Viewed 6 times in the last 48 hours
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Cabin #843594vb
                                  3
                                  Viewed 8 times in the last 48 hours
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 4
                                    Mobile Home #908185vb
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 4
                                      House #956350vb
                                      Viewed 6 times in the last 48 hours
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 3
                                        Mobile Home #920257vb
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                          House #318259vb
                                          Viewed 10 times in the last 48 hours
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 6
                                            House #870635vb
                                            3
                                            Viewed 32 times in the last 48 hours
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 9
                                              House #917111vb
                                              2
                                              Viewed 22 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (11 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                House #4023493
                                                11
                                                Viewed 18 times in the last 48 hours
                                                  Excellent! 4.7/5
                                                  (13 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Condo #1636389
                                                  13
                                                  Viewed 33 times in the last 48 hours
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Villa #416935
                                                    4
                                                    Viewed 10 times in the last 48 hours
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Villa #917246vb
                                                      1
                                                      Viewed 13 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (10 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        Villa #709251vb
                                                        10
                                                        Viewed 6 times in the last 48 hours
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          House #848669vb
                                                          1
                                                            Wonderful! 4.8/5
                                                            (23 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Villa #416941
                                                            23
                                                              Wonderful! 4.9/5
                                                              (20 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              Villa #8077992
                                                              20
                                                              Viewed 6 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (6 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                House #499807vb
                                                                6
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 7
                                                                  Bungalow #496744vb
                                                                  32
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                    Villa #6882070
                                                                    Viewed 8 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (12 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      Villa #817624vb
                                                                      12
                                                                      Viewed 38 times in the last 48 hours
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        Villa #4006182
                                                                        10
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          Villa #2395
                                                                          9
                                                                            Wonderful! 4.9/5
                                                                            (30 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            Villa #385863vb
                                                                            30
                                                                            Viewed 5 times in the last 48 hours
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Villa #476778vb
                                                                              37
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                Villa #688250vb
                                                                                1
                                                                                  Wonderful! 4.8/5
                                                                                  (28 reviews)
                                                                                  avg/night
                                                                                  • 6 BR
                                                                                  • 3 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 12
                                                                                  Villa #820475
                                                                                  28
                                                                                  Viewed 9 times in the last 48 hours
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    Villa #6109631
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                      Villa #973885
                                                                                      11
                                                                                        Wonderful! 4.9/5
                                                                                        (25 reviews)
                                                                                        avg/night
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 10
                                                                                        Villa #937954
                                                                                        25
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 8
                                                                                          Villa #412518vb
                                                                                          8
                                                                                            Wonderful! 4.9/5
                                                                                            (43 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            Villa #403940
                                                                                            43
                                                                                              Exceptional! 5.0/5
                                                                                              (8 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              Villa #78881
                                                                                              8
                                                                                              Viewed 20 times in the last 48 hours
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                Villa #8015346
                                                                                                11
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 12
                                                                                                  Villa #4247991
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    Villa #610820vb
                                                                                                    2
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 9
                                                                                                      #8118888
                                                                                                      Viewed 8 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Relaxing Villa

                                                                                                      4 of 5
                                                                                                      We stayed here for 18 nights in total after being on an 8 day Caribbean cruise in November . Our first impression when we arrived was villa looked small until we opened the door--what a very pleasant surprise . Villa was very spacious & roomy. It had a nice homely feel to it. Everything one needed in the kitchen was there to hand.Great space in both master bedroom & other double room. We liked the idea of two living room areas supplied with a television in each- very suitable for two families. We loved the pool area, even though pool was on the small side it was ample for our party of four. It was a very private area with nobody looking in & of course the hot tub was a huge bonus( we loved it for relaxing). I must say that any problems we had were attended to promptly by the management company & sorted without any issue.We found shops like Walmart & Target very accessible & reasonably close by. We found the website for the villa really really good with everything in it one needed to know. Also very useful & well documented folders in the villa were well thought out. We would have no hesitation in recommending the villa to guests of all ages. We would love to stay there again. G& C McCoy
                                                                                                      • Review Submitted: 06-Dec-2016
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      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

                                                                                                      Very clean and very well organised property. Hot tub amazing.

                                                                                                      5 of 5
                                                                                                      On first appearances the house looked perfect and nothing changed over the duration of our stay. This is our fourth villa holiday in Florida and this villa was the best presented so far. Walmart at the end of the community was so easy to get to and security were always polite and helpful. Would not hesitate to book this villa again.
                                                                                                      • Review Submitted: 28-Oct-2016
                                                                                                      • Date of Stay: Oct 2016