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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 28 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 15 times in the last 48 hours
        Wonderful! 4.9/5
        (27 reviews)
        avg/night
        • 5 BR
        • 5 BA
        • Sleeps 18
        House #452437vb
        27
        Viewed 35 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
            • 2 BR
            • 1 BA
            • Sleeps 4
            Recreational Vehicle #956770vb
            Viewed 32 times in the last 48 hours
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 4
              House #318259vb
              Viewed 9 times in the last 48 hours
                Wonderful! 4.9/5
                (12 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                Villa #817624vb
                12
                Viewed 40 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 36 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 30 times in the last 48 hours
                      Wonderful! 4.8/5
                      (13 reviews)
                      avg/night
                      • 4 BR
                      • 2 BA
                      • Sleeps 8
                      Villa #647001vb
                      13
                      Viewed 16 times in the last 48 hours
                        Excellent! 4.7/5
                        (13 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 6
                        Condo #1636389
                        13
                        Viewed 43 times in the last 48 hours
                          Wonderful! 4.9/5
                          (14 reviews)
                          avg/night
                          • 4 BR
                          • 2 BA
                          • Sleeps 10
                          Villa #8120122
                          14
                          Viewed 9 times in the last 48 hours
                            Exceptional! 5.0/5
                            (26 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            Condo #614671vb
                            26
                            Viewed 11 times in the last 48 hours
                              Wonderful! 4.8/5
                              (12 reviews)
                              avg/night
                              • 4 BR
                              • 3 BA
                              • Sleeps 8
                              Villa #1894882
                              12
                              Viewed 21 times in the last 48 hours
                                Wonderful! 4.8/5
                                (10 reviews)
                                avg/night
                                • 5 BR
                                • 4 BA
                                • Sleeps 12
                                Villa #8127090
                                10
                                Viewed 21 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (18 reviews)
                                  avg/night
                                  • 9 BR
                                  • 5 BA
                                  • Sleeps 29
                                  House #779965vb
                                  18
                                  Viewed 37 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (32 reviews)
                                    avg/night
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 8
                                    Villa #1186901
                                    32
                                    Viewed 18 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (5 reviews)
                                      avg/night
                                      • 4 BR
                                      • 3 BA
                                      • Sleeps 8
                                      Villa #402663
                                      5
                                      Viewed 46 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (23 reviews)
                                        avg/night
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 10
                                        Villa #1101043
                                        23
                                        Viewed 30 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (10 reviews)
                                          avg/night
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Villa #782848vb
                                          10
                                          Viewed 11 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (55 reviews)
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            Villa #601052
                                            55
                                            Viewed 13 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (26 reviews)
                                              avg/night
                                              • 6 BR
                                              • 4 BA
                                              • Sleeps 12
                                              Villa #3951500
                                              26
                                              Viewed 12 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (10 reviews)
                                                avg/night
                                                • 4 BR
                                                • 3 BA
                                                • Sleeps 8
                                                Villa #709251vb
                                                10
                                                Viewed 25 times in the last 48 hours
                                                  • 5 BR
                                                  • 4 BA
                                                  • Sleeps 10
                                                  Villa #3853609
                                                  15
                                                    Wonderful! 4.9/5
                                                    (17 reviews)
                                                    avg/night
                                                    • 5 BR
                                                    • 4 BA
                                                    • Sleeps 11
                                                    Villa #8124563
                                                    17
                                                    Viewed 11 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (9 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Villa #8170587
                                                      9
                                                      Viewed 5 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (17 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 1 BA
                                                        • Separate Toilets
                                                        • Sleeps 8
                                                        Villa #8162356
                                                        17
                                                        Viewed 8 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 6 BR
                                                          • 6 BA
                                                          • Sleeps 12
                                                          Villa #4090411
                                                          8
                                                          Viewed 25 times in the last 48 hours
                                                            Excellent! 4.6/5
                                                            (14 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            Condo #74574
                                                            14
                                                            Viewed 32 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (11 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #752892vb
                                                              11
                                                              Viewed 8 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (19 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 3 BA
                                                                • Sleeps 8
                                                                Villa #755129vb
                                                                19
                                                                Viewed 13 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (13 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 4 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 10
                                                                  Villa #1861429
                                                                  13
                                                                  Viewed 11 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (10 reviews)
                                                                    avg/night
                                                                    • 6 BR
                                                                    • 4 BA
                                                                    • Sleeps 12
                                                                    Villa #821343
                                                                    10
                                                                    Viewed 30 times in the last 48 hours
                                                                      Excellent! 4.4/5
                                                                      (7 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 4 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 12
                                                                      Villa #493786
                                                                      7
                                                                      Viewed 12 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (10 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 10
                                                                        Townhome #845652vb
                                                                        10
                                                                        Viewed 461 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (9 reviews)
                                                                          avg/night
                                                                          • 5 BR
                                                                          • 5 BA
                                                                          • Sleeps 12
                                                                          House #25712vb
                                                                          9
                                                                          Viewed 39 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (11 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            House #4023493
                                                                            11
                                                                            Viewed 26 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (22 reviews)
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • Sleeps 11
                                                                              House #751693vb
                                                                              22
                                                                              Viewed 20 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (11 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                Villa #8015346
                                                                                11
                                                                                Viewed 9 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (5 reviews)
                                                                                  avg/night
                                                                                  • 5 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 12
                                                                                  Villa #1907155
                                                                                  5
                                                                                  Viewed 32 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (60 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 9
                                                                                    House #390610vb
                                                                                    60
                                                                                    Viewed 9 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      Villa #3850892
                                                                                      9
                                                                                      Viewed 21 times in the last 48 hours
                                                                                        Very Good! 4.0/5
                                                                                        (5 reviews)
                                                                                        avg/night
                                                                                        • 5 BR
                                                                                        • 4 BA
                                                                                        • Separate Toilet
                                                                                        • Sleeps 12
                                                                                        Villa #3679497
                                                                                        5
                                                                                        Viewed 16 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (32 reviews)
                                                                                          avg/night
                                                                                          • 6 BR
                                                                                          • 4 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 12
                                                                                          House #586096vb
                                                                                          32
                                                                                          Viewed 17 times in the last 48 hours
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8
                                                                                            Villa #868546
                                                                                            3
                                                                                            Viewed 27 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (16 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 10
                                                                                              Villa #3530038
                                                                                              16
                                                                                              Viewed 15 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (24 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                Villa #1405658
                                                                                                24
                                                                                                Viewed 8 times in the last 48 hours
                                                                                                  • 6 BR
                                                                                                  • 5 BA
                                                                                                  • Separate Toilets
                                                                                                  • Sleeps 12
                                                                                                  Villa #1961432
                                                                                                  2
                                                                                                  Viewed 7 times in the last 48 hours
                                                                                                    Excellent! 4.6/5
                                                                                                    (7 reviews)
                                                                                                    avg/night
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 10
                                                                                                    Villa #1938475
                                                                                                    7
                                                                                                    Viewed 15 times in the last 48 hours
                                                                                                      • 3 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 6
                                                                                                      Villa #1444156
                                                                                                      3
                                                                                                      Viewed 13 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

                                                                                                      Fantastic Holiday

                                                                                                      5 of 5
                                                                                                      The Villa exceeded our expectations and the description was exactly as advertised. Rooms were very spacious and having 2 ensuites and 2 bathrooms was fantastic with 5 women and 2 men. We had a few minor problems but after contacting the owner these were fixed the next day. I would state that the owners were easy to deal with and their recommendations of restaurants was very helpful. Our favourites were Olive garden and Chilli's and the Cheesecake Factory in Millennium Mall was great as usual. Universal 30 minutes, Disney 15 -20 minutes and Busch gardens around 1 hour. We enjoyed relaxing around the pool in the evenings and the girls thoroughly enjoyed the amazing TV room. Small supermarket 5 minutes and large one 10 minutes drive. Highly recommend this Villa for being in a very quiet gated community. Frank Smith
                                                                                                      • Review Submitted: 29-Nov-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