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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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  • 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 31 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 10 times in the last 48 hours
        Wonderful! 4.9/5
        (27 reviews)
        avg/night
        • 5 BR
        • 5 BA
        • Sleeps 18
        House #452437vb
        27
        Viewed 41 times in the last 48 hours
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 4
          Mobile Home #908185vb
          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 11 times in the last 48 hours
              • 3 BR
              • 3 BA
              • Sleeps 10
              House #833008vb
              4
              Viewed 8 times in the last 48 hours
                Exceptional! 5.0/5
                (8 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                House #3842641
                8
                Viewed 12 times in the last 48 hours
                  Exceptional! 5.0/5
                  (5 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 2
                  Cottage #614884vb
                  5
                  Viewed 15 times in the last 48 hours
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    House #7020516
                    3
                    Viewed 5 times in the last 48 hours
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      House #915394vb
                      Viewed 9 times in the last 48 hours
                        avg/night
                        • 3 BR
                        • 4 BA
                        • Sleeps 6
                        House #4178419
                        Viewed 22 times in the last 48 hours
                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                          Recreational Vehicle #956770vb
                          Viewed 36 times in the last 48 hours
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Cabin #843594vb
                            3
                            Viewed 40 times in the last 48 hours
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 3
                              Cabin #868244vb
                              2 Reviews
                              Viewed 67 times in the last 48 hours
                                • 3 BR
                                • 3 BA
                                • Sleeps 6
                                House #4241926
                                1 Review
                                Viewed 7 times in the last 48 hours
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 8
                                  House #3598724
                                  3
                                  Viewed 10 times in the last 48 hours
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    House #4325842
                                    Viewed 7 times in the last 48 hours
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 4
                                      House #956350vb
                                      Viewed 11 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 7 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (12 reviews)
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 6
                                            Villa #817624vb
                                            12
                                            Viewed 39 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 29 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 37 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (9 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 3 BA
                                                  • Sleeps 10
                                                  Villa #1942578
                                                  9
                                                  Viewed 13 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (13 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    Villa #647001vb
                                                    13
                                                    Viewed 15 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (13 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Condo #1636389
                                                      13
                                                      Viewed 36 times in the last 48 hours
                                                        Wonderful! 4.8/5
                                                        (28 reviews)
                                                        avg/night
                                                        • 5 BR
                                                        • 4 BA
                                                        • Separate Toilet
                                                        • Sleeps 12
                                                        Villa #1034900
                                                        28
                                                        Viewed 11 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (14 reviews)
                                                          avg/night
                                                          • 4 BR
                                                          • 2 BA
                                                          • Sleeps 10
                                                          Villa #8120122
                                                          14
                                                          Viewed 10 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (26 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Condo #614671vb
                                                            26
                                                            Viewed 15 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (10 reviews)
                                                              avg/night
                                                              • 5 BR
                                                              • 4 BA
                                                              • Sleeps 12
                                                              Villa #8127090
                                                              10
                                                              Viewed 18 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (18 reviews)
                                                                avg/night
                                                                • 9 BR
                                                                • 5 BA
                                                                • Sleeps 29
                                                                House #779965vb
                                                                18
                                                                Viewed 28 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
                                                                    (12 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                    Villa #1894882
                                                                    12
                                                                    Viewed 13 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (5 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 8
                                                                      Villa #402663
                                                                      5
                                                                      Viewed 42 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (23 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 4 BA
                                                                        • Sleeps 10
                                                                        Villa #1101043
                                                                        23
                                                                        Viewed 32 times in the last 48 hours
                                                                          Wonderful! 4.8/5
                                                                          (10 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Villa #782848vb
                                                                          10
                                                                          Viewed 13 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (55 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            Villa #601052
                                                                            55
                                                                            Viewed 14 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (26 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 4 BA
                                                                              • Sleeps 12
                                                                              Villa #3951500
                                                                              26
                                                                              Viewed 18 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (10 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                Villa #709251vb
                                                                                10
                                                                                Viewed 22 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (15 reviews)
                                                                                  avg/night
                                                                                  • 5 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 10
                                                                                  Villa #3853609
                                                                                  15
                                                                                  Viewed 6 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (17 reviews)
                                                                                    avg/night
                                                                                    • 5 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 11
                                                                                    Villa #8124563
                                                                                    17
                                                                                    Viewed 8 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Villa #8170587
                                                                                      9
                                                                                        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 17 times in the last 48 hours
                                                                                            Excellent! 4.6/5
                                                                                            (14 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            Condo #74574
                                                                                            14
                                                                                            Viewed 37 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (11 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              Condo #752892vb
                                                                                              11
                                                                                              Viewed 7 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 14 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (10 reviews)
                                                                                                  avg/night
                                                                                                  • 6 BR
                                                                                                  • 4 BA
                                                                                                  • Sleeps 12
                                                                                                  Villa #821343
                                                                                                  10
                                                                                                  Viewed 20 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 13 times in the last 48 hours
                                                                                                      Excellent! 4.5/5
                                                                                                      (25 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Villa #3510539
                                                                                                      25
                                                                                                      Viewed 15 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      superb Southern Dunes Condo

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

                                                                                                      Great place to stay!

                                                                                                      5 of 5
                                                                                                      In quiet, beautifully maintained area. Villa and pool exactly as described, if not better. Clean, bright, spacious and well-equipped. Perfect for relaxing after outings to nearby theme parks and restaurants. Owner very helpful. Won't hesitate to recommend to friends and family.
                                                                                                      • Review Submitted: 21-Nov-2016
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      We had a fantastic stay at this beautiful villa in The Haven.

                                                                                                      5 of 5
                                                                                                      We had a really nice stay at this beautiful villa. It was very large but cosy. The villa was very clean and tidy when we arrived. It had everything we needed and the kitchen we so clean and had everything needed for dining in. There was lots of information in the villa if we needed to contact anyone and info about places near by from restaurants and supermarkets. The management company were fantastic as we had to call them regarding a query we had regarding to a battery on a smoke alarm, they had people round sorting the problem out within hours. The management company guy also come over the day after to make sure everything ok and checking to make sure the villa was ok, he was ordering something new for the games room. Our daughter was unwell during our stay and we had to use the emergency medical centre whilst there and all the details were in the folder they provided. I emailed the owner near to the end of our holiday to explain we missed almost four days of our holiday and he aloud us to stay as long as we wanted on the day of our departure. This was such a lovely kind thing we were very greatfull as it gave us more time before we got our flights in the evening. Overall the villa,management company and the owner were fantastic and I would recommend this villa to anyone especially to larger family's as its huge. There was only three of us but enjoyed the villa even though we didn't need a villa this large. A really beautiful place to stay. Kindest regards Natalie
                                                                                                      • Review Submitted: 12-Nov-2016
                                                                                                      • Date of Stay: Oct 2016