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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.

    Excellent! 4.3/5
    (35 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    House #292488vb
    35
    Viewed 53 times in the last 48 hours
      Wonderful! 4.8/5
      (5 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 6
      House #915394vb
      5
      Viewed 24 times in the last 48 hours
        Wonderful! 4.8/5
        (30 reviews)
        avg/night
        • 5 BR
        • 5 BA
        • Sleeps 18
        House #452437vb
        30
        Viewed 102 times in the last 48 hours
          Excellent! 4.5/5
          (10 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Separate Toilet
          • Sleeps 4
          Townhome #688860vb
          10
          Viewed 46 times in the last 48 hours
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 4
            Mobile Home #908185vb
            Viewed 8 times in the last 48 hours
              Very Good! 4.2/5
              (16 reviews)
              avg/night
              • 4 BR
              • 4 BA
              • Sleeps 12
              House #239029vb
              16
              Viewed 46 times in the last 48 hours
                Very Good! 4.2/5
                (10 reviews)
                avg/night
                • 4 BR
                • 2 BA
                • Sleeps 8
                House #784388vb
                10
                Viewed 19 times in the last 48 hours
                  Wonderful! 4.8/5
                  (13 reviews)
                  avg/night
                  • 4 BR
                  • 3 BA
                  • Sleeps 8
                  House #980140vb
                  13
                  Viewed 79 times in the last 48 hours
                    avg/night
                    • 3 BR
                    • 4 BA
                    • Sleeps 6
                    House #4178419
                    2
                    Viewed 27 times in the last 48 hours
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      House #4010682
                      Viewed 35 times in the last 48 hours
                        Exceptional! 5/5
                        (5 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        House #7020516
                        5
                        Viewed 18 times in the last 48 hours
                          Exceptional! 5/5
                          (6 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          Cottage #614884vb
                          6
                          Viewed 23 times in the last 48 hours
                            Exceptional! 5/5
                            (8 reviews)
                            avg/night
                            • 3 BR
                            • 3 BA
                            • Sleeps 10
                            House #833008vb
                            8
                            Viewed 37 times in the last 48 hours
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              Condo #280128vb
                              Viewed 30 times in the last 48 hours
                                • 2 BR
                                • 1 BA
                                • Sleeps 4
                                Recreational Vehicle #956770vb
                                2
                                Viewed 20 times in the last 48 hours
                                  Exceptional! 5/5
                                  (6 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 7
                                  House #513036vb
                                  6
                                  Viewed 17 times in the last 48 hours
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 3
                                    Cabin #868244vb
                                    2
                                    Viewed 44 times in the last 48 hours
                                      Exceptional! 5/5
                                      (5 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #3598724
                                      5
                                      Viewed 22 times in the last 48 hours
                                        Exceptional! 5/5
                                        (6 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Cabin #843594vb
                                        6
                                        Viewed 61 times in the last 48 hours
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #441073vb
                                          3
                                          Viewed 10 times in the last 48 hours
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 6
                                            House #4325842
                                            1
                                            Viewed 14 times in the last 48 hours
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 4
                                              House #4383110
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 3
                                                Mobile Home #920257vb
                                                  • 5 BR
                                                  • 3 BA
                                                  • Sleeps 10
                                                  House #714148vb
                                                  Viewed 23 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (24 reviews)
                                                    avg/night
                                                    • 9 BR
                                                    • 5 BA
                                                    • Sleeps 28
                                                    House #4172017
                                                    24
                                                    Viewed 315 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (39 reviews)
                                                      avg/night
                                                      • 4 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                      Villa #1186901
                                                      39
                                                      Viewed 49 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (12 reviews)
                                                        avg/night
                                                        • 5 BR
                                                        • 5 BA
                                                        • Sleeps 12
                                                        House #25712vb
                                                        12
                                                        Viewed 140 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (122 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 5 BA
                                                          • Sleeps 12
                                                          Villa #93899
                                                          122
                                                          Viewed 89 times in the last 48 hours
                                                            • 4 BR
                                                            • 3 BA
                                                            • Sleeps 9
                                                            #8118888
                                                            2
                                                            Viewed 57 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (14 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              House #4167364
                                                              14
                                                              Viewed 63 times in the last 48 hours
                                                                Excellent! 4.7/5
                                                                (15 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Condo #1636389
                                                                15
                                                                Viewed 26 times in the last 48 hours
                                                                  Exceptional! 5/5
                                                                  (6 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                  Villa #1873690
                                                                  6
                                                                  Viewed 80 times in the last 48 hours
                                                                    Excellent! 4.7/5
                                                                    (18 reviews)
                                                                    avg/night
                                                                    • 5 BR
                                                                    • 4 BA
                                                                    • Sleeps 12
                                                                    Villa #8127090
                                                                    18
                                                                    Viewed 62 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (31 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 4 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 12
                                                                      Villa #1034900
                                                                      31
                                                                      Viewed 73 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (18 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Villa #817624vb
                                                                        18
                                                                        Viewed 34 times in the last 48 hours
                                                                          Exceptional! 5/5
                                                                          (11 reviews)
                                                                          avg/night
                                                                          • 6 BR
                                                                          • 5 BA
                                                                          • Sleeps 12
                                                                          Villa #6577162
                                                                          11
                                                                          Viewed 57 times in the last 48 hours
                                                                            Exceptional! 5/5
                                                                            (5 reviews)
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 5 BA
                                                                            • Sleeps 11
                                                                            House #6919153
                                                                            5
                                                                            Viewed 94 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (15 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Condo #74574
                                                                              15
                                                                              Viewed 29 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (19 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 7
                                                                                House #268194
                                                                                19
                                                                                Viewed 23 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (14 reviews)
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  Villa #3850892
                                                                                  14
                                                                                  Viewed 53 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (17 reviews)
                                                                                    avg/night
                                                                                    • 5 BR
                                                                                    • 4 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 10
                                                                                    Villa #4257329
                                                                                    17
                                                                                    Viewed 40 times in the last 48 hours
                                                                                      Exceptional! 5/5
                                                                                      (22 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 10
                                                                                      Townhome #845652vb
                                                                                      22
                                                                                      Viewed 78 times in the last 48 hours
                                                                                        Wonderful! 4.8/5
                                                                                        (31 reviews)
                                                                                        avg/night
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Separate Toilets
                                                                                        • Sleeps 14
                                                                                        Villa #3561059
                                                                                        31
                                                                                        Viewed 204 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (22 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          Villa #8110519
                                                                                          22
                                                                                          Viewed 50 times in the last 48 hours
                                                                                            Excellent! 4.6/5
                                                                                            (10 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8
                                                                                            Villa #6772792
                                                                                            10
                                                                                            Viewed 83 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (30 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              Villa #69391
                                                                                              30
                                                                                              Viewed 54 times in the last 48 hours
                                                                                                Exceptional! 5/5
                                                                                                (11 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Condo #445097vb
                                                                                                11
                                                                                                Viewed 30 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (28 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  Villa #3665439
                                                                                                  28
                                                                                                  Viewed 30 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (13 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    Villa #8007005
                                                                                                    13
                                                                                                    Viewed 31 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (26 reviews)
                                                                                                      avg/night
                                                                                                      • 5 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 10
                                                                                                      Villa #3853609
                                                                                                      26
                                                                                                      Viewed 24 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Winter Haven Holiday Homes & Villas (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Wow!

                                                                                                      5 of 5
                                                                                                      After renting for 20 years in Orlando this is the nicest house we have ever stayed in! The house is perfect, the clubhouse is amazing and the house is a great location. Can't wait to return again!
                                                                                                      • Review Submitted: Apr 09, 2017
                                                                                                      • Date of Stay: Mar 2017

                                                                                                      Great place to stay

                                                                                                      5 of 5
                                                                                                      Stayed here for 10 days and loved every minute of it. The villa is so comfortable, felt at home from the minute we stepped through the door with it's modern decor, good sized pool, plenty of space and very comfy beds . This was our first time staying in the Davenport area and loved it. Would recommend this villa to anyone and Steve was so friendly sending us restaurant recommendations and details of nearby shops. Great place to stay.
                                                                                                      • Review Submitted: Jul 20, 2009
                                                                                                      • Date of Stay: Jun 2009