Family Friendly Holidays in Isle of Wight - Holiday Lettings

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Filters applied: Under 5s

1,797 family friendly properties

(27) Excellent 

    31

    Holiday cottage in Wootton

    Isle of Wight / Wootton

    2 4 min stay varies

    • 2 bedrooms
    • sleeps 4
    • min stay varies
    • Beach / lakeside relaxation
    • Nearest beach 1 km
    • Child friendly
    “Perfect place to relax.” Well set out on one floor, with plenty of room to chill out. We had two small dogs with us that were able to explore the garden without any worry. Although the weather wasn't very kind to us our weeks stay was most enjoyable.

    from £140 / night

    £660 - £1,485 / week

    Book View

    Responds fast!
    avg. 3 hours 25 minutes

    from £140 / night

    (41) Excellent 

      18

      Sandown holiday apartment rental

      Isle of Wight / Sandown

      2 4 min stay varies

      • 2 bedrooms
      • sleeps 4
      • min stay varies
      • Beach / lakeside relaxation
      • Nearest beach 0.5 km
      • Child friendly

      from £70 / night

      £350 - £850 / week

      Book View

      Responds fast!
      avg. 1 hour 2 minutes

      from £70 / night

      (33) Excellent 

        43

        Holiday home in Ventnor

        Isle of Wight / Ventnor

        3 7 min stay varies

        • 3 bedrooms
        • sleeps 7
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 0.3 km
        • Child friendly
        “Lovely homely house, great location” Lovely spacious comfy house. Went with a mixed family group teenagers and toddlers and the house accomodated us all perfectly, we even took the dog ! House very clean and well presented with all the bits and bobs you need. House has a lovely safe garden with great views for an evening glass of wine or two !First trip to Isle of Wright and we loved it, Location was great , we never needed to get in the car. Definetely can recomend the Perch, we will go again.

        from £150 / night

        £850 - £995 / week

        Enquire View

        from £150 / night

        (29) Excellent 

          33

          Holiday home with golf nearby in Seaview

          Isle of Wight / Seaview

          3 7 min stay varies

          • 3 bedrooms
          • sleeps 7
          • min stay varies
          • Beach / lakeside relaxation
          • Child friendly
          • Private garden

          from £121 / night

          £729 - £1,374 / week

          Book View

          Responds fast!
          avg. 2 hours 8 minutes

          from £121 / night

          (19) Very Good 

          Certificate of Excellence

            21

            Apartment rental in Totland

            Totland Bay / Totland Bay

            3 6 min stay varies

            • 3 bedrooms
            • sleeps 6
            • min stay varies
            • Beach / lakeside relaxation
            • Nearest beach 0 km
            • Child friendly

            Certificate of Excellence

            from £201 / night

            £831 - £1,712 / week

            Book View

            Responds fast!
            avg. 1 hour 37 minutes

            from £201 / night

              8

              Apartment rental in Ryde

              Isle of Wight / Ryde

              1 4 min stay varies

              • 1 bedroom
              • sleeps 4
              • min stay varies
              • Nearest beach 0.1 km
              • Child friendly
              • Car not necessary

              from £75 / night

              £487 - £607 / week

              Book View

              Responds fast!
              avg. 1 hour 58 minutes

              from £75 / night

              (5) Excellent 

                36

                East Cowes holiday home rental

                Isle of Wight / East Cowes

                3 6 min stay varies

                • 3 bedrooms
                • sleeps 6
                • min stay varies
                • Nearest beach 0.5 km
                • Child friendly
                • Car not necessary

                from £155 / night

                £2,290 / week

                Book View

                Responds fast!
                avg. 7 minutes

                from £155 / night

                (54) Excellent 

                Certificate of Excellence

                  15

                  St Lawrence, Ventnor holiday apartment let

                  Ventnor / St Lawrence, Ventnor

                  2 4 min stay varies

                  • 2 bedrooms
                  • sleeps 4
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 2 km
                  • Child friendly
                  “Fantastic accommodation - great location.” Stayed in Flat 1 for a week with partner and 11 year old. Plenty of space. Nice and clean. The view from living room and main bedroom was fantastic. We spent many hours just looking at the boats sailing past! Garden is nice and pleasant to sit in or play games, or enjoy a drink after a day out exploring the Island. Great value for money compared to other accommodation we looked at. Would definitely stay here again should we visit IOW.

                  Certificate of Excellence

                  from £58 / night

                  £275 - £844 / week

                  Book View

                  from £58 / night

                  (30) Very Good 

                    12

                    Seaview holiday cottage rental

                    Isle of Wight / Seaview

                    2 4 7 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 7 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 0.5 km
                    • Child friendly

                    from £131 / night

                    £915 / week

                    Book View

                    from £131 / night

                    (2) Excellent 

                      14

                      Ventnor holiday lodge rental

                      Isle of Wight / Ventnor

                      2 4 min stay varies

                      • 2 bedrooms
                      • sleeps 4
                      • min stay varies
                      • Nearest beach 3 km
                      • Child friendly
                      • Pet friendly

                      from £76 / night

                      £479 - £1,144 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 9 minutes

                      from £76 / night

                        9

                        Holiday cottage in Apse Heath

                        Isle of Wight / Apse Heath

                        2 4 7 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 7 nights min
                        • Child friendly
                        • Pet friendly

                        from £68 / night

                        £479 - £1,347 / week

                        Enquire View

                        from £68 / night

                        (4) Excellent 

                          16

                          Holiday cottage in Seaview

                          Isle of Wight / Seaview

                          3 6 3 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 3 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 0.5 km
                          • Child friendly

                          from £166 / night

                          £1,163 / week

                          Book View

                          from £166 / night

                            19

                            Merstone holiday cottage rental

                            Isle of Wight / Merstone

                            1 2 7 nights min

                            • 1 bedroom
                            • sleeps 2
                            • 7 nights min
                            • Child friendly

                            from £52 / night

                            £365 - £767 / week

                            Enquire View

                            from £52 / night

                            (38) Excellent 

                            Certificate of Excellence

                              29

                              Apartment rental in Shanklin

                              Isle of Wight / Shanklin

                              2 4 min stay varies

                              • 2 bedrooms
                              • sleeps 4
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Child friendly
                              • Car not necessary
                              “Seaside View Shanklin Isle of Wight” It's exactly as advertised a View of the Seaside, an EXCELLENT apartment to stay at couldn't be any closer to the beach, with nice places to eat and drink along the esplanade, facilities at the Seaside View are spot on & would have no hesitation at all going back there.

                              Certificate of Excellence

                              from £99 / night

                              £436 - £687 / week

                              Book View

                              from £99 / night

                              (24) Excellent 

                                10

                                Holiday cottage accommodation

                                Isle of Wight / Bembridge

                                4 8 7 nights min

                                • 4 bedrooms
                                • sleeps 8
                                • 7 nights min
                                • Beach / lakeside relaxation
                                • Child friendly
                                • Car not necessary
                                “Lovely Cottage” We stayed here for a week over the Easter break. The cottage is in an ideal location, very comfortable and well equipped. A short walk down the lane brings you to the beach where there is the lifeboat station and café. The beach has some sandy areas but mainly rocks and pebbles, very interesting beach, lovely to walk along. The cottage has a beach hut on the front which is equipped with deck chairs etc. The cottage is also in easy walking distance of the shops and pubs. We would recommend ‘The Crab and Lobster Inn’ which is very friendly and with very good food.

                                from £72 / night

                                £500 - £920 / week

                                Enquire View

                                from £72 / night

                                (3) Excellent 

                                  7

                                  Bonchurch holiday apartment rental

                                  Ventnor / Bonchurch

                                  2 4 min stay varies

                                  • 2 bedrooms
                                  • sleeps 4
                                  • min stay varies
                                  • Child friendly
                                  • Pet friendly

                                  from £98 / night

                                  £630 - £790 / week

                                  Book View

                                  from £98 / night

                                    10

                                    Holiday cottage in Carisbrooke

                                    Isle of Wight / Carisbrooke

                                    2 4 7 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 7 nights min
                                    • Child friendly

                                    from £57 / night

                                    £404 - £1,204 / week

                                    Enquire View

                                    from £57 / night

                                    (55) Very Good 

                                    Certificate of Excellence

                                      20

                                      Yarmouth holiday cottage rental

                                      Yarmouth / Fort Victoria

                                      2 4 min stay varies

                                      • 2 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Nearest beach 0.1 km
                                      • Child friendly
                                      “A classic british holiday break” Myself, my wife and our 6-year old Springer Spaniel had a wonderful break here. Lovely cosy cottage, great sea location, and a short walk into Yarmouth town. We recommend this property without reservation

                                      Certificate of Excellence

                                      from £103 / night

                                      £476 - £1,483 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 24 minutes

                                      from £103 / night

                                        15

                                        Holiday apartment in Shanklin

                                        Isle of Wight / Shanklin

                                        3 5 min stay varies

                                        • 3 bedrooms
                                        • sleeps 5
                                        • min stay varies
                                        • Child friendly

                                        from £49 / night

                                        £343 / week

                                        Enquire View

                                        from £49 / night

                                        (11) Very Good 

                                          23

                                          Holiday apartment in Ventnor

                                          Isle of Wight / Ventnor

                                          2 5 min stay varies

                                          • 2 bedrooms
                                          • sleeps 5
                                          • min stay varies
                                          • Beach / lakeside relaxation
                                          • Nearest beach 0.1 km
                                          • Child friendly

                                          from £92 / night

                                          £430 - £859 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 48 minutes

                                          from £92 / night

                                          (18) Very Good 

                                            10

                                            Holiday home in Gurnard

                                            Isle of Wight / Gurnard

                                            2 4 min stay varies

                                            • 2 bedrooms
                                            • sleeps 4
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Child friendly
                                            • Private garden

                                            from £69 / night

                                            £1,804 / week

                                            Book View

                                            from £69 / night

                                            (24) Excellent 

                                            Certificate of Excellence

                                              20

                                              Apartment letting in Bembridge

                                              Bembridge / St Helens, Bembridge

                                              1 4 min stay varies

                                              • 1 bedroom
                                              • sleeps 4
                                              • min stay varies
                                              • Beach / lakeside relaxation
                                              • Child friendly
                                              • Car not necessary
                                              “Island Retreat” From start to finish our stay at 'The Villas' was simply 'Great'. From the hassle free booking, straight forward instructions into the property & the welcome folder where very helpful. The holiday let was very clean, fresh and modern with the bedroom overlooking a quiet street. Plenty of extra linen & towels if required. It didn't matter that we couldn't park outside the peoperty, it was only a short walk to 'The green' & was a delightful added difference to the daily trips out. We were fortunate to have good weather and brought our bikes, which we were secured in the back yard overnight. The local area is beautiful and very easy to access on foot, with some very disirable cafes, pubs & restaurant on your doorstep. Leaflets can be found in the lounge of the holiday let. We would definetly stay here again.

                                              Certificate of Excellence

                                              from £81 / night

                                              £343 - £572 / week

                                              Book View

                                              Responds fast!
                                              avg. 1 hour 41 minutes

                                              from £81 / night

                                                11

                                                Holiday cottage rental

                                                Isle of Wight / Freshwater

                                                3 6 7 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Child friendly
                                                • Pet friendly

                                                from £52 / night

                                                £364 - £1,448 / week

                                                Enquire View

                                                from £52 / night

                                                  10

                                                  Cottage rental in St Lawrence

                                                  Ventnor / St Lawrence

                                                  4 8 7 nights min

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • 7 nights min
                                                  • Child friendly

                                                  from £69 / night

                                                  £488 - £1,984 / week

                                                  Enquire View

                                                  from £69 / night

                                                  (3) Excellent 

                                                    18

                                                    Holiday apartment in Shanklin

                                                    Isle of Wight / Shanklin

                                                    2 3 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 3
                                                    • min stay varies
                                                    • Child friendly

                                                    from £46 / night

                                                    £322 / week

                                                    Enquire View

                                                    from £46 / night

                                                    (16) Excellent 

                                                      13

                                                      Holiday apartment in Wootton

                                                      Wootton / Fishbourne

                                                      3 6 min stay varies

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Nearest beach 1 km
                                                      • Child friendly
                                                      • Pet friendly

                                                      from £92 / night

                                                      £395 - £1,140 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 29 minutes

                                                      from £92 / night

                                                      (8) Excellent 

                                                      Certificate of Excellence

                                                        12

                                                        Holiday bungalow in Freshwater

                                                        Isle of Wight / Freshwater

                                                        3 6 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Child friendly
                                                        “Great location and beautiful vuews” We had a wonderful few days on the Isle of Wight staying in this perfect bungalow - extremely clean, well equipped and perfect location with 2 young boys to entertain. The views are beautiful and with great weather we were able to enjoy the sunsets. The beach is only a short walk down and is great for kids. We had an amazing meal at The Beach Hut and would thoroughly recommend the fish and chips at the Rainbow Fish Bar in freshwater. Margaret was extremely helpful with any queries we had and always responded quickly. Thank you for a perfect holiday!

                                                        Certificate of Excellence

                                                        from £125 / night

                                                        £788 - £1,088 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 2 hours 19 minutes

                                                        from £125 / night

                                                        (21) Excellent 

                                                        Certificate of Excellence

                                                          12

                                                          Holiday apartment with golf nearby in Ryde

                                                          Ryde / Appley

                                                          2 3 5 nights min

                                                          • 2 bedrooms
                                                          • sleeps 3
                                                          • 5 nights min
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 0.5 km
                                                          • Child friendly

                                                          Certificate of Excellence

                                                          from £75 / night

                                                          £521 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 3 hours 59 minutes

                                                          from £75 / night

                                                          (16) Excellent 

                                                          Certificate of Excellence

                                                            21

                                                            Holiday home in East Cowes

                                                            Isle of Wight / East Cowes

                                                            2 4 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Child friendly

                                                            Certificate of Excellence

                                                            from £115 / night

                                                            £516 - £802 / week

                                                            Book View

                                                            from £115 / night

                                                            (17) Very Good 

                                                              20

                                                              Holiday home with golf nearby in Cowes

                                                              Isle of Wight / Cowes

                                                              3 8 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 1 km
                                                              • Child friendly
                                                              “Wonderful IOW” Had a fantastic trip to Cowes staying in a lovely house called the boathouse? The house is close to all the amenities that Cowes has to offer. The house is spacious and well decorated with a very homely feel and is spotless clean. We had a fantastic time eating and drinking with some shopping thrown in and sitting watching the beautiful boats coming and going from the harbour. I would highly recommend both this property and Cowes for a wonderful holiday.

                                                              from £115 / night

                                                              £802 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 hours 13 minutes

                                                              from £115 / night

                                                              (13) Excellent 

                                                                15

                                                                Holiday chalet in Ventnor

                                                                Isle of Wight / Ventnor

                                                                3 6 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Child friendly
                                                                • Car not necessary

                                                                from £129 / night

                                                                £679 - £1,220 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 3 hours 49 minutes

                                                                from £129 / night

                                                                (2) Excellent 

                                                                  22

                                                                  Holiday home rental

                                                                  Isle of Wight / Ryde

                                                                  4 8 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Child friendly

                                                                  from £179 / night

                                                                  £1,140 - £1,941 / week

                                                                  Book View

                                                                  from £179 / night

                                                                  (61) Excellent 

                                                                  Certificate of Excellence

                                                                    23

                                                                    Holiday log cabin with indoor pool in Ryde

                                                                    Isle of Wight / Ryde

                                                                    3 6 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 2 km
                                                                    • Swimming pool
                                                                    “Lovely Break” Beautiful accommodation and setting along with very welcoming hosts. Would recommend this to anyone considering an Isle of Wight break.

                                                                    Certificate of Excellence

                                                                    from £103 / night

                                                                    £722 - £1,603 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 1 hour 0 minutes

                                                                    from £103 / night

                                                                    (5) Excellent 

                                                                      13

                                                                      Holiday apartment in Cowes

                                                                      Isle of Wight / Cowes

                                                                      3 6 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • min stay varies
                                                                      • Child friendly

                                                                      from £126 / night

                                                                      £573 - £836 / week

                                                                      Book View

                                                                      from £126 / night

                                                                      (40) Excellent 

                                                                      Certificate of Excellence

                                                                        14

                                                                        Apartment rental in Shanklin

                                                                        Shanklin / Old Village

                                                                        2 5 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • min stay varies
                                                                        • Nearest beach 1 km
                                                                        • Child friendly
                                                                        • Car not necessary

                                                                        Certificate of Excellence

                                                                        from £98 / night

                                                                        £458 - £916 / week

                                                                        Book View

                                                                        from £98 / night

                                                                        (9) Excellent 

                                                                          14

                                                                          Merstone holiday cottage rental

                                                                          Isle of Wight / Merstone

                                                                          3 7 4 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 7
                                                                          • 4 nights min
                                                                          • Child friendly

                                                                          from £109 / night

                                                                          £647 - £991 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 1 hour 23 minutes

                                                                          from £109 / night

                                                                          (34) Excellent 

                                                                          Certificate of Excellence

                                                                            16

                                                                            Holiday chalet in Sandown

                                                                            Isle of Wight / Sandown

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Nearest beach 0.2 km
                                                                            • Child friendly
                                                                            • Pet friendly
                                                                            “Chalet 191” We enjoyed our 2 week stay in chalet 191 in Sandown. It has everything you need, it's comfy and clean. I would highly recommend staying there. Jayne, the owner is very helpful and mid way through our stay changed the beds and cleaned which was lovely! I will definitely be back

                                                                            Certificate of Excellence

                                                                            from £46 / night

                                                                            £287 - £584 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 55 minutes

                                                                            from £46 / night

                                                                            (3) Excellent 

                                                                              20

                                                                              Ventnor holiday apartment accommodation

                                                                              Isle of Wight / Ventnor

                                                                              2 5 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 5
                                                                              • min stay varies
                                                                              • Child friendly
                                                                              • Pet friendly

                                                                              from £86 / night

                                                                              £1,031 - £1,145 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 45 minutes

                                                                              from £86 / night

                                                                              (12) Very Good 

                                                                                24

                                                                                Cowes holiday home rental

                                                                                Cowes / West Cowes

                                                                                2 5 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 5
                                                                                • min stay varies
                                                                                • Beach / lakeside relaxation
                                                                                • Child friendly
                                                                                • Car not necessary

                                                                                from £109 / night

                                                                                £762 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 13 minutes

                                                                                from £109 / night

                                                                                  13

                                                                                  Carisbrooke holiday cottage rental

                                                                                  Isle of Wight / Carisbrooke

                                                                                  3 6 7 nights min

                                                                                  • 3 bedrooms
                                                                                  • sleeps 6
                                                                                  • 7 nights min
                                                                                  • Child friendly
                                                                                  • Pet friendly

                                                                                  from £61 / night

                                                                                  £429 - £1,411 / week

                                                                                  Enquire View

                                                                                  from £61 / night

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