Walking holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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393 Holiday homes

Filters applied: Walking holidays

Travellers going to Isle of Wight are booking June dates now. Secure your holiday home today and have the perfect trip.

(7) Excellent 

17

Cottage rental in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Fabulous place to stay and really helpful owners!” Just returned from a two week stay at the delightful Valerian Cottage with my wife and daughters (aged 6 and 4). The cottage is beautifully presented and extremely comfortable - more like a proper hom  …see more

from £80 / night

£450 - £950 / week

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from £80 / night

(8) Excellent 

23

Holiday chalet in Freshwater

Isle of Wight / Freshwater

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Clean comfortable with beautiful views.” Wonderful chalet. Handy for beach and lovely walks. Ideal for a quieter peaceful holiday. The chalet is a good size for a family and the owner is very helpful. It is beautifully situated on the quieter side o  …see more

from £36 / night

£250 - £450 / week

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from £36 / night

(9) Very Good 

12

Freshwater holiday bungalow rental

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Mr” This was everything promised and more a lovely holiday and great value for money clean and a nice location the road on the way in was a little bumpy but that is just being picky lots of piece and quite with a lovely view  …see more

from £33 / night

£233 - £555 / week

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from £33 / night

Featured properties

(7) Very Good 

23

Holiday chalet in Ventnor

Ventnor / Niton Undercliff

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
“Well thought out accommodation in pretty surroundings” Stayed for two nights but wish it could have been longer. The chalet has everything you could need and nicely decorated too. There's a lot of info about the area with maps and things to do and you  …see more

from £45 / night

£280 - £405 / week

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from £45 / night

(17) Excellent 

24

Holiday cottage in Wootton Bridge

Isle of Wight / Wootton Bridge

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.  …see more

from £130 / night

£695 - £1325 / week

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from £130 / night

(20) Very Good 

20

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Great Walks” WE had a great time. Chalet was clean and comfortably. Walking distance to sandown beaches and town.15 min by to car to Ryde.  …see more

from £38 / night

£225 - £475 / week

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from £38 / night

(14) Excellent 

23

Holiday home in Ryde

Isle of Wight / Ryde

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Loveley cottage in a great location” I stayed here for a week with my small dog who loved the outside courtyard. The cottage is really comfortable and clean and has everything you need for a good holiday. It is in an excellent location just minutes  …see more

from £54 / night

£375 - £800 / week

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from £54 / night

(15) Excellent 

22

St Helens holiday lodge rental

Isle of Wight / St Helens

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“beautiful property nice location” As described it was a perfect location with sea view .Clean park .well sited near complex. The lodge was very nice well equipped. Only disappointment we didn't book long enough!  …see more

from £65 / night

£395 - £1295 / week

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from £65 / night

(4) Excellent 

16

Freshwater holiday bungalow rental

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

from £38 / night

£260 - £560 / week

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from £38 / night

(13) Excellent 

20

Holiday cottage in Bonchurch

Isle of Wight / Bonchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Absolute paradise” This was our third time staying at the hideaway, will be back again next year. Such a beautiful, peaceful place can't fault it.  …see more

from £100 / night

£550 - £790 / week

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from £100 / night

(16) Excellent 

24

Holiday cottage in Shanklin

Shanklin / Old Village

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Perfect house and location” I stayed here with my 90 year old Aunt. It was perfect for her as the cottage is all on one level. There is one very shallow step up to the front door but it was easy for her to negotiate. It's very quiet yet not secluded a  …see more

from £52 / night

£360 - £700 / week

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from £52 / night

(3) Excellent 

22

Holiday caravan/mobile home in Bembridge

Isle of Wight / Bembridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“Amazing destination and accommodation - why would you go anywhere else?” I really don't want to tell everyone just how perfect this van is, or how breathtakingly beautiful the area is. I don't want to let on how amazing it feels to wander straight o  …see more

from £50 / night

£300 - £550 / week

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from £50 / night

(14) 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
“fantastic cottage, really homely” Stayed in Lane End Cottage in August of this year for a week and all I can say is it was fantastic. All the rooms were lovely and there was lots of space for the seven of us. Five adults and two children. We all had a  …see more

from £72 / night

£500 - £900 / week

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from £72 / night

(21) Excellent 

24

Apartment rental in Shanklin

Shanklin / Old Village

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.9 km
  • Ask owner if suitable for children
“The Courtyard...............Fantastic place!” Just spent a few glorious days at The Courtyard, Shanklin, IOW. Richard and Miriam were great hosts, providing lovely extras, tea, coffee, juice etc and also a wonderful and tasty homemade sponge cake....  …see more

from £88 / night

£350 - £516 / week

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from £88 / night

(1) Very Good 

12

Holiday bungalow in Freshwater

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Child friendly

from £30 / night

£190 - £590 / week

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from £30 / night

(11) Excellent 

8

Holiday log cabin with golf nearby in Whippingham

Isle of Wight / Whippingham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Private garden

from £65 / night

£325 - £450 / week

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from £65 / night

(11) Very Good 

14

Holiday chalet with golf nearby in Yaverland

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Excelent place to stay, exactly as described” We stayed for 3 nights and enjoyed our holiday very much. The house was very clean and tidy, The beach is just 5 minutes walking distance, shops and supermarket are also located nearby, Very nice and quite  …see more

from £55 / night

£259 - £520 / week

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from £55 / night

(2) Average 

30

Home rental in Nettlestone with golf nearby

Isle of Wight / Nettlestone

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Fabulous accommodation for enjoying this lovely Island” Our party of 8 adults and 2 children had a fabulous stay at Nettlestone House; very spacious and very well presented and equipped. And the lovely garden was a bonus for both playtime and the BBQ.  …see more

from £199 / night

£995 - £1995 / week

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from £199 / night

(28) Excellent 

26

Holiday caravan/mobile home with shared pool in Thorness Bay

Cowes / Thorness Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Ideal location for family break” Well equipped and comfortable caravan, nice location with views of the solent. Central site location with good vehicle access. Close to shop, bar, pool, and entertainment. We were a group of five with a 90 and 87 year  …see more

from £65 / night

£375 - £865 / week

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from £65 / night

(31) Excellent 

23

Holiday home in Yarmouth

Isle of Wight / Yarmouth

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Ideal location to visit the Illlsle of Wight” This house provides very comfortable accommodation for a party of 10. It is ideal for visiting attractions on the island. It is situated in the quiet village of Newbridge and is adjacent to a campsite whic  …see more

from £200 / night

£850 - £1775 / week

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from £200 / night

(36) Very Good 

17

Holiday chalet in Yaverland

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Seabreeze” Lovley stay at seabreeze Excellent good value for money very welcoming located on a great site , Will defently book here again Thank you for having us  …see more

from £38 / night

£225 - £475 / week

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from £38 / night

(8) Excellent 

14

Holiday apartment in Ventnor

Ventnor / Ventnor Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Brilliant apartment,brilliant location,brilliant views” Exactly what it says on'"the tin".Easy to book ,with confidence and all the support you would need-regular updates and support of "the lovely Lisa" on the island. Spacious and extremely well pre  …see more

from £145 / night

£750 - £1163 / week

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from £145 / night

(86) Excellent 

25

Holiday cottage in Ventnor

Ventnor / Niton Undercliff

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
“The best-equipped, beautiful cottage” We were six adults and two children (aged 1 years, and 3 months). We found the cottage very relaxing and spacious, with everything we could want/need for a weekend away, and a wide array of toys to keep our 1 year  …see more

from £125 / night

£595 - £1550 / week

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from £125 / night

(16) Excellent 

13

Brighstone holiday cottage rental

Isle of Wight / Brighstone

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 km
  • Private garden
“Carriers Stable - Superb” Have had a wonderful New Year break at Carriers Stable in Brigstone,Isle of White. From start to finish Vanessa and Glyn helped and communicated at short notice allowing us a break in their 5* accommodation. Everything was a  …see more

from £63 / night

£315 - £585 / week

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from £63 / night

(21) Excellent 

35

Holiday cottage in Cowes

Isle of Wight / Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
“Perfect cottage” A really lovely well equipped dog friendly cottage in a fantastic location. Great shops, pubs, dog walks and the bonus of M&S on your door step. Jenny was very helpful with the booking and the welcome pack was very much appreciated.  …see more

from £145 / night

£475 - £750 / week

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from £145 / night

(12) Excellent 

19

Holiday chalet in Niton

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 5 km
  • Car not necessary
“Fantastic place” Would give it 110% so clean and tidy and peaceful. There's everything you need in the chalet. Beautiful walks and scenery Looking forward to returning there again.  …see more

from £40 / night

£240 - £425 / week

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from £40 / night

(43) Very Good 

21

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
“Seaview Cottage - Fort Victoria w/e 31/12/2016” This is the second time that we have stayed in the cottage and was once again a perfect getaway for us and the dog and a really great place to see the New Year in. The cottage is quaint, clean and comfor  …see more

from £75 / night

£395 - £1245 / week

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from £75 / night

(5) Excellent 

27

Holiday home in Shorwell

Isle of Wight / Shorwell

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
“Church view” This was my second visit to this outstanding property in Shorwell. Both visits were with friends to walk, relax and explore more of the island. This year the highlight was a walk along the cliffs to the Needles. After a full day of fresh  …see more

from £100 / night

£600 - £1400 / week

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from £100 / night

(29) Excellent 

45

Holiday cottage rental

Ventnor / St Lawrence, Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Beautiful home in peaceful setting” Breakers Sound is a stunning house in lovely gardens with sea views. It contained everything we needed for a relaxing week. The location is very peaceful without being isolated, and lovely walks straight from the ho  …see more

from £150 / night

£525 - £1345 / week

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from £150 / night

(10) Excellent 

16

Freshwater holiday bungalow rental

Isle of Wight / Freshwater

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
“Perfect family escape!” We really enjoyed our weekend here with our nine month old. Loved that it was a bungalow so no stairs to worry about. Wish we booked longer as we didn't want to come home! Really clean and had everything we would need. Perfect  …see more

from £70 / night

£390 - £520 / week

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from £70 / night

(22) Excellent 

20

Holiday cottage in Freshwater

Freshwater / Moons Hill

2 4 7 nights min

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

from £29 / night

£200 - £780 / week

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from £29 / night

(12) Very Good 

20

Chalet rental in Gurnard

Isle of Wight / Gurnard

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Beautiful views, lovely central accommodation” My daughter stayed here & recommended it. The chalet was ideal for 2 of us and we were able to take our dog. This was great & the small lawn was fenced in so he was able to spend most of the time outside(  …see more

from £50 / night

£320 - £530 / week

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from £50 / night

(16) Very Good 

24

Holiday log cabin in Cowes

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“A peaceful total retreat from the pace of life.” If your looking for a total retreat this is it. Off the beaten tract, quiet & peaceful. Amazing views over the Solent. If you want to venture out it's location is good for many of the island's attracti  …see more

from £65 / night

£400 - £670 / week

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from £65 / night

(17) Excellent 

36

Holiday cottage rental

Isle of Wight / Bonchurch

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Mr” Well equipped. Hidden away. Lawn shaded from weather from all directions except south. Cosy. Beautiful place in a beautiful place.  …see more

from £90 / night

£450 - £1960 / week

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from £90 / night

(8) Excellent 

8

Holiday apartment in Wootton Bridge

Wootton Bridge / Fishbourne

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly

from £69 / night

£295 - £875 / week

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from £69 / night

(8) Excellent 

19

Holiday home in Ventnor

Ventnor / Niton, Isle of Wight

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £115 / night

£800 - £1500 / week

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from £115 / night

(10) Excellent 

23

Freshwater holiday bungalow rental

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

from £36 / night

£250 - £550 / week

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from £36 / night

(37) Excellent 

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
“Brilliant Holiday” We have just returned from our first family holiday on the Isle Of Wight with our two children aged 9 and 6. The Cabin is an amazing place to stay for a holiday, very clean and has everything you need. The swimming pool seemed bigge  …see more

from £93 / night

£650 - £1400 / week

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from £93 / night

(18) Very Good 

14

Holiday cottage in Ventnor

Isle of Wight / Ventnor

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“An absolutely beautiful cottage with fabulous sea view” We arrived on the day of the big snow so had the added benefit for the first day of a winters view. The cottage was cosy and warm and so beautifully decorated that we didn't feel the need to go o  …see more

from £70 / night

£490 - £880 / week

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from £70 / night

(25) Very Good 

18

Holiday caravan/mobile home in Cowes

Isle of Wight / Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly

from £50 / night

£250 - £630 / week

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from £50 / night

1