Walking holiday villas and apartments Isle of Wight

Close

View larger map

Also consider

Europe Holidays
430282 properties
United Kingdom Holidays
52622 properties
England Holidays
38011 properties
Cottages Cornwall
2983 properties
Apartments Greater London
941 properties
Cottages Cumbria / Lake District
940 properties
Houses Devon
2810 properties
Cottages Central England / Cotswolds
940 properties
Houses Dorset
819 properties
Houses Isle of Wight
507 properties
Cottages Peak District / Derbyshire
460 properties
Houses Somerset
610 properties
Houses Kent
557 properties
Houses Sussex
770 properties
Houses Norfolk
1023 properties
Cottages Isle of Man
11 properties
Northumberland
640 properties
Houses Yorkshire / Yorkshire Dales
1496 properties
Coastal Cottages
222 properties
Villas Ventnor
128 properties
Holiday homes Cowes
119 properties
Villas Shanklin
103 properties
Self catering accommodation Sandown
89 properties

Isle of Wight

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

395 Holiday homes

Filters applied: Walking holidays (395)

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

(20) Very Good 

16

Holiday apartment in Ryde

Isle of Wight / Ryde

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
“Very Nice, Up-To-Date Interior & Excellent Communication” The hayloft was an excellent place to stay for the weakened, as was attending the Isle Of White music festival. Great location between the towns and country side (very peaceful in the morning).  …see more

from £60 / night

£370 / week

Enquire View

from £60 / 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
“Superb and exquisite little gem, highly recommended” We stayed in Beachside for two magical days. It may have rained constantly but the cabin was so perfectly equipped we were happy to stay inside and cook in the very well equipped kitchen, read books  …see more

from £50 / night

£320 - £530 / week

Book View

from £50 / night

(6) Very Good 

24

Holiday home in Newport

Newport / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
“VIP accommodation for the Isle of Wight Festival” We stayed here with family and friends for 3 nights for the Isle of Wight Festival this year. Having the mooring come with the house made for a hassle free arrival and departure when the ferries and b  …see more

from £150 / night

£750 - £2400 / week

Book View

from £150 / night

(9) Excellent 

23

Cowes holiday caravan/mobile home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Swimming pool
Newly refurbished for 2016. Modern 3 bedroom caravan with 1 double bedroom, 2 twin bedrooms and pull out in lounge area. Full central heating and double glazing throughout. Shower room, and additional separate WC. Caravan facilities include fully equipped kitchen with i  …see more

from £70 / night

£365 - £750 / week

Book View

from £70 / night

(23) Very Good 

19

Apartment letting in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
Millers Rock is an attractive 2 bedroom character apartment in a privileged private road location offering panoramic seaviewsLight and airy and centrally located within 2 minutes of the beach, shops, cafes, restaurant and fishing harbour , this four star rated prope  …see more

from £80 / night

£375 - £824 / week

Enquire View

from £80 / night

(1) Excellent 

24

Holiday home in Cowes

Cowes / West Cowes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
Amazing property for up to 10 that sits just back from the waterfront and has fantastic views up and down the River Medina and to the Solent beyond from the large roof terrace - an excellent place to entertain or sit and watch the world go by. 5 bedrooms & 4 bathro  …see more

from £200 / night

£1400 - £5500 / week

Book View

from £200 / night

24

Newchurch holiday cottage rental

Sandown / Newchurch

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Characterful cottage on the Garlic Farm on the Isle of Wight. Perfectly placed for walking, cycling and family holidays. Guests enjoy a 10% discount in our renowned restaurant, use of tennis court and football pitch. 10 minutes from the beach by car.<br />Peacocks  …see more

from £175 / night

£825 - £1925 / week

Book View

from £175 / night

22

Holiday cottage in Newchurch

Sandown / Newchurch

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Tennis court, football pitch, table tennis - Discounted ferry crossings available  …see more

from £120 / night

£575 - £1275 / week

Book View

from £120 / night

(10) Very Good 

27

Holiday cottage letting

Isle of Wight / Bembridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Whether you are looking for a family beach holiday where you can forget the car and just chill in the garden or rock pool at the beach, or plan a walking, or cycling holiday exploring the island, Drayton Cottage is an ideal base - safe, secure and warm with free wifi.  …see more

from £100 / night

£325 - £800 / week

Book View

from £100 / night

(13) Excellent 

14

Niton holiday cottage rental

Isle of Wight / Niton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Rain or shine, relaxing by the fire or an exhilarating walk to the lighthouse!” Perfect setting for a peaceful break in very comfortable, well designed accommodation with private terrace and large secluded garden- sea view! Well equipped kitchen for s  …see more

from £110 / night

£575 - £1370 / week

Enquire View

from £110 / night

(11) Excellent 

23

Holiday chalet in Ventnor

Isle of Wight / Ventnor

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 4 km
“Exactly as it says Great Escape” Had a fantastic week at the Great Escape. Lovely and clean with everything needed for a comfortable stay. Beautiful Island would recommend to anyone who  …see more

from £40 / night

£240 / week

Book View

from £40 / night

(10) Very Good 

17

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“A superb apartment in a great location. Perfect.” We new the apartment was impressive from the photo's,however they do the accommodation little justice as the place needs to be seen in person. With panoramic views of the entire sea front enables Ventn  …see more

from £145 / night

£750 - £1163 / week

Book View

from £145 / night

(13) Excellent 

16

Apartment rental in Cowes

Cowes / West Cowes

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Great location, cosy and” I stayed here for a weekend and had a very comfortable and enjoyable stay. It is so continentally located by the ferry, shops, pubs and bars and it near to bus stops to see the rest of the Island. The apartment itself has e  …see more

from £100 / night

£350 - £400 / week

Book View

from £100 / night

(17) Excellent 

30

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Great holiday cottage” The Dairy was very well presented, extremely clean and very comfortable for our family with two young children. It is very well equipped with everything you need for a self catering holiday. We especially loved the hot tub, e  …see more

from £125 / night

£370 - £795 / week

Book View

from £125 / night

(39) Excellent 

32

Holiday cottage rental

Isle of Wight / Shanklin

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“This is a Gem and ticks all the boxes!” This is an immaculately clean establishment offering the choice of both B&B and self catering. It is in a great position just a few minutes walk to the beach in one direction and the town in the other. It is in  …see more

from £65 / night

£450 - £695 / week

Enquire View

from £65 / night

(24) Excellent 

14

Cottage rental 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
“Home away from home - with AMAZING views!” My wife and I stayed at Ocean View for a long weekend in middle June 2014. We found the cottage to be neat and tidy, well prepared for our stay, stylishly decorated and with amazing views spanning out across  …see more

from £99 / night

£495 - £950 / week

Enquire View

from £99 / night

(8) Excellent 

39

Holiday cottage in Seaview

Isle of Wight / Seaview

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
"The perfect self-catering holidays in Seaview on the Isle of Wight" Seaview Holidays offer luxury self-catering accommodation in a stunning, secluded location overlooking the beautiful Hersey Nature Reserve on the Isle of Wight..... We offer 2, 3 and 4 bedr  …see more

from £135 / night

£579 - £1499 / week

Book View

from £135 / night

11

Holiday cottage in Ventnor

Ventnor / Niton, Isle of Wight

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly
Situated in the small village of Niton, this cosy, period, 17th-century, terraced holiday cottage offers an ideal base for exploring all that the island has to offer. It is close to the beautiful south coast with its golden beaches, as well as being on the edge of an Ar  …see more

from £75 / night

£400 / week

Book View

from £75 / night

(7) Very Good 

24

Ryde holiday apartment rental

Ryde / Appley

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“A beautiful, well kept apartment in a great location” A really clean, comfortable, well equipped apartment (although a hairdryer would be a nice addition) in a fantastic location. Very near transport links, shops etc with a lovely sea view. I had a wo  …see more

from £100 / night

£395 - £765 / week

Book View

from £100 / night

(3) Excellent 

24

Holiday home in Bonchurch

Isle of Wight / Bonchurch

5 8 2 nights min

  • 5 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden
“Absolutely fantastic” We stayed at Garden House during the October half term and thoroughly enjoyed it, a perfect home away from home. Well placed near Ventnor and Shanklin (our favourites on the Island), and near lots of amenities. The beds were the  …see more

from £115 / night

£805 / week

Book View

from £115 / night

(2) Excellent 

8

Holiday barn in Shorwell

Isle of Wight / Shorwell

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
For those bringing bikes, surf boards and the like, a barn is available for storage.These desirable cabins nestle in downland, above the peaceful village of Shorwell, only 2 miles from yhe south coast of the Island.<br />Footpaths alongside the cottage join the Is  …see more

from £70 / night

£450 / week

Book View

from £70 / 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
Kildare is an elegant 18th Century Georgian style holiday home which sleeps 10+, retaining many original features. Located on the southern tip of the Isle of Wight in an Area of Outstanding Natural Beauty, in the beautiful village Niton.<br />The perfect retreat f  …see more

from £115 / night

£800 - £1500 / week

Book View

from £115 / night

(38) Excellent 

19

Holiday cottage in Newchurch

Sandown / Newchurch

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
“A truly lovely property.” If you want a peaceful holiday property in superb location then Brew House is for you, Tastefully decorated, very clean, comfortable and well equipped. The owners had left a lovely welcome pack which included scrumptious home  …see more

from £90 / night

£500 - £750 / week

Enquire View

from £90 / night

(7) Excellent 

23

Holiday home rental

Isle of Wight / Wootton Bridge

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
Grange Farm Self Catering, location is very peaceful,perfect for walkers,cyclists,surrounded by wild life including Red squirrels and wild birds can be seen through patio doors in the breakfast room.Visit Britain 4 star highly recommded.Beeches, pub,Farm shop close by.  …see more

from £161 / night

£1125 / week

Book View

from £161 / night

(13) Very Good 

14

Holiday cottage letting

Whitwell / Nettlecombe

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
“An excellent holiday stay” First time me and my husband have ever been to the Isle of White and totally fell in love with the place. We loved it so much even thinking of moving there within few years. Whitwell Station was a lovely accommodation and  …see more

from £90 / night

£470 - £1080 / week

Book View

from £90 / night

(4) Very Good 

22

St Helens holiday cottage rental

Isle of Wight / St Helens

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Private garden
“Fab cottage” The cottage was clean & well furnished. We were close to the beach with good restaurants and superstore close by. Neighbours friendly and helpful. The only downsides were no bath towels and nothing in the literature advising of this an  …see more

from £42 / night

£295 - £680 / week

Enquire View

from £42 / night

(9) Very Good 

13

Holiday chalet in Yaverland

Sandown / Yaverland

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Completely renovated chalet with new fitted kitchen and bathroom 32" flat screen television with rotating arm to enable you to watch TV outside chalet. Beautifully decorated giving a modern home from home styling. Sofa bed to cater for an extra person not two adul  …see more

from £100 / night

£485 / week

Book View

from £100 / night

(5) Excellent 

12

Brading holiday cottage rental

Isle of Wight / Brading

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
A quirky little character cottage backing onto open fields & located in the ancient 'Kynges Towne' of Brading. The home offers all modern comforts & the well presented accommodation has a 'light & airy' feel. Outside, there are pretty gar  …see more

from £60 / night

£275 / week

Enquire View

from £60 / night

(1) Very Good 

11

Holiday bungalow in Bembridge

Bembridge / Bembridge Village

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
This detached bungalow is situated at the head of a small cul-de-sac in a quiet residential area of the village of Bembridge. It makes an ideal holiday home being within easy walking distance of the beach at Forelands and the village shops, eateries and public houses.  …see more

from £85 / night

£395 / week

Book View

from £85 / night

(2) Excellent 

22

Cowes holiday townhouse rental

Cowes / West Cowes

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
York street as also been a popular location for those coming for sailing events as its has a very short walking distant to the Marinas<br />This property is part of the Cowes Holiday Homes portfolio where good service comes as standard  …see more

from £105 / night

£450 - £2900 / week

Book View

from £105 / night

(13) Excellent 

17

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
“Such a lovely place to spend a week... or longer!” My girlfriend and I spent a week here during Wimbledon week and were blown away by how lovely the apartment and St Helen's was. Everything about the place was better than we could have dreamed of - th  …see more

from £45 / night

£225 - £399 / week

Enquire View

from £45 / night

(10) Excellent 

18

Holiday home in Sandown

Isle of Wight / Sandown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.02 km
  • Child friendly
“Great Place for Holidays” The house is very nice. We loved the architecture - all the gatherings at ground level and bedrooms on upper. House is well equipped, and has Sainsbury, SPAR and many local stores in 2 mins walk distance. The weather wasn't g  …see more

from £150 / night

£850 - £1400 / week

Enquire View

from £150 / night

(2) Very Good 

13

Cowes holiday home let

Cowes / West Cowes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Excellent location” We are a large family consisting of three couples and two children. Ample room in the property for us all to be comfortable. Everything you can think of in property to make stay as near to home from home as possible. Location excel  …see more

from £115 / night

£550 - £3900 / week

Book View

from £115 / night

(6) Excellent 

23

Shanklin holiday apartment rental

Isle of Wight / Shanklin

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“New Years Eve” Excellent apartment with good 4 star hotel standards very close to the beach only 5 minutes walk ...  …see more

from £155 / night

£775 - £1975 / week

Book View

from £155 / night

(10) Excellent 

8

Holiday barn rental

Isle of Wight / Niton

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Recently restored 18th Century barn with sea views, under floor heating, wood burning stove, exposed 400 year old stone wall, private south facing garden, off street parking. Storage for bikes & surf boards, drying area for wetsuits.<br />The Barn is close to  …see more

from £110 / night

£575 - £1290 / week

Enquire View

from £110 / night

(26) Excellent 

8

Ventnor holiday apartment accommodation

Ventnor / Ventnor Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Car not necessary
“Great location, great views” This small apartment is a perfection destination for a romantic getaway for 2. Fantastic sea views and upper sun deck, with parking easy to find just a few minutes away. Not too far to Ventnor's amenities, with a lovely  …see more

from £64 / night

£299 - £545 / week

Enquire View

from £64 / night

(5) Excellent 

21

Bembridge holiday home let

Bembridge / Bembridge Village

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Lovely holiday home offering peace and quiet just minutes from the beach” Lovely 3-bedroomed holiday home in a quiet lane, just minutes from the beach. Very convenient with convenience store just round the corner. Would definitely recommend the prope  …see more

from £86 / night

£600 - £1250 / week

Book View

from £86 / night

(18) Very Good 

17

Holiday studio in Shanklin

Isle of Wight / Shanklin

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Good place, good price!” Nice studio apartment finished to high standard with well equipped kitchen, easy walking distance to shanklin, local pubs and restaurants. Be a bit cosy if there where four of you but great for two.  …see more

from £45 / night

£230 - £585 / week

Book View

from £45 / night

(1) Excellent 

14

Townhouse rental in Cowes

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
A great house for sailing events, corporate & holiday accommodation  …see more

from £90 / night

£425 - £2050 / week

Book View

from £90 / night

(8) Excellent 

22

Cowes holiday home rental

Cowes / West Cowes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.18 km
  • Child friendly
“Christmas in Cowes” Great house. We were a group of 9 adults and 5 children all 2 and under. This house was the perfect place to spend christmas, plenty of room and a great kitchen with everything you need including a stocked pantry, which is always h  …see more

from £295 / night

£2065 / week

Enquire View

from £295 / night