Walking holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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399 Holiday homes

Filters applied: Walking holidays

(22) Excellent 

18

Holiday log cabin in Woodside Beach

Isle of Wight / Woodside Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Best Self- Catering Accommodation I have ever stayed in!” This is most definitely the best Self-catering accommodation I have ever stayed in. Hosts Debra and Steve are most welcoming. The private garden was wonderful and visited by a host of differen
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from £60 / night

£315 - £570 / week

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from £60 / night

(10) Very Good 

15

Apartment rental in Totland

Totland Bay / Totland Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly

from £195 / night

£575 - £1275 / week

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Responds fast!
avg. 1 hour 43 minutes

from £195 / night

(11) Excellent 

13

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

£350 - £550 / week

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Responds fast!
avg. 13 minutes

from £65 / night

Featured properties

(2) Very Good 

22

Home rental in Bembridge

Isle of Wight / Bembridge

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £150 / night

£715 - £1950 / week

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from £150 / night

22

Holiday chalet rental

Isle of Wight / Seaview

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

from £54 / night

£307 - £679 / week

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Responds fast!
avg. 1 hour 21 minutes

from £54 / night

(16) Excellent 

24

Home rental in Ventnor with golf nearby

Isle of Wight / Ventnor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.75 km
  • Suitable for children age 5+
“Lovely cosy comfortable property, well presented and situated with sea views!” Stayed between Christmas and New Year during a very wet spell, but the property was warm, cosy and welcoming. Large property ideal for a family or group of friends. Proper
…see more

from £165 / night

£750 - £1300 / week

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from £165 / night

(4) Excellent 

24

Holiday chalet letting

Isle of Wight / Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Lovely place to stay” We stayed here over Easter and the weather was rather cold but this chalet was really cosy. The view is amazing and the pictures don't do it justice, I loved sitting eating and looking at the ferries that go by. The little garden
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from £90 / night

£398 - £696 / week

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from £90 / night

(1) Excellent 

15

Home rental in Ventnor

Isle of Wight / Ventnor

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden

from £125 / night

£550 - £1300 / week

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from £125 / night

(3) Excellent 

12

Holiday apartment in Cowes

Cowes / West Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden

from £95 / night

£450 - £1600 / week

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Responds fast!
avg. 1 hour 7 minutes

from £95 / night

(4) Excellent 

27

Holiday cottage rental

Freshwater / Freshwater Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Ask owner if suitable for children

from £72 / night

£360 - £560 / week

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from £72 / night

(16) Excellent 

20

Holiday home with golf nearby in Sandown

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £49 / night

£295 - £745 / week

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Responds fast!
avg. 12 minutes

from £49 / night

(7) Very Good 

13

Holiday home in Bembridge

Bembridge / Bembridge Village

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £114 / night

£795 - £2695 / week

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from £114 / night

(7) Very Good 

32

Holiday home in East Cowes

Isle of Wight / East Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Nice holiday” This property well-equipped and is ideal for small family right on the waterfront lovely island to visit. we had a great holiday with plenty of things to do around the island
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from £125 / night

£595 - £1475 / week

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Responds fast!
avg. 2 hours 23 minutes

from £125 / night

(7) Very Good 

19

Godshill holiday cottage accommodation

Isle of Wight / Godshill

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £100 / night

£340 - £1444 / week

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from £100 / night

(14) Excellent 

19

Holiday barn rental

Isle of Wight / Niton

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £85 / night

£575 - £1290 / week

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Responds fast!
avg. 1 hour 46 minutes

from £85 / 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
“Superb Apartment” This apartment is very charming and feels very homely. I felt very cosy and safe here. The apartment had everything to make your stay pleasant. Clean and fresh. My Husband and I visited with my Daughter 9 years of age. We had plenty
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from £100 / night

£395 - £765 / week

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Responds fast!
avg. 2 hours 39 minutes

from £100 / night

(1) Excellent 

12

Bembridge holiday home rental

Bembridge / Bembridge Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £185 / night

£615 - £1540 / week

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from £185 / night

(5) Excellent 

Certificate of Excellence

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
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Certificate of Excellence

from £100 / night

£600 - £1400 / week

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Responds fast!
avg. 3 hours 12 minutes

from £100 / night

(9) Excellent 

10

Cottage rental in Whippingham

Isle of Wight / Whippingham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 10 km
  • Child friendly
  • Private garden

from £49 / night

£340 - £625 / week

Enquire View

from £49 / night

(13) Excellent 

Certificate of Excellence

24

Sandown holiday apartment rental

Isle of Wight / Sandown

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Clean and well presented apartment” We stayed for three nights in October and couldn't fault it. The apartment was very clean and to a high standard. We found it was a very good base for travelling round the Island, I would definitely stay there again
…see more

Certificate of Excellence

from £35 / night

£200 - £380 / week

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Responds fast!
avg. 2 hours 57 minutes

from £35 / night

(3) Excellent 

15

Apartment rental in Shanklin

Shanklin / Old Village

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
“Superb” A very clean and comfortable apartment and beautiful gardens. Pam is a very nice and welcoming lady and nothing is too much trouble if you need anything. Will definitely be booking to go back next year at some point.
…see more

from £57 / night

£395 - £600 / week

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from £57 / night

(12) Very Good 

9

Home rental in Cowes

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
“Greta location, clean, tidy house” The location of the house was fantastic. We could access the town so easily and supermarkets and fish and chip shop were literally around the corner. The house itself was great, very clean and a well equipped kitchen
…see more

from £110 / night

£590 - £1600 / week

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from £110 / night

(16) Excellent 

24

Holiday manor house in Wroxall

Isle of Wight / Wroxall

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly

from £300 / night

£1500 - £2850 / week

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Responds fast!
avg. 2 hours 27 minutes

from £300 / night

(9) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £135 / night

£579 - £1499 / week

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from £135 / night

(22) Excellent 

Certificate of Excellence

7

Holiday lodge with golf nearby in Whippingham

Isle of Wight / Whippingham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 4 km
  • Child friendly
  • Car not necessary
“Ruth” We had to make a phone call to find it but Amber gave us clear directions. Beautiful location with plenty of space for humans and dogs, comfortable beds and great shower. Warm welcome from Amber with a welcome pack of milk, bread, butter, eggs,
…see more

Certificate of Excellence

from £95 / night

£585 - £1025 / week

Book View

from £95 / 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 - £550 / week

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Responds fast!
avg. 2 hours 3 minutes

from £30 / night

(16) Excellent 

16

Yarmouth holiday villa rental

Isle of Wight / Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Superb holiday cottage in great location” Woodland Cottage is a very well-equipped, quiet, and comfortable place to stay. We had a very enjoyable week here, and even with six of us we didn't get under each other's feet. The downstairs is bright and ai
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from £190 / night

£1125 - £2240 / week

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Responds fast!
avg. 1 hour 8 minutes

from £190 / 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
“Brill” Lovely, safe, quiet location. Cute little chalet, perfect for 2 people. All crockery/cooking stuff you need - although no oven which is a minor issue only especially if you're not staying for more than a week. Would stay here again if we were
…see more

from £40 / night

£240 / week

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from £40 / night

(19) Excellent 

Certificate of Excellence

22

Holiday cottage in Ryde

Ryde / Appley

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

Certificate of Excellence

from £85 / night

£595 - £950 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from £85 / night

(7) Very Good 

16

Cowes holiday townhouse rental

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Ideal Location !” As a group of 6, we travelled by boat from Portsmouth and moored at Cowes Yacht haven. The location is absolutely perfect for anybody travelling on their own boat as the marina is literally a minute away. The property is furnis
…see more

from £150 / night

£750 - £950 / week

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from £150 / night

(1) Excellent 

24

Holiday shepherds hut in Godshill

Isle of Wight / Godshill

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Private garden

from £75 / night

£400 / week

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Responds fast!
avg. 3 hours 48 minutes

from £75 / night

(8) Excellent 

Certificate of Excellence

13

Holiday apartment in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

Certificate of Excellence

from £110 / night

£550 - £2300 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from £110 / night

(39) 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
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from £38 / night

£225 - £470 / week

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Responds fast!
avg. 2 hours 42 minutes

from £38 / night

(14) Very Good 

Certificate of Excellence

15

Chalet letting in Cowes with shared pool

Cowes / Gurnard Pines

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Superb home from home” I had the pleasure of staying here with my family for a mini break in September. It had everything that we needed and 2 year old was really excited about the bunk beds. It was clean comfortable and plenty big enough. A lovely pl
…see more

Certificate of Excellence

from £70 / night

£350 - £600 / week

Book View

Responds fast!
avg. 1 hour 53 minutes

from £70 / night

(1) Very Good 

18

Bembridge holiday home rental

Bembridge / Bembridge Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

from £115 / night

£500 - £1250 / week

Book View

Responds fast!
avg. 3 hours 52 minutes

from £115 / night

(5) Excellent 

12

Holiday barn in Ryde

Isle of Wight / Ryde

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
“Perfect for large groups” The Granary was ideal for a large group, each room having its own en-suit. Plenty of space to socialise and very clean. The only thing I would suggest is it is better sign posted at the end of the drive as we initially drove
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from £210 / night

£900 - £2300 / week

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from £210 / night

(3) Very Good 

19

Holiday chalet in Yaverland

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“Ideal for a young family in a quiet location” Riviera Park (formerly Sandown Bay Holiday Centre) is a development of stone built chalets spread over a parkland setting contained within a former 19th century wartime-battery site. The accomodation an
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from £36 / night

£250 - £495 / week

Enquire View

from £36 / night

7

Holiday cottage rental

Isle of Wight / Wroxall

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £180 / night

£1260 / week

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Responds fast!
avg. 3 hours 57 minutes

from £180 / night

(13) Excellent 

28

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“High quality, beautifully appointed holiday barn in a peaceful location.” The barn is in great location which leaves you close to any of the islands attractions or towns. It is beautifully appointed throughout with the bonus of a hot tub in the shared
…see more

from £130 / night

£600 - £1550 / week

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Responds fast!
avg. 1 hour 51 minutes

from £130 / 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

from £175 / night

£825 - £1975 / week

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from £175 / night