Walking holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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394 Holiday homes

Filters applied: Walking holidays

(3) Excellent 

33

Holiday home in Bonchurch

Isle of Wight / Bonchurch

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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
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from £125 / night

£850 / week

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Responds fast!
avg. 2 hours 50 minutes

from £125 / night

(21) Excellent 

24

Apartment rental in Shanklin

Shanklin / Old Village

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • 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....
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from £47 / night

£325 - £516 / week

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Responds fast!
avg. 24 minutes

from £47 / night

(3) Excellent 

15

Holiday home in Bembridge

Bembridge / Bembridge Village

3 8 7 nights min

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

from £143 / night

£995 / week

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Responds fast!
avg. 3 hours 30 minutes

from £143 / 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

from £70 / night

£365 - £750 / week

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Responds fast!
avg. 3 hours 39 minutes

from £70 / night

(12) Excellent 

18

Holiday cottage rental

Cowes / West Cowes

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.08 km
  • Child friendly
“Truly a home from home” A wonderful break. Carlton Cottage is beautifully decorated, perfectly located. High attention to detail with everything thought about to make a memorable stay. With much thanks we hope to return soon.
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from £185 / night

£760 - £2600 / week

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from £185 / night

(24) Very Good 

19

Apartment letting in Ventnor

Isle of Wight / Ventnor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

from £54 / night

£375 - £839 / week

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from £54 / night

10

Holiday chalet accommodation

Isle of Wight / Sandown

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £50 / night

£300 - £510 / week

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Responds fast!
avg. 2 hours 17 minutes

from £50 / night

(37) Very Good 

21

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Brilliant Stay” The Ferry crossing was uncomplicated and organised. Dogs are allowed in the lower deck and on the sun deck which has wonderful views of the Island and the Solent. When you arrive on the Island at Yarmouth you are only 3-4 mins drive
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from £75 / night

£395 - £1245 / week

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Responds fast!
avg. 1 hour 10 minutes

from £75 / night

(12) Very Good 

20

Holiday bungalow in Freshwater

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“A home from home” Brambles Chine is a hidden secret, the road leading to it is so easy to miss the first, second and third times. This hidden holiday park is in a simply amazing location with a panoramic view from the needles in the south to Fort Albe
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from £50 / night

£270 - £560 / week

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Responds fast!
avg. 1 hour 53 minutes

from £50 / night

(2) Excellent 

10

Holiday lodge in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from £65 / night

£625 - £895 / week

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from £65 / 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 10 minutes

from £190 / 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 £75 / night

£420 - £1600 / week

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Responds fast!
avg. 3 hours 2 minutes

from £75 / night

(5) Excellent 

13

Gurnard holiday cottage rental

Isle of Wight / Gurnard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £110 / night

£575 - £2900 / week

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Responds fast!
avg. 3 hours 2 minutes

from £110 / night

(36) Excellent 

Certificate of Excellence

32

Holiday apartment in Shanklin

Shanklin / Luccombe Village

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
“Pleasant Stay and wonderful location” We had wonderful stay in this gorgeous flat... the flat was very clean and welcoming. Maria was quite helpful during the booking stage and stay as well. The location was quite convenient to go around the island. w
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Certificate of Excellence

from £80 / night

£560 / week

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Responds fast!
avg. 2 hours 26 minutes

from £80 / 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
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from £86 / night

£600 - £1250 / week

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from £86 / 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

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Responds fast!
avg. 3 hours 52 minutes

from £115 / night

(8) Very Good 

27

Thorness Bay holiday caravan/mobile home accommodation

Cowes / Thorness Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Mr” Excellent location, a clean spacious caravan very comfortable and wonderful owners who are very helpful and friendly.
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from £50 / night

£350 - £595 / week

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Responds fast!
avg. 2 hours 45 minutes

from £50 / night

(14) Excellent 

24

Holiday home in Yarmouth

Isle of Wight / Yarmouth

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
“Lovely cottage in peaceful location” Beautiful cottage with all that you need for a relaxing holiday.Perfect for adults and children alike. Bedroom is pretty and spacious.
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from £90 / night

£400 - £550 / week

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from £90 / night

(12) Excellent 

13

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Beautiful” Such a beautiful chalet with lots of space. Excellent location for children as they could just play out on the green. Lovely decor and a well equipped kitchen. Cannot find any faults at all, will hope to come back again next year..
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from £36 / night

£250 - £485 / week

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Responds fast!
avg. 1 hour 43 minutes

from £36 / night

(11) Very Good 

28

Whitwell holiday cottage rental

Isle of Wight / Whitwell

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 5 km
  • Child friendly
  • Ask about pets
“We enjoyed the cottage and would return.” This was our third trip to the wonderful Isle of Wight. We enjoyed our weeks stay at the cottage and would recommend it. The cottage is like our own little holiday home, it's a bit like the owners have just
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from £80 / night

£350 - £600 / week

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from £80 / 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

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Responds fast!
avg. 1 hour 57 minutes

from £85 / night

(10) Excellent 

18

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

(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
  • Pet friendly
“Excellent Holiday home” We stayed here for 7 days and we can't speak highly enough about the accomodation. We have two young children and we also took my Dad who is 76. It catered for all of our needs and was very child proof so don't worry about ha
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from £65 / night

£450 - £950 / week

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Responds fast!
avg. 1 hour 5 minutes

from £65 / night

(3) Very Good 

10

Holiday home in Chale

Isle of Wight / Chale

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
“Highly recommended” Stayed here for one week with my husband (and his Assistance Dog), and our 2 sons (6 & 7 years old). Honestly we were amazed by the place! Being greeted by a bottle of wine and packet of chocolate biscuits on the kitchen table
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from £131 / night

£575 - £1200 / week

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from £131 / night

(42) Excellent 

15

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
“great location, great welcome” lovely house. amazing garden with all facilities. we received a great welcome. really enjoyed the holiday.
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from £60 / night

£225 - £680 / week

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from £60 / night

(9) 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 - £1250 / week

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Responds fast!
avg. 1 hour 41 minutes

from £195 / 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 57 minutes

from £75 / night

(40) 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
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from £65 / night

£450 - £695 / week

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from £65 / night

(4) Very Good 

20

Holiday bungalow in Yaverland

Sandown / Yaverland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“Well placed, well equipped - just what we wanted.” The bungalow is easy to find, and has ample parking for two cars if necessary. The garden is spacious and mostly grassed (although our daughter did manage to find a tree to fall out of!) There is a p
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from £80 / night

£425 - £1025 / week

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Responds fast!
avg. 2 hours 27 minutes

from £80 / night

(7) Very Good 

14

Brighstone Bay holiday cottage rental

Brighstone / Brighstone Bay

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Fabulous, spotless, friendly holiday farm!” This was a great place to stay, we stayed in the converted stables and it was beautiful. 3 good sized bedrooms, very comfortable lounge with satalite tv and a well equipt kitchen with everything you could ne
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from £89 / night

£535 - £1510 / week

Enquire View

from £89 / night

(1) Excellent 

10

Holiday home with golf nearby in Cowes

Cowes / West Cowes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £152 / night

£605 - £4000 / week

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from £152 / night

(1) Excellent 

17

Barn rental in Porchfield

Isle of Wight / Porchfield

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Pet friendly

from £450 / night

£750 - £1800 / week

Enquire View

from £450 / night

(3) Very Good 

11

Holiday lodge with golf nearby in Ryde

Isle of Wight / Ryde

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km

from £40 / night

£280 - £425 / week

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Responds fast!
avg. 3 hours 30 minutes

from £40 / night

(2) Very Good 

14

Sandown holiday chalet rental

Isle of Wight / Sandown

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly

from £50 / night

£300 - £525 / week

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Responds fast!
avg. 2 hours 17 minutes

from £50 / night

19

Holiday home 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

from £100 / night

£575 - £1300 / week

Enquire View

from £100 / night

(8) 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

(2) Excellent 

13

Cowes holiday townhouse rental

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Private garden

from £95 / night

£475 - £1800 / week

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Responds fast!
avg. 3 hours 2 minutes

from £95 / 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
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from £125 / night

£450 - £795 / week

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Responds fast!
avg. 1 hour 51 minutes

from £125 / night

(14) 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
“Mrs” Fantastic stay. Keep going back. Such a great base to see the island and perfect for a couple or small family. We have also taken the parents -in-law who have taken one apartment and we the other.
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from £45 / night

£225 - £440 / week

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Responds fast!
avg. 3 hours 21 minutes

from £45 / night

(5) Excellent 

Certificate of Excellence

16

Holiday home in Sandown

Isle of Wight / Sandown

2 4 Min stay varies

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

Certificate of Excellence

from £65 / night

£240 - £631 / week

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Responds fast!
avg. 2 hours 24 minutes

from £65 / night

1