Walking holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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398 Holiday homes

Filters applied: Walking holidays

(5) Excellent 

Certificate of Excellence

15

Holiday chalet in Yaverland

Sandown / Yaverland

2 6 3 nights min

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

Certificate of Excellence

from £50 / night

£300 - £510 / week

Book View

Responds fast!
avg. 3 hours 7 minutes

from £50 / night

(9) Excellent 

Certificate of Excellence

20

Holiday home rental

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“Home from Home - by the Seaside!” The cottage was warm, cosy and had some lovely homely touches that immediately made us feel at home. The location was perfect - under 5 minutes from the Red Funnel terminal, a stone's throw from the marina and a short
…see more

Certificate of Excellence

from £80 / night

£625 - £1120 / week

Book View

Responds fast!
avg. 1 hour 9 minutes

from £80 / night

(31) Excellent 

Certificate of Excellence

8

Cottage rental in Newport

Isle of Wight / Newport

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Bella cottage Newport isle of wight” Situated on the edge of Newport a short walk into the town. Lovely secluded garden and off street parking. 2 double bedrooms one en suite and a single. Nice sized family kitchen.
…see more

Certificate of Excellence

from £80 / night

£630 - £1120 / week

Book View

Responds fast!
avg. 2 hours 5 minutes

from £80 / night

Featured properties

(7) Very Good 

Certificate of Excellence

23

Holiday cottage in Ventnor

Isle of Wight / Ventnor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“Very homely and comfortable” Very nice, very clean, good towels and bedding sheets. Good situation, very pretty house and Garden. Lots of nice details, detergent, coffee, tea, bread, butter, milk, chocolates, a welcome pack. No parking outside the ho
…see more

Certificate of Excellence

from £95 / night

£525 - £1050 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from £95 / night

23

Niton holiday home rental

Isle of Wight / Niton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £282 / night

£925 - £2025 / week

Enquire View

from £282 / night

(12) Excellent 

15

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
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from £33 / night

£233 - £570 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from £33 / night

(6) Excellent 

11

Holiday home letting

Isle of Wight / Newport

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Private garden

from £50 / night

£325 - £2080 / week

Book View

from £50 / night

13

Holiday townhouse in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary

from £70 / night

£375 - £1200 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £70 / night

(33) Excellent 

Certificate of Excellence

22

Holiday barn with golf nearby in Freshwater

Freshwater / Freshwater Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Lovely place fab location” We really enjoyed our stay here- we hadn't realised how close to the sea it was and how accessible everything is. The cottage is lovely, lots of information and a good selection of books which the kids loved. Thank you!
…see more

Certificate of Excellence

from £55 / night

£360 - £1100 / week

Book View

Responds fast!
avg. 2 hours 21 minutes

from £55 / night

(11) Excellent 

18

Holiday chalet in Ventnor Bay

Ventnor / Ventnor Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Pet friendly

from £102 / night

£416 - £542 / week

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Responds fast!
avg. 3 hours 8 minutes

from £102 / night

(6) Excellent 

21

Holiday bungalow rental

Freshwater / Freshwater Bay

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

from £36 / night

£250 - £480 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £36 / 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
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Certificate of Excellence

from £70 / night

£350 - £600 / week

Book View

Responds fast!
avg. 1 hour 53 minutes

from £70 / night

(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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Responds fast!
avg. 3 hours 36 minutes

from £150 / night

(26) Excellent 

24

Holiday tree house in Whippingham

Isle of Wight / Whippingham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children age 5+
“a holiday with a difference” We had a week away at the tree house and didn't tell the children (age range from 4 - 14) where we were staying Upon arrival they couldn't believe we were staying in a tree house. The walk down the path covered by bamboo
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from £150 / night

£550 - £1300 / week

Book View

from £150 / night

(38) 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

Book View

Responds fast!
avg. 2 hours 39 minutes

from £38 / night

(14) Excellent 

24

Godshill holiday cottage rental

Godshill / Roud

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Swimming pool
“Mrs Jan walton” Really lovely cottage tucked away in the most peaceful of locations, set in a beautiful garden with gingerbread house over looking a pond perfect for afternoon tea. As the cottage is towards the centre of the island it is a good locati
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from £79 / night

£550 - £995 / week

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from £79 / night

(21) Excellent 

Certificate of Excellence

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
“Fantastic accommodation” My parents and I stayed at The Lodge from 13th to 20th May and I have to say we absolutely fell off in love with this beautiful cottage and was very sad to leave it! It is ideally situated in a gorgeous lane, surrounded by co
…see more

Certificate of Excellence

from £52 / night

£360 - £700 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £52 / 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

Book View

Responds fast!
avg. 2 hours 19 minutes

from £36 / night

(15) Excellent 

24

Cottage rental in Totland

Totland Bay / Totland Bay

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“Spacious elegant cottage in beautiful surroundings” Little Mount was a great choice for our small family. It was spacious with a large lounge and master bedroom and well equipped. The large rambling gardens had an amazing sea view with access to the c
…see more

from £110 / night

£750 - £895 / week

Book View

from £110 / night

(1) Excellent 

12

Bonchurch holiday cottage rental

Ventnor / Bonchurch

2 4 Min stay varies

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

from £108 / night

£350 - £600 / week

Enquire View

from £108 / 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

Book View

Responds fast!
avg. 2 hours 27 minutes

from £300 / night

(7) Excellent 

20

Holiday apartment in Cowes

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 1 km
  • Suitable for children age 5+
  • Car not necessary
“Great Location and Facilities” This modern and luxurious fully equipped apartment was ideal for our stay with our 87 year old Mother, 5 mins walk from centre of Cowes, with a balcony overlooking the Harbour and a designated on site parking space. Ca
…see more

from £100 / night

£370 - £2300 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £100 / night

(6) Excellent 

22

Barn rental in Ryde

Isle of Wight / Ryde

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
“Fabulously spacious barn on working farm sleeping 12 with amazing views and” Really enjoyable stay at Kemphill Farm. Very spacious and incredibly well equipped with everything you could need. Plenty of space to sleep 12 of us young and old and each of
…see more

from £210 / night

£980 - £2400 / week

Book View

from £210 / 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
…see more

from £90 / night

£398 - £696 / week

Enquire View

from £90 / night

(1) Excellent 

13

Holiday apartment in East Cowes

Isle of Wight / East Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary

from £75 / night

£425 - £800 / week

Enquire View

from £75 / 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

Book View

from £57 / 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

Book View

Responds fast!
avg. 2 hours 23 minutes

from £125 / night

(10) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £70 / night

£390 - £520 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from £70 / night

(13) 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
“Great little house” A lovely place to stay, all you need and very well designed and decorated. Great little spot, close to lovely cafe and beach.
…see more

from £60 / night

£385 - £1575 / week

Book View

from £60 / night

(1) Excellent 

11

Caravan/mobile home rental in Bembridge

Isle of Wight / Bembridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Excellent” Lovely caravan, on a great site, close to all amenities and a nice beach is accessible from the site.
…see more

from £50 / night

£700 - £800 / week

Book View

Responds fast!
avg. 2 hours 31 minutes

from £50 / night

24

Cowes holiday guest house rental

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Suitable for children age 5+
  • Private garden

from £450 / night

£1570 - £5200 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from £450 / night

(5) Excellent 

20

Cottage rental in Whitwell

Ventnor / Whitwell

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
“A wonderful holiday in a beautiful cottage” We had a fantastic week at Maytime Cottage this August. The cottage was clean and fresh when we arrived and it is airy and spacious with loads of character. It made you feel right at home. There was good inf
…see more

from £105 / night

£450 - £890 / week

Enquire View

from £105 / night

11

Newchurch holiday lodge rental

Sandown / Newchurch

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from £214 / night

£1495 - £1545 / week

Book View

Responds fast!
avg. 3 hours 36 minutes

from £214 / night

(9) Excellent 

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 km
  • Child friendly
“Lovely, cosy and comfortable” We had a wonderful stay at the bungalow, it was cosy and comfortable. It was in a lovely spot and it would be lovely to stay again. I would defiantly recommend it.
…see more

from £45 / night

£300 - £575 / week

Book View

Responds fast!
avg. 1 hour 49 minutes

from £45 / night

(2) Excellent 

13

Holiday home in East Cowes

Isle of Wight / East Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden

from £170 / night

£425 - £850 / week

Enquire View

from £170 / night

14

Sandown holiday chalet rental

Isle of Wight / Sandown

2 4 Min stay varies

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

from £119 / night

£275 - £475 / week

Enquire View

from £119 / night

(14) Excellent 

19

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.
…see more

from £45 / night

£225 - £365 / week

Book View

Responds fast!
avg. 3 hours 54 minutes

from £45 / night

(3) 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

Book View

from £65 / night

(22) 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....
…see more

from £47 / night

£325 - £516 / week

Book View

Responds fast!
avg. 24 minutes

from £47 / night

(3) Very Good 

8

Holiday cottage in Cowes

Cowes / West Cowes

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children age 5+

from £85 / night

£350 - £2000 / week

Book View

from £85 / night

1