Cottages in Isle of Wight and Self catering accommodation – Holiday Lettings - Holiday Rentals Isle of Wight

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Isle of Wight

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981 Holiday homes

(1) Very Good 

24

Holiday home in Ventnor Bay

Ventnor / Ventnor Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £125 / night

£750 - £1005 / week

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Responds fast!
avg. 2 hours 34 minutes

from £125 / night

(3) Very Good 

21

Villa letting in Cowes

Cowes / West Cowes

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from £150 / night

£750 - £5200 / week

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Responds fast!
avg. 2 hours 28 minutes

from £150 / night

20

Holiday chalet in Ventnor Bay

Ventnor / Ventnor Bay

2 4 Min stay varies

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

from £80 / night

£380 - £768 / week

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from £80 / night

Featured properties

(3) Excellent 

20

Holiday apartment in Newchurch

Sandown / Newchurch

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Pet friendly
  • Private garden

from £60 / night

£420 / week

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Responds fast!
avg. 20 minutes

from £60 / night

(2) Very Good 

11

Cowes holiday apartment rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

from £225 / night

£750 - £2500 / week

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from £225 / night

(4) Excellent 

17

Home rental in Ventnor

Isle of Wight / Ventnor

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary

from £95 / night

£450 - £900 / week

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Responds fast!
avg. 1 hour 45 minutes

from £95 / 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

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Responds fast!
avg. 3 hours 39 minutes

from £52 / night

(3) Excellent 

12

Holiday home in Ventnor

Isle of Wight / Ventnor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask owner if suitable for children
  • Private garden
“Fantastic accommodation combined with superb weather result a holiday to remember.” The property is superbly appointed and ideally located for exploring the IOW. The views across the channel from the open living/dining room area are fantastic. A holid
…see more

from £111 / night

£775 - £1399 / week

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from £111 / night

(2) Very Good 

26

Apartment rental in Ventnor Bay

Ventnor / Ventnor Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from £90 / night

£370 - £625 / week

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Responds fast!
avg. 3 hours 59 minutes

from £90 / 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

12

Holiday apartment in Shanklin

Isle of Wight / Shanklin

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly

from £74 / night

£460 - £499 / week

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from £74 / 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

9

Chalet rental in Sandown

Isle of Wight / Sandown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly

from £30 / night

£630 / week

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from £30 / 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

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Responds fast!
avg. 2 hours 28 minutes

from £70 / 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

(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

Book View

from £72 / 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

10

Holiday home in Cowes

Isle of Wight / Cowes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

from £125 / night

£625 - £4750 / week

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Responds fast!
avg. 2 hours 28 minutes

from £125 / night

(3) Average 

16

Wootton Bridge holiday cottage rental

Isle of Wight / Wootton Bridge

3 6 7 nights min

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

from £125 / night

£875 / week

Book View

Responds fast!
avg. 2 hours 50 minutes

from £125 / night

(3) Very Good 

39

Holiday cottage in Seaview

Isle of Wight / Seaview

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £116 / night

£499 - £1015 / week

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from £116 / night

(16) Excellent 

25

Ventnor Bay holiday apartment rental

Ventnor / Ventnor Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Private garden
“Beautiful Apartment” If you want opulence then this is the place. Just loved this apartment. It was quirky but also very elegantly decorated, in a lovely location opposite the park and within easy walking distance to the town. The outside space was ve
…see more

from £63 / night

£441 / week

Book View

Responds fast!
avg. 2 hours 43 minutes

from £63 / night

(23) Very Good 

22

Cowes holiday cottage rental

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“The White House” The property location is excellent, a few minutes’ walk from the high street with excellent well known supermarkets. Fantastic local eateries with no commercial coffee shop in sight, brilliant. Cowes was unexpected but I and my family
…see more

from £73 / night

£459 - £1247 / week

Book View

Responds fast!
avg. 3 hours 11 minutes

from £73 / night

(2) Very Good 

15

Holiday apartment rental

Cowes / West Cowes

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask owner if suitable for children

from £90 / night

£375 - £1400 / week

Book View

Responds fast!
avg. 2 hours 28 minutes

from £90 / 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. 3 hours 29 minutes

from £36 / night

(5) Excellent 

15

Holiday home in Ryde

Isle of Wight / Ryde

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £95 / night

£650 - £850 / week

Book View

from £95 / night

(7) 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
“What a find !” We had a fantastic week on the IoW, seven of us in total with extended family, and Yachtsman's Rest easily accommodated us all in comfort. Plenty of bathrooms, all well placed next to bedrooms or en-suite, no kids squabbling about wh
…see more

from £150 / night

£750 - £2400 / week

Book View

Responds fast!
avg. 2 hours 6 minutes

from £150 / night

(10) Excellent 

Certificate of Excellence

22

Holiday cottage in Brighstone

Isle of Wight / Brighstone

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Lovely cottage” Everything you need, location ideal, easy to get to places to eat, village walking distance, would recommend, will go back,
…see more

Certificate of Excellence

from £99 / night

£345 - £785 / week

Book View

Responds fast!
avg. 1 hour 3 minutes

from £99 / night

(3) Excellent 

17

Holiday home in Newport

Newport / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation

from £250 / night

£950 - £2500 / week

Book View

Responds fast!
avg. 2 hours 6 minutes

from £250 / night

(6) Very Good 

Certificate of Excellence

26

Holiday apartment letting

Isle of Wight / Sandown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

Certificate of Excellence

from £35 / night

£200 - £380 / week

Book View

Responds fast!
avg. 2 hours 57 minutes

from £35 / 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.
…see more

from £185 / night

£760 - £2600 / week

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from £185 / night

(12) Excellent 

Certificate of Excellence

22

Shorwell holiday cottage rental

Isle of Wight / Shorwell

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
“Brilliant” We stayed for a week and it was like a home from home, everything you could need or want. We really enjoyed our visit to the Isle of Wight and Brookside Cottage provided a lovely haven to come back to after a day exploring.
…see more

Certificate of Excellence

from £99 / night

£385 - £985 / week

Book View

Responds fast!
avg. 1 hour 3 minutes

from £99 / night

(9) Excellent 

20

Holiday home with golf nearby in Cowes

Cowes / West Cowes

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Lovely sailing themed house in great location” Stylish decor, very comfy bedrooms and all the domestic equipment that was needed was there along with some nice Jazz CDs! Good location with teenagers as able to walk into main street of Cowes within
…see more

from £100 / night

£700 / week

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from £100 / 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

(1) Very Good 

11

Holiday apartment in Ryde

Isle of Wight / Ryde

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
“A comfortable flatlet with a convenient location in Ryde” A large main room with a comfortable bed and a well equipped kitchen. Good central heating for an out of season stay. A short walk along the seafront to get to central Ryde. There is a good wa
…see more

from £39 / night

£175 - £395 / week

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from £39 / night

(2) Very Good 

24

Shanklin holiday apartment rental

Isle of Wight / Shanklin

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 0.05 km
  • Suitable for children age 5+

from £36 / night

£207 - £453 / week

Book View

Responds fast!
avg. 18 minutes

from £36 / night

(32) Excellent 

Certificate of Excellence

27

Holiday home in Yarmouth

Isle of Wight / Yarmouth

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child 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

Certificate of Excellence

from £200 / night

£920 - £1825 / week

Book View

Responds fast!
avg. 3 hours 10 minutes

from £200 / night

(19) Very Good 

Certificate of Excellence

21

Chalet rental in Yaverland with golf nearby

Sandown / Yaverland

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“Lovely chalet” We stayed at Phil's chalet for 1 night and it was perfect. We would consider for a longer stay. The chalet had everything you need (except linen but we knew that well in advance). Very good value for money. Communication with Phil was v
…see more

Certificate of Excellence

from £20 / night

£200 - £390 / week

Book View

from £20 / night

(6) Excellent 

Certificate of Excellence

63

Seaview holiday cottage rental

Isle of Wight / Seaview

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

Certificate of Excellence

from £88 / night

£379 - £799 / week

Book View

from £88 / night

(2) Very Good 

21

Holiday chalet in Yaverland

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.2 km
  • Child friendly
  • Car not necessary
“Lovely Stay, great location” We had a lovely time here, the rooms are spacious for a chalet and there is a large outdoor grassy area that the children loved. The owner was very friendly and left plenty of information in the chalet (I.e places to go, t
…see more

from £38 / night

£225 - £470 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £38 / night

(27) 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

£360 - £630 / week

Book View

from £50 / night

1