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

(4) Average 

11

Holiday home rental

Bembridge / Bembridge Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £100 / night

£510 - £1890 / week

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Responds fast!
avg. 3 hours 36 minutes

from £100 / night

(2) Excellent 

17

Cottage rental in Billingham

Isle of Wight / Billingham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 7 km
  • Child friendly
  • Pet friendly

from £125 / night

£465 - £1209 / week

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Responds fast!
avg. 1 hour 3 minutes

from £125 / night

(8) Excellent 

14

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Same High Standard” We stayed in Carisbrooke last year and loved it and really wanted to try the newly released Albert apartment after it's extensive renovations. In fact we booked a week over the Easter holiday without even seeing any photo's. We wer
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from £80 / night

£560 / week

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Responds fast!
avg. 2 hours 43 minutes

from £80 / night

Featured properties

(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 - £590 / week

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Responds fast!
avg. 2 hours 3 minutes

from £30 / 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. 1 hour 19 minutes

from £125 / night

17

B&b rental in Wootton Bridge

Isle of Wight / Wootton Bridge

1 2 1 night min

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

from £45 / night

£280 - £595 / week

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from £45 / night

(3) Very Good 

15

Apartment rental in Cowes

Isle of Wight / Cowes

3 6 Min stay varies

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

from £140 / night

£700 - £1400 / week

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Responds fast!
avg. 1 hour 19 minutes

from £140 / 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 £165 / night

£605 - £4000 / week

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from £165 / 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
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from £100 / night

£700 / week

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from £100 / night

(11) Very Good 

24

Holiday townhouse in Cowes

Cowes / West Cowes

5 10 Min stay varies

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

from £175 / night

£800 - £4100 / week

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Responds fast!
avg. 1 hour 19 minutes

from £175 / 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
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from £42 / night

£295 - £680 / week

Enquire View

from £42 / night

(7) Excellent 

15

Holiday chalet 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

from £95 / night

£665 - £1092 / week

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from £95 / 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 £40 / night

£300 - £525 / week

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Responds fast!
avg. 3 hours 12 minutes

from £40 / night

(13) Excellent 

26

Holiday home in Sandown

Isle of Wight / Sandown

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+

from £30 / night

£195 - £431 / week

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Responds fast!
avg. 3 hours 46 minutes

from £30 / night

15

Holiday chalet with shared pool in Gurnard

Isle of Wight / Gurnard

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly

from £70 / night

£350 - £600 / week

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Responds fast!
avg. 1 hour 53 minutes

from £70 / night

(10) Excellent 

19

Cowes holiday bungalow rental

Cowes / West Cowes

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Perfect location Beautiful well equipped Bungalow” Arrived in late January for a long weekend we were exceptionally lucky with the weather.The views are stunning.The bungalow was warm cosy and spacious just like home from home so many different places
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from £70 / night

£450 - £3250 / week

Enquire View

from £70 / night

23

Holiday cottage in Whitwell

Ventnor / Whitwell

2 4 Min stay varies

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

from £46 / night

£320 - £795 / week

Enquire View

from £46 / night

(4) Excellent 

16

Home rental in Ventnor

Isle of Wight / Ventnor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
“Light, Spacious, and very helpful” The property itself was a little complex to find. Despite clear instructions being given as to its whereabouts, the driveway entrance was missed as the sign faces approaching from the south (from the direction of Bla
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from £99 / night

£1554 / week

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from £99 / night

10

Holiday cottage in Bembridge

Bembridge / Bembridge Village

2 4 Min stay varies

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

from £50 / night

£395 - £695 / week

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from £50 / night

(4) Very Good 

16

Chalet rental in Yaverland

Sandown / Yaverland

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“A good place to stay” We had a great time in this chalet there was 6 of us the little things like milk in the fridge when we got there. Also having the bath for the 2 children we had with us as they dont like a shower. Puting a £1.00 in meter was no p
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from £23 / night

£160 - £500 / week

Enquire View

from £23 / night

19

Sandown holiday apartment let

Isle of Wight / Sandown

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Suitable for children age 5+

from £60 / night

£295 - £500 / week

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Responds fast!
avg. 3 hours 10 minutes

from £60 / 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

27

Holiday home in Ventnor

Isle of Wight / Ventnor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly

from £95 / night

£660 - £1600 / week

Book View

from £95 / night

(7) Very Good 

Certificate of Excellence

15

Holiday bungalow in Nettlestone

Isle of Wight / Nettlestone

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
“Amazing!!!” Lovely place to stay, close to beach and a local shop, short drive to anywhere else on the island. Views from lounge and balcony were great, sunrise, sunset, stars and moonrise over the sea. The busy shipping channel kept my 7yr old grands
…see more

Certificate of Excellence

from £65 / night

£450 - £1050 / week

Book View

Responds fast!
avg. 3 hours 36 minutes

from £65 / 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

17

Sandown holiday chalet rental

Isle of Wight / Sandown

2 4 3 nights min

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

from £50 / night

£200 - £450 / week

Enquire View

from £50 / night

(2) Very Good 

11

Holiday lodge in Shanklin

Isle of Wight / Shanklin

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

from £60 / night

£450 - £550 / week

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Responds fast!
avg. 3 hours 56 minutes

from £60 / night

(13) 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..
…see more

from £41 / night

£285 - £520 / week

Book View

Responds fast!
avg. 1 hour 43 minutes

from £41 / 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

(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

13

Holiday cottage with golf nearby in Freshwater

Isle of Wight / Freshwater

3 5 Min stay varies

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

from £120 / night

£495 - £825 / week

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from £120 / night

15

Holiday b&b in Brading

Isle of Wight / Brading

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 4 km
  • Child friendly
  • Ask about pets

from £120 / night

£840 / week

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Responds fast!
avg. 3 hours 50 minutes

from £120 / night

(14) Excellent 

12

Holiday townhouse rental

Cowes / West Cowes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary
“Perfect Holiday Letting” My family along with my friend's family ( group of 9 ) stayed in Yachtsman for 3 nights. We all thoroughly enjoyed our stay. Amazed to see the amenities that was made available. Kitchen is fully equipped with all necessary ing
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from £200 / night

£995 - £3250 / week

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from £200 / night

(11) Excellent 

8

Newport holiday b&b rental

Isle of Wight / Newport

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 5 km
  • Ask owner if suitable for children
“Restful Relaxing Haven” I stayed for a week at this wonderful B&B. It's close to Newport but in the countryside which is the perfect location for the IOW. Tina and Terry are warm and friendly hosts who can really cook the most wonderful food. The r
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from £85 / night

£595 / week

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Responds fast!
avg. 3 hours 47 minutes

from £85 / night

(8) Excellent 

14

Ryde holiday cottage rental

Isle of Wight / Ryde

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Car not necessary

from £72 / night

£500 - £1200 / week

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from £72 / night

(9) Excellent 

23

Yarmouth holiday home rental

Yarmouth / Fort Victoria

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Very nice house and helpful owners” Would highly recommend. Very nice house in Yarmouth. Owners v helpful with recomendations of where to eat/shop etc. Very child friendly and good value. Clean and well maintained and appointed. New boiler fitted jus
…see more

from £150 / night

£800 - £1750 / week

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Responds fast!
avg. 2 hours 41 minutes

from £150 / night

13

Cowes holiday apartment rental

Isle of Wight / Cowes

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly

from £90 / night

£400 - £1500 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £90 / night

(4) Very Good 

19

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

Enquire View

from £131 / night

5

Newchurch holiday b&b rental

Sandown / Newchurch

4 2 1 night min

  • 4 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly

from £85 / night

£595 / week

Book View

from £85 / night

(10) Very Good 

24

Cowes holiday home rental

Cowes / West Cowes

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Great location - beautiful house” Just returned from a weekend stay at Halyard house. The location was perfect being right in the centre of Cowes, very near to the shops and easy to find from the Ferry. Bedrooms were cosy and comfortable. Although t
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from £100 / night

£700 / week

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from £100 / night

1