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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1,565 Holiday homes

(1) Excellent 

20

Holiday cottage in Newchurch

Sandown / Newchurch

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 km
  • Child friendly
  • Ask about pets

from £133 / night

£840 - £1,120 / week

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from £133 / night

(3) Very Good 

22

Holiday apartment in Shanklin

Isle of Wight / Shanklin

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Excellent Accommodation with very friendly owners that made stay very enjoyable.” Shanklin is a very good place to stay with nice beach, crazy golf and choice of supermarkets within short distance. I would recommend to other family's to stay here.
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from £150 / night

£1,000 - £1,305 / week

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from £150 / night

(5) Excellent 

44

Holiday chalet in Sandown

Isle of Wight / Sandown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £54 / night

£249 - £599 / week

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Responds fast!
avg. 1 hour 19 minutes

from £54 / night

(4) Excellent 

10

Holiday chalet in Sandown

Isle of Wight / Sandown

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
“Nice place to use as as base” Very clean and modernised accommodation. Well happy good value. Nice quiet location . Close to the local beach.
…see more

from £50 / night

£300 - £616 / week

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from £50 / night

(8) Excellent 

Certificate of Excellence

14

Cowes holiday home rental

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“An excellent house for a family Christmas, and a great location for summer visitors.” Twelve of us spent our family Christmas in Alban house and it was perfect. The house is lovely, great location, spotlessly clean, warm and comfortable. Carol could
…see more

Certificate of Excellence

from £700 / night

£2,500 - £4,000 / week

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from £700 / night

(8) Very Good 

Certificate of Excellence

17

Caravan/mobile home rental in Rookley with shared pool

Isle of Wight / Rookley

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
“Clean and Tidy” Caravan was exceptionally clean and tidy on arrival. Well stocked with enough plates and cutlery for the 5 of us. ( Although the table is not big enough for us to all eat at the same time). The site was clean and very quiet. We used th
…see more

Certificate of Excellence

from £80 / night

£530 - £650 / week

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Responds fast!
avg. 58 minutes

from £80 / night

5

Holiday chalet in Sandown

Isle of Wight / Sandown

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

from £50 / night

£350 / week

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from £50 / night

16

Gurnard holiday home rental

Isle of Wight / Gurnard

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 0 km
  • Child friendly
  • Pet friendly

from £145 / night

£595 - £2,170 / week

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Responds fast!
avg. 1 hour 36 minutes

from £145 / night

(1) Excellent 

12

Holiday chalet with golf nearby in Sandown

Isle of Wight / Sandown

2 6 Min stay varies

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

from £49 / night

£325 - £600 / week

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Responds fast!
avg. 1 hour 23 minutes

from £49 / night

(10) Very Good 

Certificate of Excellence

16

Ventnor holiday apartment rental

Isle of Wight / Ventnor

2 6 Min stay varies

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

Certificate of Excellence

from £80 / night

£505 - £735 / week

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Responds fast!
avg. 2 hours 38 minutes

from £80 / night

(22) Very Good 

Certificate of Excellence

25

Apartment rental in Totland

Totland Bay / Totland Bay

4 8 Min stay varies

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

Certificate of Excellence

from £225 / night

£675 - £1,725 / week

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Responds fast!
avg. 1 hour 53 minutes

from £225 / night

(5) Very Good 

11

Holiday apartment accommodation

Isle of Wight / Sandown

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £40 / night

£630 / week

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Responds fast!
avg. 2 hours 40 minutes

from £40 / night

(7) Very Good 

13

Shanklin holiday home rental

Isle of Wight / Shanklin

4 8 7 nights min

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

from £100 / night

£695 - £1,595 / week

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from £100 / night

(8) Excellent 

Certificate of Excellence

27

Holiday chalet in Sandown

Isle of Wight / Sandown

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Nearest beach 0.2 km
  • Child friendly
  • Pet friendly
“A very comfortable, well renovated chalet with everything needed for a pleasant stay.” Many thanks to Ian and Diane for providing Fossils Rest. Everything needed for a comfortable stay and creatively renovated to a high standard. Conveniently sited fo
…see more

Certificate of Excellence

from £50 / night

£250 - £475 / week

Book View

Responds fast!
avg. 1 hour 9 minutes

from £50 / night

17

Holiday bungalow in Bembridge

Isle of Wight / Bembridge

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly

from £85 / night

£710 - £1,300 / week

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from £85 / night

(9) Very Good 

21

Cowes holiday home let

Cowes / West Cowes

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Private garden

from £120 / night

£550 - £3,000 / week

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from £120 / night

(3) Very Good 

16

Apartment rental in Cowes

Isle of Wight / Cowes

3 6 Min stay varies

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

from £150 / night

£700 - £3,100 / week

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from £150 / night

(6) Very Good 

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 £105 / night

£396 - £714 / week

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Responds fast!
avg. 2 hours 17 minutes

from £105 / night

(23) Excellent 

22

Freshwater holiday home rental

Freshwater / Freshwater Bay

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Character house, in a beautiful location” Thank you Paul for letting us stay at Tower House during the week of our wedding! The house itself is beautiful with lots of quirky, original features. The location was perfect, it was just around the corner f
…see more

from £156 / night

£1,090 - £1,890 / week

Enquire View

from £156 / night

(2) Excellent 

11

Holiday apartment in Ventnor

Isle of Wight / Ventnor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £100 / night

£600 - £850 / week

Enquire View

from £100 / night

(17) Very Good 

Certificate of Excellence

20

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 0.1 km
  • Child friendly
“New year break” A fabulous apartment even while been battered by the winds the views are fantastic it has everything you could want other than sunshine
…see more

Certificate of Excellence

from £145 / night

£964 - £1,162 / week

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Responds fast!
avg. 2 hours 42 minutes

from £145 / 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 £200 / night

£990 - £2,400 / week

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from £200 / night

(8) Very Good 

11

Ventnor holiday apartment rental

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
“holiday in ventnor” excellent holiday flat in probably best position . lovely town and beautiful coastline . well stocked flat and great comfortable bed. I would highly recommend for up to four people.
…see more

from £79 / night

£550 - £945 / week

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from £79 / night

(4) Excellent 

42

Yarmouth holiday apartment rental

Isle of Wight / Yarmouth

2 4 Min stay varies

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

from £112 / night

£705 - £1,000 / week

Book View

Responds fast!
avg. 36 minutes

from £112 / night

(3) Very Good 

27

Holiday home with golf nearby in Ryde

Isle of Wight / Ryde

5 10 7 nights min

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

from £368 / night

£2,570 - £4,630 / week

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from £368 / night

(9) Very Good 

14

Brighstone Bay holiday caravan/mobile home rental

Brighstone / Brighstone Bay

3 6 Min stay varies

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

from £74 / night

£445 - £1,200 / week

Enquire View

from £74 / 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
…see more

from £90 / night

£1,554 / week

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from £90 / night

19

Holiday cottage in Brading

Isle of Wight / Brading

4 8 Min stay varies

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

from £119 / night

£475 - £1,000 / week

Enquire View

from £119 / night

(28) 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
…see more

from £75 / night

£495 - £995 / week

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Responds fast!
avg. 1 hour 22 minutes

from £75 / night

(6) Very Good 

17

Holiday home in Ryde

Isle of Wight / Ryde

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £139 / night

£660 - £1,260 / week

Enquire View

from £139 / night

(4) Excellent 

21

Holiday home in Yarmouth

Isle of Wight / Yarmouth

6 8 Min stay varies

  • 6 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

from £281 / night

£1,900 - £2,650 / week

Book View

Responds fast!
avg. 45 minutes

from £281 / night

(16) Very Good 

10

Holiday home in Gurnard

Isle of Wight / Gurnard

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • 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

£1,575 / week

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from £60 / night

(2) Average 

13

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
  • Car not necessary

from £92 / night

£450 - £700 / week

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from £92 / night

(5) Excellent 

20

Holiday apartment with golf nearby in Shanklin

Isle of Wight / Shanklin

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.05 km
  • Child friendly

from £41 / night

£245 - £577 / week

Book View

Responds fast!
avg. 1 hour 31 minutes

from £41 / night

(1) Excellent 

19

Holiday home accommodation

Isle of Wight / Ventnor

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £458 / night

£1,800 - £3,750 / week

Enquire View

from £458 / night

(3) Average 

24

Ventnor holiday apartment rental

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
“Great and well-situated holiday apartment” We enjoyed a fantastic May half-term week at Appt 3 of Ventnor Holiday Villas. The apartment was clean and all the basic requirements a family needs for a week away from home. We loved having the first floor
…see more

from £90 / night

£370 - £645 / week

Book View

Responds fast!
avg. 2 hours 32 minutes

from £90 / night

(5) Very Good 

Certificate of Excellence

12

Holiday home letting

Isle of Wight / Cowes

2 4 Min stay varies

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

Certificate of Excellence

from £90 / night

£425 - £1,725 / week

Book View

from £90 / night

(1) Excellent 

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

from £54 / night

£225 - £400 / week

Enquire View

from £54 / night

(18) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £69 / night

£379 - £625 / week

Book View

Responds fast!
avg. 1 hour 23 minutes

from £69 / night

(2) Very Good 

16

Shanklin holiday home rental

Isle of Wight / Shanklin

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £180 / night

£1,100 - £3,000 / week

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Responds fast!
avg. 2 hours 18 minutes

from £180 / night