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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1,563 Holiday homes

(6) Excellent 

Certificate of Excellence

26

Apartment rental in Ventnor Bay

Ventnor / Ventnor Bay

2 4 Min stay varies

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

Certificate of Excellence

from £90 / night

£370 - £645 / week

Book View

Responds fast!
avg. 2 hours 32 minutes

from £90 / night

(23) Excellent 

Certificate of Excellence

16

Holiday chalet in Sandown

Isle of Wight / Sandown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.2 km
  • Child friendly
  • Pet friendly
“perfect chalet” we needed somewhere pet friendly to stay for a short break while we had a reunion with family and birthday celebrations. absolutely ideal. well presented and very comfy. if it was a summer break for families it is ideal as the beach i
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Certificate of Excellence

from £40 / night

£250 - £500 / week

Book View

Responds fast!
avg. 29 minutes

from £40 / night

(2) Excellent 

20

Holiday apartment in Shanklin

Shanklin / Old Village

1 2 7 nights min

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

from £57 / night

£395 - £500 / week

Book View

Responds fast!
avg. 3 hours 24 minutes

from £57 / night

(3) Excellent 

Certificate of Excellence

22

Holiday apartment in Cowes

Isle of Wight / Cowes

2 5 Min stay varies

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

Certificate of Excellence

from £130 / night

£600 - £2,500 / week

Book View

from £130 / night

(2) Excellent 

24

Niton holiday apartment rental

Isle of Wight / Niton

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0.5 km
  • Child friendly

from £65 / night

£450 - £1,190 / week

Book View

from £65 / night

(2) 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 £65 / night

£450 - £1,195 / week

Book View

Responds fast!
avg. 1 hour 55 minutes

from £65 / night

(4) Very Good 

13

Holiday apartment in Shanklin

Isle of Wight / Shanklin

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £150 / night

£665 - £1,050 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £150 / night

(4) Very Good 

12

Holiday apartment in Bembridge

Bembridge / Bembridge Harbour

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £100 / night

£325 - £535 / week

Book View

from £100 / night

(8) Excellent 

Certificate of Excellence

12

Yarmouth holiday home rental

Isle of Wight / Yarmouth

3 6 Min stay varies

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

Certificate of Excellence

from £75 / night

£525 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £75 / night

(18) Excellent 

Certificate of Excellence

20

Holiday home with golf nearby in Sandown

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“A fantastic house in a great location, perfect for a family holiday!” We stayed at 7 Firs Court at Sandown on the Isle of Wight for a week in September. The house is lovely with everything provided for a perfect holiday for couples or families with ch
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Certificate of Excellence

from £49 / night

£295 - £745 / week

Book View

Responds fast!
avg. 12 minutes

from £49 / night

(10) Excellent 

Certificate of Excellence

23

Cowes holiday home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Private garden
“Location location location” This cottage is the perfect location. Close to seafront, parkland, cowes high street with gift shops and a little Sainsbury's / marks and spencer food outlet. So many options for eating out here too and lots going on in the
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Certificate of Excellence

from £150 / night

£900 / week

Book View

Responds fast!
avg. 1 hour 3 minutes

from £150 / night

(1) Excellent 

14

Holiday chalet in Bembridge

Isle of Wight / Bembridge

2 4 Min stay varies

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

from £74 / night

£295 - £495 / week

Enquire View

from £74 / night

(1) Very Good 

10

Holiday bungalow in Brading

Isle of Wight / Brading

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £58 / night

£400 - £525 / week

Enquire View

from £58 / night

13

Chalet rental in Bonchurch

Ventnor / Bonchurch

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £97 / night

£455 - £913 / week

Book View

Responds fast!
avg. 3 hours 31 minutes

from £97 / night

(1) Excellent 

11

Porchfield holiday cottage rental

Isle of Wight / Porchfield

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Ask about pets

from £350 / night

£450 - £1,500 / week

Enquire View

from £350 / night

(1) Excellent 

15

Sandown holiday chalet rental

Isle of Wight / Sandown

2 6 3 nights min

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

from £50 / night

£300 - £616 / week

Book View

from £50 / 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

Book View

Responds fast!
avg. 1 hour 53 minutes

from £225 / night

21

Cowes holiday home rental

Isle of Wight / Cowes

2 4 Min stay varies

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

from £100 / night

£450 - £1,700 / week

Book View

from £100 / night

16

Ventnor holiday apartment rental

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.1 km
  • Car not necessary
  • Private garden

from £90 / night

£850 - £880 / week

Book View

Responds fast!
avg. 1 hour 14 minutes

from £90 / night

(6) Excellent 

Certificate of Excellence

15

Holiday chalet in Yaverland

Sandown / Yaverland

2 6 Min stay varies

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

Certificate of Excellence

from £50 / night

£300 - £616 / week

Book View

from £50 / 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

Book View

Responds fast!
avg. 1 hour 22 minutes

from £75 / night

(10) Excellent 

Certificate of Excellence

32

Holiday home in East Cowes

Isle of Wight / East Cowes

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
“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
…see more

Certificate of Excellence

from £135 / night

£690 - £1,110 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from £135 / night

(3) Very Good 

18

Holiday home in Shanklin

Isle of Wight / Shanklin

4 8 Min stay varies

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

from £131 / night

£525 - £1,275 / week

Enquire View

from £131 / night

(54) Excellent 

Certificate of Excellence

23

Holiday log cabin with indoor pool in Ryde

Isle of Wight / Ryde

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Fantastic place for a family holiday” Had a lovely week in the cabin, we all enjoyed the pool especially my two boys. Beautiful and relaxing setting. Gill and Dave very friendly and made us feel very welcome. Hope to return soon.
…see more

Certificate of Excellence

from £96 / night

£674 - £1,400 / week

Book View

Responds fast!
avg. 1 hour 18 minutes

from £96 / night

(10) Excellent 

Certificate of Excellence

18

Holiday townhouse in Cowes

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
“Great house” I stayed in the house with my family and mum and dad and we had a fantastic week, the house is clean and big enough for a big family without feeling like your on top of each other, the garden was lovely and the house is close to a lovely
…see more

Certificate of Excellence

from £80 / night

£460 - £1,100 / week

Book View

Responds fast!
avg. 57 minutes

from £80 / night

(13) Excellent 

Certificate of Excellence

24

Holiday chalet in Niton

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 5 km
  • Car not necessary
“Terrific Little Hideaway” This is a terrific little ‘hideaway’ situated in a beautiful area. Niton itself is tucked away at the very bottom of the island and a real secret haven for walkers. It is an area of outstanding beauty and as such affords be
…see more

Certificate of Excellence

from £50 / night

£275 - £325 / week

Book View

Responds fast!
avg. 22 minutes

from £50 / night

(12) Very Good 

9

Home rental in Cowes

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
“Greta location, clean, tidy house” The location of the house was fantastic. We could access the town so easily and supermarkets and fish and chip shop were literally around the corner. The house itself was great, very clean and a well equipped kitchen
…see more

from £120 / night

£700 - £850 / week

Book View

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

Book View

from £150 / night

(37) 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

Certificate of Excellence

from £55 / night

£400 - £1,100 / week

Book View

Responds fast!
avg. 1 hour 50 minutes

from £55 / night

(47) 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 / week

Enquire View

from £65 / night

19

Sandown holiday apartment let

Isle of Wight / Sandown

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Suitable for children age 5+

from £86 / night

£600 / week

Book View

from £86 / night

(24) Excellent 

16

Holiday home 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
“Perfect in every way!” My wife and our 6 month old baby passed a delightful 3 nights at Crew's Nest n late September 2015. The house is a fantastic size and is beautifully decorated by the owners. The finish really is perfect. The owners also left an
…see more

from £175 / night

£700 - £3,070 / week

Enquire View

from £175 / night

(1) Excellent 

8

Holiday lodge in Ventnor

Isle of Wight / Ventnor

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly

from £115 / night

£805 / week

Enquire View

from £115 / night

(14) Excellent 

Certificate of Excellence

11

Sandown holiday chalet rental

Isle of Wight / Sandown

2 4 Min stay varies

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

Certificate of Excellence

from £65 / night

£500 / week

Book View

Responds fast!
avg. 8 minutes

from £65 / night

(9) Very Good 

Certificate of Excellence

12

Sandown holiday chalet rental

Isle of Wight / Sandown

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“unforgettable experience of joy.” Excellent location and beautiful place to stay.friendly owner of the chalet.no problem while staying.
…see more

Certificate of Excellence

from £50 / night

£300 - £616 / week

Book View

from £50 / night

13

Holiday apartment rental

Isle of Wight / Cowes

2 4 Min stay varies

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

from £82 / night

£375 - £625 / week

Enquire View

from £82 / night

(4) Excellent 

16

Holiday townhouse rental

Isle of Wight / Cowes

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 2 km
  • Child friendly
  • Car not necessary
“This place is so great we have been back again!” I have stayed here twice with extended family. The house is spacious and comfortable with great style. The property is located in a great spot with easy walking access to Cowes, a variety of shops, pubs
…see more

from £320 / night

£1,900 - £2,222 / week

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from £320 / 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

Book View

Responds fast!
avg. 1 hour 36 minutes

from £145 / night

(9) Very Good 

23

Holiday chalet in Niton

Isle of Wight / Niton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 5 km
  • Private garden
“Well thought out accommodation in pretty surroundings” Stayed for two nights but wish it could have been longer. The chalet has everything you could need and nicely decorated too. There's a lot of info about the area with maps and things to do and you
…see more

from £45 / night

£280 - £415 / week

Book View

Responds fast!
avg. 39 minutes

from £45 / night

24

Newchurch holiday cottage rental

Sandown / Newchurch

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from £250 / night

£1,400 - £1,975 / week

Book View

from £250 / night