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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1,581 Holiday homes

17

Calbourne holiday barn rental

Isle of Wight / Calbourne

1 2 Min stay varies

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

from £35 / night

£250 - £425 / week

Enquire View

from £35 / night

15

Holiday home in Cowes

Isle of Wight / Cowes

4 10 Min stay varies

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

from £140 / night

£650 - £4,750 / week

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from £140 / night

(2) Excellent 

12

Niton holiday chalet rental

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

from £72 / night

£236 - £337 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £72 / night

(20) Excellent 

Certificate of Excellence

30

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“An idyllic setting” We stayed for a long weekend and were thoroughly delighted by every aspect of our stay. Our hosts were friendly and accommodating; the venue pristine and comfortable and we cannot wait to go back. Highly recommended!

Certificate of Excellence

from £110 / night

£450 - £850 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from £110 / night

(18) Excellent 

Certificate of Excellence

25

Ventnor Bay holiday apartment rental

Ventnor / Ventnor Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“Perfect in every way ...” We stayed for seven nights in The Carisbrooke Apartment. We were absolutely delighted with the accommodation .... newly refurbished and tastefully decorated throughout, Gillian and Robert really have thought of everything to make this a 5-star stay! The apartment is very spacious and airy - it is impressive but does not skimp on comfort. We certainly would not hesitate to recommend it to our family and friends and our first visit won't be our last ..... we would love to return. Osborne House is located opposite Ventnor Park with the town, beach and Ventnor's Botanical Gardens within comfortable walking distance.

Certificate of Excellence

from £95 / night

£495 - £995 / week

Book View

Responds fast!
avg. 1 hour 20 minutes

from £95 / night

(14) 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
  • Nearest beach 0.3 km
  • Suitable for children age 5+

from £30 / night

£195 - £335 / week

Book View

Responds fast!
avg. 3 hours 55 minutes

from £30 / night

(1) Very Good 

10

Holiday bungalow in Brading

Isle of Wight / Brading

2 4 Min stay varies

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

from £450 / night

£400 - £525 / week

Enquire View

from £450 / 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 37 minutes

from £145 / night

(6) Excellent 

15

Apartment rental in Shanklin

Isle of Wight / Shanklin

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.5 km
  • Child friendly
  • Car not necessary

from £120 / night

£600 - £1,650 / week

Book View

Responds fast!
avg. 2 hours 48 minutes

from £120 / night

(25) Very Good 

13

Holiday apartment in Ryde

Isle of Wight / Ryde

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km

from £60 / night

£400 - £430 / week

Enquire View

from £60 / night

(52) Excellent 

27

Holiday home in Brighstone

Isle of Wight / Brighstone

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“A fantastic house, great location, with style as well as homely touches” We were a large group with ages ranging from 9 to early 80's plus a dog. The house had ample parking, comfy beds, a well equipped kitchen,cotton bed linen, fluffy towels and the two sitting rooms worked well allowing the adults and children to have time out from each other. Baked potatoes cooked in the Aga were so good we did the same again the next day. We stayed for 5 days and found more than enough to do. We would love to return one day.

from £359 / night

£2,667 - £3,700 / week

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Responds fast!
avg. 1 hour 26 minutes

from £359 / 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

(11) Very Good 

23

Holiday cottage in Ventnor

Isle of Wight / Ventnor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Child friendly
“Beautiful Cottage” We had a fabulous stay here at Ventnor . A beautiful cottage equipped with everything we needed for a lovely week in our favourite place . A great location so close to the town which has plenty of great shops , tea shops and even the best ice cream parlor and only a short walk to the beach . We also loved the garden and barbecue . Thank you Alun and Sheelagh for a lovely stay .

from £95 / night

£525 - £1,024 / week

Book View

Responds fast!
avg. 2 hours 18 minutes

from £95 / night

(15) Very Good 

17

Holiday log cabin in Woodside Beach

Isle of Wight / Woodside Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

from £60 / night

£275 - £480 / week

Enquire View

from £60 / night

(1) Excellent 

18

Holiday apartment in Ventnor

Isle of Wight / Ventnor

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.1 km
  • Child friendly
  • Car not necessary

from £145 / night

£750 - £1,163 / week

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Responds fast!
avg. 2 hours 49 minutes

from £145 / 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

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from £250 / night

19

Gurnard holiday lodge rental

Isle of Wight / Gurnard

3 6 Min stay varies

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

from £112 / night

£449 - £1,195 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £112 / night

(11) Very Good 

20

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

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

from £90 / night

£370 - £645 / week

Book View

Responds fast!
avg. 2 hours 18 minutes

from £90 / night

(3) Excellent 

17

Holiday home in Bonchurch

Ventnor / Bonchurch

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 1 km
  • Child friendly
  • Ask about pets

from £225 / night

£1,575 / week

Book View

from £225 / 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

Book View

from £100 / night

(15) Excellent 

28

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Amazing, comfortable cottage in beautiful location” From the lovely welcome to "The Old Barn" right through our whole weeks stay we had nothing bad to say. The cottage was amazing, beautifully finished and spotless within. The hot tub was a lovely added extra which my teenage daughter adored spending time in day & night. Everything you could possibly need on a week away was in the property, even DVDs and a few games to play which was a nice touch. I even managed to read a book from cover to cover from the cottages bookshelves, haven't done that in years! Great location with some nice towns and beaches within a short drive. If you want a nice family break in a superb cottage then this is the one for you, would highy recommend.

from £150 / night

£700 - £1,550 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from £150 / night

(18) Excellent 

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

from £49 / night

£295 - £745 / week

Book View

Responds fast!
avg. 12 minutes

from £49 / night

(5) Excellent 

17

Yarmouth holiday home let

Isle of Wight / Yarmouth

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“Home from Home” Very nice, clean and spacious cottage. Made feel really welcome with great Hamper, extra bonus was the christmas tree. We stayed in the Cottage over the christmas holiday and it was wonderful. The Storms did not bother us as we were very cosy inside the cottage. It was like home from home, all the kitchen appliances and utensils were supplied, nothing at all missing. The location is ideal as it is only a few minutes away from the ferry. Yarmouth is a really quaint little town, we loved it.

from £147 / night

£725 - £1,250 / week

Enquire View

from £147 / night

(1) Excellent 

24

Holiday home in Ventnor

Isle of Wight / Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.2 km
  • Child friendly
  • Car not necessary

from £80 / night

£700 / week

Book View

from £80 / night

(11) Very Good 

22

Cowes holiday home rental

Cowes / West Cowes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.18 km
  • Child friendly
“Fantastic place, great location, good value” Myself and twelve other guys stayed at Little Orchard as part of a stag weekend. There were no problems booking - the owner was very understanding, which was great as we're a group in our mid-thirties, but I was worried that the stigma of the typical stag-party-wrecking-the-place might be attached to us! The house is really fantastic - large, well-kept and with plenty of facilities for a large group: massive fridge-freezer, two large ovens, three bathrooms. It's in a great location for anyone planning to visit Cowes; just a few minutes walk to the Parade, a few more minutes to the pubs and shops beyond. From the large garden you could even see the beautiful sea, with yachts floating by. There's a barbecue too, a well-stocked larder, and comfy beds with all towels and linen were provided. I'd have no hesitation in returning to Little Orchard again, perhaps with extended family for a few day enjoying the Isle of Wight.

from £395 / night

£2,000 - £3,250 / week

Enquire View

from £395 / night

(5) Very Good 

30

Home rental in Nettlestone with golf nearby

Isle of Wight / Nettlestone

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £250 / night

£1,450 - £2,045 / week

Book View

Responds fast!
avg. 40 minutes

from £250 / night

(1) Very Good 

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 £39 / night

£225 - £400 / week

Enquire View

from £39 / night

(8) Excellent 

24

Bungalow rental in Yarmouth

Isle of Wight / Yarmouth

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

from £120 / night

£500 - £1,800 / week

Enquire View

from £120 / night

(1) Excellent 

16

Freshwater holiday tented camp rental

Isle of Wight / Freshwater

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 4 km
  • Child friendly
  • Car not necessary

from £204 / night

£945 - £1,380 / week

Book View

from £204 / night

(5) 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 £74 / night

£665 - £1,208 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £74 / night

(25) 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
“Lovely stay at the new Crew's Nest” We had previously stayed at the original Crew's Nest on St Mary's Road so we knew that we were going to be in for a lovely stay. The property has been done up beautifully and has all the little touches that make a stay special - even to an Outback gas BBQ in the garden for residents to use! You couldn't be closer to the town and all the facilities, and is also a great base from which to explore the rest of the island, which is what we did on this particular visit. In Cowes, can highly recommend Mojacs for something to eat, and Tiffins do a great bacon baguette for a bit of breakfast on the run! Will be coming back (again!)

from £175 / night

£750 - £3,070 / week

Enquire View

from £175 / night

(1) Very Good 

9

Ventnor holiday apartment rental

Isle of Wight / Ventnor

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Car not necessary

from £60 / night

£420 / week

Book View

from £60 / night

(4) Very Good 

26

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 £170 / night

£800 - £5,200 / week

Book View

from £170 / night

(17) Excellent 

24

Home rental in Ventnor with golf nearby

Isle of Wight / Ventnor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.75 km
  • Suitable for children age 5+

from £165 / night

£750 - £1,200 / week

Book View

from £165 / night

(3) Very Good 

16

Holiday apartment in Cowes

Cowes / West Cowes

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £70 / night

£340 - £950 / week

Book View

from £70 / night

36

Shanklin holiday home rental

Isle of Wight / Shanklin

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £118 / night

£826 / week

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from £118 / night

9

B&b rental in Shanklin

Isle of Wight / Shanklin

1 2 2 nights min

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

from £73 / night

£511 / week

Book View

from £73 / night

(15) Very Good 

32

Freshwater holiday apartment rental

Freshwater / Freshwater Bay

2 4 2 nights min

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

from £75 / night

£325 - £895 / week

Book View

Responds fast!
avg. 1 hour 5 minutes

from £75 / night

(23) Excellent 

Certificate of Excellence

23

Holiday cottage in Brading

Isle of Wight / Brading

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“Marmalde Cottage, the perfect Isle of Wight holiday home” The pictures of Marmalade Cottage don't do it justice, we arrived on a somewhat rainy Saturday and were greeted by Colin and Julie, how made us feel instantly welcome and were on hand to provide any help for our stay. When we entered the lovely spacious annex cottage, we found the house to be really well laid out with plenty of room for my daughter to play, they house was well equipped with lovely gardens and in a perfect location for the beaches, shops and things to do.

Certificate of Excellence

from £95 / night

£450 - £850 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £95 / night

(30) Excellent 

22

Home rental 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
“Beautiful house with lovely garden” Regatta Cottage is a lovely rental, equipped to a very high standard and clearly recently refurbished. The welcome basket was a lovely surprise and made our lives much easier particularly as we were only there for a weekend. Key pick up and return is at a local pub (in West Cowes centre near the hi speed ferry) and was nice and easy. Is about 5-10mins walk from the property. There are several keys which is useful for large groups. The garden looked lovely but we didn't really get a chance to use it, mores the pity.

from £200 / night

£750 - £2,600 / week

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from £200 / night