Watersports holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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259 Holiday homes

Filters applied: Water sports (259)

(21) Excellent 

25

Gurnard holiday home rental

Isle of Wight / Gurnard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Perfect hassle-free family getaway. Built-in garden,beach and views!” This is a beautifully presented house. Buckets and spades and teddies awaited the children, as well as cakes for all of us and wine for the grown-ups. The garden suited all needs fr  …see more

from £150 / night

£800 - £1750 / week

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from £150 / night

(82) Excellent 

25

Holiday cottage in Ventnor

Ventnor / Niton Undercliff

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
“Fantastic cottage” We had a fabulous week at Camellia Cottage at the beginning of March. Well deserving of its gold award, this cottage is very well equipped, very clean and has a very home-from-home feel. We particularly enjoyed the resident wi  …see more

from £120 / night

£570 - £1475 / week

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from £120 / night

(14) Very Good 

23

Holiday apartment in Cowes

Cowes / West Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly
Light and airy modern penthouse apartment with fantastic sea views (best in Cowes) towards Calshot Spit and the Central Solent. Close enough to the water to hear boats tack! Yards from the Royal Yacht Squadron, five minute walk along the sea front to the high street and  …see more

from £50 / night

£330 - £1525 / week

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from £50 / night

(17) Excellent 

24

Holiday cottage in Wootton Bridge

Isle of Wight / Wootton Bridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Lovely property” Had a great week at kipper cottage, cant wait to get back next year. Boat house was a real treat. House was clean and tidy. Lovely quite spot  …see more

from £135 / night

£695 - £1395 / week

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from £135 / night

(13) Excellent 

22

St Helens holiday lodge rental

Isle of Wight / St Helens

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“Fantastic stay!!” We (4 adults and one baby) stayed here for a week in february and thoroughly enjoyed every minute. The accommodation was brilliant. Everything you could need was there and the place was spotless. A definite home from home. Will g  …see more

from £65 / night

£395 - £1295 / week

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from £65 / night

(23) Excellent 

24

Ryde holiday apartment rental

Isle of Wight / Ryde

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
“Absolutely brilliant” We stayed here for a week at the end of June, the weather was poor but the apartment made up for it. the owners have thought of everything for comfort and convenience. The apartment is clean, comfortable and only 5 minute walk fr  …see more

from £50 / night

£350 - £695 / week

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from £50 / night

(29) Excellent 

45

Holiday cottage rental

Ventnor / St Lawrence, Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Absolutely beautiful cottage to spend a holiday!” This cottage is a stunning place to have a holiday. It had a real home from home feel with everything in the cottage one would need. Harry the Golden Retriever enjoyed it too having so much space to  …see more

from £150 / night

£525 - £1345 / week

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from £150 / night

(5) Excellent 

16

Cowes holiday townhouse rental

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Beautiful West Cowes holiday flat” This flat is perfectly situated on the (pedestrian-only) high street. It is literally steps away from all the amenities and sights. The flat is very cozy, well equipped, and makes you feel like you are on holiday. Tw  …see more

from £130 / night

£390 - £950 / week

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from £130 / night

(8) Excellent 

8

Holiday apartment in Wootton Bridge

Wootton Bridge / Fishbourne

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
Modern, well-equipped, purpose-built apartment.Fantastic superking fourposter bed in main bedroom.Free broadband WiFi.Convenient for Ryde and NewportNear car ferry terminals at Fishbourne (1 mile) and East Cowes (3 miles)Sleeps six without having to use a sofa-bed in th  …see more

from £66 / night

£275 - £875 / week

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from £66 / night

(35) Very Good 

17

Holiday chalet in Yaverland

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“A Little Slice of Paradise” A beautiful chalet in a gorgeous location - just a five minute walk from a lovely sandy beach. The amenities in the chalet were good and our hosts were very happy to answer any queries and make suggestions. We are r  …see more

from £32 / night

£195 - £475 / week

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from £32 / night

(22) Excellent 

16

Holiday chalet rental

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“IMMACULATE CHALET OVERLOOKING THE SEA AND CLIFFS” The chalet looked brand new and was spotlessly clean. It was in a lovely position. You could see the sea and cliffs from the settee-impressive when there was a thunderstorm and you could watch it in  …see more

from £25 / night

£175 - £550 / week

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from £25 / night

(4) Very Good 

21

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“FABULOUS LOCATION” This was our second visit to Eliabeth House and we would hapily return there because the location is perfect, being close to both the sea and town centre. The views of the sea are brilliant. I spent most of my time there watching  …see more

from £50 / night

£350 - £795 / week

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from £50 / night

(8) Excellent 

27

Holiday home in Ventnor

Isle of Wight / Ventnor

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“Lovely stay in a brilliant house in a great location.” Large, bright house with plenty of space for our group to have a very relaxing weekend. On entry house found to be very clean & tidy, rooms nicely decorated & furnished. Good range of Bedroom opti  …see more

from £155 / night

£620 - £1440 / week

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from £155 / night

(7) Excellent 

17

Cottage rental in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Fabulous place to stay and really helpful owners!” Just returned from a two week stay at the delightful Valerian Cottage with my wife and daughters (aged 6 and 4). The cottage is beautifully presented and extremely comfortable - more like a proper hom  …see more

from £80 / night

£450 - £950 / week

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from £80 / night

(42) Very Good 

24

Yarmouth holiday cottage rental

Yarmouth / Fort Victoria

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Wonderful place to relax and unwind” Spotted the cottage from the ferry on the crossing from Lymington (which was so easy). We had a car so only took 10 minutes to get there but it would have been possible to walk from the ferry if you were fit. Ver  …see more

from £75 / night

£395 - £1245 / week

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from £75 / night

(9) Excellent 

18

Sandown holiday apartment rental

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
King size bed in bedroom 1 & twin single beds in bedroom 2.  …see more

from £70 / night

£300 - £800 / week

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from £70 / night

(13) Excellent 

20

Holiday cottage in Bonchurch

Isle of Wight / Bonchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“The stay is worth repeating” We had a cozy stay in this little cottage. As a couple very good. Bedroom was a bit cold, due to the gale blowing at night with freezing temperaturers and snow. We adviced the owners to make a second door outside to hang t  …see more

from £100 / night

£550 - £790 / week

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from £100 / night

(6) Excellent 

16

Yarmouth holiday villa rental

Isle of Wight / Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Amazing - everything you could want and more ......” A fab property minutes from Yarmouth and the ferry terminal, but tucked away in the haven called Fort Victoria Country Park. Woodland Cottage is great - big enough not to feel on top of each other b  …see more

from £140 / night

£725 - £2240 / week

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from £140 / night

(3) Very Good 

26

Home letting in Bembridge

Bembridge / Bembridge Village

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Set in its own large enclosed gardens, Hedgerow is a charming, cosy and well maintained cottage, comfortably sleeping up to 10 people. Set in a quiet unmade road, Hedgerow is only a short walk from both the sea and the amenities of the lovely village of Bembridge.  …see more

from £175 / night

£750 - £2040 / week

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from £175 / night

(3) Excellent 

7

Holiday apartment in Wroxall

Isle of Wight / Wroxall

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
Semi rural set in area of outstanding natural beauty. Fabulous location for walking, cycling and horse riding. Borrow a dog or two for a walk. Great for weekend and short breaks. Beaches close by. Feeling adventurous try Paragliding, Sailing or Paddle boarding?  …see more

from £80 / night

£475 / week

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from £80 / night

(13) Excellent 

12

Holiday apartment with golf nearby in Ryde

Ryde / Appley

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Mrs” Perfect flat in ideal location bring only 8 minutes from Ryde ferry terminal. It's light airy and comfortable . Clean and warm with everything you need. Nice welcome basket in kitchen with bread cereals and biscuits plus milk in fridge . Would re  …see more

from £52 / night

£364 / week

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from £52 / night

(18) Excellent 

24

Holiday caravan/mobile home in Bembridge

Isle of Wight / Bembridge

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“An idyllic and picturesque holiday destination” This was our first time in a static caravan and so were a little unsure as to just what to expect however we were pleasantly surprised upon our initial arrival at the holiday park and also upon entering  …see more

from £100 / night

£350 - £650 / week

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from £100 / night

(36) Excellent 

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
“Brilliant Holiday” We have just returned from our first family holiday on the Isle Of Wight with our two children aged 9 and 6. The Cabin is an amazing place to stay for a holiday, very clean and has everything you need. The swimming pool seemed bigge  …see more

from £93 / night

£650 - £1400 / week

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from £93 / night

(42) Excellent 

27

Ventnor holiday apartment rental

Isle of Wight / Ventnor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Car not necessary
“Wow! What a view.” An amazing place to just relax and watch the world go by. Seashells is clean, comfortable and very good value for money. Everything you need for a relaxing holiday is here, even a welcoming bottle of wine. Lots of places to eat clos  …see more

from £70 / night

£420 - £720 / week

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from £70 / night

(18) Excellent 

21

Holiday bungalow in Freshwater

Isle of Wight / Freshwater

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“very clean, well equipped bungalow” we had a great holiday. The location was very good (sea view from the lounge). The bungalow was very well equipped and very clean. Ideally located for children - lots of space to run around outside - 3 - 4 mins wal  …see more

from £79 / night

£550 - £595 / week

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from £79 / night

(23) Excellent 

24

Holiday tree house in Whippingham

Isle of Wight / Whippingham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children age 5+
“Stunning” If you want something that is a little bit different, but also want quality ... then this is the place. We spent a fabulous week at the Treehouse. What an amazing place. The location is great, literally 15mins from the East Cowes ferry, w  …see more

from £150 / night

£550 - £1300 / week

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from £150 / night

(29) Very Good 

21

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“fabulous location” Within walking (coastal walk) distance of the lovely town of Yarmouth with its charming shops, pubs and restaurant the cottage is an ideal place to stay. Would definately recommend Saltys Restaurant and the one next to it overlookin  …see more

from £75 / night

£395 - £1245 / week

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from £75 / night

(18) Excellent 

12

Holiday chalet with shared pool, golf nearby in Gurnard

Isle of Wight / Gurnard

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Decorated to a high standard and spotless” We booked this chalet for one week, we stay on the Island every year in self catering accommodation and this was by far the best we have stayed in. The chalet is decorated to a high standard, it was absolutel  …see more

from £75 / night

£350 - £550 / week

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from £75 / night

(11) Excellent 

8

Holiday log cabin with golf nearby in Whippingham

Isle of Wight / Whippingham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Private garden
This timber built cabin makes the ideal cosy holiday retreat for two. It is well situated for exploring the whole island, and its many attractions. •The village of Whippingham is near to Queen Victoria's Osborne House, and the yachting centre of Cowes.•Pubs and res  …see more

from £75 / night

£350 - £450 / week

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from £75 / night

(25) Excellent 

15

Ryde holiday lodge rental

Isle of Wight / Ryde

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
Luxury Holiday accommodation sleeps 2 people fully equipped luxury Lodge in Ryde.  …see more

from £60 / night

£350 - £850 / week

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from £60 / night

(7) Excellent 

23

Holiday home rental

Isle of Wight / St Helens

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Mr” Wonderful peaceful location. Plenty of room in this very comfortable home for 4 adults and a child. Close to shops, restaurants and wine farms.  …see more

from £85 / night

£590 - £1600 / week

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from £85 / night

(12) Excellent 

32

Holiday home with golf nearby in Seaview

Isle of Wight / Seaview

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Exceeded my expectations” Myself and my family,absolutely loved our time spent at the Lobsters Pot, it was terrific. We couldn't fault a thing, which is rare. My little Granddaughter loved the garden, and the horses in the field too. We would certain  …see more

from £85 / night

£595 - £1099 / week

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from £85 / night

(6) Very Good 

22

Holiday cottage in Bembridge

Bembridge / Bembridge Beach

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Child friendly
“Great location.” Great location, the children loved the short bike ride to the beach. The beds were very comfortable and the rooms a good size. The utility room was very handy for rinsing swimming gear and storing our bikes. However we did feel the s  …see more

from £58 / night

£400 - £990 / week

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from £58 / night

(9) Very Good 

12

Holiday apartment in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Two bedroom apartment in an excellent waterfront location with wonderful views across the harbour and Solent beyond. Situated on the the fourth floor and accessed via a private lift or stairs.  …see more

from £130 / night

£425 - £2200 / week

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from £130 / night

(6) Excellent 

10

Holiday barn in Shorwell

Shorwell / Billingham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
The new properties have been fitted out extremely tastefully with all the mod cons including wood burner stoves for those chilly evenings, loadsa logs available ! At the property there is also secure storage for bikes, kayaks & also wash down & workshop facili  …see more

from £70 / night

£450 - £550 / week

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from £70 / night

(15) Excellent 

18

Holiday caravan/mobile home with shared pool in Bembridge

Isle of Wight / Bembridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Excellent” Stayed here for 4 nights, what a lovely clean and well equiped caravan. The bedrooms were lovely and comfortable and the 2 bathrooms were excellent. So big, and the lovely decked patio made this a really enjoyable stay. The personal touches  …see more

from £60 / night

£420 / week

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from £60 / night

(1) Excellent 

17

Holiday home in Newport

Newport / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
Outdoor pursuits include scenic walking, horse riding, fishing, cycling, water sports and golf. The island can be explored from the open-top buses that stop regularly at various collection points. Beach 5 miles. Shop 1 mile, pub and restaurant 200 yards.  …see more

from £250 / night

£850 - £2500 / week

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from £250 / 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 £180 / night

£740 - £2600 / week

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from £180 / night

(7) Very Good 

35

Holiday home in East Cowes

Isle of Wight / East Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“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

from £125 / night

£575 - £1375 / week

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from £125 / night

(16) Excellent 

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
“Perfect in every way” I stayed at the Lodge with my 90 year old Aunt. She has some mobility problems so the search for accommodation was very specific. Our needs were met perfectly. She had no trouble moving around the house or getting to and from fr  …see more

from £52 / night

£360 - £700 / week

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from £52 / night

Top Destination reviews

Eversley Luxury Apartment
Lovely luxury apartment

Lovely luxury apartment - we stayed with family and young children. Great facilities, ensuite bathrooms, lots of room. Very clean and all very new, great position for sea and town. No noise. Parking was a bit odd but sufficient as it was quiet. We … see more
Luxury Cowes Penthouse
Excellent place to stay loved it

Well worth the money.... We have recommend this to our family and friends. if you have small children some of the fine ornements are only to be looked at.... The large outside area is lovly in the sunshine. … see more
Carriers Stable - holiday cottage of high quality
Exceeded our expectations

Comfortable, clean and well-equipped cottage in a lovely part of the island. The owners had thought of everything! … see more
"TOP DECK" - STUNNING SEASIDE APARTMENT
Another fantastic stay at 'Top Deck'

Top Deck has everything needed for a relaxing holiday/break in Ventnor -great location, stunning views, good facilities and a lovely welcome pack. Everything from washing-up liquid and kitchen roll to shower gel and toilet roll is also provided, mak … see more
The Mill House
We couldn't have found a better property on the island

We were expecting a welcome pack based on the reviews we read before our arrival but it exceeded our expectations - the hot cross buns were great and the selection of Easter chocolate was a lovely surprise. We felt very much at home straight away. … see more
Waters Edge
A well designed, luxuriously equipped property, Waters Edge was just what we were looking for

Our favourite things about Waters Edge were the the views to the mainland and watching boats go by, the comfy beds, the original artwork pictures, the electric feature fireplace, and the quiet peaceful location with lots to do without having to drive … see more