Walking holiday villas and apartments Isle of Wight

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  • Bembridge (26)
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  • Gurnard (13)
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  • Whippingham (6)
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425 Holiday homes

Filters applied: Walking holidays (425)

Travellers going to Isle of Wight are booking November dates now. Secure your holiday home today and have the perfect trip.

(8) Excellent 

14

Whitwell Station Bluebell and Primrose Cottages - Nettlecombe cottage sleeps 4

Whitwell / Nettlecombe

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
Bluebell and Primrose Cottages are converted from the waiting rooms and ticket offices of the retired Victorian Railway Station. Whitwell Station is nestled within beautiful and outstanding countryside in the South Wight. Each cottage comprising of 2 bedrooms, sleeping  …see more

from £90 / night

£290 - £575 / week

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from £90 / night

(25) Excellent 

18

Seaways - Alverstone Garden Village apartment sleeps 4

Sandown / Alverstone Garden Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
The Apartment is new and has quality oak furniture,the apartment has the benefit of sea glimpses and culver cliff. The property is on the first floor. It has open plan living room with doors to a Juliet balcony. Dinning for four and a well equipped kitchen off the dinni  …see more

from £56 / night

£265 - £690 / week

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from £56 / night

(5) Very Good 

9

8 Hambrough House - Ventnor apartment sleeps 4

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
This stunning apartment is situated just above Ventnor's beach and Esplanade. There is a wide selection of restaurants, shops, cafes and bars within easy reach and far reaching views along the coastline can be enjoyed from the large open plan living-dining room and  …see more

from £86 / night

£280 - £389 / week

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from £86 / night

(11) Excellent 

24

Rose Cottage - Roud cottage sleeps 6

Godshill / Roud

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Swimming pool
Rose Cottage. Is a traditional thatched cottage in the heart of the tiny hamlet of Roud on the Isle of Wight. The Cottage stands in almost 3 acres of garden where there is a unheated swimming pool, a large pond with elevated summer house and a separate trampoline area f  …see more

from £79 / night

£550 - £995 / week

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from £79 / night

(7) Excellent 

18

Ventnor Bay Cabin - Ventnor Bay chalet sleeps 2

Ventnor / Ventnor Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Pet friendly
Ideally situated overlooking Wheelers Bay in Ventnor, this 1 bedroom detached cabin is a stone's throw away from the sea, so you are spoilt with seaviews from the villa, also with a lovely view of the chalky cliffside you feel at one with nature. This cabin is ideal fo  …see more

from £85 / night

£368 - £542 / week

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from £85 / night

24

Mill Cottage - Newchurch cottage sleeps 6

Sandown / Newchurch

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Located on The Garlic Farm nestled at the foot of Mersley Down. Mill Cottage was originally built in about 1720 and used as a mill in the 19th century. The original mill stones can be seen in the entrance to Mill Cottage which was tastefully converted into a three bedro  …see more

from £145 / night

£675 - £1310 / week

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from £145 / night

(4) Very Good 

22

Pink Beach Cottage - St Helens cottage sleeps 4

Isle of Wight / St Helens

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 2 km
  • Child friendly
  • Private garden
Pink Beach Cottage is an older style detached home situated in a quiet little road just of the village green. The accommodation is nicely presented offering two bedrooms being a double & a twin room. Downstairs there is characterful lounge with its feature fireplace,  …see more

from £83 / night

£295 - £450 / week

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from £83 / night

(2) Excellent 

21

Kingoyo #66 - Seaview chalet sleeps 4

Isle of Wight / Seaview

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
(Preferential ferry prices for all our guests: please ask for details) Our three Salterns Beach Chalets have been modernised to Premier standard to provide the most comfortable accommodation for your seaside holiday. They are superbly situated in this small development  …see more

from £58 / night

£330 - £425 / week

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from £58 / night

(13) Excellent 

16

Apartment in Central Cowes. - West Cowes apartment sleeps 4

Cowes / West Cowes

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Lovely spacious apartment located next to Shepard's Wharf Marina. 2 bedrooms, 1 shower room, large sitting room, well equipped kitchen. TV with Freeview, Xbox 360, Chromecast, Safe for valuables, Alarm system and desk for working. Close to Cowes High Street and the Chai  …see more

from £100 / night

£350 - £400 / week

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from £100 / night

(4) Very Good 

14

Afton Bank Cottage - Freshwater Bay cottage sleeps 5

Freshwater / Freshwater Bay

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
This charming semi-detached Victorian cottage is ideal for a quiet getaway with loved ones, close to beach and town, on the west coast of the Isle of Wight.The accommodation consists of a two storey cottage annexe to the owners Victorian House and is tastefully decorate  …see more

from £56 / night

£445 / week

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from £56 / night

(10) Excellent 

7

Squirrel Nutkins cabin - Whippingham log cabin sleeps 2

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 £60 / night

£350 - £450 / week

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from £60 / night

(7) Excellent 

16

Squirrels Watch - for guests with dogs - Newchurch cottage sleeps 4

Sandown / Newchurch

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Pet friendly
  • Private garden
As the title states, we are a specialist provider of self catering accommodation for those people bringing their dogs with them on holiday. Whether large or small - just one or a whole pack - we welcome you with open arms (paws).Squirrels Watch is only for those guests  …see more

from £150 / night

£700 / week

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from £150 / night

(14) Very Good 

25

The Beach House Apartment - Totland Bay apartment sleeps 8

Totland Bay / Totland Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
The Beach House apartment is situated on the ground floor of the Beach House on the esplanade of the delightful Totland Bay which sits in an area of Natural Outstanding Beauty on the North West coast of the Island. The views are unrivalled, and ever changing, looking  …see more

from £200 / night

£650 - £2000 / week

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from £200 / night

(2) Excellent 

10

Red squirrels Grange Farm - Wootton Bridge lodge sleeps 6

Isle of Wight / Wootton Bridge

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
This is a barrier free brand new build. Suitable for wheel chair users. Sleeps 5 to 6. All on one level with car parking and garden. The Lodge comprises of a Large wet room, en-suite double room and two twin rooms, Large kitchen / diner lounge. A veranda to the front  …see more

from £114 / night

£795 / week

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from £114 / night

(4) Excellent 

16

Kingfisher Cottage - Sandown house sleeps 4

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Kingfisher Cottage is tucked away in a small mews within the heart of Sandown. It has been fully refurbished and decorated to the highest standards. It will equally suit families or couples, and offers quiet and cosy accommodation just a stone's throw from local ameniti  …see more

from £54 / night

£240 - £613 / week

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from £54 / night

(1) Excellent 

24

Shepherd's Hut - Godshill shepherds hut sleeps 2

Isle of Wight / Godshill

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Car not necessary
Enjoy a romantic stay in this cosy hut with comfortable double bed and log burner is located next to the secret pond. Toilet adjacent, luxury shower room 2 mins walk. Breakfast is served in the farmhouse hall. Red squirrels and other wildlife share this spot. Godshill  …see more

from £100 / night

£700 / week

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from £100 / night

(14) Excellent 

20

7 firs court - Sandown house sleeps 5

Isle of Wight / Sandown

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
This newly constructed semi-detached house is suitable for couples and small families alike. The property benefits from off road parking for two cars and an enclosed rear garden with a raised decking area. Ideally situated a short stroll from the beach and esplanade  …see more

from £36 / night

£250 - £745 / week

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from £36 / night

(3) Very Good 

19

184 Sandown Bay Holiday Centre - Yaverland chalet sleeps 4

Sandown / Yaverland

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
A well presented holiday bungalow offering comfortable accommodation comprising two bedrooms (one double and one with 3' bunk beds), open plan lounge with sofa bed (additional sleeping for 1/2), kitchen and bathroom with shower over bath. Outside, leading out from  …see more

from £50 / night

£185 - £299 / week

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from £50 / night

(16) Excellent 

30

1 The Dairy - Yarmouth cottage sleeps 4

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
This converted Dairy Cottage is the ultimate in relaxing, set in a quiet farm location in the beautiful West Wight countryside.The cottage has its own private garden and terrace area with secure parking, and benefits from a hot tub which is shared between 3 properties o  …see more

from £110 / night

£370 - £795 / week

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from £110 / night

(6) Excellent 

30

Plum Cottage - Ventnor house sleeps 6

Isle of Wight / Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
A beautiful and stylish New England Townhouse just 5 minutes from the beach in a peaceful town location.Decorated and fully refurnished in 2014Set in a large private courtyardRear garden features conservatory and decked areasThree tastefully decorated bedroomsLarge open  …see more

from £100 / night

£640 - £820 / week

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from £100 / night

(14) Very Good 

24

Cedar Croft - Cowes log cabin sleeps 5

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Take a peaceful break away from the crowds in our quirky little cabin. Get up have a stroll along the beach, on our private bay, then sit outside and have breakfast while looking at the beautiful view and watching the boats sail by, you may want to spend time with your  …see more

from £57 / night

£400 - £670 / week

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from £57 / night

(6) Very Good 

23

Pebbles - Niton Undercliff chalet sleeps 2

Ventnor / Niton Undercliff

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
A contemporary hillside chalet in the southernmost tip of the Isle of Wight, set in beautiful gardens, with views over treetops towards the sea, and adjacent to the coastal path. Spend a relaxing week at Pebbles, a thoughtfully equipped compact terraced chalet, tucked a  …see more

from £45 / night

£270 - £405 / week

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from £45 / night

(9) Excellent 

12

holiday bungalow - Freshwater bungalow sleeps 4

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
Idyllic seaside bungalow set in Linstone Chine Holiday Village at Cliff End Freshwater on the beautiful Isle of Wight. Wii fii is available at this property. The two bedroomed bungalow is brick built with bathroom with bath and shower. The kitchen and lounge are open  …see more

from £45 / night

£310 - £575 / week

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from £45 / night

(3) Excellent 

7

Hunter Heights Self Catering - Wroxall apartment sleeps 2

Isle of Wight / Wroxall

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
Hunter Heights is a stylish home from home, this is a modern contemporary one bedroom self catering apartment. Hunter Heights is accessible by external staircase, it overlooks the spectacular Stenbury Down and Appuldurcombe Estate. The apartment has free Wi Fi, TV,  …see more

from £80 / night

£475 - £525 / week

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from £80 / night

(6) Very Good 

21

126 Sandown Bay Holiday Centre - Yaverland chalet sleeps 4

Sandown / Yaverland

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
Situated on the coast just a few minutes walk away from the beach. Lovely coastal & downland walks with views across Sandown Bay stretching out over the Enlish Channel. Own decking ideal for al fresco dining. Many local attractions & great base to explore the  …see more

from £50 / night

£195 - £309 / week

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from £50 / night

(9) Excellent 

23

BEACH RETREAT - Shanklin bungalow sleeps 2

Isle of Wight / Shanklin

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Car not necessary
BEACH RETREAT: VACANCIES. Free Wi Fi. Buses to Newport and Ryde stop outside. Beach 10 mins. Everything is central. You will love the situation. Our annexe is really just like a small bungalow. Very modern and immaculate. Home from Home. You will be very  …see more

from £65 / night

£350 - £650 / week

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from £65 / night

(12) Very Good 

20

Beachside Chalet - Gurnard chalet sleeps 2

Isle of Wight / Gurnard

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Beachside Chalet No1 is approached from a residential road, offering a safe and peaceful environment. The quiet village of Gurnard sits west along the coast from the bustling internationally renown yachting town of Cowes. HISTORY - The chalet is one of a row built in  …see more

from £43 / night

£300 - £550 / week

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from £43 / night

17

Sea Horizon, Ventnor - Ventnor house sleeps 4

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Pet friendly
This extremely well appointed and presented traditional terraced cottage offers stunning panoramic sea views from its south-facing garden with lovely decked seating areas to enjoy. This cottage has everything you need for a great holiday, and is a short distance from th  …see more

from £45 / night

£310 - £912 / week

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from £45 / night

(23) Excellent 

23

sea views close to town, safe garden pets welcome - Ventnor house sleeps 7

Isle of Wight / Ventnor

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
This 3 double bedroom house has excellent town sea and downs views and sleeps 7 people [ plus sofa bed]. The accommodation comprises of 3 double bedrooms [ 1 double bed, 2 single, 3 single beds], a bathroom with separate shower, kitchen, lounge and conservatory that l  …see more

from £175 / night

£500 / week

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from £175 / night

(12) Excellent 

19

Stickey Wicket - Niton chalet sleeps 2

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 5 km
  • Car not necessary
Sticky Wicket is a cosy one bedroom chalet set among beautiful gardens in the charming village of Niton near Ventnor. The property has one bedroom with an en-suite shower room, kitchen and lounge with sofa and tv. Situated in a row of similar south facing properties it  …see more

from £40 / night

£240 - £425 / week

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from £40 / night

(15) Excellent 

24

The Lodge - Old Village cottage sleeps 4

Shanklin / Old Village

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
This lovely character cottage is tucked away in a peaceful location but just a short walk from the picturesque Shanklin Old Villagewith its quaint thatched pub, tearooms and gift shops. Shanklin Chine is a beautiful natural wooded gorge and is a pleasant eveningstroll  …see more

from £52 / night

£360 - £700 / week

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from £52 / night

(13) Excellent 

18

Riviera Luxury B & B - Ventnor Bay b&b sleeps 6

Ventnor / Ventnor Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
SPECIAL OFFER TO ALL GUESTS OF THE RIVIERA:Upon Payment of Deposit we offer our guests a special 15% off the Red Funnel Ferry from Southampton to the Isle of Wight.The Riviera offers you the only hot tub in the UK just 10 feet away from the sea with panoramic ocean view  …see more

from £255 / night

£1785 / week

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from £255 / night

12

Osborne Court - East Cowes apartment sleeps 4

Isle of Wight / East Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Osborne Court is a two bedroom apartment situated on Cowes Parade with sea views across the Solent. The accommodation comprises of lounge leading to balcony, kitchen, family bathroom, one double bedroom and twin bedroom. The town of Cowes with its narrow streets and a  …see more

from £75 / night

£400 - £550 / week

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from £75 / night

(1) Excellent 

14

Distant Shores - Ventnor apartment sleeps 4

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
There are spectacular sea views from the balcony to one of Britain's most rugged and scenic coastlines. Inside there's a comfortable lounge, well equipped kitchen, two bedrooms; a king-sized double with amazing sea views and a twin with an en suite shower room and lovel  …see more

from £115 / night

£445 - £600 / week

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from £115 / night

(9) Excellent 

17

Little Sailing - Gurnard chalet sleeps 4

Isle of Wight / Gurnard

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
A beautiful cedar clad beach house right on the waters edge. The house is built to an extremely high quality and environmental standard. As it is highly insulated it is a very cosy stay during the winter months as well as sunny in the summer months with cool sea breeze  …see more

from £75 / night

£525 - £1100 / week

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from £75 / night

16

Green Bank with Hot Tub - West Cowes guest house sleeps 12

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Suitable for children age 5+
  • Private garden
This beautiful detached Victorian detached House comes with 6 Bedroom ,2 bathrooms & 3 shower rooms so is ideal for large families or sailing crews. It has a lovely mix of original features & modern living. The rooms are very spacious & with a mix of double  …see more

from £220 / night

£1000 - £5200 / week

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from £220 / night

(4) Very Good 

16

Isle of wight Sandown Chalet 79 - Yaverland chalet sleeps 6

Sandown / Yaverland

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Situated on the coastal path, literally steps from the national trust walkway to Culver Down. So after a stroll with spectacular sea and rural views you will find a great family pub. Location ideal for walking or cycling with many local island attractions. Great for f  …see more

from £29 / night

£200 - £300 / week

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from £29 / night

(15) Very Good 

21

Springside - Whippingham cottage sleeps 5

Isle of Wight / Whippingham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
SPRINGSIDE self catering holiday cottage, Whippingham, Isle of Wight is a quality holiday cottage set in beautiful gardens with a lovely heated swimming pool shared with owners only. The pool is 4'6" shallow end and 6'6" deep end. Built for Queen Victoria and Prince Al  …see more

from £115 / night

£695 - £1500 / week

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from £115 / night

(10) Excellent 

21

Stoneleigh Suite in Ventnor - Ventnor apartment sleeps 6

Isle of Wight / Ventnor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
Stoneleigh Suite is a spacious apartment located in a historic stone building at the bottom of St Boniface Down. There is easy access to picturesque walking routes just across the road. The views from the apartment are simply breathtaking - over St Boniface Gardens Park  …see more

from £100 / night

£600 - £700 / week

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from £100 / night

(11) Very Good 

25

Windrush - West Cowes house sleeps 17

Cowes / West Cowes

7 17 7 nights min

  • 7 bedrooms
  • Sleeps 17
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Gracious, detached, 7 bedroom property in it's own grounds. All amenities including WiFi, and TVs with Freeview. Please see video here (copy and paste into your browser): http://www.youtube.com/watch?v=IX-SG1CAyos&feature=youtu.be Originally built for the Rats  …see more

from £315 / night

£2200 - £2900 / week

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from £315 / night

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