Walking holiday villas and apartments Isle of Wight

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  • Bembridge (26)
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  • Gurnard (12)
  • Knighton, Isle of Wight (1)
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  • Porchfield (4)
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  • Ryde (19)
  • Sandown (56)
  • Seaview (14)
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  • Totland Bay (4)
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  • Whippingham (6)
  • Whitwell (5)
  • Woodside Beach (2)
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420 Holiday homes

Filters applied: Walking holidays (420)

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

(6) Excellent 

8

The Grange, Creek Gardens, Isle of Wight - Fishbourne apartment sleeps 6

Wootton Bridge / Fishbourne

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
Now with free broadband Wifi, The Grange is a purpose-built, ground floor three-bedroomed modern holiday apartment in Creek Gardens, at Wootton Bridge on the Isle of Wight. It is located on the west bank of picturesque Wootton Creek. Well equipped, with the main bedroom  …see more

from £66 / night

£275 - £875 / week

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from £66 / night

(8) Excellent 

17

Dudley House - Ventnor house sleeps 11

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
A deceptively spacious Victorian town house on 4 levels with stunning sea views close to the town and Ventnor sea front. The house is stylishly furnished and is ideal for families, with the green opposite providing a great space for outdoor games. The rear courtyard g  …see more

from £155 / night

£620 - £1440 / week

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from £155 / night

(19) Very Good 

20

Seaspray Chalet - Yaverland chalet sleeps 4

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Seaspray Chalet is fully self catering with an open plan Kitchen and lounge. It provides comfortable accommodation with two bedrooms, one double and one with bunk beds. The Bathroom has a full size bath and shower above. There is plenty of hot water and Electricity and  …see more

from £35 / night

£195 - £490 / week

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from £35 / night

(17) Very Good 

7

The Beach Retreat Eco Friendly - Gurnard log cabin sleeps 4

Isle of Wight / Gurnard

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Time to take a breather,,,,in our quirky little gem of a place, get up have a stroll along the beach, on our private bay, then sit outside and have breakfast while looking at the beautiful view, you may want to spend time with your children on the beach, go fishing ( i  …see more

from £60 / night

£420 - £550 / week

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from £60 / 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

(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

(25) Very Good 

8

Bella Cottage - Newport cottage sleeps 5

Isle of Wight / Newport

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
This period Cottage which is thought to be once a Quarry- man`s Cottage which has been recently and lovingly upgraded with all modern facilities. Located on the outskirts of Newport, the main town is easily accessible, a short walk away to many shops, restaurants, bar  …see more

from £70 / night

£520 - £1100 / week

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from £70 / night

(17) Excellent 

24

"Kipper Cottage " Waterside property - Wootton Bridge cottage sleeps 4

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
Kipper Cottage is highly rated . The cottage is comfortable and on one level accommodation for four people. There is an open-plan living room and kitchen, which are bright and spacious, tastefully furnished and have lovely views of the creek. The Cottage benefits fro  …see more

from £125 / night

£595 - £1395 / week

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from £125 / night

(23) Excellent 

12

LONGSHOREMANS COTTAGE - Sandown cottage sleeps 4

Isle of Wight / Sandown

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Longshoremans Cottage is located close to all the amenities Sandown has to offer and benefits from off road parking. It was originally converted from a boat house, whose owners earnt their living from working on the beach. The cottage is fully equipped with all the esse  …see more

from £40 / night

£235 - £420 / week

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from £40 / night

(12) Excellent 

18

Carlton Cottage - West Cowes cottage sleeps 7

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
This is a newly built, absolute gem of a cottage which is set just back from the waterfront with some Solent views. A delightful detached property fitted to the highest quality and standards. Comfortably sleeps up to 7 people in flexible accommodation to suit single or  …see more

from £180 / night

£740 - £2600 / week

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from £180 / night

(17) Excellent 

12

41 Gurnard Pines - Gurnard chalet sleeps 6

Isle of Wight / Gurnard

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Newly refurbished chalet with brand new fitted kitchen and bathroom. Fully equipped kitchen with electric oven, gas hob, fridge with a freezer compartment, microwave oven, crockery, cutlery and utensils. Iron, folding clothes horse, and vacuum cleaner. Dining area with  …see more

from £75 / night

£350 - £550 / week

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from £75 / night

12

1 Windmill Cottages - WILLOW - Bembridge Village cottage sleeps 4

Bembridge / Bembridge Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
These delightfull. newly built cottages are set in the heart of Bembridge village. When you walk in to the cottage, you get an immediate feeling that everything has been catered for. The kitchen is fully equipped, the king size bedroom upstairs is wonderfully comfortabl  …see more

from £50 / night

£395 - £695 / week

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from £50 / night

(5) Excellent 

23

Smugglers - Ventnor cottage sleeps 7

Isle of Wight / Ventnor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
OPEN ALL YEAR Smugglers is a pretty and cosy early Victorian Cottage in the centre of Ventnor, sleeping 7 people comfortably, plus a cot if required. There is a large double bedroom with a single room attached and a double room with a twin room attached. Both doubles ha  …see more

from £95 / night

£525 - £995 / week

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from £95 / 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

(22) Excellent 

20

Little Moon Cottage - Moons Hill cottage sleeps 4

Freshwater / Moons Hill

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Little Moon Cottage sits on a leafy lane at the foot of Tennyson Down with woodland to the front and rolling countryside to the rear. The garden stretches out towards the wooded slopes of the down in an AONB. It's lovely to sit at the picnic bench at the end of the  …see more

from £36 / night

£250 - £780 / week

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from £36 / night

(4) Very Good 

21

Flat 3, Elizabeth House - Ventnor apartment sleeps 5

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
Flat 3, Elizabeth House, Hambrough Road is located in the town centre just a couple of minutes' stroll down the cascade to the beach. Situated opposite the Winter Gardens, it is a great location to explore the delights of Ventnor. Many excellent pubs and restaura  …see more

from £80 / night

£350 - £795 / week

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from £80 / night

(18) Excellent 

24

Isle Of Wight Caravan Hire - Bembridge caravan/mobile home sleeps 8

Isle of Wight / Bembridge

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
*We have more statics available, so please contact us even if the calendar says unavailable*This fantastic spacious and homely static caravan is in the same area as The Other Statics we have available at Sandhills Holiday Park so if you wanted two or more families to co  …see more

from £100 / night

£350 - £650 / week

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from £100 / night

(5) Excellent 

10

Eversley Luxury Apartment - Shanklin apartment sleeps 8

Isle of Wight / Shanklin

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
A Luxurious 4 bedroom self catering holiday apartment, providing accommodation for 6 + 2 people with private roof terrace and 6 person hot tub.Located on the first and second floors this apartment offers en-suites to 3 of the bedrooms.Master Bedroom: Located on the seco  …see more

from £140 / night

£695 - £1775 / week

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from £140 / night

(10) Excellent 

16

Number 58 Brambles Chine - Freshwater bungalow sleeps 5

Isle of Wight / Freshwater

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Number 58 is a perfect holiday getaway on the beautiful Isle of Wight. Sleeping up to five people, this two bedroom self-catering semi-detached bungalow based at Brambles Chine, West Wight is just minutes from the ferry terminal in nearby Yarmouth and only yards from th  …see more

from £70 / night

£390 - £520 / week

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from £70 / night

(2) Very Good 

15

Isle of Wight Sandown Chalet 80 - Yaverland chalet sleeps 6

Sandown / Yaverland

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
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

(2) Excellent 

8

Bucks Farm (Poachers Hut) - Shorwell barn sleeps 2

Isle of Wight / Shorwell

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
A choice of three beautifully and stylishly converted barn cottages set in an idyllic rural location, surrounded by open countryside, an Area of Outstanding Natural Beauty, ideal for walkers and cyclists. Each cottage is tastefully furnished and well equipped for two pe  …see more

from £70 / night

£450 - £550 / week

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from £70 / night

(3) Excellent 

16

IOW Holiday Accommodation No 2 - Freshwater bungalow sleeps 4

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
This bungalow is located in the Linstone Chine Holiday Village, Freshwater. It has been refurbished at the beginning of 2015 and it has a marvellous, uninterrupted view over the Solent towards Hurst Castle and a few steps from the bungalow and you can see the Needles, t  …see more

from £38 / night

£260 - £560 / week

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from £38 / 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 / week

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from £80 / 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

(13) Excellent 

15

Waterside - Wootton Bridge bungalow sleeps 6

Isle of Wight / Wootton Bridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
This spacious detached 3 bedroom home is set in a stunning location with spectacular views overlooking Wootton Creek and benefits from its own floating pontoon for boats up to 32 feet allowing access to and from The Solent.The accommodation comprises a spacious lounge w  …see more

from £95 / night

£495 - £995 / week

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from £95 / night

(14) Very Good 

23

Cowes Seaview Apartment - West Cowes apartment sleeps 6

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! Free unlimited WiFi, new carpets and redecorated August 2015. Yards from the Royal Yacht Squadro  …see more

from £60 / night

£365 - £1670 / week

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from £60 / night

(11) Very Good 

15

Holiday Chalet in Gurnard with shared pools - Gurnard Pines chalet sleeps 5

Cowes / Gurnard Pines

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
We are pleased to advertise our immaculate and well maintained two bedroom Chalet in the Gurnard Pines Holiday Village that can sleep up to five persons. This Chalet comes fully equipped with all the necessary items to make your stay as close to home as possible.The mai  …see more

from £80 / night

£300 - £600 / week

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from £80 / night

(11) Very Good 

28

Dairy Cottage - Whitwell cottage sleeps 6

Isle of Wight / Whitwell

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 5 km
  • Child friendly
  • Ask about pets
Lovely 17th century stone cottage in the hamlet of Southford. The cottage stands between Stenbury Down and Niton down and several picturesque walks begin from the farm just behind the cottage. The Undercliff, Woody Bay, Ventnor, Steephill Cove and St Lawrence are all  …see more

from £80 / night

£300 - £600 / week

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from £80 / night

(5) Excellent 

25

Shepherd's Hideaway - Whippingham log cabin sleeps 6

Isle of Wight / Whippingham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
The stunning new hand-built Shepherd's Hideaway, comprises your own private cluster of beautiful oak clad Shepherd's Huts, set around a decked area in the heart of nature. Each Shepherds Hut is a different room ! Sleeping up to 6 , it is ideal for adventurous families  …see more

from £150 / night

£550 - £1200 / week

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from £150 / night

(15) Excellent 

13

Carriers Stable - holiday cottage of high quality - Brighstone cottage sleeps 2

Isle of Wight / Brighstone

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 km
  • Private garden
Carriers Stable was once a Victorian stable that has now been converted into a beautiful detached holiday cottage to accommodate ideally 2 people, and equipped to high standard, with good reviews. Normal change over day Fridays. We try to provide most items so you don't  …see more

from £62 / night

£314 - £585 / week

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from £62 / night

(58) Excellent 

20

Sea view apartment, Ventnor - Salty Holidays - Ventnor apartment sleeps 4

Isle of Wight / Ventnor

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly
Salty Holidays is the perfect spot to relax and enjoy the fantastic sea views over Ventnor bay. Facing south on a quiet private road, it is a fantastic location, only 50 meters from the beach and walking distance to the shops and restaurants. The apartment is comfortabl  …see more

from £75 / night

£400 - £825 / week

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from £75 / night

22

Yangeyange#65 - Seaview chalet sleeps 4

Isle of Wight / Seaview

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
(Preferential ferry prices for our guests: please ask for details) Our three Salterns Beach Chalets in this small development have been modernised to Premier standard to provide most comfortable accommodation for your seaside holiday. They are superbly situated with Ya  …see more

from £58 / night

£249 - £425 / week

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from £58 / night

(6) Very Good 

11

Bucks Farm (Surf Shack) - Billingham barn sleeps 2

Shorwell / Billingham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 6 km
  • Ask about pets
  • Private garden
Bucks Farm Cottages has 3 newly, purpose built barn conversions, offering unrivalled accomodation with a jaw dropping location on the south of the Island . Views extend from the Blackgang cliffs right down to Freshwater Bay ! Set in a private 'farm' community  …see more

from £70 / night

£450 - £550 / week

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from £70 / night

(4) Excellent 

11

Holiday Home in Newport, Isle of Wight - Newport house sleeps 9

Isle of Wight / Newport

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Private garden
This spacious and comfortable semi-detached house is situated in a quiet residential neighbourhood within walking distance of Newport town centre. Situated at the top of a hill, the home boasts stunning views of the island and a well-kept private garden. This home offer  …see more

from £50 / night

£325 - £1930 / week

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from £50 / night

(12) Excellent 

12

Corston House apartment - Appley apartment sleeps 3

Ryde / Appley

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Stylish, top floor, holiday apartment, in a prestigious Victorian house, located in a peaceful road, close to the sea. A short walk to Ryde's long, beautiful sandy beaches, and town centre restaurants, bars and shops. The apartment is newly furnished in a clean mod  …see more

from £52 / night

£364 - £483 / week

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from £52 / night

(6) Excellent 

14

Apartment 6, Hambrough House - Ventnor Bay apartment sleeps 6

Ventnor / Ventnor Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
Modern first floor self-catering Victorian apartment with fantastic sea and coastline views and balcony, only a stones throw from the beach and harbour and situated in the heart of Ventnor with a good choice of wine bars, fine dining and shops.Sleeps 6 in one luxury kin  …see more

from £145 / night

£750 - £1163 / week

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from £145 / 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

18

Holiday house on beach in Bembridge - Bembridge Beach house sleeps 6

Bembridge / Bembridge Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
This three storey, split level town house is part of an impressive development, which has shared communal landscaped gardens and direct access to the beach (50 meters away). The property is set in the prime position with uninterrupted views overlooking Bembridge Harbour  …see more

from £115 / night

£435 - £1190 / week

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from £115 / night

(13) Very Good 

17

Charlton House - Bonchurch house sleeps 10

Isle of Wight / Bonchurch

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Charlton House is a beautiful home set in a private and tucked away location on the edge of the highly sought after and picturesque village of Bonchurch, adjacent to the very popular Victorian town of Ventnor. Bonchurch & Ventnor has had a fair bit of media attention re  …see more

from £250 / night

£1000 - £2000 / week

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from £250 / night

(13) Excellent 

10

Lane End Cottage - Bembridge cottage sleeps 8

Isle of Wight / Bembridge

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Lane End Cottage is a beautiful detached family holiday home. The rooms are light and spacious. It has a large garden perfect for relaxing and barbecues. There is plenty of room for parking and boats etc. It is only 500 yards from the lovely Lane End Beach, with sand, r  …see more

from £69 / night

£480 - £900 / week

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from £69 / night

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