Cycling holiday villas and apartments Isle of Wight

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  • Bembridge (20)
  • Bemridge Harbour (1)
  • Bonchurch (7)
  • Brading (4)
  • Brighstone (5)
  • Brook (2)
  • Calbourne (5)
  • Cowes (48)
  • East Cowes (4)
  • Freshwater (24)
  • Godshill (5)
  • Gurnard (13)
  • Knighton, Isle of Wight (1)
  • Lake (1)
  • Nettlestone (1)
  • Newport (7)
  • Newtown (1)
  • Niton (6)
  • Porchfield (3)
  • Rookley (1)
  • Ryde (20)
  • Sandown (41)
  • Seaview (10)
  • Shanklin (36)
  • Shorwell (5)
  • St Helens (3)
  • Totland Bay (5)
  • Ventnor (54)
  • Wellow (2)
  • Whippingham (6)
  • Whitwell (5)
  • Wootton Bridge (9)
  • Wroxall (6)
  • Yarmouth (18)

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379 Holiday homes

Filters applied: Cycling holidays (379)

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

(2) Excellent 

11

4 Marinus - Cowes apartment sleeps 4

Isle of Wight / Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Superb modern two bedroom apartment on the second floor of Marinus with views over the harbour and Eastern Solent and situated adjacent to Shepards Wharf marina. Accessed via private lift or stairs, the accommodation is of a contemporary style with a fully fitted kitch  …see more

from £125 / night

£400 - £2200 / week

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from £125 / night

(10) 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

(1) Excellent 

19

8 Fife Court - West Cowes house sleeps 8

Cowes / West Cowes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This Fabulous 4 bedroom, 3 bathroom town house, within a 5 minute walk of all the amenities that Cowes has to offer. With 4 bedrooms (1 triple 1 double 1 twin & 1 single) & 3 bathrooms this house is ideally suited for larger family holiday, sailing crews or corporate  …see more

from £105 / night

£440 - £3000 / week

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from £105 / night

(4) Excellent 

20

Sunnywight Holiday Bungalows - 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 km
  • Child friendly
Welcome to the Sunnywight Holiday Bungalow. Self Catering 3 Star Accomadation in Colwell Bay, near Freshwater in the Isle of Wight.In a secluded and quiet part of The Isle of Wight, the ever popular holiday destination, and with direct access to the beach, our holiday b  …see more

from £40 / night

£275 - £485 / week

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from £40 / night

(5) Excellent 

12

151 Brambles Chine - Freshwater chalet sleeps 4

Isle of Wight / Freshwater

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
An extremely well presented holiday bungalow, situated right on the coastline with the site being surrounded by open fields. The bungalow accommodates four people comfortably, offering two bedrooms being a double & a twin room (bunk beds). The lounge is 'open p  …see more

from £56 / night

£260 - £350 / week

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from £56 / night

(13) Excellent 

14

The Stable at Buddle Place - Niton cottage sleeps 6

Isle of Wight / Niton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
The Stable at Buddle Place is a recently renovated stone built stable / coach house on one level. . It sleeps 6 in 3 bedrooms, one double with en-suite bathroom & two twin rooms with a family bathroom. There is a large sitting / dining room with sofa's, dining  …see more

from £120 / night

£575 - £1370 / week

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from £120 / night

(2) Very Good 

21

Westridge House - Ryde house sleeps 10

Isle of Wight / Ryde

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Westridge House is a one of the most exclusive homes on the island comfortably sleeping up to 10 people. The house holds 5 bedrooms, consisting of 3 double bedrooms and 2 twin bedrooms. Despite being built over 100 years ago, the house is furnished to an extremely high  …see more

from £700 / night

£2250 - £4495 / week

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from £700 / 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

19

Norwood - Brading cottage sleeps 8

Isle of Wight / Brading

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Lovingly restored by the current owners the accommodation retains many character features yet combines the benefits of modern additions which make Norwood House a perfect base for any holiday.The accommodation offers a cosy sitting room with a feature open fireplace, fl  …see more

from £135 / night

£525 - £750 / week

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from £135 / night

(12) Excellent 

28

The Old Barn - 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 luxury barn conversion recently completed is now beautifully furnished for holiday letting. The oak beamed interior compliments this original island stone barn set in a quiet farm location with outside Hot Tub in the beautiful West Wight countryside. There are two  …see more

from £130 / night

£580 - £1495 / week

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from £130 / night

8

The Wing at Fox Hollow - Wroxall house sleeps 4

Isle of Wight / Wroxall

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
Attached to the main house, there is plenty of outside space including parking for two vehicles to the side and a garden to the rear. On the ground floor there is the spacious open plan lounge/kitchen/dining room. The cottage style kitchen is well appointed with modern  …see more

from £36 / night

£250 - £410 / week

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from £36 / night

(14) Excellent 

27

Marmalade Cottage + Sea Countryside & Garden Views - Brading cottage sleeps 5

Isle of Wight / Brading

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
'Marmalade Cottage' at the top of our private gated driveway is on the edge of Brading Downs in a unique and beautiful location alongside a meadow & in lovely gardens that have panoramic views over an Area of Outstanding Natural Beauty. In a Conservation Area of Bra  …see more

from £85 / night

£425 - £845 / week

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from £85 / night

(1) Very Good 

12

Ocean View 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 0.25 km
  • Child friendly
Situated in West Wight, one of the prettiest and most unspoilt parts of the island, our Ocean View holiday bungalow is located on the coastal path above the sandy beach of Colwell Bay. Offering spectacular views of the sea and the famous Needles Lighthouse, it is only a  …see more

from £30 / night

£190 - £375 / week

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from £30 / night

(2) Excellent 

9

20 Beckford Road - West Cowes house sleeps 9

Cowes / West Cowes

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children age 5+
20 Beckford Road is a recently refurbished 4 bedroom Victorian town-house, fantastically located in central Cowes. With sea views, it is only 100 metres from the main marinas, yacht clubs and the bustling Cowes high street. Local amenities, shops, pubs and restaurants a  …see more

from £78 / night

£545 - £900 / week

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from £78 / night

(5) Very Good 

13

Sea View Apartment The Priory - Shanklin apartment sleeps 4

Isle of Wight / Shanklin

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
The apartment is part of a newly refurbished house; previously a Victorian gentleman's residence. The building is light and airy and set in two acres of grounds, in a quiet location, close to 'The old Village' Shanklin and adjacent to National Trust land.  …see more

from £98 / night

£375 - £600 / week

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from £98 / night

(1) Very Good 

24

Kokota#54 - 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 the most comfortable accommodation for your seaside holiday. They are superbly situated wit  …see more

from £58 / night

£330 - £425 / week

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from £58 / night

(1) Excellent 

14

Alban House, Cowes. overlooking the Marina - West Cowes house sleeps 12

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
A superb house in the Cowes recently refurbished to a high standard overlooking the marina with its own pontoon. The house has central heating and double glazing. This modern town house split over 4 levels has a large fully fitted kitchen including a dishwasher, fridge  …see more

from £500 / night

£2000 - £3500 / week

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from £500 / night

(1) Very Good 

8

Swallow Cottage - Gurnard cottage sleeps 4

Isle of Wight / Gurnard

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Swallow Cottage is one three properties, all with Visit Britain 4 star accommodation, at Buntshill Farm. They are situated near West Cowes and Shalfleet. Swallow Cottage is a blend of natural red brick, polished stone floors with underfloor heating and is set in open c  …see more

from £65 / night

£450 - £840 / week

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from £65 / night

(4) Excellent 

22

The Old Dairy at Kemphill Farm Ryde Isle of Wight - Ryde barn sleeps 12

Isle of Wight / Ryde

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
This fabulous renovation was carried out in 2002. Particular care has been taken to transform the interior from a 1911 milking shed into luxurious 5 star accommodation, whilst still retaining the lovely heritage features.Inside the property the spaces are extremely ligh  …see more

from £210 / night

£980 - £2400 / week

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from £210 / 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

(2) Good 

30

Nettlestone House - Nettlestone house sleeps 10

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
We think you'll love staying at Nettlestone House it has great character, is beautifully furnished, yet is family friendly and has loads of space.Nettlestone House is the main part of a substantial 220 year old stone property which offers impressive and comfortable  …see more

from £199 / night

£995 - £1995 / week

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from £199 / night

(3) Very Good 

12

Seabreeze - 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 0.2 km
  • Child friendly
The property was built in 2007 and the accommodation is built and furnished to a high standard. We have lots of guests who have been booking their holidays in Seabreeze for many years. Seabreeze is located in a quiet and peaceful location, just the thing to unwind fr  …see more

from £30 / night

£210 - £544 / week

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from £30 / night

(14) Excellent 

13

Springfield cottage - Newchurch bungalow sleeps 2

Sandown / Newchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Private garden
One bedroom bungalow in the garden near to the owners property with its own private patio. Situated in the peaceful village of Newchurch popular with walkers nature lovers and cyclists. The comfortable accomodation is all on ground level with no steps and easily acce  …see more

from £85 / night

£340 - £600 / week

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from £85 / night

(1) Excellent 

22

Littlestairs - Shanklin house sleeps 8

Isle of Wight / Shanklin

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Littlestairs is a comfortable holiday home situated in Shanklin with sea views. The accommodation offers 4 spacious double bedrooms all with en-suites (two of the bedrooms are on the ground floor). A cot is also available. The master bedroom has patio doors leading to  …see more

from £130 / night

£705 - £1595 / week

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from £130 / night

(25) Very Good 

23

The Boathouse and River Cottage, Yarmouth IOW - Yarmouth boathouse sleeps 11

Isle of Wight / Yarmouth

2 11 Min stay varies

  • 2 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
River Cottage 4 bedrooms (sleeps 7+) and The Boathouse 2 bedrooms (sleeps 4+2). Two properties at the most exclusive location on the Isle of Wight, based on the quiet waterside by the River Yar estuary and yet just 300m from the lovely harbour town. High quality proper  …see more

Pricing unknown

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Pricing unknown

(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

(11) Excellent 

23

Great Escape, 6 Westcliffe Chalets, Niton, IOW - Ventnor chalet sleeps 2

Isle of Wight / Ventnor

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 4 km
Lovely 1 bed single storey Chalet offering cosy holiday accommodation in a peaceful location overlooking beautifully maintained communal gardens with glimpses of the sea beyond the trees. Refurbished throughout just a few years ago Great Escape is modern and well prese  …see more

from £40 / night

£240 / week

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from £40 / night

(2) Excellent 

8

Holiday Chalet in Sandown / Yaverland - Sandown chalet sleeps 6

Isle of Wight / Sandown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
This is a beautiful open plan chalet that easily accommodates 6. The kitchen caters for all guests, supplying you with a table and six chairs as well as all the cooking facilities and crockery you will require. Within the lounge is a large sofa bed, Free-view TV/DVD, s  …see more

from £50 / night

£300 - £550 / week

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from £50 / night

(1) Excellent 

22

Isle of Wight Caravan Hire - Bembridge / Sandhills - Bembridge caravan/mobile home sleeps 6

Isle of Wight / Bembridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
A modern, light and open feel 6 berth caravan to let on Sandhills Holiday Park, Isle of Wight, situated just a 2 minute walk from the beach. The caravan has two bedrooms with the main bedroom having an en-suite toilet with wash basin. The main bathroom has a shower, b  …see more

from £50 / night

£300 - £550 / week

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from £50 / night

28

Spencer House Ryde - Ryde apartment sleeps 8

Isle of Wight / Ryde

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Property description Spencer House Ryde   This four bedroom modern spacious ground floor apartment is wonderfully located for the shops, bars and restaurants in cosmopolitan Ryde, with the wide sandy beaches within walking distance or a one minute drive, and is in a qu  …see more

from £100 / night

£595 - £1295 / week

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from £100 / night

(3) Excellent 

23

Sun Hill Retreat - Cowes house sleeps 6

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Private garden
This cosy cottage dating back to 1700 is situated at the top of Sun Hill .Within a minutes walk of all the amenities and yacht havens. Private parking for one guest car exists and the use of a small private garden equipped with BBQ & seating. The rear bedrooms share vi  …see more

from £150 / night

£900 / week

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from £150 / night

(3) Excellent 

28

Sea Breeze Richmond Apartments - Ventnor Bay apartment sleeps 7

Ventnor / Ventnor Bay

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
Lovely front line position second floor apartment with a large balcony enjoying superb sea views over Ventnor Bay, private side entrance with communal stairs to second floor..Entrance doors to apartment. Open plan living area with large balcony. Lounge (sofa bed conv  …see more

from £150 / night

£375 - £645 / week

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from £150 / night

(25) Very Good 

18

Sunnycott caravan park - Cowes caravan/mobile home sleeps 6

Isle of Wight / Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly
Sunnycott Cowes on the Isle of Wight is a small, quiet, rural, family owned and run Holiday Park consisting of a self-catering caravan. Sailing, horse riding and mountain bike hire are all available locally.Caravan has gas and electric heating, and is pre heated during  …see more

from £50 / night

£250 - £630 / week

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from £50 / night

(9) Very Good 

13

78 Sandown Bay Holiday Chalets - Yaverland chalet sleeps 5

Sandown / Yaverland

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Fantastic holiday chalet, in fantastic condition. This beautiful chalet is available after having undertaken a complete refit and redecoration. The chalet has been re-plastered and had a new ring main and all internal doors fitted not to mention a new kitchen and bathro  …see more

from £100 / night

£350 - £485 / week

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from £100 / night

(9) Excellent 

24

Clevelands Country House - Wroxall manor house sleeps 12

Isle of Wight / Wroxall

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Cleveland's Country House offers some of the best quality self-catering accommodation on the island. All accommodation is tastefully decorated throughout to a high standard and extremely well equipped to create a cosy, informal and relaxed atmosphere, a true home from h  …see more

from £350 / night

£1875 - £2800 / week

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from £350 / night

(9) Very Good 

16

SeaShells - Freshwater chalet sleeps 5

Isle of Wight / Freshwater

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
An open-plan lounge with dining area and kitchen, 2 bedrooms and a bathroom. Located on a 40 acre communal site. Large grassed area to the front of the property with a paved patio area which includes table and chairs allowing you to while away the hours watching the boa  …see more

from £33 / night

£199 - £495 / week

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from £33 / night

(13) Excellent 

17

1 Drayton Villas - St Helens - Bembridge apartment sleeps 4

Bembridge / St Helens, Bembridge

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Uniquely positioned on a quiet residential street which leads from St Helen's Village Green via Mill Lane to the sea. From the bottom of the lane turn left at the Old Mill and walk across the Duver to St Helens beach and sample the menu at Baywatch cafe; or turn right  …see more

from £42 / night

£225 - £299 / week

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from £42 / night

(8) Excellent 

10

1 Kings Cottage - Whippingham cottage sleeps 4

Isle of Wight / Whippingham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 10 km
  • Child friendly
  • Private garden
The well maintained cottage is located adjacent to the Royal Park of Osborne House, the home of Queen Victoria at East Cowes. The cottage offers two bedrooms and bathroom upstairs and good size lounge, kitchen and conservatory on the ground floor. Outside there is a hug  …see more

from £47 / night

£323 - £625 / week

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from £47 / 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

(11) Excellent 

12

The Yachtsman - West Cowes townhouse sleeps 10

Cowes / West Cowes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary
The Yachtsman offers high quality self-catering accommodation in the heart of nautical Cowes, close to all facilities in this vibrant seaside town. The property is ideal for sailors, walkers and cyclists, being ideally situated close to the marinas and cycle paths. D  …see more

from £200 / night

£795 - £3250 / week

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from £200 / night

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