Cycling holiday villas and apartments Isle of Wight

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Isle of Wight

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350 Holiday homes

Filters applied: Cycling holidays (350)

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

(5) Excellent 

13

Gurnard holiday cottage rental

Isle of Wight / Gurnard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
All bookings come with 15% discount of Red Funnel ferries.free Courtesy bus for sailing events or those coming on foot. Parking for 3 cars.<br />Part of the Cowes Holiday Homes portfolio where quality matters  …see more

from £120 / night

£475 - £1300 / week

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from £120 / night

(20) Very Good 

16

Holiday apartment in Ryde

Isle of Wight / Ryde

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
“Very Nice, Up-To-Date Interior & Excellent Communication” The hayloft was an excellent place to stay for the weakened, as was attending the Isle Of White music festival. Great location between the towns and country side (very peaceful in the morning).  …see more

from £60 / night

£370 / week

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from £60 / night

(10) Very Good 

17

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“A superb apartment in a great location. Perfect.” We new the apartment was impressive from the photo's,however they do the accommodation little justice as the place needs to be seen in person. With panoramic views of the entire sea front enables Ventn  …see more

from £145 / night

£750 - £1163 / week

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from £145 / night

22

Holiday chalet rental

Isle of Wight / Seaview

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
For seaside holidays at their best!<br />Weekend Nights are Friday, Saturday and Sunday. Weekday Nights are Monday, Tuesday, Wednesday and Thursday  …see more

from £43 / night

£232 - £679 / week

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from £43 / night

(14) Excellent 

22

Freshwater holiday home rental

Freshwater / Freshwater Bay

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Fantastic family holiday at The Tower House” We stayed at the Tower House in July during the first week of the school holidays. A family group of 5 adults and 6 children ranging in age from 4 to 9. Reading the description of the property, speaking to  …see more

from £143 / night

£995 - £1790 / week

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from £143 / night

(7) Very Good 

24

Ryde holiday apartment rental

Ryde / Appley

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“A beautiful, well kept apartment in a great location” A really clean, comfortable, well equipped apartment (although a hairdryer would be a nice addition) in a fantastic location. Very near transport links, shops etc with a lovely sea view. I had a wo  …see more

from £100 / night

£395 - £765 / week

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from £100 / night

(2) Excellent 

10

Holiday apartment in Brook

Isle of Wight / Brook

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly
Brook is a lovely little village in the beautiful and rural West Wight. It can offer you the perfect place for a relaxing holiday. At Brook House, we have 3 self-catering holiday properties. Northbrook, our smallest property, will give you a charming and character  …see more

from £90 / night

£300 - £995 / week

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from £90 / night

(3) Excellent 

12

Holiday apartment in Cowes

Cowes / West Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
With its off-road parking & flexible layout with 1 bathroom, 1 en suite shower room & 1 cloakroom this property is well suited for families, small groups & corporate bookings.<br />This property is part of the Cowes Holiday Homes portfolio where good  …see more

from £75 / night

£350 - £1600 / week

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from £75 / night

(5) Excellent 

22

Barn rental in Ryde

Isle of Wight / Ryde

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
“Fabulously spacious barn on working farm sleeping 12 with amazing views and” Really enjoyable stay at Kemphill Farm. Very spacious and incredibly well equipped with everything you could need. Plenty of space to sleep 12 of us young and old and each of  …see more

from £210 / night

£980 - £2400 / week

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from £210 / night

(3) Excellent 

23

Apartment letting in Wroxall

Isle of Wight / Wroxall

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Child friendly
“A very relaxing place to stay” We have stayed at Lake View twice. The property is very comfortable with good beds and plenty of room to relax. It has a well appointed kitchen with built in appliances. We love all the farm animals especially the llamas  …see more

from £150 / night

£900 / week

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from £150 / night

(21) Excellent 

7

Holiday lodge with golf nearby in Whippingham

Isle of Wight / Whippingham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 4 km
  • Child friendly
  • Car not necessary
“New Years Eve!” We stayed in Barton Lodge for a few days over New Year and it was great! (three adults two teenagers and a dog). In the run up before the stay Amber was prompt, helpful and generally brilliant at answering queries. When we arrived she  …see more

from £85 / night

£565 - £1025 / week

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from £85 / night

(12) Very Good 

20

Chalet rental in Gurnard

Isle of Wight / Gurnard

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Superb and exquisite little gem, highly recommended” We stayed in Beachside for two magical days. It may have rained constantly but the cabin was so perfectly equipped we were happy to stay inside and cook in the very well equipped kitchen, read books  …see more

from £50 / night

£320 - £530 / week

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from £50 / night

(38) Excellent 

26

Holiday home in Brighstone

Isle of Wight / Brighstone

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Lovely spacious house” Had a very nice stay in the Mill house. We all found it relaxing with lots of children. Location of the house was good for travelling around Isle of Wight. I would recommend the rental.  …see more

from £289 / night

£2026 - £3585 / week

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from £289 / night

(17) Excellent 

30

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Great holiday cottage” The Dairy was very well presented, extremely clean and very comfortable for our family with two young children. It is very well equipped with everything you need for a self catering holiday. We especially loved the hot tub, e  …see more

from £125 / night

£370 - £795 / week

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from £125 / night

(9) Excellent 

23

Cowes holiday caravan/mobile home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Swimming pool
Newly refurbished for 2016. Modern 3 bedroom caravan with 1 double bedroom, 2 twin bedrooms and pull out in lounge area. Full central heating and double glazing throughout. Shower room, and additional separate WC. Caravan facilities include fully equipped kitchen with i  …see more

from £70 / night

£365 - £750 / week

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from £70 / night

(3) Excellent 

24

Holiday home in Bonchurch

Isle of Wight / Bonchurch

5 8 2 nights min

  • 5 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden
“Absolutely fantastic” We stayed at Garden House during the October half term and thoroughly enjoyed it, a perfect home away from home. Well placed near Ventnor and Shanklin (our favourites on the Island), and near lots of amenities. The beds were the  …see more

from £115 / night

£805 / week

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from £115 / night

(24) Excellent 

14

Cottage rental in Ventnor

Isle of Wight / Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Home away from home - with AMAZING views!” My wife and I stayed at Ocean View for a long weekend in middle June 2014. We found the cottage to be neat and tidy, well prepared for our stay, stylishly decorated and with amazing views spanning out across  …see more

from £99 / night

£495 - £950 / week

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from £99 / night

(1) Excellent 

14

Shanklin holiday home rental

Shanklin / Old Village

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Car not necessary
DISCOUNT APPLIED TO SEPTEMBER 2016 RATES. You can book for 5 nights or more from £534. The cottage has been advertised for 2016 following a break, discount rate already applied. Percy cottage (Self-catering. Sleeps 4 in total. (2 bedrooms) is nestled in the pi  …see more

from £75 / night

£525 / week

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from £75 / night

(38) Excellent 

19

Holiday cottage in Newchurch

Sandown / Newchurch

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
“A truly lovely property.” If you want a peaceful holiday property in superb location then Brew House is for you, Tastefully decorated, very clean, comfortable and well equipped. The owners had left a lovely welcome pack which included scrumptious home  …see more

from £90 / night

£500 - £750 / week

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from £90 / night

(5) Excellent 

11

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Private garden
“Same High Standard” We stayed in Carisbrooke last year and loved it and really wanted to try the newly released Albert apartment after it's extensive renovations. In fact we booked a week over the Easter holiday without even seeing any photo's. We wer  …see more

from £80 / night

£475 - £745 / week

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from £80 / night

(31) Excellent 

23

Holiday home in Yarmouth

Isle of Wight / Yarmouth

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Wonderful holiday rental!” A lovely, spacious comfortable house with fantastic countryside views. We travelled with our young family and friends and all enjoyed staying at Three Gables. The kids loved the garden and played golf and boules (all provid  …see more

from £195 / night

£800 - £1775 / week

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from £195 / night

(2) Excellent 

8

Holiday barn in Shorwell

Isle of Wight / Shorwell

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
For those bringing bikes, surf boards and the like, a barn is available for storage.These desirable cabins nestle in downland, above the peaceful village of Shorwell, only 2 miles from yhe south coast of the Island.<br />Footpaths alongside the cottage join the Is  …see more

from £70 / night

£450 / week

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from £70 / night

(6) Excellent 

21

Holiday bungalow rental

Freshwater / Freshwater Bay

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Robinhill holiday bungalow is situated in the West which is a beautiful part of the island. The bungalow is in a very quiet and relaxing location, sandy Colwell Bay beach is within a few minutes walk. Walking and cycling holidays can be enjoyed any time of the year.<  …see more

from £36 / night

£250 - £480 / week

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from £36 / night

(1) Excellent 

19

Holiday home in Shanklin

Isle of Wight / Shanklin

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Great location for exploring the Island, peacefull with lovely views, countryside from the rear and sea glimpses from the front of the house. Lovely walks into Shanklin Town via the railway track or through the farm, plus America Woods seconds away.<br />Balconies  …see more

from £350 / night

£2500 / week

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from £350 / night

(6) Very Good 

24

Holiday home in Newport

Newport / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
“VIP accommodation for the Isle of Wight Festival” We stayed here with family and friends for 3 nights for the Isle of Wight Festival this year. Having the mooring come with the house made for a hassle free arrival and departure when the ferries and b  …see more

from £150 / night

£750 - £2400 / week

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from £150 / night

(13) Excellent 

16

Apartment rental in Cowes

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
“Great location, cosy and” I stayed here for a weekend and had a very comfortable and enjoyable stay. It is so continentally located by the ferry, shops, pubs and bars and it near to bus stops to see the rest of the Island. The apartment itself has e  …see more

from £100 / night

£350 - £400 / week

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from £100 / night

24

Newchurch holiday cottage rental

Sandown / Newchurch

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Characterful cottage on the Garlic Farm on the Isle of Wight. Perfectly placed for walking, cycling and family holidays. Guests enjoy a 10% discount in our renowned restaurant, use of tennis court and football pitch. 10 minutes from the beach by car.<br />Peacocks  …see more

from £175 / night

£825 - £1925 / week

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from £175 / night

(13) Very Good 

14

Holiday cottage letting

Whitwell / Nettlecombe

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
“An excellent holiday stay” First time me and my husband have ever been to the Isle of White and totally fell in love with the place. We loved it so much even thinking of moving there within few years. Whitwell Station was a lovely accommodation and  …see more

from £90 / night

£470 - £1080 / week

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from £90 / night

(6) Excellent 

63

Seaview holiday cottage rental

Isle of Wight / Seaview

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Whatever your Isle of Wight holiday needs, from family stays to short breaks for couples, Seaview Holidays can accommodate them all.  …see more

from £88 / night

£379 - £799 / week

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from £88 / night

(18) Excellent 

16

Holiday home in Cowes

Cowes / West Cowes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“The perfect base for our stay!” This was our third stay in West Cowes, having rented the 'old' Crew's Nest from Clive & Philippa twice before. The new house backs right onto the old one and was only a matter of a couple of minutes extra walk from the  …see more

from £150 / night

£550 - £3500 / week

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from £150 / night

(2) Excellent 

11

Holiday apartment in Cowes

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 which is adjacent to Shepards Wharf marina. Relax on the balcony and enjoy the ever-changing scene across the harbour and Eastern Solent. 5 minutes walk from the centre of Cowes.  …see more

from £125 / night

£400 - £2200 / week

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from £125 / night

22

Holiday cottage in Newchurch

Sandown / Newchurch

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Tennis court, football pitch, table tennis - Discounted ferry crossings available  …see more

from £120 / night

£575 - £1275 / week

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from £120 / night

12

Holiday cottage in Bembridge

Bembridge / Bembridge Village

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • 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.  …see more

from £50 / night

£695 / week

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from £50 / night

(10) Very Good 

27

Holiday cottage letting

Isle of Wight / Bembridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Whether you are looking for a family beach holiday where you can forget the car and just chill in the garden or rock pool at the beach, or plan a walking, or cycling holiday exploring the island, Drayton Cottage is an ideal base - safe, secure and warm with free wifi.  …see more

from £100 / night

£325 - £800 / week

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from £100 / night

(8) Excellent 

22

Cowes holiday home rental

Cowes / West Cowes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.18 km
  • Child friendly
“Christmas in Cowes” Great house. We were a group of 9 adults and 5 children all 2 and under. This house was the perfect place to spend christmas, plenty of room and a great kitchen with everything you need including a stocked pantry, which is always h  …see more

from £295 / night

£2065 / week

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from £295 / night

10

Home rental in Freshwater

Freshwater / Freshwater Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
Built in 2015, Tennyson Cottage, is a comfortable two bedroom home situated in Freshwater. The accommodation offers a well furnished lounge with sofa bed / diner with doors leading to an enclosed garden; a well equipped modern kitchen; downstairs wc; a double bedroom w  …see more

from £173 / night

£395 - £740 / week

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from £173 / night

(18) Very Good 

17

Holiday studio in Shanklin

Isle of Wight / Shanklin

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Good place, good price!” Nice studio apartment finished to high standard with well equipped kitchen, easy walking distance to shanklin, local pubs and restaurants. Be a bit cosy if there where four of you but great for two.  …see more

from £45 / night

£230 - £585 / week

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from £45 / night

(3) Very Good 

22

Holiday bungalow letting

Isle of Wight / Freshwater

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
A light & airy detached bungalow situated in a quiet cul-de-sac just 300yds from the popular beach at Colwell Bay. The well presented accommodation includes 3 bedrooms sleeping up to 6. The main living accommodation is open plan providing comfortable lounge seating,  …see more

from £45 / night

£318 - £825 / week

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from £45 / night

(4) Very Good 

22

St Helens holiday cottage rental

Isle of Wight / St Helens

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Private garden
“Fab cottage” The cottage was clean & well furnished. We were close to the beach with good restaurants and superstore close by. Neighbours friendly and helpful. The only downsides were no bath towels and nothing in the literature advising of this an  …see more

from £42 / night

£295 - £680 / week

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from £42 / night

(39) Excellent 

32

Holiday cottage rental

Isle of Wight / Shanklin

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“This is a Gem and ticks all the boxes!” This is an immaculately clean establishment offering the choice of both B&B and self catering. It is in a great position just a few minutes walk to the beach in one direction and the town in the other. It is in  …see more

from £65 / night

£450 - £695 / week

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from £65 / night