Cycling holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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352 Holiday homes

Filters applied: Cycling holidays (352)

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

(30) Excellent 

33

Holiday cottage in Whitwell

Isle of Wight / Whitwell

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Lovely house, beautiful garden and surroundings, brilliantly equipped.” We stayed at Ferndale with our 2 year old and tiny baby. It's a challenging travelling with small children but arriving a Ferndale we breathed a huge sigh of relief as it was so  …see more

from £150 / night

£500 - £1400 / week

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from £150 / night

(13) Excellent 

22

St Helens holiday lodge rental

Isle of Wight / St Helens

2 6 Min stay varies

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

from £65 / night

£395 - £1295 / week

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from £65 / night

(11) Excellent 

20

Holiday cottage in Yarmouth

Yarmouth / Fort Victoria

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Wight Cottage is adjacent to Fort Victoria and close to the pretty harbour town of Yarmouth. The cottage has wonderful sea views from the master bedroom and from the living room, plus plenty of outside space for safe playing, barbequing with family/friends, or simply en  …see more

from £85 / night

£595 - £1245 / week

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from £85 / night

(7) Very Good 

35

Holiday cottage in Bonchurch

Isle of Wight / Bonchurch

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Details to be aware of” Stable Cottage is in a lovely location and is well presented, clean and modern but has a few surprising omissions such as a microwave, tumble dryer, iron and ironing board although some of these are available in a shared laundr  …see more

from £10 / night

£1090 - £1990 / week

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from £10 / night

(14) Excellent 

23

Holiday home in Ryde

Isle of Wight / Ryde

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“A quaint cottage in an idyllic location” This listed quirky former coast guards cottage is an ideal bolt hole for all. All rooms offer luxury 5 star accommodation, with all mod cons thrown in with the rental price. Its central location offers the  …see more

from £54 / night

£375 - £800 / week

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from £54 / night

(8) Excellent 

58

Holiday chalet in Freshwater

Isle of Wight / Freshwater

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Comfortable, Affordable and Amazing Location” My partner and myself wanted to take our 3 young children aged 3, 6 and 9 on a week's break somewhere during half term and decided on the Isle of Wight. After looking at various accommodation options we bo  …see more

from £36 / night

£250 - £450 / week

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from £36 / night

(29) Very Good 

21

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

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

from £75 / night

£395 - £1245 / week

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from £75 / night

(14) Very Good 

23

Townhouse accommodation in Yarmouth

Yarmouth / Norton, Isle of Wight

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“This place is fantastic!” We have just spent a week at Hurst View on the Isle Of Wight, it is in an ideal spot. The ferry terminal is only 5-10mins down the road, whichwas a great stress free start to the week. The house itself is very spacious with r  …see more

from £59 / night

£410 - £970 / week

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from £59 / night

(83) Excellent 

25

Holiday cottage in Ventnor

Ventnor / Niton Undercliff

3 8 Min stay varies

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

from £120 / night

£570 - £1475 / week

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from £120 / night

(7) Excellent 

22

Holiday cottage in Brighstone

Isle of Wight / Brighstone

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Brighstone has a church, pub, restaurant, doctor's surgery, newsagent, grocery shop (including Post Office),  …see more

from £99 / night

£345 - £785 / week

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from £99 / night

(18) Excellent 

12

Holiday chalet with shared pool, golf nearby in Gurnard

Isle of Wight / Gurnard

2 6 Min stay varies

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

from £80 / night

£350 - £850 / week

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from £80 / night

(9) Excellent 

23

Freshwater holiday bungalow rental

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
only a few minutes away from the beach, stunning views, spectacular sunsets, family friendly environment with other families and children around, extensive well kept grounds, playground facilities, mini golf, homely, well maintained interior, unlimited free internet<  …see more

from £36 / night

£250 - £550 / week

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from £36 / night

(11) Excellent 

8

Holiday log cabin with golf nearby in Whippingham

Isle of Wight / Whippingham

1 2 Min stay varies

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

from £65 / night

£325 - £450 / week

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from £65 / night

(7) Excellent 

17

Cottage rental in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

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

from £80 / night

£450 - £950 / week

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from £80 / night

(20) Very Good 

20

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“A great place to start and end each day” This little chalet was a great place to lay our heads at the end of each long day exploring the island. It very quickly became "home". It was much better equipped than I had expected, with lots of little extras  …see more

from £35 / night

£225 - £475 / week

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from £35 / night

(13) Excellent 

20

Holiday cottage in Bonchurch

Isle of Wight / Bonchurch

1 2 Min stay varies

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

from £100 / night

£550 - £790 / week

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from £100 / night

(17) Excellent 

24

Holiday cottage in Wootton Bridge

Isle of Wight / Wootton Bridge

2 4 Min stay varies

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

from £135 / night

£695 - £1395 / week

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from £135 / night

(6) Very Good 

23

Holiday cottage in Ventnor

Isle of Wight / Ventnor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“Very homely and comfortable” Very nice, very clean, good towels and bedding sheets. Good situation, very pretty house and Garden. Lots of nice details, detergent, coffee, tea, bread, butter, milk, chocolates, a welcome pack. No parking outside the ho  …see more

from £95 / night

£525 - £995 / week

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from £95 / night

(28) Excellent 

22

Holiday barn with golf nearby in Freshwater

Freshwater / Freshwater Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Lovely place fab location” We really enjoyed our stay here- we hadn't realised how close to the sea it was and how accessible everything is. The cottage is lovely, lots of information and a good selection of books which the kids loved. Thank you!  …see more

from £55 / night

£360 - £1080 / week

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from £55 / night

(12) Excellent 

19

Holiday chalet in Niton

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 5 km
  • Car not necessary
“bijou, quiet, clean” Compact but everything you would need for a short break. Very clean. Lovely location. No cooker but we had one 'ping' meal using the microwave and wandered down to the local pub every other evening to eat.  …see more

from £40 / night

£240 - £425 / week

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from £40 / night

(29) Excellent 

45

Holiday cottage rental

Ventnor / St Lawrence, Ventnor

3 6 Min stay varies

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

from £150 / night

£525 - £1345 / week

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from £150 / night

(24) Excellent 

23

Holiday home in Ventnor

Isle of Wight / Ventnor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“great location. Great views.” The Perch provided myself, husband small child and mother in law with a comfortable and homely stay. The beds were comfortable and the rooms airy. The kitchen provided everything we needed and the garden although small h  …see more

from £150 / night

£495 - £895 / week

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from £150 / night

(22) Excellent 

16

Holiday chalet rental

Sandown / Yaverland

2 4 7 nights min

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

from £25 / night

£195 - £550 / week

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from £25 / night

(4) Excellent 

21

Holiday chalet in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
A unique self catering holiday in an old train ! Great for exploring the Island or just relaxing around the house watching the wildlife and the tide.Comfortable all year round and close to amenities. Off peak short lets available, please contact for more details! The pr  …see more

from £130 / night

£910 / week

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from £130 / night

(36) Very Good 

17

Holiday chalet in Yaverland

Sandown / Yaverland

2 4 Min stay varies

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

from £35 / night

£225 - £475 / week

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from £35 / night

(17) Excellent 

23

Seaview holiday home rental

Isle of Wight / Seaview

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“coastal seclusion” I stayed at Lebrel Lodge with friends for a winter weekend - I think there were about seven of us, mostly couples. It was extremely well appointed and immaculately clean. The weekend was a typical English winter one and so we someti  …see more

from £150 / night

£1045 - £1495 / week

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from £150 / night

(14) Excellent 

10

Holiday cottage accommodation

Isle of Wight / Bembridge

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Highly recommended!! Gorgeous house. We want to live there.” A beautiful cottage that's deceptively large. 1 double bedroom downstairs, 1 double and a huge twin bedroom upstairs. Large downstairs wet room and a family bathroom upstairs. Kitchen is ve  …see more

from £72 / night

£500 - £900 / week

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from £72 / night

(9) Excellent 

12

Holiday bungalow in Freshwater

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
“Lovely, cosy and comfortable” We had a wonderful stay at the bungalow, it was cosy and comfortable. It was in a lovely spot and it would be lovely to stay again. I would defiantly recommend it.  …see more

from £45 / night

£300 - £575 / week

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from £45 / night

(17) Excellent 

22

Holiday cottage in Ryde

Isle of Wight / Ryde

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Everything you could dream of in a cottage with a sea view” We were completely impressed by how well appointed the property was - it is truly a home from home, having literally everything you could possibly need. The enclosed courtyard was real peace  …see more

from £58 / night

£300 - £800 / week

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from £58 / night

(42) Excellent 

27

Ventnor holiday apartment rental

Isle of Wight / Ventnor

1 2 Min stay varies

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

from £70 / night

£420 - £720 / week

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from £70 / night

(27) Excellent 

17

Holiday apartment with golf nearby in Alverstone Garden Village

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
“A fab holiday in a great place” The apartment was very well maintained and the welcome basket is a nice touch. The beach and pier are within easy reach, only a short walk to both which makes the apartments location ideal. The beds are very comfy and t  …see more

from £46 / night

£265 - £690 / week

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from £46 / night

(13) Excellent 

12

Holiday apartment with golf nearby in Ryde

Ryde / Appley

2 3 Min stay varies

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

from £52 / night

£364 / week

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from £52 / night

(10) Excellent 

22

Shorwell holiday cottage rental

Isle of Wight / Shorwell

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
“By far the best self-catering cottage we have ever stayed at” Really enjoyed our short stay, the cottage exceeded all our expectations. Looking forward to returning for another, longer break soon.  …see more

from £99 / night

£345 - £965 / week

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from £99 / night

(16) Excellent 

13

Brighstone holiday cottage rental

Isle of Wight / Brighstone

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 km
  • Private garden
“Wonderful cottage for 2” The cottage is a wonderful place for a completely relaxing break. It was impeccably clean and very well equipped. Vanessa and Glyn were very welcoming and informative both about the cottage and local area. We were incredibl  …see more

from £63 / night

£315 - £585 / week

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from £63 / night

(18) Very Good 

16

Holiday cottage in Ventnor

Isle of Wight / Ventnor

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“An absolutely beautiful cottage with fabulous sea view” We arrived on the day of the big snow so had the added benefit for the first day of a winters view. The cottage was cosy and warm and so beautifully decorated that we didn't feel the need to go o  …see more

from £70 / night

£490 - £880 / week

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from £70 / night

(43) Very Good 

24

Yarmouth holiday cottage rental

Yarmouth / Fort Victoria

2 4 Min stay varies

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

from £75 / night

£395 - £1245 / week

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from £75 / night

(22) Excellent 

20

Holiday cottage in Freshwater

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 is a bright and sunny home in a beautiful rural location. Set on a leafy lane at the foot of Tennyson Down in an AONB with wonderful views, it is pet friendly, excellent for walking and cycling with lovely beaches and a pub with good food close by.  …see more

from £36 / night

£250 - £780 / week

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from £36 / night

(9) Excellent 

18

Sandown holiday apartment rental

Isle of Wight / Sandown

2 4 Min stay varies

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

from £70 / night

£300 - £800 / week

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from £70 / night

(21) Excellent 

24

Apartment rental in Shanklin

Shanklin / Old Village

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.9 km
  • Ask owner if suitable for children
“The Courtyard is an excellent place to stay” We were extremely comfortable during our stay as the owners, who were friendly and helpful, had thought of everything a guest might want and provided it. The property was very clean and is in a good locati  …see more

from £88 / night

£350 - £516 / week

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from £88 / night

(3) Excellent 

27

Holiday home in Shorwell

Isle of Wight / Shorwell

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
A rural village holiday getaway close to the unspoilt south west cost of the Isle of Wight. New for 2015 Church View is a stylish and modern family house set in the picturesque village of Shorwell opposite its historic church and country pub. Surrounded by beautiful cou  …see more

from £100 / night

£600 - £1350 / week

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from £100 / night