Cycling holiday villas and apartments Isle of Wight

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Isle of Wight

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357 Holiday homes

Filters applied: Cycling holidays

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

(1) Excellent 

11

Holiday apartment in Ventnor

Isle of Wight / Ventnor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Pier Top is a spacious apartment, offering flexible accommodation over three floors and catering well for a family or a group of friends.SHORT BREAKS AVAILABLE OUT OF HIGH SEASON / MINIMUM 3 NIGHTS (please ignore nightly prices on Holiday Lettings)  …see more

from £87 / night

£400 - £850 / week

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from £87 / night

(5) Very Good 

24

St Helens holiday home rental

Isle of Wight / St Helens

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Great service from company & owners” Great location, easy to get to, exactly as described, bright & light home from home, lovely garden, one small issue during the week was sorted within half a day and we left a few bits by mistake - the owners went o  …see more

from £50 / night

£348 - £835 / week

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from £50 / night

(3) Excellent 

20

Holiday home in Bembridge

Isle of Wight / Bembridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Our c1700s flint cottage is close to the sea and village amenities. Spread across 3 floors, this 3 bedroom holiday home will provide you with the comfort and relaxation you need. 1 x King size bed, 1 x double and 2 x single beds are available. The bathroom has recently  …see more

from £115 / night

£975 - £1200 / week

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from £115 / night

(16) Excellent 

23

Cottage rental in Yarmouth

Isle of Wight / Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Ask about pets
Holiday Cottage with situated on a dairy farm. Sleeps up to 8.with 4 bedrooms. Newly refurbished to a beautiful standard with all the comforts from home. Minutes from town, pubs, restaurants, activities and beaches. Hot Tub available to hire.<br />Stay on a workin  …see more

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(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

(5) Excellent 

15

Apartment rental in Knighton, Isle of Wight

Isle of Wight / Knighton, Isle of Wight

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
An individual home just brimming with character & quirky charm with exposed timbers in all the rooms. Situated in a hamlet within an area designated as an 'Area of Outstanding Natural Beauty'. Explore the local footpaths or just enjoy the country views fro  …see more

from £41 / night

£285 - £450 / week

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from £41 / night

(1) Excellent 

14

Holiday home in Cowes

Cowes / West Cowes

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
The boathouse is a modern 3 storey town house which yards from the waters edge of Cowes Town and the marina with a fabulous sundeck roof terrace overlooking the sea.  …see more

from £100 / night

£645 - £1050 / week

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from £100 / night

(1) Excellent 

15

Apartment rental in Shanklin

Shanklin / Old Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“The Priory” is an impressive former Gentlemen's residence dating back to 1864, which has been lovingly restored as superior apartments, set in a tranquil area of Shanklin, with stunning uninterrupted panoramic sea views. SHORT BREAKS NOW AVAILABLE TO  …see more

from £80 / night

£375 - £840 / week

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from £80 / night

13

Holiday home in East Cowes

Isle of Wight / East Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden
Sofa bed in conservatory, fold up bed for use in lounge, parking in front of garage to rear of property.  …see more

from £170 / night

£425 - £850 / week

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from £170 / night

(5) Very Good 

15

Holiday apartment in Shanklin

Isle of Wight / Shanklin

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Amazing apartment and amazing sea view” My husband and I traveled with my husbands parents and I can say that this apartment has definitely got the wow factor! The sea views are spectacular and we had a lovely time relaxing watching the boats and ferr  …see more

from £85 / night

£390 - £890 / week

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from £85 / night

19

Holiday home in Ventnor

Isle of Wight / Ventnor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
This beautiful south facing holiday home with fantastic sea views is comfortably furnished to a high standard. The far reaching sea views can be enjoyed from the open plan lounge, kitchen and dining areas also from the master bedroom. The first floor offers two twin bed  …see more

from £162 / night

£650 - £1800 / week

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from £162 / night

15

Apartment rental in Sandown with golf nearby

Isle of Wight / Sandown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Car not necessary
Isle of Wight. Self Catering. Sandown. Self Catering Accommodation. Apartments. Parking. Beach. Pier. Town, Cafes Pubs. Restaurants. Shops. Local Train Station. Bus Routes. Heights Leisure Centre. Garden to enjoy. Children Welcome. Dogs welcome by arrangement.<br /&g  …see more

from £55 / night

£240 - £390 / week

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from £55 / night

13

Holiday chalet in Sandown

Isle of Wight / Sandown

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
Natures Corner provides a perfect base for a family looking for a traditional seaside holiday in one of the Islands most popular seaside resorts of Sandown. This comfortable chalet is positioned on the edge of Sandown Bay Holiday centre with easy access to the beach whi  …see more

from £69 / night

£275 - £450 / week

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from £69 / night

(2) Average 

10

Holiday cottage in Calbourne

Isle of Wight / Calbourne

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
This charming two bedroom holiday home is set at the end of probably the most well know terrace on the whole of the Isle of Wight.  …see more

from £80 / night

£325 - £700 / week

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from £80 / night

(1) Very Good 

17

Holiday apartment in Sandown

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Suitable for children age 5+
Isle of Wight Self Catering Sandown Self Catering Accommodation Apartments parking Beach nearby Pier nearby Town Cafes Restaurants Pubs Shops Train Station Bus Route Leisure Centre Guest Garden Children Welcome Dogs welcome by arrangementDiscount car ferry crossings<  …see more

from £68 / night

£330 - £620 / week

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from £68 / night

13

Brading holiday cottage let

Isle of Wight / Brading

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Charnwood Cottage is a delightful character cottage that offers all the home comforts set in the heart of the village of Brading.  …see more

from £75 / night

£345 - £645 / week

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from £75 / night

(1) Excellent 

11

Shanklin holiday apartment rental

Isle of Wight / Shanklin

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
Napier apartment is the perfect holiday accommodation having superb sea views across Sandown Bay. The property is situated on the first floor and consists of a light and airy open plan lounge, a kitchen, one double bedroom and one with two single beds. There is also a  …see more

from £94 / night

£425 - £650 / week

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from £94 / night

23

Holiday home in Bembridge

Isle of Wight / Bembridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
BROOKFIELD is a substantial semi-detached Victorian villa in the heart of Bembridge village. Thoughtfully extended to provide ground floor accommodation which includes a fully fitted kitchen with 2-oven gas AGA cooker, cosy tv/snug plus expansive dining and sitting area  …see more

from £250 / night

£900 - £1895 / week

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from £250 / night

18

Holiday apartment in Ventnor

Isle of Wight / Ventnor

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
Salty Holidays is in the best location in Ventnor to relax and enjoy the stunning sea views. Facing south on a quiet road, we are only about 50m to the family friendly beach and only a 5 minute walk to town. Inspired by our love of the sea, our self catering holiday a  …see more

from £75 / night

£325 - £750 / week

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from £75 / night

(3) Excellent 

15

Apartment letting in Ventnor

Isle of Wight / Ventnor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Car not necessary
“Really a Home!” Bella Vista is one of the best holiday apartments we had so far! Really excellent and comfortable and with much interest in detail decorated. We felt immediately at home there (with the nice welcome back) and enjoyed the large kitchen,  …see more

from £85 / night

£400 - £620 / week

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from £85 / night

(1) Excellent 

16

Bungalow rental in Ventnor

Ventnor / Ventnor Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Gullsway is a fabulous 3 bedroom bungalow with outstanding sea views across the English Channel. The bungalow has been furnished to a very high standard throughout and sleeps up to 6 guests with master bedroom and en-suite shower, double bedroom (or twin as zip and lin  …see more

from £375 / night

£800 - £1550 / week

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from £375 / night

14

Holiday apartment in Newchurch

Sandown / Newchurch

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
The Annexe at Cedar Cottage is a beautifully presented self contained Annexe with its own private entrance. Situated on the squirrel trail/ cycle path it is ideal for walkers, cyclists or anyone looking for a peaceful retreat. Free Wifi. There are two wood burners. One  …see more

from £60 / night

£420 / week

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from £60 / night

(1) Very Good 

19

Holiday apartment rental

Isle of Wight / Sandown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Car not necessary
  • Ask about pets
Isle of Wight Self Catering Sandown Self Catering Accommodation Apartments Parking Beach nearby Pier Town Cafes Restaurants Pubs Shops Ideally located Train Bus Route Station Leisure Centre nearby Guest Garden Children welcome Discounted Car Ferry Crossings available.&l  …see more

from £60 / night

£295 - £500 / week

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from £60 / night

(8) Average 

18

Holiday bungalow in Seaview

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
“Pleasant stay, clean accommodation and close to the beach” Our bungalow was in a U shape with other bungalows and had good views out the front and into the middle area where it was safe for the children to play and be seen. The bungalow was a good ba  …see more

from £45 / night

£315 - £650 / week

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from £45 / night

(4) Very Good 

16

Chalet rental in Yaverland

Sandown / Yaverland

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“A good place to stay” We had a great time in this chalet there was 6 of us the little things like milk in the fridge when we got there. Also having the bath for the 2 children we had with us as they dont like a shower. Puting a £1.00 in meter was no p  …see more

from £23 / night

£160 - £500 / week

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from £23 / night

18

Holiday cottage in Newchurch

Sandown / Newchurch

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
The cottage is located on the renowned Garlic Farm and our onsite restaurant and farm shop are just a stone's throw from your door. The cottage is cosy and peaceful with private access and private patio and garden to the rear. We are close to cycle ways and footpat  …see more

from £80 / night

£425 / week

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from £80 / night

8

Shanklin holiday apartment rental

Isle of Wight / Shanklin

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
Orchardcroft, located in a leafy avenue on the fringe on Shanklin, is a one bedroom apartment its own entrance and is light, airy and comfortably furnished throughout. It comprises of a twin bedroom with a door to a small balcony; an open plan living/dining room & k  …see more

from £94 / night

£375 - £600 / week

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from £94 / night

13

Holiday cottage with golf nearby in Freshwater

Isle of Wight / Freshwater

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Roseberry Cottage is a cosy self catering holiday property located within Freshwater Bay on the Isle of Wight. There are panoramic views from Freshwater bay to 'The Needles' lighthouse & across to the mainland on a clear day and just a short stroll in the  …see more

from £120 / night

£495 - £825 / week

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from £120 / night

(2) Very Good 

15

Chalet rental in Yaverland

Sandown / Yaverland

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“we will be back” We have stayed on holiday in the Isle Of wight for many times as we have family that live on the island, So have stayed in a lot of places hotels, villas ,caravans, tents..But this is one of the best places we have stayed in the chale  …see more

from £26 / night

£160 - £500 / week

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from £26 / night

(2) Average 

17

Holiday converted chapel with golf nearby in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
This charming holiday home, a converted old chapel, provides a unique holiday experience in such an unusual property and is particularly close to Ventnor town centre and of course the esplanade and beach.Visit England Grading: 3 stars  …see more

from £174 / night

£375 - £745 / week

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from £174 / night

23

Holiday cottage in Newchurch

Sandown / Newchurch

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Paddock Cottage is ideal for a couple. It is a conversion of one end of an old threshing barn at The Garlic Farm on the Isle of Wight. It consists of a sitting room with large sofa bed with adjoining kitchen, a double bedded room with en-suite bathroom. French windows o  …see more

from £75 / night

£375 - £655 / week

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from £75 / night

(1) Excellent 

10

Holiday apartment in Shanklin

Isle of Wight / Shanklin

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Car not necessary
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach  …see more

from £85 / night

£340 - £750 / week

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from £85 / night

4

Holiday apartment in Shanklin

Isle of Wight / Shanklin

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
The Garden Apartment at Lyon Court has just been refurbished to a very high standard and takes up the entire storey at garden level. With the ceiling height in excess of 8 feet in most rooms, stylish dimmable LED downlights throughout and large windows and doors, it ma  …see more

from £180 / night

£900 - £2200 / week

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from £180 / night

12

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Set in the Undercliff area of Outstanding Natural Beauty, Seaview Holiday Apartment stands in peaceful secluded terraced gardens. The apartment faces south across the Undercliff offering superb views of the English Channel. Steephill Cove & Woody Bay are only a ten  …see more

from £60 / night

£245 - £620 / week

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from £60 / night

(13) Excellent 

18

Isle of Wight / Godshill

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 6 km
  • Child friendly
  • Car not necessary

 …see more

from £189 / night

£1323 / week

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from £189 / night

(2) Excellent 

19

Isle of Wight / Ventnor

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Child friendly

 …see more

from £130 / night

£595 - £1475 / week

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from £130 / night

(1) Very Good 

12

Isle of Wight / Calbourne

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden

 …see more

from £105 / night

£450 / week

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from £105 / night