Cycling holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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364 Holiday homes

Filters applied: Cycling holidays

(26) Excellent 

15

Ryde holiday lodge rental

Isle of Wight / Ryde

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km

from £60 / night

£350 - £504 / week

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Responds fast!
avg. 1 hour 45 minutes

from £60 / night

(1) Excellent 

20

Holiday cottage in Newchurch

Sandown / Newchurch

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 km
  • Child friendly
  • Ask about pets

from £120 / night

£675 - £1100 / week

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from £120 / night

10

Holiday chalet accommodation

Isle of Wight / Sandown

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £50 / night

£300 - £510 / week

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Responds fast!
avg. 3 hours 7 minutes

from £50 / night

Featured properties

(3) Very Good 

11

Holiday lodge with golf nearby in Ryde

Isle of Wight / Ryde

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km

from £40 / night

£280 - £425 / week

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Responds fast!
avg. 3 hours 36 minutes

from £40 / night

(32) Excellent 

Certificate of Excellence

27

Holiday home in Yarmouth

Isle of Wight / Yarmouth

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
“Ideal location to visit the Illlsle of Wight” This house provides very comfortable accommodation for a party of 10. It is ideal for visiting attractions on the island. It is situated in the quiet village of Newbridge and is adjacent to a campsite whic
…see more

Certificate of Excellence

from £200 / night

£920 - £1825 / week

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Responds fast!
avg. 3 hours 10 minutes

from £200 / 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
  • Pet friendly
“Excellent Holiday home” We stayed here for 7 days and we can't speak highly enough about the accomodation. We have two young children and we also took my Dad who is 76. It catered for all of our needs and was very child proof so don't worry about ha
…see more

from £65 / night

£450 - £950 / week

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Responds fast!
avg. 1 hour 5 minutes

from £65 / night

(1) Excellent 

12

Bonchurch holiday cottage rental

Ventnor / Bonchurch

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Private garden

from £108 / night

£350 - £600 / week

Enquire View

from £108 / night

17

Holiday home in Gurnard

Isle of Wight / Gurnard

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £179 / night

£1250 - £1445 / week

Enquire View

from £179 / night

21

Cottage rental in Newchurch

Sandown / Newchurch

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from £80 / night

£480 - £830 / week

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from £80 / night

(16) Excellent 

16

Yarmouth holiday villa rental

Isle of Wight / Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Superb holiday cottage in great location” Woodland Cottage is a very well-equipped, quiet, and comfortable place to stay. We had a very enjoyable week here, and even with six of us we didn't get under each other's feet. The downstairs is bright and ai
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from £190 / night

£1125 - £2240 / week

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Responds fast!
avg. 1 hour 8 minutes

from £190 / night

(11) Excellent 

13

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

from £65 / night

£350 - £550 / week

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Responds fast!
avg. 13 minutes

from £65 / night

(13) Excellent 

Certificate of Excellence

21

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
“Fantastic place” Would give it 110% so clean and tidy and peaceful. There's everything you need in the chalet. Beautiful walks and scenery Looking forward to returning there again.
…see more

Certificate of Excellence

from £40 / night

£240 - £300 / week

Book View

Responds fast!
avg. 55 minutes

from £40 / night

(6) Very Good 

Certificate of Excellence

26

Holiday apartment letting

Isle of Wight / Sandown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

Certificate of Excellence

from £35 / night

£200 - £380 / week

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Responds fast!
avg. 2 hours 57 minutes

from £35 / night

(6) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £88 / night

£379 - £799 / week

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from £88 / night

(15) 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
“Exceptional” Fantastic accommodation, great location, spotless, lovely homely touches, fantastic owners who have really thought the accommodation through and go the extra mile to ensure you have a relaxing time. Great value, will be booking again very
…see more

from £52 / night

£364 / week

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from £52 / night

(3) Very Good 

22

Holiday apartment in Shanklin

Isle of Wight / Shanklin

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Excellent Accommodation with very friendly owners that made stay very enjoyable.” Shanklin is a very good place to stay with nice beach, crazy golf and choice of supermarkets within short distance. I would recommend to other family's to stay here.
…see more

from £150 / night

£1000 - £1475 / week

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Responds fast!
avg. 3 hours 56 minutes

from £150 / night

(16) Excellent 

Certificate of Excellence

27

Holiday cottage in Brading

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
“Had a wonderful stay - Clean and Spacious with warm welcome by Colin and Julie” Colin and Julie gave us warmest welcome and made sure we have a comfortable stay. The house was spacious, kept very tidy and had everything we needed. It was nice to have
…see more

Certificate of Excellence

from £95 / night

£650 - £915 / week

Book View

Responds fast!
avg. 2 hours 25 minutes

from £95 / night

(11) Excellent 

23

Holiday chalet in Ventnor

Isle of Wight / Ventnor

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 4 km
“Brill” Lovely, safe, quiet location. Cute little chalet, perfect for 2 people. All crockery/cooking stuff you need - although no oven which is a minor issue only especially if you're not staying for more than a week. Would stay here again if we were
…see more

from £40 / night

£240 / week

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from £40 / night

23

Niton holiday home rental

Isle of Wight / Niton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £282 / night

£925 - £2025 / week

Enquire View

from £282 / night

(3) Excellent 

20

Holiday apartment in Newchurch

Sandown / Newchurch

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Pet friendly
  • Private garden

from £60 / night

£420 / week

Book View

Responds fast!
avg. 20 minutes

from £60 / night

(1) Excellent 

28

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

from £180 / night

£1530 - £2200 / week

Book View

from £180 / night

7

Holiday cottage rental

Isle of Wight / Wroxall

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £180 / night

£1260 / week

Book View

Responds fast!
avg. 3 hours 57 minutes

from £180 / night

(3) Very Good 

30

Home rental in Nettlestone with golf nearby

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
“Fabulous accommodation for enjoying this lovely Island” Our party of 8 adults and 2 children had a fabulous stay at Nettlestone House; very spacious and very well presented and equipped. And the lovely garden was a bonus for both playtime and the BBQ.
…see more

from £199 / night

£995 - £1995 / week

Book View

Responds fast!
avg. 1 hour 4 minutes

from £199 / night

(3) Very Good 

39

Holiday cottage in Seaview

Isle of Wight / Seaview

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £116 / night

£499 - £1015 / week

Book View

from £116 / 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

Enquire View

from £42 / night

(2) Very Good 

10

Shanklin holiday apartment rental

Isle of Wight / Shanklin

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
“Amazing Apartment” We stayed at this "apartment" without realising that it was actually larger in size than our 3 bedroom house! Obviously the owners have furnished it to their personal standards, and just about everything we needed was there ( inclu
…see more

from £150 / night

£750 - £1250 / week

Book View

from £150 / night

(3) Excellent 

33

Holiday home in Bonchurch

Ventnor / Bonchurch

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 £125 / night

£850 / week

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Responds fast!
avg. 2 hours 50 minutes

from £125 / night

(9) Excellent 

23

Yarmouth holiday home rental

Yarmouth / Fort Victoria

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Very nice house and helpful owners” Would highly recommend. Very nice house in Yarmouth. Owners v helpful with recomendations of where to eat/shop etc. Very child friendly and good value. Clean and well maintained and appointed. New boiler fitted jus
…see more

from £150 / night

£800 - £1750 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £150 / night

(15) Very Good 

18

Holiday home in Bonchurch

Ventnor / Bonchurch

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £250 / night

£1000 - £1995 / week

Book View

Responds fast!
avg. 47 minutes

from £250 / night

(22) Excellent 

Certificate of Excellence

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
“Ruth” We had to make a phone call to find it but Amber gave us clear directions. Beautiful location with plenty of space for humans and dogs, comfortable beds and great shower. Warm welcome from Amber with a welcome pack of milk, bread, butter, eggs,
…see more

Certificate of Excellence

from £95 / night

£585 - £1025 / week

Book View

from £95 / night

(25) Excellent 

22

Home rental in Cowes

Cowes / West Cowes

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“family Holiday” We returned to the Isle of Wight after many years and have had the most relaxing time the accommodation was excellent and well stocked we found parking a daily challenge but so did everyone else it did not spoil the holiday and never i
…see more

from £150 / night

£750 - £2500 / week

Book View

from £150 / night

(15) Excellent 

23

Holiday home in Ryde

Isle of Wight / Ryde

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Loveley cottage in a great location” I stayed here for a week with my small dog who loved the outside courtyard. The cottage is really comfortable and clean and has everything you need for a good holiday. It is in an excellent location just minutes
…see more

from £100 / night

£400 - £750 / week

Book View

Responds fast!
avg. 1 hour 23 minutes

from £100 / 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
“Superb Apartment” This apartment is very charming and feels very homely. I felt very cosy and safe here. The apartment had everything to make your stay pleasant. Clean and fresh. My Husband and I visited with my Daughter 9 years of age. We had plenty
…see more

from £100 / night

£395 - £765 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £100 / night

(16) Excellent 

25

Ventnor Bay holiday apartment rental

Ventnor / Ventnor Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Private garden
“Beautiful Apartment” If you want opulence then this is the place. Just loved this apartment. It was quirky but also very elegantly decorated, in a lovely location opposite the park and within easy walking distance to the town. The outside space was ve
…see more

from £63 / night

£441 / week

Book View

Responds fast!
avg. 2 hours 43 minutes

from £63 / night

(7) 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
“What a find !” We had a fantastic week on the IoW, seven of us in total with extended family, and Yachtsman's Rest easily accommodated us all in comfort. Plenty of bathrooms, all well placed next to bedrooms or en-suite, no kids squabbling about wh
…see more

from £150 / night

£750 - £2400 / week

Book View

Responds fast!
avg. 2 hours 6 minutes

from £150 / night

(15) Excellent 

24

Cottage rental in Totland

Totland Bay / Totland Bay

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“Spacious elegant cottage in beautiful surroundings” Little Mount was a great choice for our small family. It was spacious with a large lounge and master bedroom and well equipped. The large rambling gardens had an amazing sea view with access to the c
…see more

from £110 / night

£750 - £895 / week

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from £110 / night

(42) Excellent 

23

Holiday log cabin with indoor pool in Ryde

Isle of Wight / Ryde

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Highly recommended” We have just had a fantastic week at the cabin. Clean and cosy. Pool is fantastic. Beautiful gardens. We visited some great places on the island and it was so lovely to come back and chill out in the pool. Gilly & Dave were so welc
…see more

from £93 / night

£650 - £1400 / week

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Responds fast!
avg. 1 hour 45 minutes

from £93 / night

(21) Excellent 

21

Holiday apartment with golf nearby in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Best in IOW !!!” It was one of the best stay ever.. the apartment is so clean, colourful, spacious, lovely home décor and fully equipped kitchen.. there was nothing to be missed or regretted ! Perfect for family ! It has best views also you could hear
…see more

from £80 / night

£400 - £790 / week

Enquire View

from £80 / night

(5) Excellent 

12

Holiday barn in Ryde

Isle of Wight / Ryde

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
“Perfect for large groups” The Granary was ideal for a large group, each room having its own en-suit. Plenty of space to socialise and very clean. The only thing I would suggest is it is better sign posted at the end of the drive as we initially drove
…see more

from £210 / night

£900 - £2300 / week

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from £210 / night

(2) Very Good 

21

Holiday home with golf nearby in Ryde

Isle of Wight / Ryde

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £600 / night

£1995 - £4695 / week

Book View

Responds fast!
avg. 3 hours 36 minutes

from £600 / night

1