Cycling holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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351 Holiday homes

Filters applied: Cycling holidays

(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
“Beautiful home in peaceful setting” Breakers Sound is a stunning house in lovely gardens with sea views. It contained everything we needed for a relaxing week. The location is very peaceful without being isolated, and lovely walks straight from the ho
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from £150 / night

£525 - £1345 / week

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from £150 / night

(8) Excellent 

28

Holiday home in Ventnor

Isle of Wight / Ventnor

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“Lovely stay in a brilliant house in a great location.” Large, bright house with plenty of space for our group to have a very relaxing weekend. On entry house found to be very clean & tidy, rooms nicely decorated & furnished. Good range of Bedroom opti
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from £155 / night

£620 - £1440 / week

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Responds fast!
avg. 55 minutes

from £155 / night

(25) Excellent 

25

Gurnard holiday home rental

Isle of Wight / Gurnard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Perfect in everyway!” Location is ideal with the beach on the doorstep! Attractions on the island cater for all the family and are within easy reach. Property was a home from home with added luxuries of its location. Carol, our host was so welcom
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from £150 / night

£1000 - £1750 / week

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Responds fast!
avg. 3 hours 3 minutes

from £150 / night

Featured properties

(15) 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
“beautiful property nice location” As described it was a perfect location with sea view .Clean park .well sited near complex. The lodge was very nice well equipped. Only disappointment we didn't book long enough!
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from £90 / night

£595 - £1295 / week

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Responds fast!
avg. 1 hour 4 minutes

from £90 / 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
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from £140 / night

£900 - £1990 / week

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Responds fast!
avg. 3 hours 45 minutes

from £140 / night

(5) Very Good 

23

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“FABULOUS LOCATION” This was our second visit to Eliabeth House and we would hapily return there because the location is perfect, being close to both the sea and town centre. The views of the sea are brilliant. I spent most of my time there watching
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from £75 / night

£385 - £795 / week

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from £75 / night

(18) 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
“Perfect place to relax.” Well set out on one floor, with plenty of room to chill out. We had two small dogs with us that were able to explore the garden without any worry. Although the weather wasn't very kind to us our weeks stay was most enjoyable.
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from £135 / night

£695 - £1325 / week

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from £135 / night

(4) Excellent 

33

Ventnor holiday apartment rental

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly
“Beautiful apartment & lovely break” The apartment was decorated beautifully,spacious, spotlessly clean and well stocked with everything you could ever want or need for a short break. Johnathan and Susan, the owners of the apartment, live in the hou
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from £60 / night

£420 - £650 / week

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Responds fast!
avg. 3 hours 19 minutes

from £60 / night

(9) Very Good 

24

Cowes holiday home rental

Cowes / West Cowes

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Great location - beautiful house” Just returned from a weekend stay at Halyard house. The location was perfect being right in the centre of Cowes, very near to the shops and easy to find from the Ferry. Bedrooms were cosy and comfortable. Although t
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from £100 / night

£700 / week

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from £100 / night

(28) Excellent 

26

Holiday caravan/mobile home with shared pool in Thorness Bay

Cowes / Thorness Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Ideal location for family break” Well equipped and comfortable caravan, nice location with views of the solent. Central site location with good vehicle access. Close to shop, bar, pool, and entertainment. We were a group of five with a 90 and 87 year
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from £65 / night

£375 - £770 / week

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Responds fast!
avg. 1 hour 23 minutes

from £65 / night

(6) Excellent 

30

Ventnor holiday home rental

Isle of Wight / Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Highly recommended” Lovely, spotlessly clean accommodation situated in a quiet central location. We all enjoyed our stay at Plum Cottage and would definitely recommend..
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from £110 / night

£600 - £1090 / week

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Responds fast!
avg. 3 hours 45 minutes

from £110 / night

(22) Excellent 

35

Holiday cottage in Cowes

Isle of Wight / Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
“Perfect cottage” A really lovely well equipped dog friendly cottage in a fantastic location. Great shops, pubs, dog walks and the bonus of M&S on your door step. Jenny was very helpful with the booking and the welcome pack was very much appreciated.
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from £145 / night

£475 - £750 / week

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Responds fast!
avg. 3 hours 48 minutes

from £145 / night

(3) Excellent 

14

Cowes holiday home rental

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
“An excellent house for a family Christmas, and a great location for summer visitors.” Twelve of us spent our family Christmas in Alban house and it was perfect. The house is lovely, great location, spotlessly clean, warm and comfortable. Carol could
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from £500 / night

£1600 - £3500 / week

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Responds fast!
avg. 3 hours 3 minutes

from £500 / night

(8) Excellent 

14

Holiday apartment in Ventnor

Ventnor / Ventnor Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Brilliant apartment,brilliant location,brilliant views” Exactly what it says on'"the tin".Easy to book ,with confidence and all the support you would need-regular updates and support of "the lovely Lisa" on the island. Spacious and extremely well pre
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from £145 / night

£750 - £1163 / week

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Responds fast!
avg. 2 hours 23 minutes

from £145 / 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
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from £150 / night

£1045 - £1495 / week

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Responds fast!
avg. 2 hours 8 minutes

from £150 / night

(9) Excellent 

20

Holiday home rental

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“Home from Home - by the Seaside!” The cottage was warm, cosy and had some lovely homely touches that immediately made us feel at home. The location was perfect - under 5 minutes from the Red Funnel terminal, a stone's throw from the marina and a short
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from £80 / night

£625 - £1120 / week

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Responds fast!
avg. 37 minutes

from £80 / night

(16) Very Good 

24

Holiday log cabin in Cowes

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“A peaceful total retreat from the pace of life.” If your looking for a total retreat this is it. Off the beaten tract, quiet & peaceful. Amazing views over the Solent. If you want to venture out it's location is good for many of the island's attracti
…see more

from £65 / night

£400 - £670 / week

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from £65 / night

(10) Excellent 

23

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
“Clean comfortable with beautiful views.” Wonderful chalet. Handy for beach and lovely walks. Ideal for a quieter peaceful holiday. The chalet is a good size for a family and the owner is very helpful. It is beautifully situated on the quieter side o
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from £36 / night

£250 - £450 / week

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from £36 / night

(3) Excellent 

16

Holiday cottage with golf nearby in Totland

Totland Bay / Totland Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £70 / night

£350 - £850 / week

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Responds fast!
avg. 1 hour 17 minutes

from £70 / night

(3) Very Good 

7

Holiday caravan/mobile home in Shanklin

Isle of Wight / Shanklin

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“Lovely week” The caravan is in a lovely plot which is quiet and private. The site is clean and tidy although we only used the caravan to sleep and spent the days out exploring. We have a 2 year old and claire sorted out a travel cot and everything w
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from £50 / night

£300 / week

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from £50 / 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
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from £80 / night

£450 - £950 / week

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from £80 / night

(5) 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
“Church view” This was my second visit to this outstanding property in Shorwell. Both visits were with friends to walk, relax and explore more of the island. This year the highlight was a walk along the cliffs to the Needles. After a full day of fresh
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from £100 / night

£600 - £1400 / week

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Responds fast!
avg. 3 hours 12 minutes

from £100 / night

(21) Very Good 

16

Holiday apartment in Ryde

Isle of Wight / Ryde

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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).
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from £60 / night

£370 - £400 / week

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from £60 / night

(9) Average 

9

Holiday bungalow with shared pool in Gurnard

Isle of Wight / Gurnard

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Brillant” We visited gurnard pines for a weeks holiday,such a lovely week fantastic weather. Appartment/chalet was clean, had everything we needed especially for having children which was great! There is a huge bit of green for kids to play out on, be
…see more

from £60 / night

£420 / week

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from £60 / night

(2) Excellent 

59

Bembridge holiday lodge rental

Isle of Wight / Bembridge

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £65 / night

£455 / week

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Responds fast!
avg. 2 hours 41 minutes

from £65 / night

(14) Excellent 

15

Holiday bungalow in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“Great Location” Location was perfect , from initial proximity to the ferry a few minutes around the corner, to the view from the the balcony ( where we spent most of the time in the property!) particularly when the tide is in, and a very short drive t
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from £70 / night

£495 - £995 / week

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Responds fast!
avg. 1 hour 51 minutes

from £70 / night

(24) Excellent 

43

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
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from £150 / night

£500 - £895 / week

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from £150 / night

(16) 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
“Excellent facilities, in a unique setting” The facilities were excellent and the accommodation very close to the sea. There were two very good restaurants close by which had been recommended by the owner.
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from £100 / night

£550 - £790 / week

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Responds fast!
avg. 3 hours 49 minutes

from £100 / night

(62) Excellent 

20

Ventnor holiday apartment rental

Isle of Wight / Ventnor

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly
“Wished I could have stayed longer..” Thank you to Dawn and Guy for a lovely, if all too short, stay at Marina Apartments. The location was very specal, with fabulous sea views and all the amenities of Ventnor right on your doorstep, including a beach
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from £75 / night

£400 - £825 / week

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Responds fast!
avg. 2 hours 55 minutes

from £75 / night

(38) 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
“Seabreeze” Lovley stay at seabreeze Excellent good value for money very welcoming located on a great site , Will defently book here again Thank you for having us
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from £38 / night

£225 - £475 / week

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Responds fast!
avg. 1 hour 22 minutes

from £38 / night

(3) Very Good 

8

Holiday cottage in Cowes

Cowes / West Cowes

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children age 5+

from £85 / night

£350 - £2000 / week

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from £85 / night

(2) Average 

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.
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from £199 / night

£995 - £1995 / week

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Responds fast!
avg. 1 hour 4 minutes

from £199 / night

(4) Excellent 

11

Holiday home letting

Isle of Wight / Newport

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Private garden

from £50 / night

£325 - £1930 / week

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from £50 / 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

from £70 / night

£490 - £780 / week

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from £70 / night

(25) 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 34 minutes

from £60 / night

(15) Very Good 

22

Cottage rental in Whippingham with golf nearby

Isle of Wight / Whippingham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
“Fantastic family holiday!” Stayed for a week and had the most amazing time, couldn't ask for better accommodation and attention to detail. Shelley and Paul were friendly and helpful and nothing was too much trouble. The swimming pool was the highlig
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from £125 / night

£795 - £1500 / week

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Responds fast!
avg. 39 minutes

from £125 / night

(88) 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
“Another fantastic week at Camellia Cottage.” An perfect as ever - the new beds & dishwasher an added bonus. Best cottage on the Island. We'll be back again in October!
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from £125 / night

£595 - £1550 / week

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Responds fast!
avg. 59 minutes

from £125 / night

(7) Very Good 

23

Holiday chalet in Ventnor

Ventnor / Niton Undercliff

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
“Well thought out accommodation in pretty surroundings” Stayed for two nights but wish it could have been longer. The chalet has everything you could need and nicely decorated too. There's a lot of info about the area with maps and things to do and you
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from £45 / night

£280 - £415 / week

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from £45 / night

(13) Excellent 

19

Holiday cottage in Calbourne

Isle of Wight / Calbourne

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
“Lovely and very well-equipped cottage” Had a great stay here during the IoW festival, it's a really comfortable property, very well-equipped and beautifully furnished. Only 10 mins to Newport but in a peaceful area surrounded by fields. We've alread
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from £100 / night

£400 - £800 / week

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Responds fast!
avg. 1 hour 54 minutes

from £100 / 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

from £75 / night

£325 - £750 / week

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from £75 / night

1