Cycling holiday villas and apartments Isle of Wight | Holiday Lettings

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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.

(14) 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

(84) 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 - £1550 / week

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from £120 / night

(8) Excellent 

13

Holiday cottage in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“We had a lovely stay” Salt Air Cottage was lovely and Miriam had thought of everything to make our stay pleasant. The cottage was well kitted out and there were lots of little touches like phone charges, games to play, DVDs to watch and music to list  …see more

from £75 / night

£475 - £595 / week

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from £75 / night

(8) Excellent 

70

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

(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

(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

£335 - £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

(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

(11) Excellent 

9

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

(31) 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

(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

(12) 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
“Warm & welcoming with fabulous grounds” We stayed for one week and explored the island. It's a great spot to discover inland highlights like Robin Hill Country Park & the coast at Brook and Yarmouth. The cottage is really cosy with a twin room upsta  …see more

from £100 / night

£400 - £800 / 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

(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

(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

(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

£500 - £895 / week

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from £150 / night

(1) Excellent 

22

Holiday caravan/mobile home in Bembridge

Isle of Wight / Bembridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“Amazing destination and accommodation - why would you go anywhere else?” I really don't want to tell everyone just how perfect this van is, or how breathtakingly beautiful the area is. I don't want to let on how amazing it feels to wander straight o  …see more

from £50 / night

£300 - £550 / week

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from £50 / 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

(7) 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

(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

(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

£550 - £1400 / week

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from £150 / 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

(17) Excellent 

36

Holiday cottage rental

Isle of Wight / Bonchurch

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“A perfect choice” A delightful cottage, from which we hosted our daughter's wedding at East Dene. We couldn't have picked a better location, helped by superb weather, which enhanced this gem of a property even more.  …see more

from £90 / night

£450 - £1960 / week

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from £90 / 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

(22) 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 hassle-free family getaway. Built-in garden,beach and views!” This is a beautifully presented house. Buckets and spades and teddies awaited the children, as well as cakes for all of us and wine for the grown-ups. The garden suited all needs fr  …see more

from £150 / night

£900 - £1750 / week

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from £150 / 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
“A charming experience” The Salisbury was a wonderful place to stay, it was well equipped with utensils, tea equipment and more. The living area was great with sky tv and a charming little electric fire place which gives the property great character.  …see more

from £65 / night

£375 - £865 / week

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from £65 / night

(4) Excellent 

20

Holiday bungalow in Freshwater

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Wow! What a find!” I stayed in this bungalow for a week with my partner and our 11 year old daughter and it was nothing short of perfect! The location is stunning with a glorious beach only a stone's throw away where we spent every evening rock po  …see more

from £43 / night

£300 - £485 / week

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from £43 / night

(7) Very Good 

23

Holiday chalet in Ventnor

Ventnor / Niton Undercliff

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
“Perfect for a relaxing break” Pebbles is a chalet decorated in a seaside theme it was just like staying in a beach hut with everything we could possibly need. The area is beautiful with perfect coastal walks. The village is a five minute walk away wit  …see more

from £45 / night

£280 - £405 / week

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from £45 / night

(20) 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
“Fantastic location, gorgeous home and lovely host” From the moment we arrived on the Ferry Jenny ensured we had all the information we needed which made our holiday so much easier. The cottage is super central and near some great bars and pubs. The co  …see more

from £145 / night

£475 - £1550 / week

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from £145 / night

(61) 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  …see more

from £75 / night

£400 - £825 / week

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from £75 / night

(10) Very Good 

16

Holiday chalet rental

Isle of Wight / Freshwater

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Lovely relaxing stay” We thoroughly enjoyed our stay here and would definitely be keen to return in the near future. The accommodation is bright and spacious, and a great size for a small family. Comfy beds, and a cot bed which was very useful to us.  …see more

from £30 / night

£242 - £492 / week

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from £30 / 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  …see more

from £145 / night

£750 - £1163 / week

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from £145 / night

(10) Excellent 

16

Freshwater holiday bungalow rental

Isle of Wight / Freshwater

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
“Perfect family escape!” We really enjoyed our weekend here with our nine month old. Loved that it was a bungalow so no stairs to worry about. Wish we booked longer as we didn't want to come home! Really clean and had everything we would need. Perfect  …see more

from £70 / night

£390 - £520 / week

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from £70 / 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

(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 £40 / night

£280 - £780 / week

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from £40 / night

(12) 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
“Amazing - everything you could want and more ......” A fab property minutes from Yarmouth and the ferry terminal, but tucked away in the haven called Fort Victoria Country Park. Woodland Cottage is great - big enough not to feel on top of each other b  …see more

from £145 / night

£795 - £2240 / week

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from £145 / 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 £150 / night

£900 - £1990 / week

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from £150 / 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

(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  …see more

from £50 / night

£350 - £795 / week

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from £50 / 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
This spacious and comfortable semi-detached house is situated in a quiet residential neighbourhood within walking distance of Newport town centre. Situated at the top of a hill, the home boasts stunning views of the island and a well-kept private garden.  …see more

from £50 / night

£325 - £1930 / week

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from £50 / night