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29 Holiday homes in Isle of Wight

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Filters applied: City breaks (29)

29 Results  |  
16 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £42 /night

£292 - £477 / week

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Late Deal: save up to £110

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Lovely spacious apartment located next to Shepard's Wharf Marina. 2 bedrooms, 1 shower room, large sitting room, well equipped kitchen. Tv with Freeview, free wifi, Xbox 360, Desk with monitor for working. Close to Cowes High Street. Free use of 4 picnic chairs and matching table. Free use of 4 person picnic backpack. Child Safety gate  …see more

9 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £61 /night

£424 - £1696 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Recently Renovated Cottage In Central West Cowes Perfect Location For Yacht Haven, High Speed Ferry Or Car Ferries  …see more

13 Photos

Townhouse | 3 Bedrooms | sleeps 9

3 Nights min stay

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from £35 /night

£239 - £2491 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
This is property is situated in one of the most popular roads for Cowes week & other sailing lets  …see more

Featured properties

18 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £65 /night

£453 - £1855 / week

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Late Deal: save up to £144

Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
42A opened its doors to the delight of holiday makers in 2013. A stunning 2 bedroom apartment perfectly placed in the heart of Old Cowes, moments from the sea, and a 3 minute walk to the Yacht Haven. EMAIL THE OWNER FOR MORE GREAT PRICES  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 2

Short stays welcome

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from £40 /night

£280 - £350 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Not suitable for children
  • Car not necessary
  • No pets allowed
Luxury self-catering apartment on ground floor for discerning couple; part of 1844 Victorian Grade 2 listed building. Five minute walk to the High Street in Ryde Ten minute walk to beach, train station + hovercraft; 10 metres to bus stop (access to most of the island)  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £136 /night

£950 - £1450 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.6 km
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
  • Private garden
1844 VICTORIAN GRADE 2 LISTED BUILDING ALL THE LUXURIES OF MODERN LIVING CLOSE TO HIGH STREET A beautiful house tastefully furnished and well maintained Four spacious bedrooms and two bathrooms South-facing garden and patio for sunbathing and barbecues Large kitchen with all amenities; separate dining-room; separate ground floor toilet; off-street parking  …see more

8 Photos

Cottage | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £45 /night

£313 - £721 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Pink Beach Cottage is a detached cottage situated in a quiet little road just off the St Helens village green. The well presented accommodation includes two bedrooms being a double & a twin room. In addition, swell fitted modern kitchen, a separate dining room.  …see more

20 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £122 /night

£850 - £1500 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
EASTER : 10% DISCOUNT. Prime Waterfront Location. Wonderful modern property in small mews development with balcony and fantastic views over the harbour and Solent beyond. Accommodation of very good standard in contemporary style. Very comfortable for 6 or 8 guests.  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £122 /night

£848 - £1272 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car advised
  • No pets allowed
30PS is the ideal place for a break with family or friends on the Isle of Wight, located just a stone's throw of the stunning Ventnor sea front, and within easy reach of the islands award winning beaches, leading attractions, breathtaking cycle tracks and much more.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

3 Nights min stay

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from £50 /night

£350 - £675 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Stunning contemporary top floor apartment with 2 bedrooms, by a beautiful beach, with sea views over The Solent to Portsmouth, and rear views over Ryde town. Situated in a conservation area in a listed building, very well located and has a dedicated parking space. The apartment is tastefully decorated, is light and airy and well located for all travel routes  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

7 Nights min stay

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from £35 /night

£245 - £760 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Millers Rock, Ventnor, is a luxury 2 bedroom, 4 star, self catering, character apartment with panoramic seaviews, occupying a privileged private road location adjacent to shops, restaurants, beach and harbour, with private parking, book online at www.millersrock.co.uk  …see more

13 Photos

Cottage | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £57 /night

£395 - £795 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Delightful self-catering cottages set in the heart of Bembridge, one of the Islands most attractive and interesting villages  …see more

14 Photos

House | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £72 /night

£500 - £950 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This charming detached two/ three bedroom house is situated in a quiet residential area of the village of Bembridge  …see more

18 Photos

House | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £122 /night

£850 - £1600 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • No pets allowed
Fantastic contemporary property in prestigious waterside development with great views over the Solent and only a short walk away from the Royal yacht clubs and Cowes town centre.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £66 /night

£460 - £480 / week

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Key info:

  • Nearest beach 2 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
A stunningly presented two bedroom apartment in the heart of Cowes. Seconds from the marinas. Two bedrooms both with 'zip and link' beds sleeping 4 with the addition of a huge sofa bed in the lounge if required. Modern and bright. WIFI and all mod cons.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 8

1 night min stay

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from £37 /night

£255 - £318 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Stunning sea views/ocean views, small garden, 50 meters from the seaside, Accommodates up to 8 people, beach nearby, swimming pool (heated from May), tennis court, a minigolf course, a Michelin-rated restaurant in close proximity, easy access to Ventnor Garden, Shanklin Very large 2-bedroom flat with stunning sea views, close to the beach Great location in a quiet area  …see more

17 Photos

House | 5 Bedrooms | sleeps 12

Excellent 5/5 

2 Nights min stay

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from £115 /night

£800 - £5000 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Situated in the popular York St in central Cowes. Perfect family holiday home or regatta rental. Flexible accommodation with annexe. Newly decorated and furnished with pretty garden.  …see more

15 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £65 /night

£450 - £500 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Ideal for sailing accommodation of vacations, this charming property is in a quiet mews development and has the added benefit of a garage  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £32 /night

£222 - £260 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Stunning sea views/ocean views, small garden, 50 meters from the seaside, Accommodates up to 8 people, swimming pool heated from May, Wi-Fi internet, tennis court, a minigolf course, a Michelin-rated restaurant in close proximity, easy access to Ventnor Garden, Shanklin  …see more

7 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £53 /night

£366 - £535 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
A tranquil setting amongst the woods ideal for couples or families. Ideal location close to bike routes, public transport and ferries with some super walks.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £32 /night

£223 - £260 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Stunning sea views/ocean views, small garden, 50 meters from the seaside, Accommodates up to 8 people, swimming pool (heated from May), all weather tennis court, a minigolf course, a Michelin-rated restaurant in close proximity, easy access to Ventnor Garden, Shanklin  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 5

3 Nights min stay

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from £140 /night

£975 - £1750 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
GowithOh - Comfortable 1 bedroom apartment 200m from Trafalgar Square  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £225 /night

£1575 - £2716 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
GowithOh - Stylish one bedroom apartment in the heart of Covent Garden  …see more

19 Photos

Studio | sleeps 2

3 Nights min stay

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from £200 /night

£1400 - £2541 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
GowithOh - Contemporary duplex studio apartment next to Covent Garden  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £134 /night

£938 - £1688 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
GowithOh - Contemporary 1 bedroom apartment 200M from Trafalgar Square  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 5

3 Nights min stay

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from £140 /night

£975 - £1750 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
GowithOh - Modern 1 bedroom apartment 200M from Trafalgar Square  …see more

15 Photos

House | 2 Bedrooms | sleeps 4

Very Good 4/5 

3 Nights min stay

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from £61 /night

£422 - £961 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Perfectly positioned on East Cowes harbour just 10 meters from the sea. A 2 bedroom house sleeping 4 people. Panoramic harbour views and to West Cowes. Finished to a high standard throughout. Front elevated patio overlooking harbour.  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £225 /night

£1575 - £2716 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
GowithOh - Fantastic one bedroom apartment in the Covent Garden area  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 6

3 Nights min stay

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from £140 /night

£975 - £1750 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
GowithOh - Convenient 1 bedroom apartment 200M from Trafalgar Square  …see more

Offering over 500 miles of footpaths, and stretches of stunning coastline, the Isle of Wight is perfect for a walking holiday or a family break. Enjoy the unspoilt scenery, or have an activity filled vacation with sailing, windsurfing and paragliding all on offer locally. The island is famous for the annual Cowes week event in late August, and in May it hosts the largest walking festival anywhere in the UK.