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Isle of Wight Holidays & City Breaks - Holiday Lettings

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25 properties suitable for city breaks and holidays

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Bembridge holiday bungalow rental

Bembridge bungalow

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“perfect place for family holiday” The location was amazing, the beach was 5 minute away. the house was neat and clean and spacious. the homeowner was quick in replying all of my queries. We were really impressed with the whole house layout. rooms were spacious, clean, they have few board games in the house which my 7-year-old son loved. I would highly recommend this place and for sure will book this place for my next holidays.

from £126 / night

£911 - £1,203 / week

1 / 27

Holiday home in Wootton

Wootton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £137 / night

£441 - £1,025 / week

1 / 19

Holiday b&b in Shanklin

Shanklin b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £92 / night

£642 / week

1 / 65

Shanklin holiday caravan/mobile home rental

Shanklin caravan/mobile home

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £172 / night

£1,145 / week

1 / 11

Holiday cottage in St Helens

St Helens cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £128 / night

£437 - £1,434 / week

1 / 28

Lighthouse rental in Niton

Niton lighthouse

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £245 / night

£1,046 - £2,095 / week

1 / 18

Cottage rental in Norton

Norton cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £164 / night

£550 - £1,996 / week

1 / 32

Holiday bungalow in Cowes

Cowes bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £201 / night

£1,403 / week

1 / 25

Holiday home with golf nearby in Ventnor

Ventnor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £141 / night

£461 - £1,528 / week

1 / 23

Carisbrooke holiday home accommodation

Carisbrooke house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £144 / night

£667 - £2,005 / week

1 / 19

Holiday home in Ryde

Ryde house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £160 / night

£479 - £1,470 / week

1 / 25

Holiday home in Luccombe

Luccombe house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £272 / night

£1,900 / week

1 / 19

Holiday cottage in Bembridge

Bembridge cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £206 / night

£617 - £2,779 / week

1 / 51

Ventnor holiday home rental

Ventnor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £252 / night

£1,764 / week

1 / 37

Holiday lighthouse in Niton

Niton lighthouse

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £245 / night

£1,046 - £2,095 / week

1 / 16

Holiday home in Ventnor

Ventnor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £406 / night

£1,922 - £4,337 / week

1 / 18

Holiday lighthouse in Niton

Niton lighthouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £243 / night

£1,037 - £1,687 / week

1 / 14

Holiday apartment in Shanklin

Shanklin apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £229 / night

£1,455 - £2,428 / week

1 / 17

Holiday home in St Helens

St Helens house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £325 / night

£1,386 / week

1 / 16

Holiday apartment in Newchurch

Newchurch apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £98 / night

£682 / week

1 / 23

Shanklin holiday log cabin rental

Shanklin log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £126 / night

£779 - £1,340 / week

1 / 5

Holiday apartment in Shanklin

Shanklin apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £344 / night

£2,233 - £3,836 / week

1 / 24

Holiday apartment in Cowes

Cowes apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Lovely central location!” 42a Cowes town centre is an absolute pleasure to stay in! The location is fantastic just a stones throw away from the red Jet ferry terminal and you're on the high street itself surrounded by gorgeous gift shops, lovely pubs and a great choice of restaurants. The apartment itself Is beautiful we absolutely loved the nautical theme throughout, it was clean and modern, whilst feeling incrediably homely! We slept very well and the beds are super comfy! It's the added touches that make it...a DVD Collection, milk, sugar, biscuits, and I have to say the chilling wine fridge was very well-received! The only thing I would suggest for improvement is to have a facility for recycling, as there wasn't any recycling bags for us to use for glass etc. We would definitley love to stay again and will be recommending to anyone who is looking to stay on the Isle of wight rather then stay in a guest house. A perfect apartment to catch up with friends as we did, or for couples and families.

from £126 / night

£802 - £1,042 / week

1 / 18

Apartment rental in Shanklin

Shanklin apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Everything you could want in a holiday flat on the isle of Wight” The Courtyard is very close to the old village in Shanklin with local amenities (convenience store and lots of restaurants) in easy walking distance. The flat is quiet, well-furnished and located next to the garden at the rear of a large Victorian house. The owners Richard and Miriam are very friendly and helpful and have thought of just about everything including a lovely cake to welcome visitors.

from £81 / night

£706 - £866 / week

1 / 22

Cottage rental in Totland

Totland cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £239 / night

£1,668 / week

1 / 73

Great rentals within 20 miles that match your search

Holiday apartment with golf nearby in Lymington

Lymington apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £229 / night

£1,718 - £2,680 / week

1 / 6

Bungalow rental in Bursledon

Bursledon bungalow

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

from £131 / night

£916 / week

1 / 32

Apartment rental in Portsmouth

Portsmouth apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £201 / night

£1,432 - £1,592 / week

1 / 14

Southsea holiday apartment rental

Southsea apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £138 / night

£825 - £905 / week

1 / 45

Holiday home in Lymington

Lymington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 15

from £401 / night

£2,806 / week

1 / 30

Hamble holiday home rental

Hamble house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £101 / night

£706 / week

1 / 12

Holiday cottage rental

Lymington cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £158 / night

£991 / week

1 / 25

Holiday studio in Portsmouth

Portsmouth studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £114 / night

£630 / week

1 / 20

Southampton holiday apartment rental

Southampton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £126 / night

£859 - £1,340 / week

1 / 51

Portsmouth holiday studio rental

Portsmouth studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £114 / night

£630 / week

1 / 21

Lymington holiday apartment rental

Lymington apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £114 / night

£794 / week

1 / 46

Southampton holiday apartment rental

Southampton apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £114 / night

£1,144 - £1,946 / week

1 / 19

Holiday apartment with shared pool in Brockenhurst

Brockenhurst apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £115 / night

£801 / week

1 / 12

Holiday apartment with golf nearby in Portsmouth

Portsmouth apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £114 / night

£794 / week

1 / 14

Holiday apartment in Southampton

Southampton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £115 / night

£745 / week

1 / 16

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