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Isle of Wight Holidays & City Breaks - Holiday Lettings

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76 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 £109 / night

£802 - £1,317 / week

1 / 27

Holiday apartment in Shanklin

Shanklin apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £161 / night

£1,329 - £2,199 / week

1 / 17

Holiday apartment in Shanklin

Shanklin apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £252 / night

£2,039 - £3,390 / week

1 / 24

Holiday b&b in Shanklin

Shanklin b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £95 / night

£666 / week

1 / 58

Shanklin holiday caravan/mobile home rental

Shanklin caravan/mobile home

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £201 / night

£1,374 / week

1 / 11

Holiday home in Niton

Niton house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £204 / night

£978 - £2,059 / week

1 / 11

Holiday home in Wootton

Wootton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £137 / night

£441 - £1,260 / week

1 / 13

Ryde holiday home rental

Ryde house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from £1,047 / night

£4,428 - £7,862 / week

1 / 22

Lighthouse rental in Niton

Niton lighthouse

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £200 / night

£979 - £1,968 / week

1 / 18

Holiday home in St Helens

St Helens house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £135 / night

£507 - £1,687 / week

1 / 16

Holiday cottage in St Helens

St Helens cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £116 / night

£403 - £1,415 / week

1 / 28

Carisbrooke holiday home accommodation

Carisbrooke house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £130 / night

£620 - £2,198 / week

1 / 19

Holiday home rental

Shanklin house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £229 / night

£1,002 - £1,603 / week

1 / 29

Holiday home in Ventnor

Ventnor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £391 / night

£1,814 - £4,623 / week

1 / 18

Holiday home in Ryde

Ryde house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £144 / night

£432 - £1,582 / week

1 / 25

Holiday apartment in Newchurch

Newchurch apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £86 / night

£602 / week

1 / 23

Holiday home in Seaview

Seaview house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from £315 / night

£2,388 / week

1 / 17

Holiday home in Ryde

Ryde house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £117 / night

£487 - £1,060 / week

1 / 16

Holiday lighthouse in Niton

Niton lighthouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £197 / night

£971 - £1,584 / week

1 / 14

Holiday lighthouse in Niton

Niton lighthouse

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £200 / night

£979 - £1,791 / week

1 / 16

Shanklin holiday log cabin rental

Shanklin log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £103 / night

£779 - £1,191 / week

1 / 5

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

Holiday cottage in Bembridge

Bembridge cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £190 / night

£568 - £2,699 / week

1 / 51

Cottage rental in Totland

Totland cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £239 / night

£1,668 / week

1 / 73

Freshwater holiday home rental

Freshwater house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

“Tower House is charming, spacoius and full of character.” Tower House is within easy walking distance of the beach, Tennyson Down and a good convenience store. A Victorian property with Victorian links all around Tennyson's home, Charles Dodgson and Alice Liddle's holiday properties and Julia Margaret Cameron's Dimbola Lodge. The piano café is the former residence of Tennyson's piano tuner.

from £285 / night

£1,990 - £2,445 / week

1 / 21

Cottage rental in Norton

Norton cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £147 / night

£484 - £1,996 / week

1 / 32

Holiday home in Ventnor

Ventnor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £143 / night

£428 - £1,553 / week

1 / 23

Apartment rental in Cowes

Cowes apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Perfect” We had a great stay in West Cowes, James’s apartment is perfectly situated with many fantastic restaurants, pubs and a supermarket only a short walk away. The apartment itself is very well equipped and has everything you could need, it is also clean and very well kept. James was very helpful and commutative in the lead up to our stay and advised on Island parking etc. Would love to visit again and would definitely recommend. Many thanks to James for sharing his apartment with us. Dan and Denise.

from £155 / night

£802 / week

1 / 20

Great rentals within 20 miles that match your search

Apartment rental in Southsea with golf nearby

Southsea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £91 / night

£455 - £630 / week

1 / 20

Hamble holiday home rental

Hamble house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £92 / night

£642 / week

1 / 12

Holiday home with golf nearby in Southsea

Southsea house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £436 / night

£2,519 / week

1 / 19

Portsmouth holiday home rental

Portsmouth house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

from £115 / night

£802 / week

1 / 23

Holiday apartment in Southsea

Southsea apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £150 / night

£950 - £1,200 / week

1 / 19

Holiday caravan/mobile home in Lymington

Lymington caravan/mobile home

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £81 / night

£401 - £722 / week

1 / 18

Holiday apartment in Old Portsmouth

Old Portsmouth apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £128 / night

£750 - £1,249 / week

1 / 24

Holiday apartment with golf nearby in Lymington

Lymington apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £229 / night

£1,718 - £2,966 / week

1 / 6

Holiday apartment in Portsmouth

Portsmouth apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

from £166 / night

£905 / week

1 / 27

Bungalow rental in Bursledon

Bursledon bungalow

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

from £115 / night

£802 / 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

Holiday home in Lymington

Lymington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 15

from £344 / night

£2,405 / week

1 / 30

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