Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

Watersports Holidays in Isle of Wight - Holiday Lettings

All filters (1)

Filters (1)

Clear filters

414 properties with watersports onsite or nearby

Applied filters (1)

Holiday bungalow in Freshwater

Freshwater bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Perfect spot for morning swims and sunset views.” A quiet location with beach access. Lovely views and sunsets. The chalet has everything we needed and the owners were very helpful, leaving extra beach towels for us. Easy to get to from the Lymington - Yarmouth ferry.

from £81 / night

£430 - £802 / week

1 / 18

Holiday apartment in Ventnor

Ventnor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful stay” We have just returned from a wonderful stay at Top Deck in ventnor, in a fabulous Position overlooking the sea. The apartment ( which is amazing so don't be put off by approaching it from the back) has absolutely everything you would possible need including so many thoughtful extras, we spent lots of time watching passing ships and fishing boats with the telescope And binoculars provided it was great. And the view from the roof terrace is breathtaking.Serena and Michaels communication from booking through to the end of our break was brilliant and we were informed of exactly everything we needed to know, there was so much information about the apartment, reading materials, info on the island and places to visit you were sure of a great time, and of course all the little thoughtful extras fresh flowers, fresh bread , fresh fruit, milk, wine, juice, cake I could go on and on. We just can't wait to return and do that lovely walk to steephill cove and enjoy our crab pasty !! Fresh fried fish of the day off the harbour, our tapas in the Met, and fish pie in the spyglass, plus the hundreds of things the island has to offer. Thank you soooo much Serena and Michael x

from £109 / night

£624 - £773 / week

1 / 26

Yarmouth holiday villa rental

Yarmouth villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great house/cottage & holiday!” Lovely cottage with beautiful views of the sea. It had everything we needed inside & plenty of outside space to sit & have drinks & bbq. Yarmouth Village is only 20 min walk or few mins drive, no problems parking in the village.

from £189 / night

£956 - £2,949 / week

1 / 26

Holiday bungalow rental

Freshwater bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £69 / night

£390 - £716 / week

1 / 10

Holiday home in Niton, Isle of Wight

Niton, Isle of Wight house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £180 / night

£1,260 - £2,061 / week

1 / 18

Lodge rental in Bembridge

Bembridge lodge

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Amazing Lodge” The lodge was very comfortable and clean. It was equipped with everything you would ever need including an ice maker. Had a wonderful stay we loved walking to the secluded beach - Priory Bay.

from £115 / night

£802 / week

1 / 22

Holiday home in Sandown

Sandown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Just great!!” We spent a lovely long weekend here in January. We enjoyed the walk to the beach, the hot tub and the apartment was great. Many thanks

from £149 / night

£1,042 / week

1 / 30

Holiday apartment in Wroxall

Wroxall apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £81 / night

£516 - £831 / week

1 / 37

Holiday apartment in Cowes

Cowes apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £144 / night

£687 - £2,691 / week

1 / 15

Holiday cottage in Cowes

Cowes cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“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. I would definitely recommend this great holiday cottage.

from £172 / night

£802 - £1,203 / week

1 / 35

Holiday cottage in Yarmouth

Yarmouth cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Excellent accommodation - location and local people” Good walks at rear and front of the property on this dog friendly island. Property overlooks the sea with fenced green area (for Victoria cottages residents) where rabbits and children can play. In this area dogs must be on a lead for safety and hygiene reasons. Very short walk through this green takes you to the sea where dogs can wander freely. Walk to the left and beach is okay for sandcastles but nowhere is safe for swimming. Only two of us, plus dog, but cottage would comfortably house 4 adults. Very smart, clean and quiet. Only small fenced front garden if your dog is an escape artist but the wood at back has good trails that lead to view of Needles and eventually coastal path. We love the area and cottage .... BUT don't expect to find supermarkets in good supply. However there is a Co op in Freshwater. 15 mins walk into Yarmouth good for eating and tourism but quite small.

from £103 / night

£527 - £1,632 / week

1 / 21

Cottage rental in Ventnor

Ventnor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Tranquility base” We had a long weekend at Ocean View, off season in March. The cottage is really cosy, in extremely good order, very clean and the sea views are wonderful. It also has a small patio in the front where, as the weather was kind, we sat and drank wine in the early evening. Debby, the owner, was very helpful with local information and has a good knowledge of where to eat and drink (under no circumstances omit a visit to the Taverners in Godshill). We're going to try and book Ocean View again for a return visit in the summer.

from £114 / night

£859 - £1,432 / week

1 / 21

Home rental in Cowes

Cowes house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Perfect Holiday Rental” From the first contact with Amanda I knew this place was going to be great. Amanda was very prompt and helpful in answering emails and throughout the booking process. The cottage itself is amazing. A huge kitchen, lovely backyard and very comfy beds! Everything you could think of is catered for including kitchen equipment, dvd's, and sensor lights on the landing! I highly recommend this Cottage for it's great location to West Cowes centre and homely feel. There is already talk of going back next year we had such a great stay.

from £144 / night

£1,603 / week

1 / 17

Holiday chalet in Sandown

Sandown chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £81 / night

£544 - £745 / week

1 / 21

Sandown holiday chalet rental

Sandown chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £84 / night

£527 - £779 / week

1 / 19

St Lawrence, Ventnor holiday apartment let

St Lawrence, Ventnor apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Fantastic accommodation - great location.” Stayed in Flat 1 for a week with partner and 11 year old. Plenty of space. Nice and clean. The view from living room and main bedroom was fantastic. We spent many hours just looking at the boats sailing past! Garden is nice and pleasant to sit in or play games, or enjoy a drink after a day out exploring the Island. Great value for money compared to other accommodation we looked at. Would definitely stay here again should we visit IOW.

from £81 / night

£418 - £1,023 / week

1 / 17

Ventnor holiday penthouse rental

Ventnor penthouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £287 / night

£2,004 / week

1 / 32

Bungalow rental in Ryde

Ryde bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Excellent cottage, good location, thoughtful owners.” The cottage is really good for young families as they have so many toys, games and DVDs for the kids to enjoy on wet days, and the play den in the garden is really well equipped with toys. It is really beautifully furnished, exceptionally clean and tidy and the location is excellent for the beach and exploring the Island. Had a lovely week in spite of the weather. Would definitely go back.

from £229 / night

£831 - £1,718 / week

1 / 31

Sandown holiday chalet rental

Sandown chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £58 / night

£745 / week

1 / 20

Holiday cottage in Ventnor

Ventnor cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £115 / night

£802 - £859 / week

1 / 13

Cottage rental in Newport

Newport cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Amazing stay !” Second time we've been back to this lovely cottage and it certainly won't be our last! Delightful stay , clean and cosy and Lynn made it so easy with the Ferry!

from £138 / night

£882 / week

1 / 12

Holiday lodge with shared pool in Gurnard

Gurnard lodge

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £115 / night

£802 / week

1 / 15

Home rental in Wootton with golf nearby

Wootton house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £109 / night

£716 / week

1 / 15

Sandown holiday chalet rental

Sandown chalet

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £81 / night

£561 / week

1 / 18

Holiday bungalow in Yarmouth

Yarmouth bungalow

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £241 / night

£1,718 - £2,977 / week

1 / 30

Holiday chalet in Yaverland

Yaverland chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £132 / night

£859 / week

1 / 13

Holiday home in Shanklin

Shanklin house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £153 / night

£687 - £1,660 / week

1 / 31

Sandown holiday home let

Sandown house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £121 / night

£831 - £1,088 / week

1 / 16

Home rental in Shorwell

Shorwell house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £108 / night

£754 - £1,924 / week

1 / 44

Holiday cottage in Newchurch

Newchurch cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Lovely cosy house” Perhaps the best equiped holidayhome I ever rented. Due to the big floods of last winter the kitchen is brandnew and has all you can wish for. And otherwise Ali will help you out. Beds are good as well. The children loved al the toys ( train, playmobil, puzzles and lots more). Bikes available, also for children. Beautifull big patio full of flowers. The weather was so good (hot summer weather) that sometimes I missed the openness for some wind (and a view) but in cooler weather the patio will be a real benefit. Beaches in easy reach.

from £126 / night

£1,031 / week

1 / 36

Holiday cottage in Wootton

Wootton cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“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.

from £195 / night

£815 - £1,560 / week

1 / 24

Holiday home in Shorwell

Shorwell house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

“Wonderful house and holiday” The house was absolutely perfect for us with a 3 and 1 year old. Beautifully decorated and very spacious. Perfect home for a family holiday. Ideally located for everything we wanted to see and do. Would 100% recommend.

from £144 / night

£745 - £1,947 / week

1 / 27

Holiday home with golf nearby in Cowes

Cowes house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Great Weekend” We stayed at Wight Cottage, a party of 6 adults & there was everything we could have imagined we'd need. Welcome pack was a really lovely touch and very 'welcome' ! Cottage exactly as per the photos, extremely comfortable, immaculately clean with all mod cons. Very convenient for the centre of town. Highly recommended.

from £229 / night

£1,603 / week

1 / 24

Yarmouth holiday apartment rental

Yarmouth apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £103 / night

£722 / week

1 / 42

Holiday chalet with golf nearby in Yaverland

Yaverland chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £92 / night

£447 - £802 / week

1 / 20

Holiday home in Shanklin

Shanklin house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £131 / night

£916 - £1,832 / week

1 / 55

Sandown holiday chalet rental

Sandown chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £65 / night

£321 - £768 / week

1 / 21

Holiday home in Ventnor

Ventnor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

from £229 / night

£916 - £2,519 / week

1 / 22

Holiday bungalow in Freshwater

Freshwater bungalow

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £86 / night

£504 - £1,231 / week

1 / 16

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

×

Also consider