List your home
Apply filters
£ to

Price

£10 - 500+

Price per night

£ to per night

Location

  • England Clear
  • Isle of Wight Clear

Location

Isle of Wight

  • Show all locations
  • Bembridge (29)
  • Bemridge Harbour (3)
  • Bonchurch (11)
  • Brading (2)
  • Brighstone (7)
  • Calbourne (4)
  • Cowes (58)
  • East Cowes (6)
  • Freshwater (21)
  • Godshill (4)
  • Gurnard (18)
  • Knighton, Isle of Wight (1)
  • Lake (1)
  • Merstone (2)
  • Nettlestone (1)
  • Newport (6)
  • Newtown (1)
  • Niton (2)
  • Northwood (2)
  • Porchfield (1)
  • Rookley (1)
  • Ryde (25)
  • Saint Helens (1)
  • Sandown (45)
  • Seaview (14)
  • Shanklin (35)
  • Shorwell (6)
  • St Helens (4)
  • Totland Bay (9)
  • Ventnor (68)
  • Whippingham (6)
  • Whitwell (10)
  • Woodside Beach (1)
  • Wootton Bridge (10)
  • Wroxall (7)
  • Yarmouth (28)

more +

less -

Bedrooms

Show all

  • Show all
  • Studio
  • 1 Bedroom
  • 2 Bedrooms
  • 3 Bedrooms
  • 4 Bedrooms
  • 5 Bedrooms
  • 6 Bedrooms
  • 7 Bedrooms
  • 8 Bedrooms
  • 9 Bedrooms
  • 10 Bedrooms
  • 11 Bedrooms
  • 12 Bedrooms
  • 13 Bedrooms
  • 14 Bedrooms
  • 15+ Bedrooms

more +

less -

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

Filters applied: Cycling holidays (450)

32 of 450 Results

Sort by: Default

  • Default
  • Price low to high
  • Price high to low
  • Reviews

from £140 / night

£980 - £1995 / week

View

1 / 11

Holiday cottage in Isle of Wight

Cowes / West Cowes

Cottage / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Not suitable for children
  • No pets allowed

Add to shortlist

from £140 / night

£980 - £1995 / week

View

Beautiful town cottage sleeping 4 guests in the heart of Cowes Old Town with car ferry travel*, luxury welcome hamper and free parking included. *only on stays of 3 nights or longer Regret that this property does not accept children or pets  …see more

from £68 / night

£475 - £1195 / week

View

(3) Excellent 5/5 

1 / 35

Holiday home in Isle of Wight

Isle of Wight / East Cowes

House / 2 Bedrooms / sleeps 5

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £68 / night

£475 - £1195 / week

View

Waterfront Cottage with sensational Sea & River Medina views Modern interior with nautical flavour, right on the water's edge & central, easy access to ferries, shops, restaurants, pubs, national heritage sites. Perfect base to explore the island. Superfast Broadband. Perfect for families. For sailors, property is very near UKSA and marina(s). Great viewing vantage point.  …see more

from £193 / night

£1350 - £5500 / week

View

(1) Excellent 5/5 

1 / 24

Holiday home in Cowes

Isle of Wight / Cowes

House / 5 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £193 / night

£1350 - £5500 / week

View

Amazing property for up to 10 that sits just back from the waterfront and has fantastic views up and down the River Medina and to the Solent beyond from the large roof terrace - an excellent place to entertain or sit and watch the world go by. 5 bedrooms & 4 bathrooms. Lift access and off-road parking for 2 cars. Ask about fares on Red Funnel ferries.  …see more

Featured properties

from £70 / night

£485 - £975 / week

View

(1) Excellent 5/5 

1 / 20

Isle of Wight holiday home let

Isle of Wight / East Cowes

House / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £70 / night

£485 - £975 / week

View

For those wanting to enjoy a waterside holiday on The Esplanade. with spectacular views of Cowes, the Solent, an assortment of shipping and wonderful sunsets. Sleeps 6 in 3 bedrooms This Grade 2 listed 'Old Coastguard Boat House' is situated in a conservation area on the relaxed seafront.  …see more

from £115 / night

£800 - £1750 / week

View

(10) Excellent 5/5 

1 / 23

Yarmouth holiday home rental

Yarmouth / Fort Victoria

House / 4 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £115 / night

£800 - £1750 / week

View

Isle of Wight Yarmouth Southern England Solent country breaks sea seaside beach sunny There are two foldaway/carrycots for babies.small infants and a children's chair.  …see more

from £108 / night

£750 - £1950 / week

View

(4) Excellent 5/5 

1 / 24

Shanklin holiday apartment rental

Isle of Wight / Shanklin

Apartment / 3 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £108 / night

£750 - £1950 / week

View

Contemporary & spacious luxury apartment. Stunning sea views, pillow top beds, dishwasher, washer/dryer, TV & DVDS in each room, plus amazing private terrace & hot tub. Master En-Suite with spa bath. Free Wi-Fi. Free use of Luccombe Hotels Leisure Club. Mins walk beach  …see more

from £108 / night

£750 - £1163 / week

View

(2) Excellent 5/5 

1 / 14

Holiday apartment in Ventnor

Ventnor / Ventnor Bay

Apartment / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £108 / night

£750 - £1163 / week

View

Modern 3 bedroom Victorian first floor apartment with fantastic sea and coastline views with large balcony.  …see more

from £200 / night

£1400 - £2450 / week

View

(1) Very Good 4/5 

1 / 9

Holiday villa in Ventnor

Ventnor / Ventnor Bay

Villa / 5 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed

Very Good 4/5 

Add to shortlist

from £200 / night

£1400 - £2450 / week

View

Villa Lavinia is part of the award winning The Hambrough. With five double rooms, three bathrooms, utility room, large kitchen lounge also a newly landscaped garden with full sea views from Alexandra Road. Retaining much of its original Victorian charm. Shorter stay options available - please send a message to enquire about availability and prices.  …see more

from £96 / night

£670 - £1750 / week

View

(1) Excellent 5/5 

1 / 10

Isle of Wight holiday apartment let

Isle of Wight / Shanklin

Apartment / 4 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £96 / night

£670 - £1750 / week

View

Luxurious apartment for 6 +2 people with private roof terrace & hot tub. TV/DVDs in every room. Dishwasher & Washer/Dryer Located on 1st & 2nd floors with en-suites to 3 bedrooms. FREE W--Fi. Free unlimited use of Luccombe Hotels Leisure Club. Few minutes walk to beach  …see more

from £108 / night

£750 - £1250 / week

View

(1) Excellent 5/5 

1 / 11

Shanklin holiday apartment rental

Isle of Wight / Shanklin

Apartment / 3 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Suitable for children over 5
  • Car not necessary
  • No pets allowed

Excellent 5/5 

Add to shortlist

Not on the map

from £108 / night

£750 - £1250 / week

View

Fantastic Property with the definite Wow Factor! Exclusive Location Walking Distance to Old Village, Cricket Ground, Park & Beach! FREE WI-FI  …see more

from £114 / night

£795 - £3250 / week

View

(6) Excellent 5/5 

1 / 12

Holiday townhouse rental

Cowes / West Cowes

Townhouse / 4 Bedrooms / sleeps 10

  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £114 / night

£795 - £3250 / week

View

VisitEngland 4* self catering accommodation in the heart of Cowes, ideal as a base ashore for sailors and for those wanting a base on the Island from which to explore. With a drying room and ample undercover storage The Yachtsman is also ideal for walkers & cyclists. An Accessibility Statement has been prepared for the property. Please contact us to request a copy.  …see more

from £50 / night

£350 - £620 / week

View

(7) Excellent 5/5 

1 / 22

Whitwell holiday cottage rental

Isle of Wight / Whitwell

Cottage / 2 Bedrooms / sleeps 6

  • Nearest beach 5 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £50 / night

£350 - £620 / week

View

Lovely cosy 17th century stone cottage tucked away just outside the village of Whitwell. Pretty courtyard garden which catches the afternoon sun, modern bathroom and kitchen and two double bedrooms. The cottage is a ten minute drive from the seaside town of Ventnor.  …see more

from £108 / night

£750 - £1163 / week

View

(5) Very Good 4.5/5 

1 / 17

Holiday apartment in Ventnor

Isle of Wight / Ventnor

Apartment / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary

Very Good 4.5/5 

Add to shortlist

from £108 / night

£750 - £1163 / week

View

Contemporary, 5 Star, Gold Award, luxury, self-catering Victorian apartment with panoramic sea views and large balcony. Ideal for a 3 or 4 day luxury retreat only a stones throw from the beach and harbour.  …see more

from £115 / night

£800 - £1500 / week

View

(5) Excellent 5/5 

1 / 19

Holiday home in Isle of Wight

Ventnor / Niton, Isle of Wight

House / 4 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £115 / night

£800 - £1500 / week

View

Kildare is an elegant 18th Century Georgian style holiday home which sleeps 10+, retaining many original features. Located on the southern tip of the Isle of Wight in an Area of Outstanding Natural Beauty, in the beautiful village Niton. The perfect retreat for families or groups of friends to relax in comfort & style.  …see more

from £40 / night

£280 - £532 / week

View

1 / 16

Holiday apartment in Isle of Wight

Ventnor / Ventnor Bay

Apartment / 1 Bedroom / sleeps 2

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed

Add to shortlist

from £40 / night

£280 - £532 / week

View

Brunswick holiday apartments are: In Ventnor town where shops are unique and restaurants are varied and plentiful 500 yards from the beach and coastal path and other great walks 20 yards from the bus stop Free tourist parking permits bike storage BBQ & free WIFI A Great central location to explore the islands attractions or just relax and enjoy the unique climate.  …see more

from £103 / night

£715 - £2500 / week

View

(21) Excellent 5/5 

1 / 22

Home rental in Cowes

Cowes / West Cowes

House / 3 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

Add to shortlist

from £103 / night

£715 - £2500 / week

View

A delightful Victorian terraced house 5 minutes walk to Cowes town centre. Decorated in a contemporary and uncluttered style. Well equipped modern kitchen. Light and spacious lounge and dining area. Garden with table and chairs for 8, parasol, hammock and BBQ. Free wifi. Travel cot and high chair available. Welcome basket on arrival.  …see more

from £126 / night

£880 - £2300 / week

View

(1) Excellent 5/5 

1 / 12

Holiday barn in Ryde

Isle of Wight / Ryde

Barn / 5 Bedrooms / sleeps 10

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden

Excellent 5/5 

Add to shortlist

from £126 / night

£880 - £2300 / week

View

A truly stunning, 5 star, Gold Award barn conversion sleeping 10 people+ cot in 5 bedrooms all with their own ensuite / private bathrooms. Wonderful original oak-beamed ceiling with fabulous gantry walkway over to a viewing platform up in the eaves! Wi-fi availble. A Bio-mass wood boiler heats all the hot water and heating with pine sourced from our own woodland.  …see more

from £84 / night

£585 - £1185 / week

View

(2) Excellent 5/5 

1 / 20

Isle of Wight holiday chalet rental

Isle of Wight / Bemridge Harbour

Chalet / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Suitable for children over 5
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £84 / night

£585 - £1185 / week

View

The Retreat is a waterside new build timber framed property, offering a double bedroom with en-suite wet room and twin bedded room with adjacent bath/shower. All linen and towels are provided free of charge. The Retreat is located in St Helens village, Isle of Wight.  …see more

from £71 / night

£495 - £895 / week

View

(4) Excellent 5/5 

1 / 15

Holiday bungalow in Isle of Wight

Isle of Wight / Wootton Bridge

Bungalow / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Great for children of all ages
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £71 / night

£495 - £895 / week

View

Waterside holiday Bungalow that sleeps 6 with creek view and moorings for your boat Moorings available for your boat just ask for details and price  …see more

from £132 / night

£920 - £2370 / week

View

(2) Very Good 4.5/5 

1 / 22

Barn rental in Ryde

Isle of Wight / Ryde

Barn / 5 Bedrooms / sleeps 12

  • Nearest beach 3 km
  • Great for children of all ages
  • Car advised
  • No pets allowed

Very Good 4.5/5 

Add to shortlist

from £132 / night

£920 - £2370 / week

View

This 5 Star Gold fabulous barn conversion has 5 bedrooms and 5 bathrooms and sleeps 12 people very comfortably. Enjoy wonderful views out over rolling countryside through the floor to gable windows, have a BBQ on your patio or take a walk over the farm to the woodland. Wi-Fi available. Friday change over, flexible out of season.  …see more

from £108 / night

£750 - £1950 / week

View

(15) Excellent 5/5 

1 / 23

Holiday apartment in Isle of Wight

Isle of Wight / Shanklin

Apartment / 3 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £108 / night

£750 - £1950 / week

View

Luxurious, spacious & contemporary sea-facing apartment. Private roof patio & hot tub, pillow top beds & spa bath master en-suite. Washer/dryer, dishwasher, fridge & freezer. Free Wi-fi. Free Unlimited free use of Luccombe Hotels Leisure Club. Few minutes walk to beach.  …see more

from £53 / night

£370 - £500 / week

View

(7) Excellent 5/5 

1 / 20

Cottage rental in Lake

Isle of Wight / Lake

Cottage / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Not suitable for children
  • Car not necessary

Excellent 5/5 

Add to shortlist

from £53 / night

£370 - £500 / week

View

Only 5 minutes walk from Lake station or a bus stop you don't even need to bring the car to enjoy a relaxing break Within 5 minutes walk is the Cliff path where you can choose to stroll down to either Shanklin by turning right or Sandown by turning left. stairs are a narrow and a little steep, the garden has a patio area with a table and chairs (parasol) & shed  …see more

from £57 / night

£395 - £2500 / week

View

(1) Excellent 5/5 

1 / 21

Isle of Wight holiday townhouse rental

Cowes / West Cowes

Townhouse / 3 Bedrooms / sleeps 10

  • Great for children of all ages
  • No pets allowed
  • Private garden

Excellent 5/5 

Add to shortlist

from £57 / night

£395 - £2500 / week

View

York street as also been a popular location for those coming for sailing events as its has a very short walking distant to the Marinas This property is part of the Cowes Holiday Homes portfolio where good service comes as standard  …see more

from £50 / night

£350 - £723 / week

View

(2) Very Good 4.5/5 

1 / 23

Holiday chalet in Yarmouth

Isle of Wight / Yarmouth

Chalet / 4 Bedrooms / sleeps 8

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden

Very Good 4.5/5 

Add to shortlist

from £50 / night

£350 - £723 / week

View

Westfield Farm comprises a spacious chalet bungalow with panoramic views over its 5 acres of fields. Extensive gardens, and outbuildings include stables, goatshed and pole barn. Situated in an Area of Outstanding Natural Beauty.  …see more

from £21 / night

£145 - £530 / week

View

(1) Very Good 4/5 

1 / 18

Chalet rental in Isle of Wight with shared pool

Isle of Wight / Bonchurch

Chalet / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • No pets allowed

Very Good 4/5 

Add to shortlist

from £21 / night

£145 - £530 / week

View

Our Sea View holiday chalet is set in an elevated and peaceful location on the south coast of the Isle of Wight. Ideal for couples and families wanting a relaxing and peaceful holiday. The chalet offers spectacular sea views from the lounge and private patio.  …see more

from £57 / night

£395 - £2850 / week

View

(1) Very Good 4/5 

1 / 10

Holiday home in Isle of Wight

Cowes / West Cowes

House / 4 Bedrooms / sleeps 7

  • Great for children of all ages
  • No pets allowed
  • Private garden

Very Good 4/5 

Add to shortlist

from £57 / night

£395 - £2850 / week

View

with its flexible layout & off road parking this property lends itself for large families, corporate booking & sailing events. All bookings with us come with linen & towels provided & we can also provide you with a 15% discount code for Red Funnel vehicle crossings.  …see more

from £36 / night

£250 - £625 / week

View

(17) Very Good 4.5/5 

1 / 18

Holiday caravan/mobile home in Isle of Wight

Isle of Wight / Cowes

Caravan/Mobile Home / 2 Bedrooms / sleeps 6

  • Nearest beach 2 km
  • Great for children of all ages
  • Car advised
  • Pets welcome

Very Good 4.5/5 

Add to shortlist

from £36 / night

£250 - £625 / week

View

Sunnycott Peaceful, beautiful location, lovely caravan, 2 miles from Cowes. good pub within walking distance. Great place to explore the Isle of Wight from. Sailing, horse riding and mountain bike hire are all available locally.  …see more

from £58 / night

£400 - £875 / week

View

(3) Very Good 4.5/5 

1 / 22

Holiday cottage in Isle of Wight

Isle of Wight / Brighstone

Cottage / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

Add to shortlist

from £58 / night

£400 - £875 / week

View

Briarley Cottage is 4 star, self-catering holiday accommodation on the Isle of Wight. A charming Grade II listed thatched cottage, Briarley Cottage is situated in Brighstone, the quintessential Isle of Wight village. Briarley Cottage is child friendly and dog friendly. Built in the 1700's this 2 bedroom cottage is a delightful “home away from home” full of old world charm.  …see more

from £36 / night

£250 - £795 / week

View

(2) Excellent 5/5 

1 / 8

Holiday apartment in Isle of Wight

Wootton Bridge / Fishbourne

Apartment / 3 Bedrooms / sleeps 6

  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £36 / night

£250 - £795 / week

View

Modern, well-equipped, purpose-built apartment. Fantastic superking fourposter bed in main bedroom. Free broadband WiFi. Convenient for Ryde and Newport Near car ferry terminals at Fishbourne (1 mile) and East Cowes (3 miles) Sleeps six without having to use a sofa-bed in the sitting room - the Grange has three proper bedrooms!  …see more

from £58 / night

£400 - £800 / week

View

(4) Excellent 5/5 

1 / 15

Holiday cottage rental

Isle of Wight / Ryde

Cottage / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £58 / night

£400 - £800 / week

View

The cottage / house is situated in Ryde on the Isle of Wight. Sleeps 4 in total. Beach nearby. Restaurants, cafes, bars, public swimming pool, boating lake, Ice skating rink nearby. Car parking nearby. None smoking. No pets. Freeview. Wi Fi.  …see more

from £62 / night

£430 - £1000 / week

View

(15) Very Good 4.5/5 

1 / 22

Cowes holiday cottage rental

Cowes / West Cowes

Cottage / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary

Very Good 4.5/5 

Add to shortlist

from £62 / night

£430 - £1000 / week

View

The Cottage is located on a quite street very close to the waters edge, but has very easy access to the rest of the Island. Its cool in summer and wam in winter.  …see more

from £42 / night

£290 - £550 / week

View

1 / 15

Chalet letting in Isle of Wight with shared pool

Cowes / Gurnard Pines

Chalet / 2 Bedrooms / sleeps 5

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

Add to shortlist

from £42 / night

£290 - £550 / week

View

Immaculate and well appointed 2 bedroom chalet. Ideally located for Cowes and within easy reach of all Isle of Wight attractions. Gurnard Holiday village contains leisure activities including indoor and outdoor swimming pools,gym,children activities,bar and restaurant The Isle of Wight has numerous beaches including Shanklin, Sandown and Ventnor  …see more
first

Also consider

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page