Cycling holiday villas and apartments Isle of Wight

Close

View larger map

Also consider

Europe Holidays
425072 properties
United Kingdom Holidays
57024 properties
England Holidays
41528 properties
Cottages Cornwall
2983 properties
Apartments Greater London
941 properties
Cottages Cumbria / Lake District
940 properties
Houses Devon
2810 properties
Cottages Central England / Cotswolds
940 properties
Houses Dorset
819 properties
Houses Isle of Wight
507 properties
Cottages Peak District / Derbyshire
460 properties
Houses Somerset
610 properties
Houses Kent
557 properties
Houses Sussex
770 properties
Houses Norfolk
1023 properties
Cottages Isle of Man
11 properties
Northumberland
640 properties
Houses Yorkshire / Yorkshire Dales
1496 properties
Coastal Cottages
222 properties
Villas Ventnor
123 properties
Holiday homes Cowes
122 properties
Villas Shanklin
104 properties
Self catering accommodation Sandown
96 properties

Isle of Wight

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
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

357 Holiday homes

Filters applied: Cycling holidays

Travellers going to Isle of Wight are booking June dates now. Secure your holiday home today and have the perfect trip.

(1)  

11

Holiday chalet with golf nearby in Yaverland

Sandown / Yaverland

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
isle of wight, self catering chalet, beautiful views 5 mins walk to sandy beach<br />fully equipped, electric FREE  …see more

from £32 / night

£220 - £500 / week

Book View

from £32 / night

(7) Excellent 

20

Holiday cottage rental

Freshwater / Moons Hill

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly
Sunbeam Cottage is a bright and sunny home in a beautiful rural location. Set on a leafy lane at the foot of Tennyson Down in an AONB with wonderful views, it is pet friendly, excellent for walking and cycling with lovely beaches and a pub with good food close by.  …see more

from £53 / night

£370 - £720 / week

Book View

from £53 / night

(6) Excellent 

21

Holiday bungalow rental

Freshwater / Freshwater Bay

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Robinhill holiday bungalow is situated in the West which is a beautiful part of the island. The bungalow is in a very quiet and relaxing location, sandy Colwell Bay beach is within a few minutes walk. Walking and cycling holidays can be enjoyed any time of the year.<  …see more

from £36 / night

£250 - £480 / week

Book View

from £36 / night

(1) Excellent 

29

Holiday caravan/mobile home in Bembridge

Isle of Wight / Bembridge

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Double glazed with central heating. (Radiators in all the rooms). Fully equipped kitchen with gas cooker, fridge with icebox, microwave, toaster & kettle to cater for 8 guests. Beds made up on arrival (Towels not provided). Private beach with Cafe during the summer  …see more

from £55 / night

£385 / week

Book View

from £55 / night

(7) Excellent 

24

Bungalow rental in Yarmouth

Isle of Wight / Yarmouth

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
Large bungalow with peaceful country views near beaches. 2 downstairs bedrooms and downstairs shower room accessible for restricted mobility. 2 ensuite upstairs bedrooms, for 3 generations or 2 families.Sunny private patio provides outdoors dining and relaxing area. Geo  …see more

from £120 / night

£650 - £1750 / week

Enquire View

from £120 / night

(5) Excellent 

20

Holiday cottage in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Private garden
Beautiful town cottage sleeping 4 guests in the heart of Cowes Old Town with luxury welcome hamper and free parking included. Regret that this property does not accept children or pets  …see more

from £150 / night

£1050 - £2200 / week

Book View

from £150 / night

11

Caravan/mobile home rental in Bembridge

Isle of Wight / Bembridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Available for holiday hire, is our large 4 bedroom static caravan set in the stunning surroundings of Whitecliff Bay Holiday Park in Bembridge. The caravan is very spacious, with 4 separate bedrooms, an open plan living and dining area, shower room with toilet and also  …see more

from £50 / night

£525 - £800 / week

Book View

from £50 / night

(8) Excellent 

10

Cottage rental in Whippingham

Isle of Wight / Whippingham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 10 km
  • Child friendly
  • Private garden
Self-catering countryside cottage, equipped to a high standard, with excellent views across fields. Located along a private lane, very secluded - the base for great holidays on the Isle of Wight - great for chilling out!! Ideal for couple & families seeking relaxati  …see more

from £49 / night

£340 - £625 / week

Enquire View

from £49 / night

(6) Excellent 

63

Seaview holiday cottage rental

Isle of Wight / Seaview

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Whatever your Isle of Wight holiday needs, from family stays to short breaks for couples, Seaview Holidays can accommodate them all.  …see more

from £88 / night

£379 - £799 / week

Book View

from £88 / night

(2) Excellent 

8

Holiday chalet in Sandown

Isle of Wight / Sandown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
This is a beautiful open plan chalet that easily accommodates 6. The kitchen caters for all guests, supplying you with a table and six chairs as well as all the cooking facilities and crockery you will require. Within the lounge is a large sofa bed, Free-view TV/DVD, s  …see more

from £50 / night

£390 - £550 / week

Book View

from £50 / night

(2) Excellent 

10

Holiday apartment in Brook

Isle of Wight / Brook

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly
Brook is a lovely little village in the beautiful and rural West Wight. It can offer you the perfect place for a relaxing holiday. At Brook House, we have 3 self-catering holiday properties. Northbrook, our smallest property, will give you a charming and character  …see more

from £90 / night

£300 - £995 / week

Book View

from £90 / night

(5) Excellent 

20

Cottage rental in Whitwell

Isle of Wight / Whitwell

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
“A wonderful holiday in a beautiful cottage” We had a fantastic week at Maytime Cottage this August. The cottage was clean and fresh when we arrived and it is airy and spacious with loads of character. It made you feel right at home. There was good inf  …see more

from £105 / night

£420 - £890 / week

Enquire View

from £105 / night

(2) Excellent 

32

Ventnor holiday apartment rental

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly
Navarino Villa Apartment is set on the ground floor of a Victorian house. In an Area of Outstanding Natural Beauty (AONB), nestling at the base of St Boniface Downs, the apartment enjoys spectacular views of the Downs. Navarino Villa apartment combines the best of moder  …see more

from £60 / night

£420 - £630 / week

Book View

from £60 / night

(2) Excellent 

8

Cowes holiday townhouse rental

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Private garden
Due to its location so near to town, this property would be well suited for those not bringing a car coming across on the Red Jet, for those with a car permits can be provided for on street parking.<br />This property is part of the Cowes Holiday Homes portfolio w  …see more

from £95 / night

£460 - £1800 / week

Book View

from £95 / night

(1) Excellent 

11

Shanklin holiday apartment rental

Isle of Wight / Shanklin

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
“Amazing Apartment” We stayed at this "apartment" without realising that it was actually larger in size than our 3 bedroom house! Obviously the owners have furnished it to their personal standards, and just about everything we needed was there ( inclu  …see more

from £122 / night

£850 - £1250 / week

Book View

from £122 / night

(13) Very Good 

26

Holiday home with golf nearby in Cowes

Cowes / West Cowes

7 17 Min stay varies

  • 7 bedrooms
  • Sleeps 17
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“Perfect house for large group, and close to Cowes pubs etc.” We have just spent a fabulous week at Windrush over New Year 2016. There were 3 families (12 in total + dog) and could have fitted in a few more as well! Windrush is a lovely old house wit  …see more

from £315 / night

£1800 - £9000 / week

Book View

from £315 / night

(9) Excellent 

11

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“The chalet was lovely & clean. Owners were lovely people.” We went here on the 17th of September till the 24th so it was nice & quiet with all the children having gone back to school. The accommodation was lovely & clean. Everything you wanted was the  …see more

from £36 / night

£250 - £485 / week

Book View

from £36 / night

(1) Excellent 

12

Bembridge holiday home rental

Bembridge / Bembridge Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Ledge View is a beautiful newly-upgraded property sleeping up to 8 people just seconds from the sea in Bembridge, Isle of Wight. The house is in a fantastic location, due to its proximity to the stunning Forelands beach.  …see more

from £185 / night

£610 - £1540 / week

Book View

from £185 / night

(1) Excellent 

59

Bembridge holiday lodge rental

Isle of Wight / Bembridge

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
A 6 berth Superior Lodge which can comfortably accommodate 6 adults. Benefits from a separate cloakroom in addition to the family shower room. Parking adjacent to the unit. A travel cot and high chair are available for use by our younger guests. SITE PASSES Can be p  …see more

from £60 / night

£420 / week

Book View

from £60 / night

(12) Excellent 

18

Holiday cottage rental

Cowes / West Cowes

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.08 km
  • Child friendly
“Truly a home from home” A wonderful break. Carlton Cottage is beautifully decorated, perfectly located. High attention to detail with everything thought about to make a memorable stay. With much thanks we hope to return soon.  …see more

from £180 / night

£760 - £2600 / week

Book View

from £180 / night

(41) Excellent 

16

Ventnor holiday apartment let

Ventnor / St Lawrence, Ventnor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“great location, great welcome” lovely house. amazing garden with all facilities. we received a great welcome. really enjoyed the holiday.  …see more

from £50 / night

£225 - £820 / week

Enquire View

from £50 / night

(3) Excellent 

13

Caravan/mobile home rental in Bembridge with shared pool

Isle of Wight / Bembridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Cosy but spacious enough for six” Very comfortable 2-night stay. Caravan is modern and smart with good facilities. It's on the inland side of Hillway Road, so it's a good 10-minute walk to the beach and 5 minutes to the main site facilities (clubhouse  …see more

from £40 / night

£280 / week

Book View

from £40 / night

(24) Excellent 

22

Home rental in Cowes

Cowes / West Cowes

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“family Holiday” We returned to the Isle of Wight after many years and have had the most relaxing time the accommodation was excellent and well stocked we found parking a daily challenge but so did everyone else it did not spoil the holiday and never i  …see more

from £150 / night

£750 - £2500 / week

Book View

from £150 / night

(18) Very Good 

17

Holiday studio in Shanklin

Isle of Wight / Shanklin

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Lovely little hideaway.” We had a great few days away in Shanklin and stayed there with our toddler. We'd definitely stay in this studio apartment again. Many thanks for everything.  …see more

from £45 / night

£230 - £585 / week

Book View

from £45 / night

(1) Excellent 

14

Shanklin holiday home rental

Shanklin / Old Village

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Car not necessary
DISCOUNT APPLIED TO SEPTEMBER 2016 RATES. You can book for 5 nights or more from £534. The cottage has been advertised for 2016 following a break, discount rate already applied. Percy cottage (Self-catering. Sleeps 4 in total. (2 bedrooms) is nestled in the pi  …see more

from £75 / night

£525 / week

Book View

from £75 / night

(6) Very Good 

24

Holiday home in Newport

Newport / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
“What a find !” We had a fantastic week on the IoW, seven of us in total with extended family, and Yachtsman's Rest easily accommodated us all in comfort. Plenty of bathrooms, all well placed next to bedrooms or en-suite, no kids squabbling about wh  …see more

from £150 / night

£750 - £2400 / week

Book View

from £150 / night

(3) Very Good 

12

Holiday barn in Ryde

Isle of Wight / Ryde

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
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.<br  …see more

from £130 / night

£900 - £2250 / week

Book View

from £130 / night

(13) Very Good 

17

Holiday home in Bonchurch

Isle of Wight / Bonchurch

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Charlton House is a beautiful home set in a private and tucked away location on the edge of the highly sought after and picturesque village of Bonchurch, adjacent to the very popular Victorian town of Ventnor. Bonchurch & Ventnor has had a fair bit of media attentio  …see more

from £250 / night

£1250 - £1995 / week

Book View

from £250 / night

(15) Very Good 

24

Holiday home in Totland

Totland Bay / Totland Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Nice House” Craiglea is a nice house, in a nice village, 5 minutes walk from the sea , very handy for shops, good parking, and an enclosed garden  …see more

from £116 / night

£570 / week

Book View

from £116 / night

(3) Excellent 

12

Holiday apartment in Cowes

Cowes / West Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
With its off-road parking & flexible layout with 1 bathroom, 1 en suite shower room & 1 cloakroom this property is well suited for families, small groups & corporate bookings.<br />This property is part of the Cowes Holiday Homes portfolio where good  …see more

from £75 / night

£350 - £1600 / week

Book View

from £75 / night

(23) Excellent 

14

Cottage rental in Ventnor

Isle of Wight / Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Excellent Holiday home” We stayed here for 7 days and we can't speak highly enough about the accomodation. We have two young children and we also took my Dad who is 76. It catered for all of our needs and was very child proof so don't worry about ha  …see more

from £65 / night

£450 - £950 / week

Book View

from £65 / night

(5) Excellent 

11

Holiday chalet in Freshwater

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Excellent stay and location” A fabulous chalet with fantastic mod cons, a lovely welcome basket greeted us which was lovely. The chalet was great as was the location, the children enjoyed playing football on the field and climbing frames. The Isle of  …see more

from £39 / night

£275 - £595 / week

Enquire View

from £39 / night

(13) Excellent 

16

Apartment rental in Cowes

Cowes / West Cowes

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Great location, cosy and” I stayed here for a weekend and had a very comfortable and enjoyable stay. It is so continentally located by the ferry, shops, pubs and bars and it near to bus stops to see the rest of the Island. The apartment itself has e  …see more

from £100 / night

£350 - £450 / week

Book View

from £100 / night

(1) Excellent 

24

Holiday home in Cowes

Cowes / West Cowes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
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 bathro  …see more

from £200 / night

£1400 - £5500 / week

Book View

from £200 / night

(4) Excellent 

27

Holiday cottage rental

Freshwater / Freshwater Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Ask owner if suitable for children
Rabbit's Bothie is in the conservation area at the heart of the Tennyson Mile at Freshwater Bay. Sheltered on both sides by the soaring white cliffs of the Tennyson Heritage Coast, the bay has smugglers' caves, dramatic rocks and a sandy beach at low tide.<  …see more

from £72 / night

£360 - £560 / week

Book View

from £72 / night

(9) Very Good 

24

Cowes holiday home rental

Cowes / West Cowes

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Great location - beautiful house” Just returned from a weekend stay at Halyard house. The location was perfect being right in the centre of Cowes, very near to the shops and easy to find from the Ferry. Bedrooms were cosy and comfortable. Although t  …see more

from £100 / night

£700 / week

Book View

from £100 / night

(12) Excellent 

13

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Beautiful” Such a beautiful chalet with lots of space. Excellent location for children as they could just play out on the green. Lovely decor and a well equipped kitchen. Cannot find any faults at all, will hope to come back again next year..  …see more

from £36 / night

£250 - £485 / week

Book View

from £36 / night

(25) Excellent 

28

Holiday bungalow with golf nearby in Sandown

Isle of Wight / Sandown

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Home from home in a brilliant location!” Enjoyed a short winter break at Sudbury. Lovely bungalow, very well equipped and spotlessly clean. Central heating brilliant (Needed as break taken in December!) Highly recommend, in a great location, few minu  …see more

from £74 / night

£380 - £1010 / week

Enquire View

from £74 / night

(1) Excellent 

19

Holiday home in Cowes

Cowes / West Cowes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
The property is ideally base for those holidaying on the Island or for sailing crews who like quality accommodation & great for those coming to work on the island.<br />This property is part of the Cowes Holiday Homes portfolio where good service comes as stan  …see more

from £105 / night

£450 - £3000 / week

Book View

from £105 / night

(8) Excellent 

22

Cowes holiday home rental

Cowes / West Cowes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.18 km
  • Child friendly
“Christmas in Cowes” Great house. We were a group of 9 adults and 5 children all 2 and under. This house was the perfect place to spend christmas, plenty of room and a great kitchen with everything you need including a stocked pantry, which is always h  …see more

from £295 / night

£2065 / week

Enquire View

from £295 / night