Cycling holiday villas and apartments Isle of Wight

Close

View larger map

Also consider

Europe Holidays
431300 properties
United Kingdom Holidays
49822 properties
England Holidays
35393 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
Holiday homes Cowes
120 properties
Villas Ventnor
102 properties
Self catering accommodation Sandown
91 properties
Villas Shanklin
86 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

305 Holiday homes

Filters applied: Cycling holidays (305)

(5) Excellent 

12

Freshwater holiday bungalow rental

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Great value for money!” We enjoyed our stay at this bungalow, good outlook, could see coast of dorset, easy access to coastal path. Would recommend highly, friendly owners and good value for money!  …see more

from £33 / night

£233 - £555 / week

Book View

from £33 / night

16

Bembridge holiday townhouse rental

Bembridge / Bembridge Harbour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly
FOUR STAR, VISIT BRITAIN GRADE, SELF CATERING YACHTSMAN's Residence. 50 metres Yacht Club, Marina & Sandy Beach, Spacious & modernised Family home, Sleeps Six in comfort. Redecorated 2011.WELL APPOINTED, 3 BEDROOM 3 Floor HARBOUR HOME. Gro  …see more

from £99 / night

£440 - £695 / week

Enquire View

from £99 / night

(11) Excellent 

8

Holiday log cabin with golf nearby in Whippingham

Isle of Wight / Whippingham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Private garden
This timber built cabin makes the ideal cosy holiday retreat for two. It is well situated for exploring the whole island, and its many attractions. •The village of Whippingham is near to Queen Victoria's Osborne House, and the yachting centre of Cowes.•Pubs and res  …see more

from £75 / night

£350 - £450 / week

Book View

from £75 / night

(13) Excellent 

15

Holiday bungalow in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“Bungalow with fabulous views” We had a very enjoyable weeks stay in July 2016. The holiday home is spacious, very clean and comfortable. It had everything needed for the four of us except I do think it should be made clear that Gary only provides hand  …see more

from £95 / night

£495 - £995 / week

Book View

from £95 / 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

£300 - £550 / week

Book View

from £50 / night

(22) Excellent 

20

Holiday cottage in Freshwater

Freshwater / Moons Hill

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Little Moon 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 £36 / night

£250 - £780 / week

Book View

from £36 / night

(20) Excellent 

19

Cowes holiday cottage rental

Isle of Wight / Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Homely little cottage in the heart of Cowes” A beautiful little cottage right in the heart of Cowes, within easy walking distance to all shops, pubs and resteraunts. Beautifully decorated and very comfortable accommodation. The only drawback is the p  …see more

from £55 / night

£1575 / week

Book View

from £55 / night

(2) Average 

30

Home rental in Nettlestone with golf nearby

Isle of Wight / Nettlestone

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Fabulous accommodation for enjoying this lovely Island” Our party of 8 adults and 2 children had a fabulous stay at Nettlestone House; very spacious and very well presented and equipped. And the lovely garden was a bonus for both playtime and the BBQ.  …see more

from £199 / night

£995 - £1995 / week

Book View

from £199 / night

(17) Excellent 

22

Holiday cottage in Ryde

Isle of Wight / Ryde

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Everything you could dream of in a cottage with a sea view” We were completely impressed by how well appointed the property was - it is truly a home from home, having literally everything you could possibly need. The enclosed courtyard was real peace  …see more

from £58 / night

£300 - £800 / week

Book View

from £58 / night

(10) Excellent 

17

Gurnard holiday chalet rental

Isle of Wight / Gurnard

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Fantastic” Little Sailing is in a prime location on the edge of the Solent. It is well equipped and has everything needed for a perfect stay. The views from the huge windows are wonderful. There is a pub serving food within a very short walk.  …see more

from £75 / night

£525 - £1100 / week

Enquire View

from £75 / 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 attention re  …see more

from £250 / night

£1000 - £2000 / week

Book View

from £250 / 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 - £400 / week

Book View

from £100 / night

(2) Excellent 

30

Holiday home in Yarmouth

Isle of Wight / Yarmouth

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
'Boathouse' and 'River Cottage' properties Yarmouth.The most exclusive area on the Isle of Wight, based on the quiet waterside by the River Yar estuary. Breathtaking surrounding views from sunrise to sunset, over one of the loveliest wildlife sanctua  …see more

from £215 / night

£1500 / week

Enquire View

from £215 / night

(25) Very Good 

18

Holiday caravan/mobile home in Cowes

Isle of Wight / Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Pet friendly
SunnycottPeaceful, 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 £50 / night

£250 - £630 / week

Book View

from £50 / night

(3) Very Good 

8

Holiday cottage in Cowes

Cowes / West Cowes

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children age 5+
Fantastic 3 bedroom cottage (sleeps 8) in the heart of Cowes, minutes from the marina, shops, restaurants, bars and high speed ferry. Great for families or groups of friends. Please ask about RedFunnel ferry bookings. No pets or smokers please.  …see more

from £85 / night

£350 - £2000 / week

Book View

from £85 / night

(9) Excellent 

24

Holiday manor house in Wroxall

Isle of Wight / Wroxall

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
Property is well equipped, free WiFi throughout, comprehensive selection of Wii/ board games and you can even borrow a dog to walk...There is safe secure bike storage, drying room for outdoor gear and bike wash down facilities. A warm welcome awaits you!Cyclists, walker  …see more

from £350 / night

£1875 - £2800 / week

Book View

from £350 / night

12

Holiday cottage in Bembridge

Bembridge / Bembridge Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
These delightfull. newly built cottages are set in the heart of Bembridge village. When you walk in to the cottage, you get an immediate feeling that everything has been catered for.  …see more

from £50 / night

£395 - £695 / week

Book View

from £50 / night

(17) Excellent 

30

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Great holiday cottage” The Dairy was very well presented, extremely clean and very comfortable for our family with two young children. It is very well equipped with everything you need for a self catering holiday. We especially loved the hot tub, e  …see more

from £125 / night

£370 - £795 / week

Book View

from £125 / night

(5) Excellent 

25

Holiday log cabin accommodation

Isle of Wight / Whippingham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Fabulous little hideaway” We booked this for the weekend as a girls trip away and we wanted to stay somewhere different so this ticked all the boxes. I had emailed Fiona numerous times before our stay with various queries and she was always prompt to  …see more

from £150 / night

£550 - £1200 / week

Book View

from £150 / night

(2) Excellent 

10

Holiday lodge in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
This is a barrier free brand new build. Suitable for wheel chair users. Sleeps 5 to 6. All on one level with car parking and garden. The Lodge comprises of a Large wet room, en-suite double room and two twin rooms, Large kitchen / diner lounge. A veranda to the front  …see more

from £114 / night

£795 / week

Book View

from £114 / night

(16) Excellent 

13

Holiday bungalow in Newchurch

Sandown / Newchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Private garden
“Blissful break in Newchurch..” Our son treated us to a week's break on the Isle of Wight for our 25th Wedding Anniversary and what a fantastic surprise it was. The accommodation was second to none and the owners, Hilary and David, the perfect hosts. T  …see more

from £85 / night

£340 - £600 / week

Book View

from £85 / night

16

Cowes holiday guest house rental

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Suitable for children age 5+
  • Private garden
With its elevated position some of the rooms have views over Cowes & the Solent & it comes with its own parking space & good size garden.This property is part of the Cowes Holiday Homes portfolio where good service comes as standard  …see more

from £250 / night

£1200 - £5200 / week

Book View

from £250 / night

(4) Excellent 

11

Holiday home letting

Isle of Wight / Newport

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Private garden
This spacious and comfortable semi-detached house is situated in a quiet residential neighbourhood within walking distance of Newport town centre. Situated at the top of a hill, the home boasts stunning views of the island and a well-kept private garden.  …see more

from £50 / night

£325 - £1930 / week

Book View

from £50 / 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 picture  …see more

from £65 / night

£455 / week

Book View

from £65 / night

(2) Very Good 

39

Holiday cottage in Seaview

Isle of Wight / Seaview

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • 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 £116 / night

£499 - £1015 / week

Book View

from £116 / night

(38) Excellent 

19

Holiday cottage in Newchurch

Sandown / Newchurch

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
“A truly lovely property.” If you want a peaceful holiday property in superb location then Brew House is for you, Tastefully decorated, very clean, comfortable and well equipped. The owners had left a lovely welcome pack which included scrumptious home  …see more

from £85 / night

£500 - £750 / week

Enquire View

from £85 / night

(19) Excellent 

22

Holiday cottage in Ryde

Ryde / Appley

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Sleeps 4, cottage has 2 bedrooms, bathroom, kitchen, lounge, conservatory dining room, patio garden & bbq  …see more

from £85 / night

£595 - £950 / week

Book View

from £85 / 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

(11) Very Good 

16

Home rental in Cowes with golf nearby

Cowes / West Cowes

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“lovely little house, located very close to cowes” Had a great stay, well equipped and easy to find. Added bonus of wi-fi. Would stay again. Sweet house good for average size family. Clean and attractive property. Extra features of TV in each bedro  …see more

from £85 / night

£355 - £650 / week

Book View

from £85 / night

(10) Very Good 

10

Wootton Bridge holiday chalet rental

Isle of Wight / Wootton Bridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“Clean reasonably well equipped chalet good base for holiday.” Good communication leading up to stay, very good communication during stay. Very happy with chalet.Would be happy to use the accommodation again. Little bit out of the way but I guess that'  …see more

from £59 / night

£295 - £535 / week

Book View

from £59 / night

(2) Very Good 

16

Holiday bungalow with shared pool in Gurnard

Isle of Wight / Gurnard

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Gurnard bungalow a must” This was our first time in the small property at the holiday camp. It is in a fairly secluded position. Our first impression as we walked through the door was the cleanliness. The lounge/diner with small kitchen area was well  …see more

from £45 / night

£205 - £420 / week

Book View

from £45 / night

(16) Excellent 

24

Holiday cottage in Shanklin

Shanklin / Old Village

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Perfect in every way” I stayed at the Lodge with my 90 year old Aunt. She has some mobility problems so the search for accommodation was very specific. Our needs were met perfectly. She had no trouble moving around the house or getting to and from fr  …see more

from £52 / night

£360 - £700 / week

Book View

from £52 / night

(3) Excellent 

23

Cowes holiday home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Private garden
“Superb!!!” We stayed at the lovely Sun Hill in August for a couple of nights and as a family we were so happy. The house is immaculately clean and is equipped with everything that you could need. The owners kept us well informed and were so helpful  …see more

from £150 / night

£900 / week

Book View

from £150 / night

24

Newchurch holiday cottage rental

Sandown / Newchurch

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Characterful cottage on the Garlic Farm on the Isle of Wight. Perfectly placed for walking, cycling and family holidays. Guests enjoy a 10% discount in our renowned restaurant, use of tennis court and football pitch. 10 minutes from the beach by car.Peacocks, red squirr  …see more

from £175 / night

£825 - £1925 / week

Book View

from £175 / night

(1) Excellent 

19

Holiday home in Shanklin

Isle of Wight / Shanklin

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Great location for exploring the Island, peacefull with lovely views, countryside from the rear and sea glimpses from the front of the house. Lovely walks into Shanklin Town via the railway track or through the farm, plus America Woods seconds away.Balconies accessed fr  …see more

from £395 / night

£2500 - £2750 / week

Book View

from £395 / 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 relaxation.  …see more

from £49 / night

£340 - £625 / week

Enquire View

from £49 / night

(15) Excellent 

20

Holiday home with golf nearby in Sandown

Isle of Wight / Sandown

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
2 bedroom new build sleeps up to 5 sandown off road parking 5 seater corner sofa downstairs toilet and upstairs bathroom isle of wight holiday let close to beach and train safe decking wifi enclosed garden summer sun  …see more

from £36 / night

£250 - £745 / week

Book View

from £36 / night

(17) Excellent 

20

Studio rental in Ventnor with golf nearby

Isle of Wight / Ventnor

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
“Perfect - Fresh and light an enjoyable holiday” Excellent location, with stunning views. Apartment well looked after, clean and tidy. A delightful holiday with all the necessary facilities. 5 Minute walk to the seaside. 5 Stars  …see more

from £80 / night

£400 - £675 / week

Enquire View

from £80 / night

(5) Excellent 

15

Apartment rental in Knighton, Isle of Wight

Isle of Wight / Knighton, Isle of Wight

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
An individual home just brimming with character & quirky charm with exposed timbers in all the rooms. Situated in a hamlet within an area designated as an 'Area of Outstanding Natural Beauty'. Explore the local footpaths or just enjoy the country views from your balcony  …see more

from £39 / night

£275 - £395 / week

Enquire View

from £39 / night

(11) Excellent 

23

Holiday chalet in Ventnor

Isle of Wight / Ventnor

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 4 km
“Exactly as it says Great Escape” Had a fantastic week at the Great Escape. Lovely and clean with everything needed for a comfortable stay. Beautiful Island would recommend to anyone who  …see more

from £40 / night

£240 / week

Book View

from £40 / night