Walking holiday villas and apartments Isle of Wight | Holiday Lettings

Close

View larger map

Also consider

Europe Holidays
452666 properties
United Kingdom Holidays
57916 properties
England Holidays
42277 properties
Isle of Wight Holidays
993 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
149 properties
Holiday homes Cowes
131 properties
Villas Shanklin
112 properties
Self catering accommodation Sandown
108 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

399 Holiday homes

Filters applied: Walking holidays

(16) Excellent 

22

St Helens holiday lodge rental

Isle of Wight / St Helens

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“beautiful property nice location” As described it was a perfect location with sea view .Clean park .well sited near complex. The lodge was very nice well equipped. Only disappointment we didn't book long enough!
…see more

from £90 / night

£695 - £2045 / week

Book View

Responds fast!
avg. 1 hour 16 minutes

from £90 / night

(7) Very Good 

35

Holiday cottage in Bonchurch

Ventnor / Bonchurch

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Details to be aware of” Stable Cottage is in a lovely location and is well presented, clean and modern but has a few surprising omissions such as a microwave, tumble dryer, iron and ironing board although some of these are available in a shared laundr
…see more

from £150 / night

£900 - £1890 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £150 / night

(22) Excellent 

35

Holiday cottage in Cowes

Isle of Wight / Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
“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.
…see more

from £145 / night

£475 - £750 / week

Book View

Responds fast!
avg. 2 hours 24 minutes

from £145 / night

Featured properties

(4) Excellent 

14

Cowes holiday home rental

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“An excellent house for a family Christmas, and a great location for summer visitors.” Twelve of us spent our family Christmas in Alban house and it was perfect. The house is lovely, great location, spotlessly clean, warm and comfortable. Carol could
…see more

from £500 / night

£2000 - £3500 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from £500 / night

(10) Excellent 

28

Holiday home in Ventnor

Isle of Wight / Ventnor

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“Lovely stay in a brilliant house in a great location.” Large, bright house with plenty of space for our group to have a very relaxing weekend. On entry house found to be very clean & tidy, rooms nicely decorated & furnished. Good range of Bedroom opti
…see more

from £155 / night

£620 - £1440 / week

Book View

Responds fast!
avg. 56 minutes

from £155 / night

(18) Excellent 

36

Holiday cottage rental

Ventnor / Bonchurch

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Mr” Well equipped. Hidden away. Lawn shaded from weather from all directions except south. Cosy. Beautiful place in a beautiful place.
…see more

from £90 / night

£450 - £1960 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £90 / night

(17) Excellent 

20

Holiday cottage in Bonchurch

Ventnor / Bonchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Excellent facilities, in a unique setting” The facilities were excellent and the accommodation very close to the sea. There were two very good restaurants close by which had been recommended by the owner.
…see more

from £110 / night

£550 - £790 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £110 / night

(29) Excellent 

45

Holiday cottage rental

Ventnor / St Lawrence, Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Beautiful home in peaceful setting” Breakers Sound is a stunning house in lovely gardens with sea views. It contained everything we needed for a relaxing week. The location is very peaceful without being isolated, and lovely walks straight from the ho
…see more

from £150 / night

£525 - £1345 / week

Book View

from £150 / night

(24) Excellent 

43

Holiday home in Ventnor

Isle of Wight / Ventnor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“great location. Great views.” The Perch provided myself, husband small child and mother in law with a comfortable and homely stay. The beds were comfortable and the rooms airy. The kitchen provided everything we needed and the garden although small h
…see more

from £150 / night

£500 - £895 / week

Enquire View

from £150 / night

(19) Excellent 

23

Seaview holiday home rental

Isle of Wight / Seaview

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“coastal seclusion” I stayed at Lebrel Lodge with friends for a winter weekend - I think there were about seven of us, mostly couples. It was extremely well appointed and immaculately clean. The weekend was a typical English winter one and so we someti
…see more

from £150 / night

£1045 - £1495 / week

Book View

Responds fast!
avg. 2 hours 14 minutes

from £150 / night

(28) Excellent 

26

Holiday caravan/mobile home with shared pool in Thorness Bay

Cowes / Thorness Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Ideal location for family break” Well equipped and comfortable caravan, nice location with views of the solent. Central site location with good vehicle access. Close to shop, bar, pool, and entertainment. We were a group of five with a 90 and 87 year
…see more

from £65 / night

£375 - £770 / week

Book View

Responds fast!
avg. 1 hour 11 minutes

from £65 / night

(20) Excellent 

14

Holiday cottage in Ventnor

Isle of Wight / Ventnor

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“An absolutely beautiful cottage with fabulous sea view” We arrived on the day of the big snow so had the added benefit for the first day of a winters view. The cottage was cosy and warm and so beautifully decorated that we didn't feel the need to go o
…see more

from £70 / night

£490 - £940 / week

Book View

from £70 / night

(7) Excellent 

30

Ventnor holiday home rental

Isle of Wight / Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Delighted” What a great find. Originally I had booked to stay at Seawinds in Gurnard but received a call 3 weeks before our holiday to say the owner had double booked. I chose plum cottage at short notice; I wouldn't usually have picked it as I lik
…see more

from £110 / night

£700 - £1090 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £110 / night

(22) Excellent 

24

Apartment rental in Shanklin

Shanklin / Old Village

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.9 km
  • Ask owner if suitable for children
“The Courtyard...............Fantastic place!” Just spent a few glorious days at The Courtyard, Shanklin, IOW. Richard and Miriam were great hosts, providing lovely extras, tea, coffee, juice etc and also a wonderful and tasty homemade sponge cake....
…see more

from £47 / night

£325 - £516 / week

Book View

Responds fast!
avg. 24 minutes

from £47 / night

(28) Excellent 

17

Holiday apartment with golf nearby in Alverstone Garden Village

Sandown / Alverstone Garden Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“A fab holiday in a great place” The apartment was very well maintained and the welcome basket is a nice touch. The beach and pier are within easy reach, only a short walk to both which makes the apartments location ideal. The beds are very comfy and t
…see more

from £53 / night

£289 - £705 / week

Book View

Responds fast!
avg. 1 hour 0 minutes

from £53 / night

(19) Very Good 

24

Holiday log cabin in Cowes

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“A peaceful total retreat from the pace of life.” If your looking for a total retreat this is it. Off the beaten tract, quiet & peaceful. Amazing views over the Solent. If you want to venture out it's location is good for many of the island's attracti
…see more

from £65 / night

£400 - £670 / week

Book View

from £65 / night

(16) Excellent 

10

Holiday cottage accommodation

Isle of Wight / Bembridge

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Lovely cottage in a wonderful location” I cannot recommend this beautiful cottage enough. Booking was so simple with Peter always just an email away if I had any questions. The cottage had so much room and such a beautiful garden to enjoy the sunshine
…see more

from £72 / night

£500 - £900 / week

Enquire View

from £72 / night

(11) Excellent 

18

Holiday chalet in Ventnor Bay

Ventnor / Ventnor Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Pet friendly

from £102 / night

£416 - £542 / week

Book View

Responds fast!
avg. 3 hours 8 minutes

from £102 / night

(9) Excellent 

Certificate of Excellence

20

Holiday home rental

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“Home from Home - by the Seaside!” The cottage was warm, cosy and had some lovely homely touches that immediately made us feel at home. The location was perfect - under 5 minutes from the Red Funnel terminal, a stone's throw from the marina and a short
…see more

Certificate of Excellence

from £80 / night

£625 - £1120 / week

Book View

Responds fast!
avg. 1 hour 9 minutes

from £80 / night

(6) 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

from £50 / night

£325 - £2080 / week

Book View

from £50 / night

(13) Excellent 

23

Holiday chalet in Freshwater

Isle of Wight / Freshwater

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Freshwater IOW holiday” The Summerhouse in Freshwater was comfy, clean and well equipped with a beautiful sea view. Had a lovely week exploring IOW and if weather had been better would have loved exploring the nearby beach. Our 3 year old granddaught
…see more

from £36 / night

£250 - £450 / week

Book View

from £36 / night

18

Holiday apartment in Ventnor

Isle of Wight / Ventnor

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £75 / night

£325 - £750 / week

Book View

from £75 / 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

from £55 / night

£385 / week

Book View

Responds fast!
avg. 2 hours 55 minutes

from £55 / night

(20) Excellent 

24

Holiday cottage in Wootton Bridge

Isle of Wight / Wootton Bridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“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.
…see more

from £130 / night

£695 - £1395 / week

Book View

from £130 / night

(42) Excellent 

27

Holiday home in Brighstone

Isle of Wight / Brighstone

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“We couldn't have found a better property on the island” We were expecting a welcome pack based on the reviews we read before our arrival but it exceeded our expectations - the hot cross buns were great and the selection of Easter chocolate was a lovel
…see more

from £350 / night

£2667 - £3585 / week

Book View

Responds fast!
avg. 2 hours 3 minutes

from £350 / night

(10) Excellent 

Certificate of Excellence

14

Holiday apartment in Ventnor Bay

Ventnor / Ventnor Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Brilliant apartment,brilliant location,brilliant views” Exactly what it says on'"the tin".Easy to book ,with confidence and all the support you would need-regular updates and support of "the lovely Lisa" on the island. Spacious and extremely well pre
…see more

Certificate of Excellence

from £145 / night

£750 - £1163 / week

Book View

Responds fast!
avg. 41 minutes

from £145 / night

(1) Excellent 

10

Wroxall holiday home rental

Isle of Wight / Wroxall

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Private garden

from £50 / night

£250 - £475 / week

Enquire View

from £50 / night

(32) Excellent 

33

Holiday cottage in Whitwell

Ventnor / Whitwell

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“A wonderful family home in a beautiful rural location, dawn was spectacular” We spent a long weekend here with friends. even in November there are so many places to explore and excellent pubs to eat at. The garden in fantastic and would be wonderful f
…see more

from £150 / night

£550 - £1350 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £150 / night

(3) Very Good 

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

Responds fast!
avg. 1 hour 4 minutes

from £199 / night

(14) Very Good 

23

Townhouse accommodation in Yarmouth

Yarmouth / Norton, Isle of Wight

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“This place is fantastic!” We have just spent a week at Hurst View on the Isle Of Wight, it is in an ideal spot. The ferry terminal is only 5-10mins down the road, whichwas a great stress free start to the week. The house itself is very spacious with r
…see more

from £59 / night

£410 - £895 / week

Enquire View

from £59 / 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

from £93 / night

£650 - £780 / week

Book View

from £93 / night

(95) Excellent 

25

Holiday cottage in Niton Undercliff

Ventnor / Niton Undercliff

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
“Perfect” The cottage is beautiful and equipped with everything you could possibly need for a perfect family holiday, but what made it special was the extra thoughtful touches we would never have expected, like welcome gifts for us and for the children
…see more

from £125 / night

£595 - £1550 / week

Book View

Responds fast!
avg. 59 minutes

from £125 / night

(1) Excellent 

24

Shanklin holiday home rental

Shanklin / Old Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Car not necessary

from £50 / night

£335 - £595 / week

Book View

from £50 / night

(6) Excellent 

10

Shanklin holiday apartment let

Isle of Wight / Shanklin

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Lovely luxury apartment” Lovely luxury apartment - we stayed with family and young children. Great facilities, ensuite bathrooms, lots of room. Very clean and all very new, great position for sea and town. No noise. Parking was a bit odd but sufficien
…see more

from £140 / night

£695 - £1850 / week

Book View

from £140 / night

(14) Excellent 

18

Sandown holiday apartment rental

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Stay at Rosie's place” Our stay at Rosie's place was excellent. It was very clean and all the amenities we could have wanted. It is also close to the beach and centre of town. Would recommend this accommodation.
…see more

from £70 / night

£350 - £850 / week

Book View

Responds fast!
avg. 43 minutes

from £70 / night

(47) Very Good 

21

Yarmouth holiday cottage rental

Yarmouth / Fort Victoria

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Cosy , well equipped cottage overlooking the Solent.” Lovely well equipped cottage. Very comfortable beds. Great view across the solent. Nice grassy area out front for kids to play on, and to watch rabbits running around. This is a great location wi
…see more

from £75 / night

£395 - £1245 / week

Book View

Responds fast!
avg. 1 hour 8 minutes

from £75 / night

(20) Excellent 

Certificate of Excellence

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
“Very comfortable relaxing holiday” Enjoyed our stay in this very clean comfortable cottage very convenient for shops,restuarents & exploring the island..we didn't take our car & found it easy to get around from here. The furnishings are very nice & al
…see more

Certificate of Excellence

from £58 / night

£300 - £800 / week

Book View

Responds fast!
avg. 2 hours 9 minutes

from £58 / night

(1) Excellent 

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
“Excellent” Lovely caravan, on a great site, close to all amenities and a nice beach is accessible from the site.
…see more

from £50 / night

£700 - £800 / week

Book View

Responds fast!
avg. 2 hours 31 minutes

from £50 / night

(27) Excellent 

25

Gurnard holiday home rental

Isle of Wight / Gurnard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Perfect house, perfect location!” We spent a week in this gorgeous house celebrating Mum's 80th. We loved everything! From the fresh flowers, home made cake & scones, clotted cream, lemon curd, sausages we found waiting for us to the amazing water v
…see more

from £150 / night

£1000 - £1750 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from £150 / night

(8) Excellent 

12

Holiday apartment in Ventnor

Isle of Wight / Ventnor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Pet friendly

from £40 / night

£260 - £370 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from £40 / night