50 Best Isle of Wight Cottages on Holiday Lettings - Holiday cottages

Close

View larger map

Also consider

Enter dates for more accurate prices

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

1,745 Vacation rentals

(12) Very Good 

Certificate of Excellence

23

Vacation chalet in Niton

Isle of Wight / Niton

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 5 mi
  • Private garden
A contemporary hillside chalet in the southernmost tip of the Isle of Wight, set in beautiful gardens, with views over treetops towards the sea, and adjacent to the coastal path. Spend a relaxing week at Pebbles, a thoughtfully equipped compact terraced chalet, tucked a …see more

Certificate of Excellence

from $59 / night

$362 - $537 / week

Book View

Responds fast!
avg. 1 hour 36 minutes

from $59 / night

(30) Excellent 

43

Vacation 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 mi
  • Child friendly
This 3 double bedroom house has excellent town sea and downs views and sleeps 7 people [ plus sofa bed]. The accommodation comprises of 3 double bedrooms [ 1 double bed, 2 single, 3 single beds], a bathroom with separate shower, kitchen, lounge and conservatory that l …see more

from $195 / night

$584 - $1,291 / week

Inquire View

from $195 / night

(54) Excellent 

Certificate of Excellence

15

St Lawrence, Ventnor Vacation apartment rental

Ventnor / St Lawrence, Ventnor

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Set in the Undercliff area of Outstanding Natural Beauty, Woodcliffe stands in peaceful secluded gardens. The apartment faces south across the Undercliff offering superb views of the English Channel. Steephill Cove is nearby, while Ventnor offers the usual seaside attr …see more

Certificate of Excellence

from $78 / night

$291 - $521 / week

Book View

from $78 / night

(10) Very Good 

23

Vacation apartment in Ventnor

Isle of Wight / Ventnor

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Flat 3, Elizabeth House, Hambrough Road is located in the town centre just a couple of minutes' stroll down the cascade to the beach. Situated opposite the Winter Gardens, it is a great location to explore the delights of Ventnor. Many excellent pubs and restaurants a …see more

from $65 / night

$322 - $1,024 / week

Book View

Responds fast!
avg. 3 hours 4 minutes

from $65 / night

(16) Very Good 

15

Apartment rental in Totland

Totland Bay / Totland Bay

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
This luxurious spacious apartment is literally a stone's throw from the sea. It is almost like being on board a luxury cruise liner with stunning views of the unspoilt pretty Totland Bay. There are 2 bathrooms, large lounge/ dining room, king size, double and a twin r …see more

from $252 / night

$938 - $1,649 / week

Book View

Responds fast!
avg. 1 hour 12 minutes

from $252 / night

(37) Excellent 

18

Sandown Vacation 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 mi
  • Child friendly
Rosie's Place is a spacious and airy split level apartment within walking distance of the beach and High Street with 2 private off road car spaces. When it's not let out Rosie's Place is our holiday home and so we have furnished it and equipped it to the highest stand …see more

from $91 / night

$451 - $1,160 / week

Book View

Responds fast!
avg. 58 minutes

from $91 / night

(22) Excellent 

Certificate of Excellence

20

Apartment rental in Bembridge

Bembridge / St Helens, Bembridge

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Uniquely positioned on a quiet residential street which leads from St Helen's Village Green via Mill Lane to the sea. From the bottom of the lane turn left at the Old Mill and walk across the Duver to St Helens beach and sample the menu at Baywatch cafe; or turn right …see more

Certificate of Excellence

from $67 / night

$316 - $619 / week

Book View

Responds fast!
avg. 2 hours 52 minutes

from $67 / night

(21) Excellent 

10

Vacation 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
Lane End Cottage is a beautiful detached family holiday home. The rooms are light and spacious. It has a large garden perfect for relaxing and barbecues. There is plenty of room for parking and boats etc. It is only 500 yards from the lovely Lane End Beach, with sand, r …see more

from $92 / night

$644 / week

Inquire View

from $92 / night

(28) Excellent 

33

Vacation home with golf nearby in Seaview

Isle of Wight / Seaview

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
The Lobster Pot is a wonderful, newly renovated family friendly chalet cottage with sea views, in Seaview. Just a short walk to several renowned and award winning beaches such as Priory Bay, Seagrove Bay, Seaview Beach, The Duver and Bembridge Beach. The beaches are pre …see more

from $136 / night

$899 - $1,552 / week

Book View

from $136 / night

(58) Excellent 

37

Vacation 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
The Mill House is a beautiful detached Georgian farmhouse situated in a quiet country lane. It has spectacular views across fields to the downs and is a ten-minute walk from the sea at Brighstone Bay. Across the lane is a pleasant ten-minute walk beside the stream, whi …see more

from $463 / night

$3,994 - $4,618 / week

Book View

Responds fast!
avg. 1 hour 16 minutes

from $463 / night

19

Vacation apartment rental

Isle of Wight / Cowes

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
This light and airy second floor apartment is ideally situated to enjoy the popular town of Cowes and provides a wonderful spot to unwind and take in the superb views of the passing sailing activity. Decorated in a 'seaside' theme, the accommodation includes a separate …see more

from $251 / night

$655 - $1,307 / week

Inquire View

from $251 / night

(27) Excellent 

31

Vacation cottage in Wootton

Isle of Wight / Wootton

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Kipper Cottage is highly rated . The cottage is comfortable and on one level accommodation for four people. There is an open-plan living room and kitchen, which are bright and spacious, tastefully furnished and have lovely views of the creek. The Cottage benefits fro …see more

from $181 / night

$851 - $1,830 / week

Book View

from $181 / night

8

Apartment rental in Ryde

Isle of Wight / Ryde

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Car not necessary
The perfectly located apartment for leisure or work. Directly opposite pristine beaches and close to transport links: hovercraft and catermaran, this apartment has all you need for a short or long let. Stunning views of the ever moving and busy Solent will keep you ent …see more

from $98 / night

$619 - $644 / week

Book View

Responds fast!
avg. 44 minutes

from $98 / night

(4) Excellent 

Certificate of Excellence

28

Shorwell Vacation cottage rental

Isle of Wight / Shorwell

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 4 mi
  • Child friendly
  • Private garden
Quality and style flows through this stunning cottage which has been lovingly renovated to a high standard and is centrally located in the ancient rural village of Shorwell, on the west coast of the Isle of Wight. A landmark house within the village, the cottage was bui …see more

Certificate of Excellence

from $163 / night

$1,008 - $1,779 / week

Book View

Responds fast!
avg. 52 minutes

from $163 / night

8

Cottage rental in Calbourne

Isle of Wight / Calbourne

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
This property is located in one of the Isle of Wight's best-loved beauty spots,iconic Winkle Street in the village of Calbourne. A stream runs directly outside the cottage,which is a lovely spot to relax and enjoy a picnic,or perhaps walk along to nearby Calbourne Wa …see more

from $68 / night

$476 - $1,372 / week

Inquire View

from $68 / night

(19) Very Good 

29

Barn rental in Bonchurch

Ventnor / Bonchurch

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Strawberries, our lovingly restored two bedroom cottage is based on a former strawberry farm set on the southern slopes of St Boniface Down. The cottage is cascading with seaside charm whilst featuring a modern open plan interior and huge south facing windows. The cen …see more

from $182 / night

$1,103 - $1,803 / week

Book View

Responds fast!
avg. 1 hour 50 minutes

from $182 / night

(14) Very Good 

Certificate of Excellence

8

Vacation caravan/mobile home in St Helens

Isle of Wight / St Helens

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
Privately owned static caravan on St Helens Holiday Park. Comfortable accommodation sleeps 6/8 people. 3 bedrooms (1 double bedroom, 2 twin bedrooms plus double pull out bed in lounge. Fully equipped with central heating, double glazing, electric shower, Freeview TV. Th …see more

Certificate of Excellence

from $76 / night

$532 / week

Book View

Responds fast!
avg. 34 minutes

from $76 / night

(3) Very Good 

14

Vacation apartment in Ventnor

Isle of Wight / Ventnor

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Set in the Undercliff area of Outstanding Natural Beauty, Seaview Holiday Apartment stands in peaceful secluded terraced gardens. The apartment faces south across the Undercliff offering superb views of the English Channel. Steephill Cove & Woody Bay are only a ten min …see more

from $85 / night

$344 - $934 / week

Book View

from $85 / night

(4) Excellent 

19

Vacation cottage in Seaview

Isle of Wight / Seaview

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
"The perfect self-catering holidays in Seaview on the Isle of Wight" Seaview Holidays offer luxury self-catering accommodation in a stunning, secluded location overlooking the beautiful Hersey Nature Reserve on the Isle of Wight..... We offer 2, 3 and 4 bedroom holida …see more

from $188 / night

$1,313 / week

Book View

from $188 / night

15

Newchurch Vacation cottage rental

Sandown / Newchurch

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child friendly
  • Private garden
Little Mersley Farmhouse is located on the Garlic Farm nestled at the foot of Mersley Down in the Arreton Valley, an area of outstanding natural beauty. Following a sensitive renovation, it is now available as our largest most well appointed cottage. The property sleeps …see more

from $246 / night

$1,132 - $2,851 / week

Book View

from $246 / night

(13) Excellent 

21

Vacation apartment in Cowes

Isle of Wight / Cowes

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 1 mi
  • Suitable for children age 5+
  • Car not necessary
The apartment is in quite a new development , with spectacular and panoramic views over the Solent and River Medina. It overlooks a busy marina with its many yachts. It is very close to the quaint and bustling centre of Cowes, with plenty of individual shops, restaurant …see more

from $129 / night

$509 - $2,570 / week

Book View

Responds fast!
avg. 2 hours 54 minutes

from $129 / night

21

Seaview Vacation chalet rental

Isle of Wight / Seaview

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
(Preferential ferry prices for our guests: please ask for details) Our three Salterns Beach Chalets in this small development have been modernised to Premier standard to provide most comfortable accommodation for your seaside holiday. They are superbly situated with Ya …see more

from $84 / night

$589 / week

Book View

from $84 / night

(33) Very Good 

Certificate of Excellence

24

Home rental in Ventnor Bay with golf nearby

Ventnor / Ventnor Bay

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Child friendly
Our Victorian cottage has been decorated and furnished to a high standard in a sympathetic style in keeping with its period. It's upside down layout maximises the living space and town and ocean view - probably one of the best sea views on the island! The cottage front …see more

Certificate of Excellence

from $111 / night

$513 - $902 / week

Book View

Responds fast!
avg. 1 hour 13 minutes

from $111 / night

(71) Excellent 

Certificate of Excellence

21

Ventnor Vacation apartment rental

Isle of Wight / Ventnor

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Child friendly
Salty Holidays is the perfect spot to relax and enjoy the fantastic sea views over Ventnor bay. Facing south on a quiet private road, it is a fantastic location, only 50 meters from the beach and walking distance to the shops and restaurants. The apartment is comfortabl …see more

Certificate of Excellence

from $97 / night

$516 - $1,095 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from $97 / night

(18) Excellent 

Certificate of Excellence

24

Sandown Vacation apartment rental

Isle of Wight / Sandown

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Apartment three , completely refurbished in 2013 offers modern and spotlessly clean accommodation, comprising shower room, kitchen diner and living room. The bedroom can either be prepared for your arrival as a twin or as a six foot wide king size with french doors lea …see more

Certificate of Excellence

from $39 / night

$272 / week

Book View

Responds fast!
avg. 2 hours 36 minutes

from $39 / night

(35) Excellent 

Certificate of Excellence

29

Apartment rental in Shanklin

Isle of Wight / Shanklin

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Seaside View holiday apartment ideally situated a stones throw from the beach. From the minute you arrive you can sit and relax. Watching the sea whatever the season, it is always transfixing, either from the comfort of the open plan kitchen, lounge, diner or from your …see more

Certificate of Excellence

from $111 / night

$490 - $773 / week

Book View

from $111 / night

(30) Very Good 

12

Seaview Vacation cottage rental

Isle of Wight / Seaview

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
"The perfect self-catering holidays in Seaview on the Isle of Wight" Seaview Holidays offer luxury self-catering accommodation in a stunning, secluded location overlooking the beautiful Hersey Nature Reserve on the Isle of Wight..... We offer 2, 3 and 4 bedroom holida …see more

from $148 / night

$1,037 / week

Book View

from $148 / night

12

Vacation home rental

Isle of Wight / Ventnor

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Private garden
Sea view sea view sea view is what my house offers together with large enclosed terraced garden to enjoy that view on slightly different levels which are all lawned. Watch the sunrise from your pillow, the moonlight shimmering on the sea or the midday sun reflecting o …see more

from $357 / night

$1,557 / week

Book View

from $357 / night

(25) Excellent 

Certificate of Excellence

51

Vacation manor house in Wroxall

Isle of Wight / Wroxall

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 5 mi
  • Child friendly
Cleveland's Country House offers some of the best quality self-catering accommodation on the island. All accommodation is tastefully decorated and extremely well equipped to create a relaxed atmosphere, a true home from home experience. The grand entrance hall of the …see more

Certificate of Excellence

from $324 / night

$2,263 - $3,814 / week

Book View

Responds fast!
avg. 14 minutes

from $324 / night

(31) Excellent 

Certificate of Excellence

19

Vacation 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 mi
  • Child friendly
The house is perfect for: • a family holiday - just 2 minutes walk from the beach, private parking, pubs & restaurants & cafés within 5 minutes walking distance. • sunbathing in the garden while enjoying the sight and sound of the sea. • wonderful coastal walks, botani …see more

Certificate of Excellence

from $222 / night

$636 - $1,278 / week

Book View

from $222 / night

(11) Very Good 

16

Cowes Vacation townhouse rental

Cowes / West Cowes

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Lovely relaxing townhouse overlooking Cowes Marina with fabulous views of the Solent beyond, situated right in the heart of Cowes. Three bedrooms, two bathrooms, spacious sitting room and kitchen with huge window over marina. Flat screen freeview TV's, Wifi throughout, …see more

from $168 / night

$518 - $1,229 / week

Book View

Responds fast!
avg. 3 hours 8 minutes

from $168 / night

(9) Excellent 

35

Vacation cottage in Bonchurch

Ventnor / Bonchurch

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Stable Cottage is located at the end of a quiet private lane to the east of the timeless village of Bonchurch. The cottage is a perfect retreat for a family holiday with Monks Bay a two minutes wander down the coastal path. The cottage was renovated in 2013. Through c …see more

from $207 / night

$970 - $2,444 / week

Book View

Responds fast!
avg. 1 hour 50 minutes

from $207 / night

(20) Excellent 

Certificate of Excellence

13

Vacation apartment in Brading

Isle of Wight / Brading

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 2 mi
  • Ask about children
  • Car not necessary
Our first floor holiday apartment has 2 rooms (bedroom with en-suite and kitchen/diner). It has its own private entrance, car parking and garden space. For those without a car it is an excellent base for both walking and cycling - arrangements can be made to pick up cli …see more

Certificate of Excellence

from $72 / night

$500 / week

Book View

from $72 / night

(10) Very Good 

14

Vacation home in Totland

Isle of Wight / Totland Bay

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Roselands on the Isle of Wight:This lovely, clean, new build three bedroom Isle of Wight holiday home is located in a private cul-de sac within the little village of Totland, on the west of the island. The house comprises:- Large living room (TV DVD player) with double …see more

from $64 / night

$347 - $1,082 / week

Book View

from $64 / night

16

Vacation apartment in Shanklin

Isle of Wight / Shanklin

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
Memorable holidays on the island are often created by a visit to Shanklin with her great beaches and well known esplanade - and this two bedroom apartment is perfect for those who want to have first class sea views, be yards from a sandy beach and have good cafes and re …see more

from $72 / night

$485 - $821 / week

Book View

from $72 / night

(4) Excellent 

14

Home rental in Freshwater with golf nearby

Freshwater / Freshwater Bay

6 15 7 nights min

  • 6 bedrooms
  • sleeps 15
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Gate House is situated in the heart of Freshwater Bay, an area of outstanding natural beauty in the west Wight. The house not only overlooks the sea but is also located at the foot of Tennyson Down and the Heritage Coastal Trail. It backs onto Afton Marsh and …see more

from $368 / night

$2,570 / week

Book View

Responds fast!
avg. 46 minutes

from $368 / night

(3) Excellent 

39

East Cowes Vacation home rental

Isle of Wight / East Cowes

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Car not necessary
Award winning Old School House conversion with river views on the banks of the River Medina, the house offers parking for ONE vehicle only directly outside the house. Pet friendly. Beautifully decorated, exposed brickwork, vaulted ceiling, tall sash windows. Excellent …see more

from $143 / night

$908 - $2,595 / week

Book View

Responds fast!
avg. 7 minutes

from $143 / night

(12) Excellent 

Certificate of Excellence

16

Vacation chalet with golf nearby in Yaverland

Sandown / Yaverland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Car not necessary
Seascape is a brick -built, double-glazed chalet that is new to the rental market for 2018 and no expense has been spared to make this chalet among the best you will find. The chalet is situated in a peaceful location with fantastic sea views across Sandown Bay, and is …see more

Certificate of Excellence

from $59 / night

$194 - $711 / week

Book View

Responds fast!
avg. 16 minutes

from $59 / night

(50) Excellent 

Certificate of Excellence

33

Vacation home in Yarmouth

Isle of Wight / Yarmouth

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Looking to spend time with friends and family this New Year? We have have availability. Minimum stay 3 nights Please check out w' threegableswestwight for all my latest offers **Book a short break 3rd November -14th December and get free ferry from …see more

Certificate of Excellence

from $245 / night

$1,128 - $2,480 / week

Book View

Responds fast!
avg. 2 hours 27 minutes

from $245 / night

(3) Excellent 

20

Ventnor Vacation apartment accommodation

Isle of Wight / Ventnor

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Pet friendly
The flat is situated on the ground floor of Esplanade House which is a detached Victorian property. It is approximately 35 metres from the sand/shingle beach and close to many cafes, retaurants and nice pubs. It is a short walk from the town centre where there are man …see more

from $84 / night

$1,160 - $1,289 / week

Book View

Responds fast!
avg. 2 hours 33 minutes

from $84 / night