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

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Beach rentals Ventnor
201 properties
Villas Shanklin
141 properties
Holiday rentals Cowes
132 properties
Apartments Sandown
121 properties
Self catering Bembridge
65 properties
Vacation rentals Freshwater
60 properties
Yarmouth
51 properties
Ryde
51 properties
Wootton
28 properties
Seaview
28 properties
Totland Bay
23 properties
Newport
22 properties
Brighstone
19 properties
St Helens
16 properties
Gurnard
15 properties
Niton
15 properties
Brading
13 properties
Chale
13 properties
Shorwell
12 properties
East Cowes
12 properties

Isle of Wight

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1,788 Vacation rentals

(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 $91 / night

$636 - $1,145 / week

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from $91 / night

(22) Excellent 

20

Vacation cottage in Bonchurch

Ventnor / Bonchurch

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
The Hideaway exhibits all the charm of a traditional rural cottage whilst featuring a stylish contemporary interior. The project, completed in spring 2010 and redecorated in 2015 was a perfect opportunity to create a charming coastal retreat. Open plan cottage Upstair …see more

from $140 / night

$878 - $1,005 / week

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avg. 2 hours 35 minutes

from $140 / night

(2) Excellent 

19

Vacation apartment in Shanklin

Isle of Wight / Shanklin

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach is …see more

from $107 / night

$935 - $1,602 / week

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avg. 3 hours 36 minutes

from $107 / night

(6) Excellent 

Certificate of Excellence

11

Vacation home in Seaview

Isle of Wight / Seaview

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Montrose is a carefully renovated detached family home. Within the village of Seaview close to the local restaurants and shops and a short walk to the beach and Yacht club. With lots of the character retained it has the modern facilities for all the generations of the …see more

Certificate of Excellence

from $178 / night

$1,272 - $2,289 / week

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from $178 / night

(24) Excellent 

32

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 $166 / night

$840 - $1,806 / week

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from $166 / night

(18) 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 $255 / night

$878 - $1,513 / week

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avg. 2 hours 40 minutes

from $255 / night

(11) Excellent 

30

Ventnor Vacation 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 mi
  • Child friendly
A beautiful and stylish New England Townhouse just 5 minutes from the beach in a peaceful town location. Decorated and fully refurnished in 2016 Set in a large private courtyard Rear garden features conservatory and decked areas Three tastefully decorated bedrooms Larg …see more

from $153 / night

$893 - $1,397 / week

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avg. 2 hours 35 minutes

from $153 / night

(22) 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 $134 / night

$887 - $1,531 / week

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from $134 / night

(22) Excellent 

36

Vacation cottage rental

Ventnor / Bonchurch

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Carmel is set down a private lane on the south coast of the Isle of Wight just a stones throw from secluded Monks Bay. The property faces due south with seaviews from the cottage and the surrounding gardens. Carmel has been furnished in a modern style to compliment many …see more

from $178 / night

$1,005 - $2,518 / week

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avg. 2 hours 35 minutes

from $178 / night

(6) Very Good 

21

Vacation chalet rental

Isle of Wight / Seaview

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
(Preferential ferry prices for all our guests: please ask for details) Our three Salterns Beach Chalets have been modernised to Premier standard to provide the most comfortable accommodation for your seaside holiday. They are superbly situated in this small development …see more

from $69 / night

$391 - $824 / week

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from $69 / night

(32) 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 $89 / night

$445 - $1,145 / week

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avg. 1 hour 12 minutes

from $89 / night

(22) Excellent 

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

from $64 / night

$312 - $508 / week

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from $64 / night

(42) Excellent 

40

Vacation cottage rental

Ventnor / St Lawrence, Ventnor

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
SPECIAL JUNE 2018 LATE AVAILABILITY OFFER W/C FRIDAY 1ST JUNE 2018 TO 8TH JUNE 2018 REDUCED TO £550.00 W/C FRIDAY 8TH JUNE 2018 TO 15TH JUNE 2018 REDUCED TO £550.00 W/C FRIDAY 15TH JUNE 2018 TO 22ND JUNE 2018 REDUCED TO £550.00 SPECIAL JULY 2018 LATE AVAILABILITY …see more

from $191 / night

$668 - $1,647 / week

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from $191 / night

(9) 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 $64 / night

$318 - $1,011 / week

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avg. 3 hours 6 minutes

from $64 / night

(14) Excellent 

13

Cottage rental in Bonchurch

Ventnor / Bonchurch

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Pet friendly
Pay by card or PayPal, through the Holiday Lettings website, to be covered by Payment Protection. Never pay by bank or wire transfer. Description from owner Description An idyllic retreat in the heart of one of the Isle of Wight's prettiest villages, Grebe Cottage was c …see more

from $166 / night

$1,208 - $1,246 / week

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avg. 27 minutes

from $166 / night

(24) Excellent 

29

Seaview Vacation 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 mi
  • Swimming pool
A stylish modern home with a walk-in 'wow' factor. Set in a fantastic location - enjoy a woodland walk in the grounds, or the seclusion of a private patio and garden. Our lovely holiday home is available to share. Ideal for all the family, secure 8 acre grounds for th …see more

from $190 / night

$1,329 - $1,901 / week

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avg. 1 hour 46 minutes

from $190 / night

(29) 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 $192 / night

$574 - $1,270 / week

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from $192 / night

(22) 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 $146 / night

$1,016 / week

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from $146 / night

(14) Excellent 

Certificate of Excellence

16

St Helens Vacation caravan/mobile home rental

Isle of Wight / St Helens

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
The Retreat is a privately owned three bedroom static caravan set in the St Helens Holiday Park which is child friendly and car free and features a heated outdoor pool, games room, launderette and play areas. The Retreat is double glazed with full gas central heating an …see more

Certificate of Excellence

from $58 / night

$401 / week

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from $58 / night

(2) Excellent 

4

Vacation apartment in Ryde

Isle of Wight / Ryde

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Flatlet 6 A Stylish studio Apartment situated on the lower ground floor. It is within a large Victorian residence that has been carefully transformed into 6 stylish self catering apartments. Flatlet 6 comprises of a full size pull down double bed with a separate bedro …see more

from $101 / night

$300 - $632 / week

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avg. 2 hours 54 minutes

from $101 / night

13

Chalet rental in Sandown

Isle of Wight / Sandown

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
150 Sandown Bay Holiday Centre is located in a quiet area of the park with parking behind and lots of lovely grass and fields to the front. The chalet is not as modern as some of them but has plenty of British Sea Side Holiday charm. The Chalet has 2 bedrooms, 1 with a …see more

from $68 / night

$472 / week

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avg. 3 hours 51 minutes

from $68 / night

(1) Excellent 

22

Vacation home rental

Isle of Wight / Ryde

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
New to Trip Advisor Tea Tree Cottage is fabulously convenient if you want to explore the Isle of Wight, and not even need to bring a car with you! Its a 5 minutes taxi ride from Ryde Pier Head with its rail links to Portsmouth Harbour and on to London Waterloo Station. …see more

from $180 / night

$1,259 - $1,526 / week

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from $180 / night

(30) Excellent 

Certificate of Excellence

20

Vacation bungalow in Wootton

Isle of Wight / Wootton

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
This spacious detached 3 bedroom home is set in a stunning location with spectacular views overlooking Wootton Creek and benefits from its own floating pontoon for boats up to 32 feet allowing access to and from The Solent. The accommodation comprises a spacious lounge …see more

Certificate of Excellence

from $140 / night

$757 - $1,265 / week

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Responds fast!
avg. 1 hour 36 minutes

from $140 / night

(11) Very Good 

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

from $58 / night

$356 - $528 / week

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avg. 56 minutes

from $58 / night

(8) Excellent 

29

Home rental in Bembridge

Bembridge / Bembridge Village

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.7 mi
  • Child friendly
Hedgerow is a charming detached thatched house, close to both the beaches and village centre of Bembridge, located on a quiet private road. It is set in a large attractive enclosed garden with mature shrubs and trees, and has a wooden climbing frame for younger childre …see more

from $339 / night

$1,653 - $2,734 / week

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avg. 56 minutes

from $339 / night

18

Calbourne Vacation barn rental

Isle of Wight / Calbourne

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
This charming newly converted barn is set in the grounds of ‘Street Place Farm', tucked away in this wonderful rural West Wight position. The farm is surrounded by open fields providing the ideal location for walkers and nature lovers. Next to the barn there is a sizeab …see more

from $574 / night

$574 - $797 / week

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from $574 / night

(1) 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. Pet friendly. Beautifully decorated, exposed brickwork, vaulted ceiling, tall sash windows. Excellent location for touring the island. The floating bridge to Cowes is 20 second …see more

from $140 / night

$890 - $2,543 / week

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avg. 10 minutes

from $140 / night

13

Cowes Vacation apartment rental

Isle of Wight / Cowes

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
This beautiful 3rd floor 1 bedroom open plan apartment in the popular Marinus development is only 2 minutes walk from the marina & town. Comes with views across the harbour from the lounge & balcony & with the use of the sofa bed in the lounge can sleep up to 4 Mast …see more

from $121 / night

$541 - $763 / week

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from $121 / night

(4) Excellent 

10

Shanklin Vacation apartment rental

Isle of Wight / Shanklin

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
FANTASTIC PROPERTY IN EXCLUSIVE LOCATION WALKING DISTANCE TO OLD VILLAGE, BEACH, PARK, CRICKET GROUND FREE WIFI AVAILABLE IN PROPERTY DISCOUNTED FERRY CROSSINGS AVAILABLE (SOUTHAMPTON-EAST COWES ROUTE) This unique apartment, which is close to 1500 sq feet, in size i …see more

from $223 / night

$1,081 - $1,653 / week

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from $223 / night

(8) Very Good 

27

Vacation cottage rental

Freshwater / Freshwater Bay

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Ask about children
Rabbit's Bothie, a self-catering holiday cottage in Freshwater Bay on the Isle of Wight, is just three minutes' walk from the photography museum at Dimbola; St Agnes church with its thatched roof; and Orchard's, the village grocer. Self-catering for two with wifi …see more

from $92 / night

$458 - $712 / week

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from $92 / night

(2) Excellent 

5

Vacation home in Newport

Isle of Wight / Newport

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
This is a cosy and fully equipped 1 bedroom mews house located within easy walking distance of town centre shops and restaurants, together with bus routes to all other places on the Isle of Wight. There is parking for a small car (e.g VW Golf max) if required. All mod …see more

from $64 / night

$445 / week

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Responds fast!
avg. 3 hours 28 minutes

from $64 / night

(13) 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 $248 / night

$922 - $1,621 / week

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Responds fast!
avg. 1 hour 49 minutes

from $248 / night

(7) Excellent 

31

Vacation apartment in Shanklin

Isle of Wight / Shanklin

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
The Garden Apartment at Lyon Court has just been refurbished to a very high standard and takes up the entire storey at garden level. With the ceiling height in excess of 8 feet in most rooms, stylish dimmable LED downlights throughout and large windows and doors, it ma …see more

from $201 / night

$1,736 - $3,071 / week

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Responds fast!
avg. 3 hours 24 minutes

from $201 / night

(7) Excellent 

13

Shanklin Vacation home rental

Shanklin / Luccombe Village

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
There really is something for everyone here with a charming snug/bedroom area, a fantastic private balcony from the master suite, a wonderful timber built terrace with table and chairs, a quite unique bar-be-cue hut, as well as extensive lawned gardens with various tree …see more

from $363 / night

$2,537 / week

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from $363 / night

(4) Excellent 

16

Vacation apartment in Cowes

Cowes / West Cowes

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden
This beautiful modern maisonette over 2 floors is situated in Mill Hill road has views over Cowes & the Solent and within comfortable walking distance of marinas. The accommodation is of a modern high standard & well-presented throughout, the top floor comprises of 2 b …see more

from $117 / night

$522 - $890 / week

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from $117 / night

(3) Very Good 

43

Vacation home with golf nearby in Ryde

Isle of Wight / Ryde

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Westridge House is a one of the most exclusive homes on the island comfortably sleeping up to 10 people. The house holds 5 bedrooms, consisting of 3 double bedrooms and 2 twin bedrooms. Despite being built over 100 years ago, the house is furnished to an extremely high …see more

from $467 / night

$3,268 - $5,887 / week

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from $467 / night

(39) Excellent 

33

Vacation cottage in Whitwell

Ventnor / Whitwell

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Ferndale is a large, charming, four bedroom Victorian cottage on the Isle of Wight, set in idyllic countryside, with a beautiful garden, stunning views of surrounding fields and walks from the doorstep. The house was recently refurbished to a very high standard and has …see more

from $191 / night

$636 - $1,717 / week

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Responds fast!
avg. 3 hours 6 minutes

from $191 / night

(9) Excellent 

14

Vacation apartment in Cowes

Cowes / West Cowes

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This highly sought after apartment is beautifully decorated throughout with a lovely nautical theme in the living room. Enjoy dining out on the spacious balcony, overlooking the harbour. A perfect place to start the day with breakfast or wind down in the evenings under …see more

from $140 / night

$636 - $1,145 / week

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from $140 / night

(9) Excellent 

24

Vacation home in Bonchurch

Ventnor / Bonchurch

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
'Boutique hotel meets Country House' is how one reviewer described our lovely home with sea views in Bonchurch, a beautiful village on the south of the island. The village was recently voted No 5 in The Times list of ' 50 Best Places to Live By the Sea'. They said: "Why …see more

from $491 / night

$3,433 / week

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from $491 / night

(2) Excellent 

48

Vacation home in Ventnor

Isle of Wight / Ventnor

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Car not necessary
Our home is well presented, convenient & comfortable - a 3 storey town house located close to shops, restaurants & pubs and is a 5 minute walk to the beach. Within walking distance are the downs, Steephill Cove, the botanic gardens and a lovely park. We offer free wi- …see more

from $224 / night

$1,389 / week

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Responds fast!
avg. 2 hours 46 minutes

from $224 / night