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

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Beach rentals Ventnor
127 properties
Holiday rentals Cowes
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Villas Shanklin
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Apartments Sandown
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Ryde
58 properties
Holiday cottages Bembridge
51 properties
Yarmouth
49 properties
Vacation rentals Freshwater
49 properties
Seaview
39 properties
Wootton Bridge
22 properties
Niton
17 properties
Totland Bay
16 properties
Gurnard
15 properties
Newport
14 properties
Bonchurch
12 properties
Brading
12 properties
Whitwell
10 properties
St Helens
10 properties
Brighstone
10 properties
East Cowes
10 properties

Isle of Wight

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900 Vacation rentals

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(30) Excellent 

33

Vacation cottage in Whitwell

Isle of Wight / 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 $185 / night

$615 - $1722 / week

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from $185 / night

(13) Excellent 

22

St Helens Vacation 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 mi
  • Swimming pool
Admiral Park 8 is a super New Hampshire 40x16 luxury lodge. It comes with the highest spec and we are confident you'll love it. .....The lodge overlooks Bembridge Bay with sandy beaches, marina and nature reserve. (The main picture is an identical lodge in a differ  …see more

from $80 / night

$486 - $1593 / week

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from $80 / night

(11) Excellent 

20

Vacation cottage in Yarmouth

Yarmouth / Fort Victoria

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Wight Cottage is adjacent to Fort Victoria and close to the pretty harbour town of Yarmouth. The cottage has wonderful sea views from the master bedroom and from the living room, plus plenty of outside space for safe playing, barbequing with family/friends, or simply en  …see more

from $105 / night

$732 - $1532 / week

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from $105 / night

(7) Very Good 

35

Vacation cottage in Bonchurch

Isle of Wight / 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 $13 / night

$1341 - $2448 / week

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from $13 / night

(14) Excellent 

23

Vacation home in Ryde

Isle of Wight / Ryde

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
coastguard cottage is a self catering holiday home is situated 1 minute level walk from the safe glorious sandy beaches of Ryde, Isle of Wight. It has 2 bedrooms 1 king and 2 singles, there is also a sofa bed that could accommodate an extra guest or two. Both bedrooms h  …see more

from $66 / night

$462 - $984 / week

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from $66 / night

(8) Excellent 

58

Vacation 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 mi
  • Child friendly
The Summerhouse is a spacious, self catering, semi detached chalet located on a peaceful, naturally landscaped holiday park in Brambles Chine, part of the Isle of Wight's area of outstanding natural beauty. Situated only 150 meters from the sea it provides spectacu  …see more

from $44 / night

$308 - $554 / week

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from $44 / night

(29) Very Good 

21

Vacation cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Charming coastguard cottage situated at Fort Victoria Country Park near Yarmouth and Freshwater on the picturesque West coast of the Isle of Wight. enjoying stunning sea views across the Solent. The recently refurbished seaside cottage offers an excellent base for a sel  …see more

from $93 / night

$486 - $1532 / week

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from $93 / 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 mi
  • Child friendly
Awarded a 4 Star accreditation from VisitEngland Hurst View offers high quality Self Catering holiday accomodation for up to 6 guests in this end of terrace townhouse. Hurst View offers high quality holiday accommodation in the attractive and popular holiday resort of N  …see more

from $73 / night

$505 - $1194 / week

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from $73 / night

(18) Excellent 

39

Vacation apartment in Shanklin

Shanklin / Old Village

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
5 The Priory is a luxury 1 bedroom ground floor apartment situated in a Victorian former gentlemen's residence overlooking Shanklin and Sandown Bay. The building stands above lush woodland grounds and is situated in a quiet yet convenient position on the coastal pa  …see more

from $74 / night

$400 - $769 / week

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from $74 / night

(5) Very Good 

11

Ventnor Vacation apartment rental

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Beach Home Ventnor is an ideal British holiday location sleeping up to 4 people in a tranquil setting. It offers spectacular, panoramic views of the beach at Ventnor Bay, the cliff tops and far out to sea. The beach can be reached within 1 minute from the end of the gar  …see more

from $88 / night

$615 - $1138 / week

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from $88 / night

(83) Excellent 

25

Vacation cottage in Ventnor

Ventnor / Niton Undercliff

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Child friendly
Four Star - Gold Award - Character accommodation, easily sleeping eight guests. Perfect for the extended family, or two families wishing to share. A real home from home, offering everything you could want. With a traditional welcoming pub a 5 minute walk away it is a pe  …see more

from $148 / night

$702 - $1815 / week

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from $148 / night

11

Porchfield Vacation caravan/mobile home rental

Isle of Wight / Porchfield

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
We are proud to offer a 3 bedroom Static caravan on Thorness bay caravan holiday park on the beautiful Isle of Wight. 1 Double master bedroom and 2 twin rooms and then a double sofa bed in lounge. Benefits from own private decking area and ample parking. Holiday site ha  …see more

from $56 / night

$1169 / week

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from $56 / night

(7) Excellent 

22

Vacation cottage in Brighstone

Isle of Wight / Brighstone

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Charming Grade II listed character cottage, quietly situated on the edge of the pretty village of Brighstone, 1/2 mile from the sea. 2 The Granary originally formed part of Brighstone Mill and dates back to 1700. Converted in 1990, the living room is on the first floor  …see more

from $122 / night

$425 - $966 / week

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from $122 / night

(18) Excellent 

12

Vacation chalet with shared pool, golf nearby in Gurnard

Isle of Wight / Gurnard

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Newly refurbished chalet with brand new fitted kitchen and bathroom. Fully equipped kitchen with electric oven, gas hob, fridge with a freezer compartment, microwave oven, crockery, cutlery and utensils. Iron, folding clothes horse, and vacuum cleaner. Dining area with  …see more

from $99 / night

$431 - $1046 / week

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from $99 / night

(9) Excellent 

23

Freshwater Vacation bungalow rental

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Sunnyside Bungalow faces South and the sun streams in all day through the big picture window. Not only that, but it has one of the best locations of any bungalow on this private holiday park.A few paces away are the cliffs overlooking the beach of Colwell Bay an  …see more

from $44 / night

$308 - $677 / week

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from $44 / night

(11) Excellent 

8

Vacation 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 mi
  • 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.•P  …see more

from $80 / night

$400 - $554 / week

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from $80 / night

(7) Excellent 

17

Cottage rental in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Recently refurbished and new to the holiday market, Valerian Cottage built of Island Stone in 1830, and originally forming part of a larger house, sits prettily at the top of Tulse Hill in the Centre of Ventnor giving easy access to the town with its many restaurants, s  …see more

from $99 / night

$554 - $1169 / week

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from $99 / night

(20) Very Good 

20

Yaverland Vacation chalet rental

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Seaspray Chalet is fully self catering with an open plan Kitchen and lounge. It provides comfortable accommodation with two bedrooms, one double and one with bunk beds. The Bathroom has a full size bath and shower above. There is plenty of hot water and Electricity and  …see more

from $44 / night

$277 - $585 / week

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from $44 / night

(13) Excellent 

20

Vacation cottage in Bonchurch

Isle of Wight / Bonchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $123 / night

$677 - $972 / week

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from $123 / night

(17) Excellent 

24

Vacation 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 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 $167 / night

$855 - $1716 / week

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from $167 / night

(6) Very Good 

23

Vacation cottage in Ventnor

Isle of Wight / Ventnor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
OPEN ALL YEAR Smugglers is a pretty and cosy early Victorian Cottage in the centre of Ventnor, sleeping 7 people comfortably, plus a cot if required. There is a large double bedroom with a single room attached and a double room with a twin room attached. Both doubles ha  …see more

from $117 / night

$646 - $1224 / week

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from $117 / night

(1) Excellent 

25

Apartment rental in Ventnor

Ventnor / Ventnor Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Overlooking the sea, Apartment 4 is situated in a purpose built block of Holiday Apartments. With a sliding patio door opening onto a sea facing balcony ideal for sun lovers. On town level-just a few minutes walk away from the restaurants, shops and beach of Ventnor. T  …see more

from $111 / night

$456 - $769 / week

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from $111 / night

(28) Excellent 

22

Vacation barn with golf nearby in Freshwater

Freshwater / Freshwater Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
We can book you discount Redfunnel ferry tickets. Stable Cottage, set in the grounds of Afton Farmhouse, is in an 'Area of Outstanding Natural Beauty' on the west of the Isle of Wight. Awarded a 4 star rating by visit England. Afton, on the outskirts of Fre  …see more

from $68 / night

$443 - $1329 / week

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from $68 / night

(12) Excellent 

19

Vacation chalet in Niton

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 5 mi
  • Car not necessary
Sticky Wicket is a cosy one bedroom chalet set among beautiful gardens in the charming village of Niton near Ventnor. The property has one bedroom with an en-suite shower room, kitchen and lounge with sofa and tv. Situated in a row of similar south facing properties it  …see more

from $50 / night

$296 - $523 / week

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from $50 / night

(29) Excellent 

45

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
March 2015. Breakers Sound has just been completely redecorated throughout with new carpets and curtains for your enjoyment and comfortThis quintessential English cottage nestles in the heart of the St Lawrence Undercliffe. A sought after location officially rec  …see more

from $185 / night

$646 - $1655 / week

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from $185 / night

(10) Excellent 

26

Vacation chalet in Yaverland

Sandown / Yaverland

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Wight Waves is a brick-built, newly double-glazed chalet, with Eco heating for the colder weather, and we have completely renovated it to a high standard. This is the second season we have offered it for holiday rental. It is one of the few chalets on the site with its  …see more

from $62 / night

$246 - $609 / week

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from $62 / night

(24) Excellent 

23

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 $185 / night

$609 - $1101 / week

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from $185 / night

(17) Excellent 

12

Vacation caravan/mobile home rental

Isle of Wight / Bembridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Luxury Caravan sleeping in comfort for 6 people. Fully central Heated and double glassed. Decking out front for BBQ's etc. Set on the stunning bay at Whitcliff Bay Holiday park, Isle of Wight which provides private beach and 2 pools. Full entertainment package avai  …see more

from $56 / night

$388 / week

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from $56 / night

(22) Excellent 

16

Vacation chalet rental

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
The chalet is modern and well equipped for a family of 4, it has sea views from the front and side windows, and over looks the beautiful cliffs of Culver down.It is situated on the edge of national trust land which is accessible from the site with many miles of  …see more

from $31 / night

$240 - $677 / week

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from $31 / night

(4) Excellent 

21

Vacation chalet in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Suntrap is a very unusual and unique holiday home on the Isle of Wight. The house is decorated, furnished and equipped to a very high standard encloses an old railway carriage. The carriage was originally built in the 1880's and after years of operation in Lincoln  …see more

from $160 / night

$1120 / week

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from $160 / night

(36) Very Good 

17

Vacation chalet in Yaverland

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Seabreeze Chalet is fully self catering with an open plan Kitchen and lounge. It provides comfortable accommodation with two bedrooms, one double and one with bunk beds. The Bathroom has a full size bath and shower above. There is plenty of hot water and Electricity and  …see more

from $44 / night

$277 - $585 / week

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from $44 / night

(17) Excellent 

23

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. My lovely holiday home is available to share. Ideal for all the family, secure 8 acre groun  …see more

from $184 / night

$1286 - $1839 / week

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from $184 / night

(2) Very Good 

15

Vacation apartment rental

Cowes / West Cowes

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
This stylish apartment within Osborne Court is situated on Cowes Parade & has amazing views across The Solent. Its a short walk to the main town, marina's, shops, restaurants, pubs & Red Jet Hi speed terminal. The apartment is of a high standard internally  …see more

from $99 / night

$431 - $1722 / week

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from $99 / night

(14) 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 $88 / night

$615 - $1107 / week

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from $88 / night

(9) Excellent 

12

Vacation bungalow in Freshwater

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Idyllic seaside bungalow set in Linstone Chine Holiday Village at Cliff End Freshwater on the beautiful Isle of Wight. Wii fii is available at this property. The two bedroomed bungalow is brick built with bathroom with bath and shower. The kitchen and lounge are open  …see more

from $56 / night

$369 - $708 / week

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from $56 / night

(17) Excellent 

22

Vacation 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 mi
  • Child friendly
Built in 1850 West View is a mews cottage which has been moderrnised and refurbished to a high standard making it an ideal base for an Isle of Wight holiday. It is close to the beaches, opposite the tennis club, central to all the shops and attractions of Ryde, 10 minut  …see more

from $72 / night

$369 - $984 / week

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from $72 / night

(42) Excellent 

27

Ventnor Vacation apartment rental

Isle of Wight / Ventnor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Car not necessary
'Seashells' epitomises beach side living, with spectacular sea views from the lounge and bedroom. We chose it particularly for its warm and welcoming ambience and perfect location. Constantly updated, this relaxing apartment could suit a romantic getaway for t  …see more

from $87 / night

$517 - $886 / week

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from $87 / night

(27) Excellent 

17

Vacation 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 mi
  • Child friendly
The Apartment is new and has quality oak furniture,the apartment has the benefit of sea glimpses and culver cliff. The property is on the first floor. It has open plan living room with doors to a Juliet balcony. Dinning for four and a well equipped kitchen off the dinni  …see more

from $57 / night

$326 - $849 / week

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from $57 / night

(13) Excellent 

12

Vacation apartment with golf nearby in Ryde

Ryde / Appley

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Stylish, top floor, holiday apartment, in a prestigious Victorian house, located in a peaceful road, close to the sea. A short walk to Ryde's long, beautiful sandy beaches, and town centre restaurants, bars and shops. The apartment is newly furnished in a clean  …see more

from $64 / night

$448 / week

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from $64 / night

(10) Very Good 

12

Vacation apartment in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Two bedroom apartment in an excellent waterfront location with wonderful views across Shepards Marina and the Solent beyond. A Quay Management property situated on the the fourth floor and accessed via a private lift or stairs. Within 5 minutes easy walk of the centre o  …see more

from $160 / night

$523 - $2706 / week

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from $160 / night