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

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Beach rentals Ventnor
124 properties
Holiday rentals Cowes
121 properties
Villas Shanklin
108 properties
Apartments Sandown
101 properties
Ryde
62 properties
Self catering Bembridge
59 properties
Vacation rentals Freshwater
50 properties
Yarmouth
48 properties
Seaview
43 properties
Wootton Bridge
23 properties
Niton
17 properties
Newport
15 properties
Totland Bay
14 properties
Gurnard
13 properties
St Helens
13 properties
Bonchurch
12 properties
Brading
12 properties
Whitwell
11 properties
East Cowes
10 properties
Brighstone
9 properties

Isle of Wight

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935 Vacation rentals

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(15) 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 $82 / night

$494 - $1619 / week

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from $82 / night

(9) Very Good 

20

Vacation apartment in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Stunning sea views from this two bedroomed Self contained Apartment. Situated within walking distance of the Town and beach but offering uninterrupted sea views. The Apartments has two bedrooms, one double and one twin. Bathroom with Shower and Bidet.Fully fitted ki  …see more

from $107 / night

$463 - $782 / week

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from $107 / 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 $48 / night

$282 - $594 / week

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from $48 / night

Featured properties

(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 $100 / night

$563 - $1188 / week

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from $100 / night

(23) Excellent 

25

Gurnard Vacation home rental

Isle of Wight / Gurnard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
A fantastic light spacious home with a large mature garden reaching down to the beach providing wonderful sea views of the Solent and beyond. The property has been completely refurbished to a high standard and provides 4 double bedrooms all with fantastic views, bathro  …see more

from $188 / night

$1125 - $2188 / week

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from $188 / night

(7) Very Good 

23

Vacation chalet in Ventnor

Ventnor / Niton Undercliff

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
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 $57 / night

$350 - $507 / week

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from $57 / night

(23) Excellent 

24

Ryde Vacation apartment rental

Isle of Wight / Ryde

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Our recently renovated 2 bedroom spacious raised ground floor apartment is minutes walk from the centre of Ryde's shops, restaurants, bars, cinema. Located in the quiet conservation area Vernon Square.This lovely square can be used by residents for picnics etc.Easy  …see more

from $67 / night

$469 - $869 / week

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from $67 / 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 $188 / night

$657 - $1682 / week

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from $188 / night

(4) Excellent 

16

Freshwater Vacation bungalow rental

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
This bungalow is located in the Linstone Chine Holiday Village, Freshwater. It has been refurbished at the beginning of 2015 and it has a marvellous, uninterrupted view over the Solent towards Hurst Castle and a few steps from the bungalow and you can see the Needles, t  …see more

from $63 / night

$338 - $700 / week

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from $63 / night

(19) 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 $82 / night

$425 - $782 / week

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from $82 / 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 $175 / night

$1125 - $2488 / week

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from $175 / night

(1) Excellent 

7

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

from $175 / night

$1250 - $2188 / week

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from $175 / night

(25) Excellent 

15

Ryde Vacation lodge rental

Isle of Wight / Ryde

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
This welcoming lodge really is a home from home all recently refurbished to a very high luxury standard. (Over 25 only).The accommodation sleeps 2 and the lodge is situated in a secluded area surrounded by woodland, yet not far from the beautiful sandy beaches and ch  …see more

from $75 / night

$438 - $630 / week

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from $75 / night

(4) Excellent 

16

St Helens Vacation caravan/mobile home rental

Isle of Wight / St Helens

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

from $50 / night

$350 / week

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from $50 / 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 $58 / night

$332 - $863 / week

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from $58 / night

(12) Excellent 

19

Vacation cottage in Calbourne

Isle of Wight / Calbourne

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Set in a rural location in the grounds of an 18th century farmhouse with 1.5 acres of land. the Old Brewhouse is a delightful 2 bedroomed converted brewhouse which won a design award following completion. The accommodation comprises a ground floor double bedroom with a  …see more

from $125 / night

$500 - $1000 / week

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from $125 / night

(4) Excellent 

20

Vacation bungalow in Freshwater

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Welcome to the Sunnywight Holiday Bungalow. Self Catering 3 Star Accomadation in Colwell Bay, near Freshwater in the Isle of Wight.In a secluded and quiet part of The Isle of Wight, the ever popular holiday destination, and with direct access to the beach, our h  …see more

from $54 / night

$375 - $607 / week

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from $54 / 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 $163 / night

$869 - $1657 / week

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from $163 / night

(10) 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 $45 / night

$313 - $688 / week

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from $45 / night

(16) Very Good 

24

Vacation 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
Take a peaceful break away from the crowds in our quirky little cabin. Get up have a stroll along the beach, on our private bay, then sit outside and have breakfast while looking at the beautiful view and watching the boats sail by, you may want to spend time with your  …see more

from $82 / night

$500 - $838 / week

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from $82 / night

(13) Excellent 

15

Vacation bungalow in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
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

from $88 / night

$619 - $1244 / week

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from $88 / night

(10) Excellent 

16

Freshwater Vacation bungalow rental

Isle of Wight / Freshwater

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Number 58 is a perfect holiday getaway on the beautiful Isle of Wight. Sleeping up to five people, this two bedroom self-catering semi-detached bungalow based at Brambles Chine, West Wight is just minutes from the ferry terminal in nearby Yarmouth and only yards from th  …see more

from $88 / night

$488 - $650 / week

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from $88 / night

(8) Excellent 

8

Vacation apartment in Wootton Bridge

Wootton Bridge / Fishbourne

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
Now with free broadband Wifi, The Grange is a purpose-built, ground floor three-bedroomed modern holiday apartment in Creek Gardens, at Wootton Bridge on the Isle of Wight. It is located on the west bank of picturesque Wootton Creek. Well equipped, with the main bedroom  …see more

from $87 / night

$369 - $1094 / week

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from $87 / night

(10) Very Good 

27

Vacation cottage rental

Isle of Wight / Bembridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
A super sunny flat back garden with BBQ, couch, chairs, and bench on a large patio. Private and safe the garden is perfect for relaxing. Drayton cottage is a lovely warm Victorian semi detached cottage with private parking within easy walking of the beach. This means yo  …see more

from $125 / night

$438 - $1000 / week

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from $125 / night

(16) Excellent 

13

Brighstone Vacation cottage rental

Isle of Wight / Brighstone

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
  • Private garden
Carriers Stable was once a Victorian stable that has now been converted into a beautiful detached holiday cottage to accommodate ideally 2 people, and equipped to high standard, with good reviews. Normal change over day Fridays. We try to provide most items so you don&#  …see more

from $79 / night

$394 - $732 / week

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from $79 / 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 $187 / night

$1307 - $1869 / week

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from $187 / night

(3) Excellent 

13

Caravan/mobile home rental in Bembridge with shared pool

Isle of Wight / Bembridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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 $57 / night

$394 / week

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from $57 / night

(6) Excellent 

20

Vacation lodge in Newchurch

Sandown / Newchurch

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Pet friendly
  • Private garden
Newchurch Nook is a beautiful open plan, self catering lodge. Can also accommodate 1 baby in a travel cot. A well behaved dog is welcome. Situated on the Squirrel trail/ cycle path , ideal for walkers, cyclists or anyone looking for a peaceful retreat. Free wifi. There  …see more

from $75 / night

$525 / week

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from $75 / night

(6) Excellent 

10

Shanklin Vacation apartment rental

Isle of Wight / Shanklin

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
A Luxurious 4 bedroom self catering holiday apartment, providing accommodation for 6 + 2 people with private roof terrace and 6 person hot tub.Located on the first and second floors this apartment offers en-suites to 3 of the bedrooms.Master Bedroom: Loc  …see more

from $175 / night

$869 - $2219 / week

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from $175 / night

(8) Excellent 

28

Vacation 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 mi
  • Child friendly
A deceptively spacious Victorian town house on 4 levels with stunning sea views close to the town and Ventnor sea front. The house is stylishly furnished and is ideal for families, with the green opposite providing a great space for outdoor games. The rear courtyard g  …see more

from $194 / night

$775 - $1800 / week

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from $194 / night

(2) Very Good 

9

Apartment accommodation in Bembridge

Bembridge / Bembridge Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
2 Driftwood is a charming 1 bedroom apartment with fantastic views of the sea that sleeps up to 4 people. The property is set in a unique position in Bembridge, seconds from the coastline with magnificent views of the solent. 2 Driftwood is within walking distance of lo  …see more

from $125 / night

$332 - $613 / week

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from $125 / night

(5) 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 restaura  …see more

from $63 / night

$438 - $994 / week

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from $63 / 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 $63 / night

$250 - $619 / week

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from $63 / night

(16) Excellent 

24

Vacation cottage in Shanklin

Shanklin / Old Village

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This lovely character cottage is tucked away in a peaceful location but just a short walk from the picturesque Shanklin Old Villagewith its quaint thatched pub, tearooms and gift shops. Shanklin Chine is a beautiful natural wooded gorge and is a pleasant eveningstroll  …see more

from $65 / night

$450 - $875 / week

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from $65 / night

(9) Very Good 

12

Freshwater Vacation bungalow rental

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
The property was built in 2007 and the accommodation is built and furnished to a high standard. We have lots of guests who have been booking their holidays in Seabreeze for many years. Seabreeze is located in a quiet and peaceful location, just the thing to unwind fr  …see more

from $42 / night

$292 - $694 / week

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from $42 / night

(21) Excellent 

24

Apartment rental in Shanklin

Shanklin / Old Village

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.9 mi
  • Ask about children
One bedroom ground floor apartment with king size bed and freesat television. Bathroom containing a free standing shower and bath, lounge with double size sofa bed and freesat television. Kitchen with gas grill and double oven separate fridge and freezer also a dishwash  …see more

from $110 / night

$438 - $645 / week

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from $110 / night

(12) Very Good 

20

Chalet rental in Gurnard

Isle of Wight / Gurnard

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Beachside Chalet No1 is approached from a residential road, offering a safe and peaceful environment. The quiet village of Gurnard sits west along the coast from the bustling internationally renown yachting town of Cowes. HISTORY - The chalet is one of a row built in  …see more

from $63 / night

$400 - $663 / week

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from $63 / night

18

Cowes Vacation home rental

Isle of Wight / Cowes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Large Victorian property with Cowes Yacht Haven on the doorstep and a short stroll into the town centre. French country style furnishings, stripped original wooden floors, interesting features, and comfortable living space for 10 - or possibly 11. Accommodation comprise  …see more

from $282 / night

$1125 - $5832 / week

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from $282 / night

(3) Excellent 

15

Apartment rental in Shanklin

Shanklin / Old Village

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
This beautifully presented one bedroom ground floor garden apartment is set in a quiet location in the grounds of an Edwardian house in the coastal resort of Shanklin. It is attached to the owners house, but cleverly arranged for maximum privacy as has its own separate  …see more

from $71 / night

$494 - $750 / week

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from $71 / night

(9) Excellent 

20

Vacation home rental

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
A beautifully presented Victorian Fishermans Cottage in Cowes, Isle of Wight. A charming 2 bedroom Victorian Cottage within easy walking distance to Shephard's Wharf marina and only a few minutes walk from the town centre. The cottage has a good size double bedroo  …see more

from $100 / night

$782 - $1400 / week

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from $100 / night

Cottages and self catering accommodation in Isle of Wight

Why Isle of Wight?

The Isle of Wight is just off England's south coast and is less than two hours from London via the Isle of Wight Ferry. It's home to picturesque villages, traditional seaside towns and some of the most beautiful beaches in the UK. Its mild climate and family-friendly attractions make it the ideal choice for a UK break near the sea. So, whether you're looking for a romantic cottage in Cowes, a seaside apartment in Sandown or family-sized townhouse in Ryde, the Isle of Wight has some fantastic holiday rentals to choose from.

Fantastic days out

There's so much to see and do in the Isle of Wight, you'll want to come back year after year. For a fun-filled family day out, head to Blackgang Chine. This enchanting theme park overlooking the south coast is set in beautiful gardens. From fairytale castles to life-sized dinosaurs, a day out here is like something straight from a storybook and will inspire imaginations.

Take your little monkeys to Monkey Haven, an award-winning sanctuary for birds, reptiles and, of course, monkeys, in Newport. To see Shanklin in miniature, visit the charming Model Village in Godshill; the attention to detail is simply incredible. And if you fancy a bit (well, a lot) of stately grandeur, then how about a day out at Queen Victoria's holiday home, Osborne House?

Beside the seaside

There are some beautiful beaches on the Isle of Wight. Some highlights include the peaceful beach at St Helens, the family-friendly beach at Sandown with its pier and amusement arcades, and the unspoilt Brighstone Bay. If watersports are your thing, Ryde beach is great for swimming, sailing and windsurfing, so you can easily spend the whole day out in the waves. And if you're looking for a romantic place to take your significant other, Steephill Cove is a peaceful idyll with a fantastic seafood restaurant nearby.
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