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

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Beach rentals Ventnor
167 properties
Villas Shanklin
125 properties
Apartments Sandown
124 properties
Holiday rentals Cowes
121 properties
Self catering Bembridge
59 properties
Vacation rentals Freshwater
55 properties
Yarmouth
53 properties
Ryde
49 properties
Seaview
26 properties
Wootton Bridge
25 properties
Newport
25 properties
Totland Bay
19 properties
Gurnard
14 properties
Niton
14 properties
St Helens
13 properties
Brading
12 properties
Chale
11 properties
East Cowes
11 properties
Brighstone
11 properties
Shorwell
10 properties

Isle of Wight

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1,600 Vacation rentals

(23) Excellent 

Certificate of Excellence

32

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

Certificate of Excellence

from $149 / night

$937 - $1,880 / week

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from $149 / night

(2) Excellent 

9

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 $80 / night

$317 - $667 / week

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from $80 / night

(19) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $142 / night

$937 - $1,346 / week

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from $142 / night

(17) Excellent 

Certificate of Excellence

21

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 Isle of Wight holiday cottage on edge of 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, this is an upside down cottage as the livi …see more

Certificate of Excellence

from $132 / night

$465 - $1,206 / week

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avg. 1 hour 25 minutes

from $132 / night

(8) 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 $68 / night

$338 - $1,073 / week

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avg. 2 hours 23 minutes

from $68 / night

(8) Excellent 

Certificate of Excellence

11

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
Sunny Beach #3 is a spacious two bed apartment with large balcony overlooking the sandy beaches of Shanklin. Situated on the first floor, the beach is literally metres away with safe, sandy beaches & promenade stretching miles in either direction An open plan livi …see more

Certificate of Excellence

from $149 / night

$802 - $1,678 / week

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from $149 / night

(29) Excellent 

Certificate of Excellence

20

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
  • 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 $129 / night

$668 - $1,343 / week

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avg. 2 hours 43 minutes

from $129 / 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 $189 / night

$1,011 - $2,668 / week

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avg. 1 hour 59 minutes

from $189 / night

7

Vacation cottage rental

Isle of Wight / Wroxall

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Sleeps 4 in 2 bedrooms + 1 on camp bed Delightful detached cottage in the heart of an Area of Outstanding Natural Beauty, close to the picturesque village of Godshill on a working livestock farm bordering Appuldurcombe estate. 10 minute drive from Shanklin's sandy …see more

from $176 / night

$944 - $1,213 / week

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from $176 / night

(7) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $88 / night

$365 - $756 / week

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Responds fast!
avg. 3 hours 22 minutes

from $88 / night

8

Vacation apartment in Ryde

Isle of Wight / Ryde

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
Flatlet 3 A cosy studio Apartment situated on the first floor. It is within a large Victorian residence that has been carefully transformed into 6 stylish self catering apartments. Freeview colour tv/dvd. Central heating and double glazing. Fully fitted kitchen with f …see more

from $53 / night

$237 - $533 / week

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from $53 / night

22

Home rental in Cowes

Isle of Wight / Cowes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
This property is situated in a quiet road just a short walk to the town centre, with wonderful views of Cowes & the Solent from the top bedroom balcony & from the middle floor lounge. There is a good sized family kitchen dining room on the ground floor with steps down …see more

from $176 / night

$844 - $4,048 / week

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from $176 / night

(6) Excellent 

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 $97 / night

$485 - $755 / week

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from $97 / night

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 $317 / night

$1,468 / week

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Responds fast!
avg. 3 hours 3 minutes

from $317 / night

(37) 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
January 2018. Breakers Sound has just had all new bed linens, duvet, pillows and towels for your comfort. March 2015. Breakers Sound has just been completely redecorated throughout with new carpets and curtains for your enjoyment and comfort This quintessential Englis …see more

from $203 / night

$708 - $1,745 / week

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from $203 / night

(23) 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 $202 / night

$1,410 - $2,017 / week

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avg. 1 hour 48 minutes

from $202 / night

16

Lodge rental in Whippingham with golf nearby

Isle of Wight / Whippingham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Private garden
Our cabin is a new addition to our holiday let business, reviews for our excellent performance can be found on 'Squirrel nutkins cabin'. Woodside makes the ideal cosy holiday retreat for four, not suitable for children under 10yrs. It is well situated for exploring the …see more

from $101 / night

$802 - $1,011 / week

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Responds fast!
avg. 35 minutes

from $101 / night

(20) Excellent 

Certificate of Excellence

25

Vacation apartment rental

Isle of Wight / Shanklin

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
This family friendly apartment is ideally located centrally near beaches, shops, amusements and all amenities including the Railway Station. Great location for children as ground level and easy access for pushchairs. Easy Parking available The Ivy Apartments have been …see more

Certificate of Excellence

from $149 / night

$911 - $1,080 / week

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from $149 / night

(11) Excellent 

12

Vacation cottage in Ryde

Isle of Wight / Ryde

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 3 mi
  • Child friendly
5-Star Gold Award winner, recommended in 'TOP 25 BRITISH HOLIDAY RENTALS' by the TIMES NEWSPAPER. A beautifully presented 17th century barn conversion on a working farm, with 3 large en-suit double/twin bedrooms, one on ground floor and two on first floor, overlooking M …see more

from $116 / night

$812 - $1,623 / week

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from $116 / night

(19) 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 mode …see more

from $84 / night

$585 / week

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from $84 / night

(36) Excellent 

Certificate of Excellence

12

Vacation caravan/mobile home rental

Isle of Wight / Bembridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 mi
  • 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 available …see more

Certificate of Excellence

from $54 / night

$378 / week

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Responds fast!
avg. 2 hours 14 minutes

from $54 / night

(5) Excellent 

12

Vacation apartment in Shanklin

Isle of Wight / Shanklin

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Chine House Apartment is a first floor self-contained apartment in the heart of Old Village Shanklin with private terraced south facing garden great for sun bathing or al fresco dining. Gas central heated apartment with private entrance, free parking with access to free …see more

from $107 / night

$647 - $768 / week

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avg. 2 hours 17 minutes

from $107 / night

(2) Very Good 

9

Apartment accommodation in Bembridge

Bembridge / Bembridge Beach

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • 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 $135 / night

$539 / week

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from $135 / night

(19) 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 $97 / night

$674 - $1,213 / week

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from $97 / night

(7) Excellent 

12

Vacation home in Ventnor

Isle of Wight / Ventnor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Private garden
Overlook commands a breathtaking birds eye view of the Victorian town of Ventnor and a panoramic sweep of the English Channel beyond. The house, which has been architect designed and finished to a very high standard, looks out in all directions through walls of glass, n …see more

from $150 / night

$1,045 - $1,885 / week

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from $150 / night

22

Vacation chalet rental

Isle of Wight / Seaview

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • 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 $73 / night

$414 - $915 / week

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avg. 2 hours 48 minutes

from $73 / night

(28) 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 $203 / night

$674 - $1,213 / week

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from $203 / night

(17) Excellent 

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 $176 / night

$932 - $1,607 / week

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avg. 1 hour 57 minutes

from $176 / night

(8) Excellent 

17

Vacation cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.2 mi
  • Child friendly
  • Car not necessary
Serendipity is a gorgeous Victoria-era cottage overlooking the sea set in an idyllic and peaceful setting next to the beach and a nature conservation area. The cottage has been recently (2016) renovated to a very high standard throughout. Both the living room and the b …see more

from $128 / night

$533 - $1,678 / week

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avg. 1 hour 23 minutes

from $128 / night

(7) 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 $243 / night

$1,042 - $2,749 / week

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avg. 44 minutes

from $243 / night

(10) Excellent 

14

Vacation apartment in Shanklin

Isle of Wight / Shanklin

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Private garden
New modern holiday apartments Fantastic area 3 minutes walk to the beach Bus and train station and town and Shanklin old village and chine all within short walking distance All mod cons internet tvs in every room Power shower in a luxurious bathroom Kitchen all equ …see more

from $176 / night

$1,109 - $1,582 / week

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from $176 / night

(1) Excellent 

11

Vacation apartment in Ryde

Isle of Wight / Ryde

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Flatlet 4 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 4 comprises of a full size pull down double bed in the lounge area. A …see more

from $93 / night

$317 - $667 / week

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from $93 / night

(23) Excellent 

Certificate of Excellence

23

Vacation chalet in Freshwater

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
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 spectacular v …see more

Certificate of Excellence

from $49 / night

$338 - $608 / week

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Responds fast!
avg. 2 hours 5 minutes

from $49 / night

(1) Excellent 

28

Vacation bungalow in Niton

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 2 mi
  • Pet friendly
KIVUVU, believed to be a Bantu word meaning peace, which is exactly what we hope you find here. Kivuvu is a detached bungalow next to our house. You have your own fenced garden and patio area, to the front is another small patio with a tap and hose available for washing …see more

from $88 / night

$613 / week

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from $88 / night

(16) Excellent 

16

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 0.2 mi
  • Child friendly
NEEDLEPOINT is a delightful family owned bungalow situated in west wight just 3 miles from the historic town of Yarmouth and ferry port. Needle Point is set on a quiet secluded part of the Lindstone Chine Holiday Park just 2 minutes from the private beach and adjoining …see more

from $53 / night

$371 - $741 / week

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avg. 3 hours 1 minutes

from $53 / night

(1) Very Good 

9

Ventnor Vacation apartment rental

Isle of Wight / Ventnor

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Car not necessary
Cantabile is  a one bedroom holiday apartment with a  king sized bed, en-suite bathroom, open plan living area & views across the town towards the sea and up to the downs behind Ventnor.   Located in the centre of the town with easy access to beach, town centre and dow …see more

from $105 / night

$736 / week

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from $105 / night

(20) Excellent 

Certificate of Excellence

30

Vacation cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
This converted Dairy Cottage is the ultimate in relaxing, set in a quiet farm location in the beautiful West Wight countryside. The cottage has its own private garden and terrace area with secure parking, and benefits from a hot tub which is shared between 3 prop …see more

Certificate of Excellence

from $155 / night

$674 - $1,146 / week

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Responds fast!
avg. 1 hour 34 minutes

from $155 / night

(50) Excellent 

15

St Lawrence, Ventnor Vacation apartment rental

Ventnor / St Lawrence, 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, 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

from $68 / night

$304 - $869 / week

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from $68 / night

(9) 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 $162 / night

$802 - $1,476 / week

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avg. 1 hour 59 minutes

from $162 / night

13

Vacation apartment rental

Isle of Wight / Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
‘Solent Views’ is a two bedroom apartment situated on Cowes Parade with the Royal Yacht Squadron nearby. This light and airy third floor apartment comprises of a lounge that leads to a balcony, kitchen, family bathroom, one double bedroom and one twin bedroom with wash …see more

from $111 / night

$506 - $843 / week

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from $111 / night