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

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Beach rentals Ventnor
157 properties
Villas Shanklin
124 properties
Holiday rentals Cowes
121 properties
Apartments Sandown
117 properties
Self catering Bembridge
61 properties
Yarmouth
52 properties
Vacation rentals Freshwater
50 properties
Ryde
48 properties
Seaview
25 properties
Wootton Bridge
25 properties
Newport
24 properties
Totland Bay
17 properties
Niton
13 properties
Brading
12 properties
Gurnard
12 properties
St Helens
12 properties
Brighstone
11 properties
East Cowes
11 properties
Chale
11 properties
Shorwell
10 properties

Isle of Wight

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1,527 Vacation rentals

(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 $70 / night

$378 - $784 / week

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Responds fast!
avg. 2 hours 16 minutes

from $70 / night

(27) 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 $210 / night

$700 - $1,260 / week

Inquire View

from $210 / night

(5) Excellent 

19

Vacation home in Cowes

Isle of Wight / Cowes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
Firefly House is a 4 bedroom period townhouse with 2 parking spaces, just a few minutes walk from the historic towncentre, waterfront and marinas of Cowes, home of UK yacht racing, and gateway to the Isle of Wight. It has been beautifully renovated to retain its Vict …see more

from $245 / night

$1,715 / week

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avg. 2 hours 12 minutes

from $245 / night

(5) Excellent 

Certificate of Excellence

15

Vacation bungalow in Freshwater

Isle of Wight / Freshwater

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
3 bedrooms with stunning sea and countryside views, direct access to beach Brambles Farm Bungalow is located in West Wight, a beautiful part of the Island, with miles of heritage coastline, scenic walks, cycle tracks and breathtaking views from Tennyson Down, Headon Wa …see more

Certificate of Excellence

from $105 / night

$490 - $1,190 / week

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avg. 2 hours 18 minutes

from $105 / 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 $168 / night

$973 - $1,533 / week

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avg. 1 hour 50 minutes

from $168 / 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 $175 / night

$1,372 / week

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avg. 28 minutes

from $175 / night

(6) 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 $252 / night

$1,083 - $2,856 / week

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avg. 42 minutes

from $252 / 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 $196 / night

$1,106 - $2,772 / week

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avg. 1 hour 50 minutes

from $196 / night

(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 $154 / night

$910 - $1,953 / week

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from $154 / night

(19) Excellent 

20

Vacation cottage in Bonchurch

Ventnor / 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 $140 / night

$784 - $1,106 / week

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avg. 1 hour 50 minutes

from $140 / night

(7) Excellent 

14

Merstone Vacation cottage rental

Isle of Wight / Merstone

3 7 4 nights min

  • 3 bedrooms
  • Sleeps 7
  • 4 nights min
  • Child friendly
If you like walking or cycling, then this property is ideally situated. Centrally located on the Island, this converted Barn offers comfort with all modern amenities. Wood floors throughout and beams in the comfy lounge with an open plan kitchen and dining area. Suro …see more

from $168 / night

$1,050 / week

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avg. 2 hours 49 minutes

from $168 / 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 $100 / night

$700 - $1,260 / week

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from $100 / night

(23) Excellent 

19

Vacation cottage in Ventnor

Isle of Wight / Ventnor

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
The house is perfect for: • a family holiday - just 2 minutes walk from the beach, private parking, pubs & restaurants & cafés within 5 minutes walking distance. • sunbathing in the garden while enjoying the sight and sound of the sea. • wonderful coastal walks, botani …see more

from $98 / night

$686 - $1,246 / week

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avg. 3 hours 38 minutes

from $98 / night

(22) Very Good 

Certificate of Excellence

25

Apartment rental in Totland

Totland Bay / Totland Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
The Beach House apartment is situated on the ground floor of the Beach House on the esplanade of the delightful Totland Bay which sits in an area of Natural Outstanding Beauty on the North West coast of the Island. The views are unrivalled, and ever changing, looking …see more

Certificate of Excellence

from $315 / night

$945 - $2,415 / week

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avg. 2 hours 42 minutes

from $315 / night

(33) 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 comfort This quintessential English cottage nestles in the heart of the St Lawrence Undercliffe. A sought after location officially recognise …see more

from $210 / night

$735 - $1,813 / week

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from $210 / night

(3) Very Good 

15

Apartment rental in Cowes

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This remarkably decorated apartment is great for families with a large living area and three good sized bedrooms. The benefit of two balconies either side means you can choose whether to soak up the sun or enjoy some shade. The balcony off of the kitchen is a perfect pl …see more

from $231 / night

$980 - $4,340 / week

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from $231 / night

(4) Very Good 

12

Vacation apartment in Bembridge

Bembridge / Bembridge Harbour

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
1 Driftwood is a delightful and bright first floor apartment set in a unique location enjoying panoramic views of The Solent and is adjacent to the beach and coastal walks. Bembridge Ledge is accessed across the grassland in front of the property or via Fishermans Walk. …see more

from $140 / night

$350 - $749 / week

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from $140 / night

(19) Excellent 

Certificate of Excellence

22

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

Certificate of Excellence

from $66 / night

$588 / week

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Responds fast!
avg. 38 minutes

from $66 / night

(21) 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. Our lovely holiday home is available to share. Ideal for all the family, secure 8 acre grounds for th …see more

from $209 / night

$1,463 - $2,093 / week

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avg. 2 hours 40 minutes

from $209 / night

(16) 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 $168 / night

$910 - $1,666 / week

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avg. 1 hour 50 minutes

from $168 / night

19

Vacation cottage in Brading

Isle of Wight / Brading

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Dating back to 1811 and originally a fisherman’s cottage, this beautiful 3 storey character holiday home has been lovingly restored by the current owners with the accommodation retaining many character features yet combining the benefits of modern additions. The accomm …see more

from $229 / night

$735 - $1,470 / week

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from $229 / night

16

Vacation caravan/mobile home in Rookley

Isle of Wight / Rookley

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Welcome to our lovely, family run caravan on Rookley country park in the Isle of Wight. Newly refurbished for 2017 with a fun, seaside theme, everything brand new including bedding, flooring and all kitchen appliances. Site includes two fishing lakes, indoor & outdoor …see more

from $42 / night

$294 - $840 / week

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from $42 / 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 $55 / night

$385 - $770 / week

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avg. 2 hours 36 minutes

from $55 / night

(11) Excellent 

19

Cowes Vacation bungalow rental

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Stunning views of the Solent and Southampton Water. Watch the world sail by from the lounge window.This bungalow is situated on an elevated position close to the Royal Yacht Squadron in Cowes. It is just a 5 minute walk from the bustling centre of Cowes, with its numero …see more

from $154 / night

$735 - $2,060 / week

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from $154 / night

(6) Very Good 

11

Cowes Vacation caravan/mobile home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Our caravan is situated a couple of minutes walk from all the site amenities and a 10 minute walk to the beach. Our private family owned caravan with 3 bedrooms to sleep 6 people. It has all the amenities needed and bedding is included. It is a great place to bring the …see more

from $110 / night

$560 - $973 / week

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from $110 / night

(11) Excellent 

21

Vacation apartment in Cowes

Isle of Wight / Cowes

2 5 Min stay varies

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

from $140 / night

$546 - $2,793 / week

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Responds fast!
avg. 1 hour 48 minutes

from $140 / night

(6) Excellent 

Certificate of Excellence

27

Vacation home in Shorwell

Isle of Wight / Shorwell

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Private garden
A rural village holiday getaway close to the unspoilt south west cost of the Isle of Wight. New for 2015 Church View is a stylish and modern family house set in the picturesque village of Shorwell opposite its historic church and country pub. Surrounded by beautiful cou …see more

Certificate of Excellence

from $140 / night

$840 - $1,960 / week

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Responds fast!
avg. 3 hours 34 minutes

from $140 / night

(8) Very Good 

Certificate of Excellence

17

Vacation chalet in Niton

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
The Long Hop 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 e …see more

Certificate of Excellence

from $70 / night

$385 - $455 / week

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Responds fast!
avg. 21 minutes

from $70 / night

(7) Excellent 

Certificate of Excellence

12

Sandown Vacation chalet rental

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Car not necessary
Comfortable and clean holiday chalet for a family or couple on a site which overlooks the beautiful Sandown Bay. Carpeted lounge and bedrooms Heaters in all rooms (including electric fire stove in lounge) Linen provided for all beds (plus duvets and pillows) TV with in …see more

Certificate of Excellence

from $35 / night

$154 - $672 / week

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Responds fast!
avg. 1 hour 11 minutes

from $35 / night

(7) Excellent 

12

Sandown Vacation apartment rental

Isle of Wight / Sandown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
The luxury 3 bed apartment with stunning sea views is located in a desirable area on Sandown seafront.It is situated on the top floor (7th Floor) of an exclusive development offering panoramic sea views with secure allocated parking for 1 car in the south of the beautif …see more

from $98 / night

$630 - $1,820 / week

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from $98 / night

(18) Excellent 

Certificate of Excellence

22

Shorwell Vacation cottage rental

Isle of Wight / Shorwell

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Private garden
Character Isle of Wight cottage located in the picture postcard village of Shorwell, opposite the excellent Crown Inn. The cottage dates from 1800 and has been modernised to create a cosy and spacious "home from home" holiday cottage with a beautiful lawned garden, broo …see more

Certificate of Excellence

from $139 / night

$511 - $1,449 / week

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Responds fast!
avg. 1 hour 12 minutes

from $139 / night

(3) Excellent 

44

Vacation chalet in Sandown

Isle of Wight / Sandown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Lantern Cove is a family owned holiday rental. It has recently undergone full refurbishment resulting in a modern, bright and well equipped property. We are just 5 minutes from the beach and the site is set in a peaceful location, surrounded by countryside views. We als …see more

from $76 / night

$349 - $727 / week

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from $76 / night

(16) 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 $139 / night

$483 - $1,071 / week

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avg. 1 hour 12 minutes

from $139 / night

29

Vacation home in Newport

Isle of Wight / Newport

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Child friendly
  • Private garden
ACCOMMODATION Entered on the ground floor into a reception hall with access to a ground floor wet room with shower, easy reach sink and WC with optional toilet frame, seat riser, grab rails and a shower wheelchair all available on request. A large bedroom with king si …see more

from $353 / night

$2,468 / week

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from $353 / night

(17) Excellent 

21

Vacation chalet rental

Isle of Wight / Sandown

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Pet friendly and with free WiFi, 'Fossils Reach' is situated on a quiet part of the holiday park. It's not overlooked, and has a grassed area to the front with sea glimpses viewed through the trees. Local wildlife includes rabbits, foxes, pheasants and the occasional …see more

from $70 / night

$350 - $735 / week

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Responds fast!
avg. 1 hour 41 minutes

from $70 / night

(27) Excellent 

Certificate of Excellence

7

Vacation lodge with golf nearby in Whippingham

Isle of Wight / Whippingham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 4 mi
  • Child friendly
  • Car not necessary
The Victorian lodge house is one of a pair situated within the Barton Estate close to Osborne House which was Queen Victoria's holiday residence of choice. It has been beautifully and lovingly refurbished with your comfort in mind. The house sleeps 6 and offers flexib …see more

Certificate of Excellence

from $140 / night

$1,435 / week

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Responds fast!
avg. 2 hours 30 minutes

from $140 / 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 $70 / night

$350 - $1,113 / week

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Responds fast!
avg. 2 hours 54 minutes

from $70 / night

(9) Excellent 

33

Bungalow rental in Ryde with golf nearby

Isle of Wight / Ryde

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Appleysands is a detached, modern property set in a very quiet Close just a 5 minutes stroll down a leafy lane to the FAB soft, sandy Appley beach. A toy filled playden in a child safe, enclosed garden to keep children happy while you relax on the Decking and breathe …see more

from $140 / night

$630 - $1,470 / week

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Responds fast!
avg. 2 hours 59 minutes

from $140 / night

(9) Excellent 

35

Vacation cottage in Bonchurch

Ventnor / Bonchurch

4 8 Min stay varies

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

from $210 / night

$910 - $2,772 / week

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Responds fast!
avg. 1 hour 50 minutes

from $210 / night

(28) Excellent 

14

Apartment rental in Shanklin

Shanklin / Old Village

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Car not necessary
Luxury ground floor apartment within a beautiful old Victorian Priory, enveloped in breath taking scenery.Ocean Deck is situated on the coastal path, set within two acres of woodland overlooking the sea.Double doors from the lounge/diner open onto a large secluded decki …see more

from $119 / night

$560 - $1,120 / week

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from $119 / night