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

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Holiday rentals Cowes
127 properties
Beach rentals Ventnor
125 properties
Villas Shanklin
109 properties
Apartments Sandown
104 properties
Self catering Bembridge
66 properties
Ryde
64 properties
Vacation rentals Freshwater
54 properties
Yarmouth
53 properties
Seaview
42 properties
Wootton Bridge
24 properties
Totland Bay
17 properties
Niton
17 properties
Newport
16 properties
St Helens
13 properties
Gurnard
12 properties
Brading
12 properties
Bonchurch
12 properties
Whitwell
10 properties
Shorwell
10 properties
East Cowes
10 properties

Isle of Wight

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957 Vacation rentals

(28) Excellent 

26

Vacation caravan/mobile home with shared pool in Thorness Bay

Cowes / Thorness Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
The Salisbury is a beautifully spacious, bright and airy (2011 model) 38' x 12' 3 bedroom caravan. It is ideally suited for families and can accommodate a maximum of 4 adults and 2 children is non-smoking and we do not allow pets. It boasts double glazing and full do …see more

from $85 / night

$488 - $1001 / week

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from $85 / 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 $390 / night

$1203 - $6065 / week

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from $390 / 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 $98 / night

$683 - $1203 / week

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from $98 / night

(17) Excellent 

36

Vacation cottage rental

Isle of Wight / 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 $117 / night

$585 - $2548 / week

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from $117 / 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 comfort This quintessential English cottage nestles in the heart of the St Lawrence Undercliffe. A sought after location officially rec …see more

from $195 / night

$683 - $1749 / week

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from $195 / 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 $202 / night

$806 - $1872 / week

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from $202 / night

(7) 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 $143 / night

$910 - $1417 / week

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from $143 / night

(18) Very Good 

14

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 $92 / night

$637 - $1222 / week

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from $92 / 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 $77 / night

$533 - $1164 / week

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from $77 / night

(26) 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 $195 / night

$1300 - $2275 / week

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from $195 / night

(3) Excellent 

14

Cowes Vacation home rental

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
A superb house in the Cowes recently refurbished to a high standard overlooking the marina with its own pontoon. The house has central heating and double glazing. This modern town house split over 4 levels has a large fully fitted kitchen including a dishwasher, fridge …see more

from $650 / night

$2600 - $4550 / week

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from $650 / night

(16) 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 $143 / night

$715 - $1027 / week

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from $143 / night

9

Vacation cottage rental

Bembridge / Bembridge Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
These delightfull. newly built cottages are set in the heart of Bembridge village. When you walk in to the cottage, you get an immediate feeling that everything has been catered for. The kitchen is fully equipped, the king size bedroom upstairs is wonderfully comfortabl …see more

from $65 / night

$514 - $904 / week

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from $65 / night

(24) 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 $195 / night

$650 - $1164 / week

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from $195 / night

(3) Very Good 

8

Vacation cottage in Cowes

Cowes / West Cowes

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Suitable for children age 5+
A period terraced cottage, located in central Cowes, just 3 minutes walk from the RedJet, just off the High Street. An excellent base for sailing, exploring the island or just enjoying the local amenities, of which there are numerous restaurants, bars, cafes and a high …see more

from $111 / night

$455 - $2600 / week

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from $111 / night

(7) Excellent 

20

Vacation cottage rental

Freshwater / Moons Hill

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Pet friendly
Sunbeam Cottage sits on a leafy lane at the foot of Tennyson Down with woodland to the front and rolling countryside to the rear. The garden stretches out towards the wooded slopes of the down in an AONB. It's lovely to sit at the picnic bench in the top garden with a d …see more

from $121 / night

$845 - $936 / week

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from $121 / night

(6) 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 $98 / night

$501 - $1034 / week

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from $98 / night

(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 different s …see more

from $117 / night

$774 - $1684 / week

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from $117 / night

(29) Excellent 

8

Cottage rental in Newport

Isle of Wight / Newport

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This period Cottage which is thought to be once a Quarry- man`s Cottage which has been recently and lovingly upgraded with all modern facilities. Located on the outskirts of Newport, the main town is easily accessible, a short walk away to many shops, restaurants, bar …see more

from $104 / night

$819 - $1457 / week

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from $104 / night

(18) 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 $169 / night

$904 - $1814 / week

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from $169 / night

(6) Excellent 

24

St Helens Vacation caravan/mobile home rental

Isle of Wight / St Helens

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Pet friendly
Privately owned static caravan on St Helens Holiday Park. Comfortable accommodation sleeps 5/7 people. 3 bedrooms (1 double bedroom, 1 twin bedroom, 1 single bedroom plus double pull out bed in lounge. Fully equipped with central heating, double glazing, electric shower …see more

from $103 / night

$719 / week

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from $103 / night

(19) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $67 / night

$468 - $910 / week

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from $67 / night

(17) 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't …see more

from $82 / night

$410 - $761 / week

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from $82 / night

(15) Excellent 

24

Vacation manor house in Wroxall

Isle of Wight / Wroxall

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Cleveland's Country House offers some of the best quality self-catering accommodation on the island. All accommodation is tastefully decorated and extremely well equipped to create a relaxed atmosphere, a true home from home experience. The grand entrance hall of the …see more

from $387 / night

$1935 - $3677 / week

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from $387 / 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. Our lovely holiday home is available to share. Ideal for all the family, secure 8 acre grounds for th …see more

from $195 / night

$1359 - $1944 / week

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from $195 / night

(22) Excellent 

20

Vacation cottage in Freshwater

Freshwater / Moons Hill

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Little Moon Cottage sits on a leafy lane at the foot of Tennyson Down with woodland to the front and rolling countryside to the rear. The garden stretches out towards the wooded slopes of the down in an AONB. It's lovely to sit at the picnic bench at the end of the gard …see more

from $93 / night

$650 - $1014 / week

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from $93 / night

(28) 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 $73 / night

$437 - $917 / week

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from $73 / night

13

Cowes Vacation home rental

Isle of Wight / Cowes

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
Claremont Cottage is a charming self catering townhouse nestled on Sun Hill in the heart of downtown Cowes and is a perfect location to be based for a short break or family holiday on the Isle of Wight. Offering flexible availability throughout the whole of 2016 it is l …see more

from $162 / night

$626 - $3161 / week

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from $162 / night

(15) 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 $93 / night

$650 - $1170 / week

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from $93 / night

(15) Very Good 

29

Barn rental in Bonchurch

Isle of Wight / 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 $169 / night

$650 - $1417 / week

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from $169 / night

13

Vacation townhouse in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
This centrally located cottage is great for small groups or sailing crews who want to be in the heart of the action Its located just behind The Coast Bar, It has recently been refurbished to a very high standard with lovely laminate flooring & new beds. Due to its loc …see more

from $92 / night

$488 - $1560 / week

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from $92 / night

(2) Excellent 

13

Caravan/mobile home rental in St Helens

Isle of Wight / St Helens

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Privately owned static caravan on St Helens Holiday Park. Comfortable accommodation sleeps 6/8 people. 3 bedrooms (1 double bedroom, 2 twin bedrooms plus double pull out bed in lounge. Fully equipped with central heating, double glazing, electric shower, Freeview TV. Th …see more

from $103 / night

$719 / week

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from $103 / night

(13) 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 $169 / night

$715 - $2860 / week

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from $169 / night

(5) Excellent 

11

Vacation home rental

Isle of Wight / Newport

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Private garden
This spacious and comfortable semi-detached house is situated in a quiet residential neighbourhood within walking distance of Newport town centre. Situated at the top of a hill, the home boasts stunning views of the island and a well-kept private garden. This ho …see more

from $65 / night

$423 - $2509 / week

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from $65 / night

(7) Excellent 

23

Vacation home rental

Isle of Wight / St Helens

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Harbour View is a unique four bedroom semi-detached beach house located at the end of the St Helens Duver, overlooking Bembridge Harbour on the Isle of Wight. A National Trust protected area of natural beauty, surrounded by sand dunes, coastal woods and the sea. A perf …see more

from $112 / night

$780 - $2145 / week

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from $112 / night

(13) Very Good 

10

Vacation home in Gurnard

Isle of Wight / Gurnard

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
A boutique beach house featured in COAST magazine (see photos) offering simple, comfortable and chic living, set over 2 floors with a multitude of sunny outside spaces and decks with sea views, set in the sought after area of old Gurnard just yards from the sandy beach. …see more

from $78 / night

$497 - $2032 / week

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from $78 / night

(2) Good 

30

Home rental in Nettlestone with golf nearby

Isle of Wight / Nettlestone

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
We think you'll love staying at Nettlestone House it has great character, is beautifully furnished, yet is family friendly and has loads of space. Nettlestone House is the main part of a substantial 220 year old stone property which offers impressive and comforta …see more

from $259 / night

$1294 - $2594 / week

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from $259 / night

(24) 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 walk …see more

from $74 / night

$514 - $904 / week

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from $74 / 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 $195 / night

$1170 - $2587 / week

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from $195 / night

(14) Excellent 

23

Vacation home in Ryde

Isle of Wight / Ryde

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $130 / night

$520 - $975 / week

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from $130 / 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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