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

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Holiday rentals Cowes
120 properties
Beach rentals Ventnor
102 properties
Apartments Sandown
91 properties
Villas Shanklin
86 properties
Ryde
52 properties
Vacation rentals Freshwater
44 properties
Yarmouth
41 properties
Holiday cottages Bembridge
39 properties
Seaview
34 properties
Newport
18 properties
Niton
16 properties
Wootton Bridge
15 properties
Gurnard
13 properties
Totland Bay
13 properties
Shorwell
12 properties
Whitwell
11 properties
Bonchurch
10 properties
St Helens
10 properties
Brighstone
10 properties
Godshill
8 properties

Isle of Wight

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802 Vacation rentals

(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 $191 / night

$667 - $1709 / week

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from $191 / night

(18) Very Good 

16

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  …see more

from $89 / night

$623 - $1118 / week

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from $89 / night

(7) Excellent 

17

Cottage rental in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

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

from $102 / night

$572 - $1207 / week

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from $102 / night

(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
Thorness Bay is spread out across fields, framed on one side by the sea with stunning views. With the Park open 12 months of the year and a full entertainment season running from Easter to the end of October Thorness Bay makes an ideal family centered holiday or the p  …see more

from $83 / night

$477 - $1099 / week

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from $83 / night

(8) Excellent 

37

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 $197 / night

$788 - $1829 / week

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from $197 / night

(30) Excellent 

33

Vacation cottage in Whitwell

Isle of Wight / Whitwell

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Ferndale is a large, charming, four bedroom Victorian cottage on the Isle of Wight, set in idyllic countryside, with a beautiful garden, stunning views of surrounding fields and walks from the doorstep. The house was recently refurbished to a very high standard and has  …see more

from $191 / night

$635 - $1778 / week

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from $191 / night

(42) Excellent 

27

Ventnor Vacation apartment rental

Isle of Wight / Ventnor

1 2 Min stay varies

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

from $89 / night

$534 - $915 / week

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from $89 / night

(82) Excellent 

25

Vacation cottage in Ventnor

Ventnor / Niton Undercliff

3 8 Min stay varies

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

from $153 / night

$724 - $1874 / week

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from $153 / night

(18) Excellent 

24

Vacation caravan/mobile home in Bembridge

Isle of Wight / Bembridge

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
*We have more statics available, so please contact us even if the calendar says unavailable*This fantastic spacious and homely static caravan is in the same area as The Other Statics we have available at Sandhills Holiday Park so if you wanted two or more famili  …see more

from $127 / night

$445 - $826 / week

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from $127 / night

(15) 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 $13 / night

$585 - $2490 / week

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from $13 / night

17

Vacation home in Bonchurch

Isle of Wight / Bonchurch

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
This pretty, period cottage in a unique position just 2 minutes above Monks Bay Beach is the perfect destination for a family getaway at any time of the year. With spectacular sea views from every room, a large garden and within walking distance along the sea wall to V  …see more

from $254 / night

$1175 - $2223 / week

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from $254 / night

(21) 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
  • Child friendly
  • Car not necessary
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 $191 / night

$1016 - $2223 / week

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from $191 / night

(3) Excellent 

27

Wroxall Vacation cottage rental

Isle of Wight / Wroxall

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Manor Farm Cottage is a detached 3 bedroom traditional stone cottage located about 3 miles from Ventnor on the southern tip of the Isle of Wight. Nestled in the surrounding downs away from it all the cottage is the perfect family bolthole. It is a luxury home from hom  …see more

from $254 / night

$826 - $2032 / week

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from $254 / night

(6) Excellent 

16

Yarmouth Vacation villa rental

Isle of Wight / Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Woodlands Cottage is a stunning four bedroom property overlooking the sea and set in well over an acre of it's own private woodland on the west coast of the Isle of Wight. The property is incredibly tranquil and secluded. The master bedroom has a very spacious wooden d  …see more

from $178 / night

$921 - $2845 / week

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from $178 / 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 $172 / night

$883 - $1772 / week

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from $172 / night

(14) Excellent 

23

Vacation home in Ryde

Isle of Wight / Ryde

2 6 7 nights min

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

from $69 / night

$477 - $1016 / week

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from $69 / night

(7) Very Good 

35

Vacation cottage in Bonchurch

Isle of Wight / Bonchurch

4 8 Min stay varies

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

from $13 / night

$1385 - $2528 / week

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from $13 / night

(15) 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 $79 / night

$399 - $743 / week

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from $79 / night

(23) Excellent 

24

Vacation tree house in Whippingham

Isle of Wight / Whippingham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Suitable for children age 5+
Come and stay in a cosy and exciting little house in the trees. Fantastic for adventurous families, but equally wonderful as a romantic break for couples, or a quirky treat for groups of friends. Enjoy the privacy and peace of living right in the heart of natur  …see more

from $191 / night

$699 - $1651 / week

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from $191 / night

(5) Very Good 

24

St Helens Vacation home rental

Isle of Wight / St Helens

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
A refurbished holiday home fronting the village green and with downland views from the back bedroom. The home offers 3 bedrooms (2 x doubles & one with 2 x bunks), lounge, separate dining area, fitted kitchen, rear lobby and family bathroom. The accommodation is b  …see more

from $64 / night

$442 - $718 / week

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from $64 / 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 $89 / night

$496 - $661 / week

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from $89 / 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 $59 / night

$337 - $877 / week

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from $59 / 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 grounds for the  …see more

from $190 / night

$1328 - $1899 / week

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from $190 / night

(5) Excellent 

16

Cowes Vacation townhouse rental

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Lovely relaxing townhouse overlooking Cowes Marina with fabulous views of the Solent beyond, situated right in the heart of Cowes. Three bedrooms, two bathrooms, spacious sitting room and kitchen with huge window over marina. Flat screen freeview TV's, Wifi through  …see more

from $166 / night

$496 - $1207 / week

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from $166 / night

(36) Excellent 

23

Vacation log cabin with indoor pool in Ryde

Isle of Wight / Ryde

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
The cabin is set in a tranquil quite setting. Well behaved children welcome.It really is a home from home with the added luxury of your own heated swimming pool and sauna. The accommodation sleeps 4 adults and 2 children. The cabin is situated in a secluded area surro  …see more

from $119 / night

$826 - $1778 / week

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from $119 / night

(14) Excellent 

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 $147 / night

$572 - $1385 / week

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from $147 / 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 $91 / night

$635 - $1175 / week

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from $91 / night

(35) Very Good 

17

Vacation chalet in Yaverland

Sandown / Yaverland

2 4 Min stay varies

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

from $41 / night

$248 - $604 / week

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from $41 / night

(29) Very Good 

21

Vacation cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

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

from $96 / night

$502 - $1582 / week

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from $96 / night

(4) Excellent 

13

Cottage rental in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
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 $166 / night

$731 - $1080 / week

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from $166 / night

(17) 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 path on  …see more

from $77 / night

$413 - $794 / week

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from $77 / 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 walk  …see more

from $64 / night

$445 - $883 / week

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from $64 / night

(9) Excellent 

18

Sandown Vacation apartment rental

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Rosie's Place is a spacious and airy split level apartment within walking distance of the beach and High Street with 2 private off road car spaces. When it's not let out Rosie's Place is our holiday home and so we have furnished it and equipped it to the highest stand  …see more

from $89 / night

$381 - $1016 / week

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from $89 / night

(14) Very Good 

23

Vacation apartment in Cowes

Cowes / West Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Child friendly
Light and airy modern penthouse apartment with fantastic sea views (best in Cowes) towards Calshot Spit and the Central Solent. Close enough to the water to hear boats tack! Yards from the Royal Yacht Squadron, five minute walk along the sea front to the high street and  …see more

from $64 / night

$420 - $1937 / week

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from $64 / night

(4) Very Good 

21

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 $64 / night

$445 - $1010 / week

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from $64 / night

(4) Excellent 

8

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
This is a spacious two bed apartment on the first floor, with a large balcony overlooking the sea., the beach is literally metres away with safe, sandy beaches & promenade stretching miles in either direction Open plan living area with corner sofa, larg  …see more

from $134 / night

$705 - $1461 / week

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from $134 / night

(11) Excellent 

20

Vacation cottage in Yarmouth

Yarmouth / Fort Victoria

2 4 7 nights min

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

from $108 / night

$756 - $1582 / week

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from $108 / night

(2) Excellent 

8

Vacation caravan/mobile home in St Helens

Isle of Wight / St Helens

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
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 $63 / night

$436 - $614 / week

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from $63 / night

(13) Excellent 

22

St Helens Vacation lodge rental

Isle of Wight / St Helens

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Admiral Park 8 is a super New Hampshire 40x16 luxury lodge. It comes with the highest spec and we are confident you'll love it. .....The lodge overlooks Bembridge Bay with sandy beaches, marina and nature reserve. (The main picture is an identical lodge in a different s  …see more

from $83 / night

$502 - $1645 / week

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from $83 / night

(18) Excellent 

21

Vacation bungalow in Freshwater

Isle of Wight / Freshwater

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Brambles Farm Bungalow is set in a peaceful, rural location and has far reaching sea views. There is access to the beach and coastal paths from the garden. You can watch the boats sail by, enjoy BBQ's and see spectacular sunsets from the patio furnished with table, chai  …see more

from $100 / night

$699 - $756 / week

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from $100 / night