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

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1,655 Vacation rentals

(1) Excellent 

14

Ventnor Vacation lodge rental

Isle of Wight / Ventnor

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
The perfect property for an escape to the country, The Lodge is a beautiful modern retreat set in beautiful Isle of Wight countryside. With direct access to the downs straight from the doorstep, The Lodge is a firm favourite with walkers and dog owners. Inside, The Lodg …see more

from $96 / night

$503 - $1,034 / week

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avg. 3 hours 41 minutes

from $96 / night

(3) Excellent 

36

East Cowes Vacation home rental

Isle of Wight / East Cowes

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Car not necessary
Award winning Old School House conversion with river views on the banks of the River Medina, the house offers parking for ONE vehicle only directly outside the house. Pet friendly. Beautifully decorated, exposed brickwork, vaulted ceiling, tall sash windows. Excellent …see more

from $163 / night

$1,035 - $2,957 / week

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avg. 8 minutes

from $163 / night

(54) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $74 / night

$355 - $1,090 / week

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from $74 / night

(21) 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

$646 - $1,188 / week

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from $93 / night

(27) Excellent 

31

Vacation cottage in Wootton

Isle of Wight / Wootton

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 $181 / night

$853 - $1,834 / week

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from $181 / night

(39) 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 1st floor 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 hig …see more

from $91 / night

$452 - $1,098 / week

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avg. 58 minutes

from $91 / night

(30) 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 $194 / night

$581 - $1,285 / week

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from $194 / night

(4) Excellent 

Certificate of Excellence

28

Shorwell Vacation cottage rental

Isle of Wight / Shorwell

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 4 mi
  • Child friendly
  • Private garden
Quality and style flows through this stunning cottage which has been lovingly renovated to a high standard and is centrally located in the ancient rural village of Shorwell, on the west coast of the Isle of Wight. A landmark house within the village, the cottage was bui …see more

Certificate of Excellence

from $185 / night

$1,149 - $1,775 / week

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avg. 51 minutes

from $185 / night

(28) Excellent 

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

from $156 / night

$1,028 - $1,775 / week

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from $156 / night

9

Vacation cottage in Apse Heath

Isle of Wight / Apse Heath

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
This cottage is situated alongside five other cottages in a small rural hamlet,just 1.5 miles from the Isle of Wight’s east coast. The tranquil location makes it the perfect choice for those who want to relax and enjoy a break from the hustle and bustle of daily life …see more

from $80 / night

$556 - $1,676 / week

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from $80 / night

(18) 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 $89 / night

$2,329 / week

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from $89 / night

(11) 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 $111 / night

$555 - $1,109 / week

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avg. 3 hours 4 minutes

from $111 / night

(12) Very Good 

Certificate of Excellence

23

Vacation chalet in Niton

Isle of Wight / Niton

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 5 mi
  • Private garden
A contemporary hillside chalet in the southernmost tip of the Isle of Wight, set in beautiful gardens, with views over treetops towards the sea, and adjacent to the coastal path. Spend a relaxing week at Pebbles, a thoughtfully equipped compact terraced chalet, tucked a …see more

Certificate of Excellence

from $67 / night

$414 - $614 / week

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avg. 1 hour 32 minutes

from $67 / night

(35) Excellent 

Certificate of Excellence

29

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
  • Car not necessary
Seaside View holiday apartment ideally situated a stones throw from the beach. From the minute you arrive you can sit and relax. Watching the sea whatever the season, it is always transfixing, either from the comfort of the open plan kitchen, lounge, diner or from your …see more

Certificate of Excellence

from $128 / night

$562 - $887 / week

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avg. 3 hours 26 minutes

from $128 / night

19

Merstone Vacation cottage rental

Isle of Wight / Merstone

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly
This property is located in a fantastic central position on the Isle of Wight,making it easy for guests to access all of the island’s top attractions and beaches. The area immediately around the cottage comprises of peaceful fields with zig-zagging footpaths leading …see more

from $60 / night

$420 - $934 / week

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from $60 / night

10

Apartment rental in Ryde

Isle of Wight / Ryde

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Car not necessary
The perfectly located apartment for leisure or work. Directly opposite pristine beaches and close to transport links: hovercraft and catermaran, this apartment has all you need for a short or long let. Stunning views of the ever moving and busy Solent will keep you ent …see more

from $113 / night

$710 - $740 / week

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avg. 1 hour 2 minutes

from $113 / night

(1) Excellent 

19

Ventnor Vacation villa rental

Isle of Wight / Ventnor

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
You can’t beat the healing nature of the sea, if you are lucky enough to get the opportunity to stay at this villa you will not only get to hear the soothing of the sea, you will awake to the panoramic sea view in the morning and generally see the sun rise above the sea …see more

from $170 / night

$781 - $1,294 / week

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avg. 1 hour 42 minutes

from $170 / night

(3) Excellent 

7

Bonchurch Vacation apartment rental

Ventnor / Bonchurch

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly
Unique old world Pub/Restaurant with one holiday apartment, enclosed in a continental style courtyard. The apartment is across the courtyard from the Bar. There are 11 steps leading up to the entrance. There is a large lounge, dining room with kitchenette ( no oven ) …see more

from $126 / night

$814 - $1,021 / week

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from $126 / night

(4) Excellent 

19

Vacation cottage in Seaview

Isle of Wight / Seaview

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
"The perfect self-catering holidays in Seaview on the Isle of Wight" Seaview Holidays offer luxury self-catering accommodation in a stunning, secluded location overlooking the beautiful Hersey Nature Reserve on the Isle of Wight..... We offer 2, 3 and 4 bedroom holida …see more

from $215 / night

$1,501 / week

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from $215 / night

(17) Very Good 

21

Apartment rental in Totland

Totland Bay / Totland Bay

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
This luxurious spacious apartment is literally a stone's throw from the sea. It is almost like being on board a luxury cruise liner with stunning views of the unspoilt pretty Totland Bay. There are 2 bathrooms, large lounge/ dining room, bedroom with a king size bed, …see more

from $289 / night

$1,074 - $1,918 / week

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avg. 43 minutes

from $289 / night

11

Vacation cottage rental

Isle of Wight / Freshwater

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Freshwater is three miles away from Yarmouth,known for its maritime story and its ferry port and marina. Freshwater is just over half-an-hour’s drive from Newport - the busiest town on the island. It’s the perfect base from which to explore the Needles Landmark Attra …see more

from $62 / night

$429 - $1,613 / week

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from $62 / night

(13) 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 $148 / night

$584 - $2,950 / week

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avg. 2 hours 36 minutes

from $148 / night

9

Vacation cottage in Carisbrooke

Isle of Wight / Carisbrooke

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly
Situated on a farm in the beautiful South Wight countryside,this property enjoys lovely views across nearby lakes and open countryside to Ventnor Downs. Set out on foot or bicycle to follow one of the many paths and trails that lie close to the farm,following the Riv …see more

from $66 / night

$459 - $1,392 / week

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from $66 / night

(23) Excellent 

Certificate of Excellence

20

Apartment rental in Bembridge

Bembridge / St Helens, Bembridge

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Uniquely positioned on a quiet residential street which leads from St Helen's Village Green via Mill Lane to the sea. From the bottom of the lane turn left at the Old Mill and walk across the Duver to St Helens beach and sample the menu at Baywatch cafe; or turn right …see more

Certificate of Excellence

from $96 / night

$333 - $738 / week

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Responds fast!
avg. 1 hour 45 minutes

from $96 / night

(13) Excellent 

15

Vacation chalet in Ventnor

Isle of Wight / Ventnor

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
RECENTLY RENOVATED! BOOK WHILST THERE IS STILL AVAILABILITY THIS YEAR! Come and relax at this 3 bedroom detached villa. This high spec villa was recently completely refurbished with all new modern fixtures and fittings. It has been brilliantly transformed into a …see more

from $159 / night

$814 - $1,575 / week

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from $159 / night

(29) Excellent 

Certificate of Excellence

16

Vacation chalet in Sandown

Isle of Wight / Sandown

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0.2 mi
  • Child friendly
  • Pet friendly
Chalet 191 is situated in a peaceful location, just a few minutes walk either by road or coastal footpath to beautiful, safe, sandy beaches. From the site there are stunning views of Culver Cliffs and Sandown Bay. The shops and attractions of Sandown are a 3 minute driv …see more

Certificate of Excellence

from $52 / night

$370 - $740 / week

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Responds fast!
avg. 21 minutes

from $52 / night

(4) Excellent 

Certificate of Excellence

25

Vacation apartment accommodation

Ventnor / Ventnor Bay

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Child friendly
Our apartment is in the best location in Ventnor, only about 50 meters to the family friendly beach and only a 5 minute walk to town. Inspired by our love of the sea, the apartment is decorated with lovely coastal themes and is equipped with kitchen, lounge, dining ro …see more

Certificate of Excellence

from $148 / night

$814 - $1,405 / week

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Responds fast!
avg. 2 hours 39 minutes

from $148 / night

15

Vacation cottage in Fishbourne

Isle of Wight / Fishbourne

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly
One of two cottages recently renovated,this property embodies country style and living. It lies within an excellent walking and cycling area,with footpaths and tracks extending in various directions,including to the coast at Wootton Creek,the woods at Briddlesford Co …see more

from $67 / night

$468 - $939 / week

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from $67 / night

12

Cottage rental in Whitwell

Ventnor / Whitwell

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Child friendly
Situated in an attractive courtyard,this property is surrounded by open fields stretching out towards the Downs. A short stroll will bring you to the nearby village of Godshill,home to a variety of tearooms,restaurants and pubs. A wonderful walking area,footpaths lea …see more

from $77 / night

$534 - $1,831 / week

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from $77 / night

(58) Excellent 

Certificate of Excellence

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 quiet setting. Well behaved children welcome.It really is a home from home with the added luxury of your own heated swimming pool.. The accommodation sleeps 4 adults and 2 children. The cabin is situated in a secluded area surrounded by …see more

Certificate of Excellence

from $133 / night

$932 - $2,070 / week

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Responds fast!
avg. 2 hours 11 minutes

from $133 / night

(15) Excellent 

13

Vacation apartment in Wootton

Wootton / Fishbourne

3 6 min stay varies

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

from $119 / night

$510 - $1,471 / week

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avg. 2 hours 35 minutes

from $119 / night

21

Cottage rental in Gurnard

Isle of Wight / Gurnard

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child friendly
This property is located in the Gurnard area of Cowes. This popular residential area is home to a fantastic golf course which is situated at the end of the property’s garden,the clubhouse to which is situated just 200 metres away. Cowes is renowned for its excellent …see more

from $170 / night

$1,187 - $3,445 / week

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from $170 / night

10

Carisbrooke Vacation cottage rental

Isle of Wight / Carisbrooke

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
This cottage enjoys a quiet location on the owner's farm in the village of Carisbrooke. The village is known for its impressive castle,where visitors can not only visit the Norman walls and keep,but also look around the beautiful Princess Beatrice Gardens and the tra …see more

from $74 / night

$517 - $1,632 / week

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from $74 / night

(3) Very Good 

12

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 1 A cosy and secluded studio Apartment situated on the second 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 …see more

from $67 / night

$348 - $584 / week

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Responds fast!
avg. 3 hours 24 minutes

from $67 / night

9

Vacation cottage rental

Ventnor / Whitwell

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly
This cottage enjoys a quiet rural location,surrounded by fields,at the bottom of Appuldurcombe Down overlooking the picturesque village of Godshill. A short,pleasant walk along the wooded footpath from the cottage brings guests directly to the village,where they will …see more

from $64 / night

$446 - $798 / week

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from $64 / night

(18) Excellent 

Certificate of Excellence

24

Sandown Vacation apartment rental

Isle of Wight / Sandown

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Apartment three , completely refurbished in 2013 offers modern and spotlessly clean accommodation, comprising shower room, kitchen diner and living room. The bedroom can either be prepared for your arrival as a twin or as a six foot wide king size with french doors lea …see more

Certificate of Excellence

from $49 / night

$342 / week

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Responds fast!
avg. 2 hours 36 minutes

from $49 / night

(47) Excellent 

Certificate of Excellence

43

Vacation apartment in Shanklin

Shanklin / Luccombe Village

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
The Priory is a large, handsome Victorian residence at Luccombe (comprising of eleven apartments) situated on the edge of Shanklin, on a spectacular stretch of cliffs. The apartment is located on the top (second) floor with far reaching views over Shanklin and Sandown …see more

Certificate of Excellence

from $133 / night

$932 / week

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from $133 / night

(17) Excellent 

Certificate of Excellence

16

Freshwater Vacation bungalow rental

Isle of Wight / Freshwater

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • 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

Certificate of Excellence

from $119 / night

$732 / week

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Responds fast!
avg. 2 hours 13 minutes

from $119 / night

(30) Very Good 

12

Seaview Vacation cottage rental

Isle of Wight / Seaview

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
"The perfect self-catering holidays in Seaview on the Isle of Wight" Seaview Holidays offer luxury self-catering accommodation in a stunning, secluded location overlooking the beautiful Hersey Nature Reserve on the Isle of Wight..... We offer 2, 3 and 4 bedroom holida …see more

from $169 / night

$1,182 / week

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from $169 / night

(12) Very Good 

24

Cowes Vacation home rental

Cowes / West Cowes

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Town centre location ! In the heart of the action...yet peaceful and tucked away ! Stunning 2 bedroom house in the heart of Cowes old town offering contemporary seaside accomodation sleeping up to 7 guests ( 5 plus 2 on sofa bed ). Bedroom 1 consists of twin beds th …see more

from $170 / night

$1,186 / week

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Responds fast!
avg. 3 hours 57 minutes

from $170 / night

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