Short city breaks Isle of Wight | Holiday Lettings UK

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Isle of Wight

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24 Holiday homes

Filters applied: City breaks

Travellers going to Isle of Wight are booking June dates now. Secure your holiday home today and have the perfect trip.

(14) Excellent 

27

Holiday cottage in Brading

Isle of Wight / Brading

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“Had a wonderful stay - Clean and Spacious with warm welcome by Colin and Julie” Colin and Julie gave us warmest welcome and made sure we have a comfortable stay. The house was spacious, kept very tidy and had everything we needed. It was nice to have  …see more

from £105 / night

£675 - £820 / week

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from £105 / night

(28) Excellent 

22

Holiday barn with golf nearby in Freshwater

Freshwater / Freshwater Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Lovely place fab location” We really enjoyed our stay here- we hadn't realised how close to the sea it was and how accessible everything is. The cottage is lovely, lots of information and a good selection of books which the kids loved. Thank you!  …see more

from £55 / night

£360 - £1100 / week

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from £55 / night

(13) Very Good 

15

Chalet letting in Cowes with shared pool

Cowes / Gurnard Pines

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Lovely chalet, good facilities.” A lovely home from home. We stayed for 4 nights over the weekend of the Isle of White Festival. We didn't want to camp at the festival & this chalet was the perfect alternative on a budget. With 4 adults and a 5 month  …see more

from £80 / night

£300 - £600 / week

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from £80 / night

(3) Excellent 

14

Holiday apartment with golf nearby in Ryde

Isle of Wight / Ryde

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Isle Of Wight 2 Bedroom Apartment in tranquil setting amongst the woods ideal for couples or families. Ideal location close to bike routes, public transport and ferries with some super walks.  …see more

from £70 / night

£560 - £700 / week

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from £70 / night

(21) Excellent 

18

Holiday apartment in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+
“Comfy, central and clean.” Stayed only for 3 nights but would have loved to of stayed longer. Lovely light comfortable flat. A little bit of noise at night but I guess that is to be expected when you stay in any central location. Will come back aga  …see more

from £90 / night

£1260 / week

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from £90 / night

(5) Excellent 

20

Holiday cottage in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Private garden
Beautiful town cottage sleeping 4 guests in the heart of Cowes Old Town with luxury welcome hamper and free parking included. Regret that this property does not accept children or pets  …see more

from £150 / night

£1050 - £2200 / week

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from £150 / night

13

Holiday 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  …see more

from £70 / night

£305 - £1200 / week

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from £70 / night

(3) Excellent 

23

Cowes holiday home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Private garden
“Superb!!!” We stayed at the lovely Sun Hill in August for a couple of nights and as a family we were so happy. The house is immaculately clean and is equipped with everything that you could need. The owners kept us well informed and were so helpful  …see more

from £150 / night

£900 - £2400 / week

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from £150 / night

(2) Excellent 

23

Holiday yurt in Newchurch

Sandown / Newchurch

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 8 km
  • Child friendly
  • Ask about pets
We have 3 luxury yurts hidden in a private field in a unique and beautiful location on the Isle of Wight. The yurts were constructed on the Isle of Wight. They are 6 metres in diametre and have a mezzanine deck with kingsize double bed and two full size single mattress  …see more

from £80 / night

£495 - £775 / week

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from £80 / night

(7) Very Good 

24

Ryde holiday apartment rental

Ryde / Appley

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“A beautiful, well kept apartment in a great location” A really clean, comfortable, well equipped apartment (although a hairdryer would be a nice addition) in a fantastic location. Very near transport links, shops etc with a lovely sea view. I had a wo  …see more

from £100 / night

£395 - £765 / week

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from £100 / night

(11) Very Good 

9

Home rental in Cowes

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
“Greta location, clean, tidy house” The location of the house was fantastic. We could access the town so easily and supermarkets and fish and chip shop were literally around the corner. The house itself was great, very clean and a well equipped kitchen  …see more

from £90 / night

£450 - £1600 / week

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from £90 / night

8

Holiday apartment in Shanklin

Isle of Wight / Shanklin

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into 5 individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. Flat 1  …see more

from £110 / night

£500 - £1000 / week

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from £110 / night

(23) Very Good 

19

Apartment letting in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
Millers Rock is an attractive 2 bedroom character apartment in a privileged private road location offering panoramic seaviewsLight and airy and centrally located within 2 minutes of the beach, shops, cafes, restaurant and fishing harbour , this four star rated prope  …see more

from £80 / night

£375 - £794 / week

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from £80 / night

(14) Excellent 

22

Freshwater holiday home rental

Freshwater / Freshwater Bay

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Fantastic family holiday at The Tower House” We stayed at the Tower House in July during the first week of the school holidays. A family group of 5 adults and 6 children ranging in age from 4 to 9. Reading the description of the property, speaking to  …see more

from £143 / night

£995 - £1790 / week

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from £143 / night

16

Holiday cottage in Ventnor

Ventnor / Niton, Isle of Wight

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden
In association with Trinity House, Rural Retreats are pleased to present St Catherine's Lighthouse. Situated just outside the hamlet of Niton, approximately 10 minutes' drive from the popular coastal resort of Ventnor, the southern most point of the Isle of Wi  …see more

from £149 / night

£1037 - £1933 / week

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from £149 / night

6

Holiday apartment in Shanklin

Isle of Wight / Shanklin

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach  …see more

from £110 / night

£500 - £1000 / week

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from £110 / night

(2) Excellent 

22

Cowes holiday townhouse rental

Cowes / West Cowes

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
York street as also been a popular location for those coming for sailing events as its has a very short walking distant to the Marinas<br />This property is part of the Cowes Holiday Homes portfolio where good service comes as standard  …see more

from £105 / night

£450 - £2900 / week

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from £105 / night

(2) Excellent 

10

Holiday lodge in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
This is a barrier free brand new build. Suitable for wheel chair users. Sleeps 5 to 6. All on one level with car parking and garden. The Lodge comprises of a Large wet room, en-suite double room and two twin rooms, Large kitchen / diner lounge. A veranda to the front  …see more

from £65 / night

£595 - £895 / week

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from £65 / night

(13) Excellent 

16

Apartment rental in Cowes

Cowes / West Cowes

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Great location, cosy and” I stayed here for a weekend and had a very comfortable and enjoyable stay. It is so continentally located by the ferry, shops, pubs and bars and it near to bus stops to see the rest of the Island. The apartment itself has e  …see more

from £100 / night

£350 - £450 / week

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from £100 / night

5

Shanklin holiday log cabin rental

Isle of Wight / Shanklin

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Private garden
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach  …see more

from £100 / night

£420 - £750 / week

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from £100 / night

(3) Average 

15

Holiday cottage in Bembridge

Bembridge / St Helens, Bembridge

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Delightful self-catering cottages set in the heart of Bembridge, one of the Islands most attractive and interesting villages  …see more

from £43 / night

£295 - £750 / week

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from £43 / night

15

Holiday home rental

Isle of Wight / Sandown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Car not necessary
  • Private garden
Tweedy Pie is a fabulous newly built one bedroom holiday home in Sandown. Situated in the heart of Sandown, Tweedy Pie is nicely tucked away on a private driveway with parking. It is walking distance to the lovely sandy beaches, town centre, restaurants and transporta  …see more

from £55 / night

£350 - £700 / week

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from £55 / night

(1) Excellent 

10

Holiday apartment in Shanklin

Isle of Wight / Shanklin

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Car not necessary
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach  …see more

from £85 / night

£340 - £750 / week

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from £85 / night

4

Holiday apartment in Shanklin

Isle of Wight / Shanklin

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
The Garden Apartment at Lyon Court has just been refurbished to a very high standard and takes up the entire storey at garden level. With the ceiling height in excess of 8 feet in most rooms, stylish dimmable LED downlights throughout and large windows and doors, it ma  …see more

from £180 / night

£900 - £2200 / week

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from £180 / night