Holiday cottages with 5 bedrooms in Isle of Wight

Holiday cottages with 5 bedrooms in Isle of Wight

Browse the 12 large holiday cottages with 5 bedrooms in Isle of Wight that we’ve selected for our portfolio.  Read more Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 12 self catering cottages with 5 bedrooms in Isle of Wight

Kingston Barns

  • Sleeps 15 + 4 cots in 4 properties
  • Changeover Sat

7 nights from £2371

St Andrews is a 6 bedroom, dog friendly holiday home with hot tub near the beach in Yarmouth, Isle of Wight.
  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2727

St Andrews

4641

6 bedroom, dog friendly holiday home with hot tub near the beach in Yarmouth, Isle of Wight.


Wow! This spectacular converted church has the makings for the most amazing holiday, set in an elevated position with panoramic views across the surrounding countryside and a glimp...

  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2727

Kingston Barns

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £1802

Mattingley Farm

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1402

Redworth is a 5 bedroom self catering home near the beach in Bembridge, Isle of Wight.
  • Sleeps 11 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £2032

Redworth

4541

5 bedroom self catering home near the beach in Bembridge, Isle of Wight.


This impressive five bedroom house is located on Ducie Avenue, a charming unmade road leading to the beach, in the village of Bembridge. Located within a few minutes walk of the lo...

  • Sleeps 11 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £2032

West Ingle is a 5 bedroom self catering home near the beach in Seaview, Isle of Wight.
  • Sleeps 11 + cot
  • No pets
  • Changeover Sat

7 nights from £1701

West Ingle

3693

5 bedroom self catering home near the beach in Seaview, Isle of Wight.


A beautiful Edwardian house, brimming with charm and original features, with magnificent sea views from almost every room, the terrace and garden. The open plan kitchen/dining-room...

  • Sleeps 11 + cot
  • No pets
  • Changeover Sat

7 nights from £1701

Cara Cottage is a 5 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2226

Cara Cottage

4846

5 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.


Welcome to Cara Cottage, a stunning detached property located in the heart of Bembridge village. This eye-catching holiday home with soft pink 'Spanish inspired' exterior is beauti...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2226

Solent Heights is a 5 bedroom dog-friendly self catering cottage near the beach in Cowes, Isle of Wight
  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2006

Solent Heights

3946

5 bedroom dog-friendly self catering cottage near the beach in Cowes, Isle of Wight


A beautifully designed, contemporary home in the popular sailing town of Cowes, Solent Heights boasts sea views and quality finishes throughout. Set over four floors - including ba...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2006

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

Seacrest House is a 5 bedroom, rural self catering cottage near the beach in Ryde, Isle of Wight.
  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £1438

Seacrest House

3653

5 bedroom, rural self catering cottage near the beach in Ryde, Isle of Wight.


This stunning three-storey holiday home is in the enviable position of being only a few minutes' stroll from the beach and also the centre of Ryde town. Built in the early part of ...

  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £1438

Pepita is a 5 bedroom dog friendly cottage with sea views in Seaview.
  • Sleeps 9 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1469 *

Pepita

5719

5 bedroom dog friendly cottage with sea views in Seaview.


With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...

  • Sleeps 9 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1469 *

Load more

A holiday cottage in Isle of Wight with five bedrooms makes the perfect base for a family reunion or a group of friends to get away together. With a range of bedroom types available, there are plenty of options to choose from: doubles, singles, twins and the occasional bunk. But never a sofa bed or put-me-up – we only accommodate as many people as there are proper beds. Use the filters on the left to help find the right one for you.

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