Holiday cottages with 5 bedrooms in Isle of Wight

Holiday cottages with 5 bedrooms in Isle of Wight

Browse the 10 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 10 self catering cottages with 5 bedrooms in Isle of Wight

Kingston Barns

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

7 nights from £2394

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 £2702

St Andrews

4641

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


Looking for a truly unique getaway? This beautiful, converted church offers an unforgettable Isle of Wight escape, blending historic charm with modern convenience. Perched in an el...

  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2702

Kingston Barns

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

7 nights from £1806

Mattingley Farm

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

7 nights from £1404

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 £1788

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 £1788

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 £2228

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 £2228

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

7 nights from £2008

Solent Heights

3946

5 bedroom 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 £2008

Pepita is a 5 bedroom, dog friendly holiday 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 holiday 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 *

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

6 Seafield Terrace is a 5 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £801 *

6 Seafield Terrace

3562

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


6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...

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

7 nights from £801 *

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  • 20% off

    25 Apr 2025 - 2 May 2025

    From £1092.00 £873.60

Mallards is a 5 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £878

Mallards

3627

5 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight.


Mallards is a spacious, three-storey Edwardian house in Seaview village and a much-loved family home. Enjoying a great location just yards from the seafront, it's the perfect choic...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £878

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.