Cottages on the Isle of Wight Sleeping 5 People

Choose from 71 luxury cottages for 5 people on the Isle of Wight

Windy Ridge is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1000

Windy Ridge

4464

4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.


Tucked away in the idyllic setting of Seagrove Bay and just steps away from the beach, Windy Ridge is a stunning semi-detached house with wonderful sea views from both the ground a...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1000

Creekside is a 5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.
  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1157

Creekside

3588

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Aptly named and perfectly positioned on the banks of pretty Wootton Creek on the north coast of the Isle of Wight, Creekside is a gorgeous waterfront holiday home with delightful v...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1157

Orchard House is a 4 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight
  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1223

Orchard House

3641

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


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

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

7 nights from £1223

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  • 25% off

    20 Jun 2026 - 27 Jun 2026

    From £1933.00 £1449.75

  • 25% off

    27 Jun 2026 - 4 Jul 2026

    From £2050.00 £1537.50

  • 25% off

    4 Jul 2026 - 11 Jul 2026

    From £2200.00 £1650.00

Saye House is a 4 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1294

Saye House

4573

4 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


Just a few minutes from idyllic Seagrove Bay, Saye House has been stylishly renovated to a high standard offering a wonderful place to enjoy a well-earned rest on the Isle of Wight...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1294

View
  • 50% off

    2 Jul 2026 - 6 Jul 2026

    From £1449.28 £724.64

Choose from our exclusive collection at the best prices with real time availability.

Pitt Corner is a 4 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 £1607

Pitt Corner

3644

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


A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is a roomy retreat, with plenty of space for the family to spread...

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

7 nights from £1607

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 £2300

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 £2300

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 £2132

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 £2132

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.


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 £2727

Colwell Bay Cottages

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1680

Kingston Barns

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

7 nights from £1824

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