We have 87 self catering cottages for a family holiday on the Isle of Wight to show you.
7 nights from £572 *
Modwena
44683 bedroom, dog friendly self catering cottage near the sea in Yarmouth, Isle of Wight.
This gorgeous three bedroom cottage is in the picturesque town of Yarmouth just a few minutes' walk from the village centre and historic pier. Located on the west coast of the Isla...
7 nights from £572 *
7 nights from £574
Yardley
36972 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...
7 nights from £574
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £603 *
Lucaya
36214 bedroom self catering cottage near the beach in Ryde, Isle of Wight.
Welcome to Lucaya, a smart town house for eight set over three floors, a great space with a pretty enclosed rear patio and lawn, the ideal stay for a family looking for a seaside b...
7 nights from £603 *
7 nights from £604
Spinnakers
36592 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.
Situated in a peaceful, private estate just a short stroll from the charming seaside town of Yarmouth, Spinnakers is a cosy, single-storey semi-detached holiday home with well-kept...
7 nights from £604
7 nights from £606
The Dairy
45362 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The dairy is a warm and welcoming barn conversion perfect for slow mornings, costal adventures and cosy evenings by the fire. Being is the largest of the four barns at Kingston, an...
7 nights from £606
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20% off
27 Jun 2026 - 4 Jul 2026
From £879.00 £703.20
7 nights from £609
The Pigsty
45382 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
Tucked away in a picturesque and peaceful spot just outside the village of Shorwell, this charming barn conversion makes a wonderful base for a relaxed getaway. The Pigsty at Kings...
7 nights from £609
7 nights from £609
The Stables
45372 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
The heart of the property is an inviting open plan living space where the sitting, dining and kitchen areas are thoughtfully brought together. Soft natural light filters in through...
7 nights from £609
7 nights from £628
Winkle Cottage
43952 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
This gorgeous terraced cottage, situated in the Conservation Area of the old town of Cowes, is just a few minutes' walk from the centre of town, offering the perfect family holiday...
7 nights from £628
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20% off
26 Jun 2026 - 3 Jul 2026
From £961.00 £768.80
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
7 nights from £650
Pebbles
43982 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Seaview is a wonderful place for an Isle of Wight holiday and Pebbles is perfectly situated in the heart of the village on a quiet residential street just a stone's throw away from...
7 nights from £650
7 nights from £657
2 St Josephs
35302 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
With sea views from the terrace and fresh, modern decor throughout, 2 St Josephs is a holiday maker's home-from-home. It is the perfect getaway for a small family, a couple or two ...
7 nights from £657
