Holiday cottages with 5 bedrooms in Isle of Wight
Browse the 9 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 9 self catering cottages with 5 bedrooms in Isle of Wight
Kingston Barns
7 nights from £2664 booking fees included
7 nights from £2790 booking fees included
St Andrews
46416 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...
7 nights from £2790
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.
Kingston Barns
7 nights from £2013 booking fees included
7 nights from £2195 booking fees included
Redworth
45415 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...
7 nights from £2195
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £2363 booking fees included
Cara Cottage
48465 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...
7 nights from £2363
7 nights from £1220 booking fees included
Creekside
35885 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...
7 nights from £1220
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15% off
17 Jul 2026 - 24 Jul 2026
From £2107.00 £1853.95 booking fees included
7 nights from £1561 * booking fees included
Pepita
57195 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,...
7 nights from £1561 *
7 nights from £847 * booking fees included
6 Seafield Terrace
35625 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...
7 nights from £847 *
7 nights from £940 booking fees included
Mallards
36275 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the sought-after village of Seaview, just a short stroll from the beach and village centre, Mallards is a charming three-storey detached Edwardian town house ...
7 nights from £940
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.
