by Wyndham Vacation Rentals

Isle of Wight

For a tiny island, the Isle of Wight really knows how to pack a punch. Every summer, tens of thousands of music fans descent on Newport to enjoy three days of dancing, singing, and dressing up. For one weekend, the entire island is home to the UK’s biggest open-air party, and the atmosphere is infectious.

But the rest of the year, visitors will find a very different Isle of Wight: a beautiful, peaceful, and sophisticated part of England which is the perfect location for a quiet weekend away or a family vacation.

Holiday cottages with pools are the best way of experiencing all the hidden nooks and crannies of this unique island, with its tiny stone villages, long golden beaches, and world-class restaurants.

As one of the most southerly parts of the UK, the Isle of Wight is a great place to simply soak up the summer sun at your own cottage with a swimming pool, or on the pretty beaches by Yarmouth or Ventnor. Cottage with pools also allow you to venture off the beaten track, and discover some of the hidden gems that have not yet become popular tourist attractions. On the east of the island, visit the pretty village of Bembridge, with its stone windmill and coastal views. Or cycle through the pristine countryside of the Isle of Wight AONB, stopping off at the thatched village of Brighstone for a pint at The Three Bishops on your way home.

Kids and families will particularly appreciate the island’s cottages with private pools, where you can plan out your daily adventures by the poolside. Rent a sailboat at Cowes and spend the day drifting along the Solent, or stopping off at coastal towns such as Shanklin, Ryde and Seaview. Or walk along the shoreline looking for crabs and fossils. The island is known as the ‘Dinosaur Capital’ of Great Britain due to the abundance of fossils which can be found along the rocky coastline. Budding palaeontologists can hunt for their own dinosaur bones at Compton Bay, near Freshwater, or around Yaverland Beach near Sandown, and guided fossil walks are often offered by visiting scientists and researchers.

When you have your own base on the island, it won’t be long before it feels like home, and you’ll find yourself returning year after year.

Get better search results by telling us when you want to book
Add a date
2 cottages are available
  • Shorwell, Isle of Wight
    Shorwell, Isle of Wight×

    Cheverton Farm - Brummell Barn

    Shorwell, Isle of Wight

    Ref: PYV
    Key Features:
    - Wifi - Swimming pool - Car parking on site - Pub within 1 mile

    Nestling in the beautiful Bowcombe Valley, just 4 miles from the nearest south coast beach, are these two...

    Prices from
    Pets included
    Pets go free
  • Totland, near Freshwater, Isle of Wight
    Totland, near Freshwater, Isle of Wight×


    Totland, near Freshwater, Isle of Wight

    Ref: 28885
    Key Features:
    - Hot Tub - Wifi - Swimming pool - Car parking on site - Pub within 1 mile - Pets go free - Detached Property - Open Fire

    Private heated indoor swimming pool

    Wychwood is set on the cliff-top in an Area of Outstanding Natural...

    Prices from
    Pets included
    Pets go free

Looking for something with a little more?

Cotages with Hot tubs Cottages part of our Luxury collection Something with a swimming pool A place near the Coast

Subscribe to our latest deals & offers