Holiday cottages with pools on the Isle of Wight

Holiday cottages with pools on the Isle of Wight

Complete your holiday to the Isle of Wight with the added luxury of a swimming pool. Whether you choose indoor or outdoor, you’ll wonder how you enjoyed your past holidays without one. We have 12 holiday cottages with pools to enjoy on the Isle of Wight.Read more

The ultimate family friendly holiday needs a swimming pool. Splash around with the kids on rainy days to tire them out or get into the routine of an evening swim for everybody. If you’re on holiday with a big group this is a lovely way to gather everyone together to catch up. Get the kids to entertain themselves by practicing handstands, playing games in the water and fetching heavy objects from the bottom of the pool. They’ll spend hours bobbing up and down, giving you some time to relax with a good book while watching them enjoy the waters.

A romantic couples holiday can be made by a pool. Relax by the poolside together, spending mornings gliding through the calm waters before heading back to your holiday cottage only a stone’s throw away to enjoy breakfast together. A pool will get you out of the cottage without needing to hop in the car saving you the stress of trying to navigate an area you might not be familiar with.

Whatever you’re looking for from your holiday on the Isle of Wight, a pool gives you an extra option for something to do without having to leave your cottage.

We have 12 luxury self catering cottages with pools to rent on the Isle of Wight

Farm Cottage is a 2 bedroom, dog friendly cottage near Ventnor.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

From £110 per night

Farm Cottage

5718

2 bedroom, dog friendly cottage near Ventnor.


For those looking for a peaceful and calming cottage then look no further than Farm Cottage, it's set in the delightful grounds of the owners' home and has been furnished with care...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

From £110 per night

The Stables is a 1 bedroom, dog friendly holiday cottage close to the beach, near Ventnor.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £72 per night

The Stables

5651

1 bedroom, dog friendly holiday cottage close to the beach, near Ventnor.


Welcome to The Stables, a romantic getaway for two! Close to the seaside town of Ventnor, with its beautiful beachfront, you can explore this corner of the Island and then retreat ...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £72 per night

Sunrise and Stars is a Dog friendly shepherds hut with a hot tub near Ventnor.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £85 per night

Sunrise and Stars

5672

Dog friendly shepherds hut with a hot tub near Ventnor.


Step into an oasis of peace and tranquility on the Isle of Wight at Sunrise and Stars, a beautifully crafted hideaway with a pool for private use and a hot tub, surrounded by capti...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £85 per night

Driftwood is a A dog friendly luxury retreat with private hot tub sleeping 4.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £617 *

Driftwood

5613

A dog friendly luxury retreat with private hot tub sleeping 4.


Whisk yourself away to this pretty retreat on the glorious Isle of Wight, new to the portfolio this spring and perfect for couples, small families and four-legged companions who lo...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £617 *

Colwell Bay Cottages

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

7 nights from £1234

Escape Away is a A luxury retreat with private hot tub and use of swimming pool.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £617 *

Escape Away

5612

A luxury retreat with private hot tub and use of swimming pool.


New to the Classic portfolio, very close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base you...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £617 *

The Drey is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight
  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £780

The Drey

5139

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


Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...

  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £780

Little Forelands is a 5 bedroom self catering cottage with sea views in Bembridge, Isle of Wight
  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £2397

Little Forelands

4474

5 bedroom self catering cottage with sea views in Bembridge, Isle of Wight


This absolutely lovely family home in Bembridge, on the east coast of the Isle of Wight, has a large garden and stunning sea views. With a gated entrance Little Forelands is privat...

  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £2397

Need more time? Reserve any cottage for up to 24 hours before booking.

Sunset Cottage is a 3 bedroom self catering cottage near Ventnor, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £906 *

Sunset Cottage

4319

3 bedroom self catering cottage near Ventnor, Isle of Wight


Looking for the ultimate homestay for a family holiday, a celebratory escape for a couple, or simply an excuse to get together with friends, Sunset Cottage has holiday luxury cover...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £906 *

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  • 20% off

    13 Sep 2024 - 20 Sep 2024

    From £1250.00 £1000.00

  • 20% off

    20 Sep 2024 - 27 Sep 2024

    From £1250.00 £1000.00

  • 20% off

    27 Sep 2024 - 4 Oct 2024

    From £1250.00 £1000.00

  • 20% off

    4 Oct 2024 - 11 Oct 2024

    From £1250.00 £1000.00

  • 20% off

    11 Oct 2024 - 18 Oct 2024

    From £1785.00 £1428.00

Shore House is a 3 bedroom self catering cottage with sea views in Seaview, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1118

Shore House

3778

3 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A seaside sanctuary, Shore House is a beautifully decorated three-storey house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1118

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