Holiday Cottages with Outdoor Pools

Escape to another world when you float on the calm waters of your outdoor pool. Amongst our collection of holiday homes with outdoor swimming pools, you can wake up in luxury self-catering accommodation and head out to take a splash in your own outdoor swimming pool. Spend your days by the poolside and let your worries soak away. This is the holiday home you've been waiting for.Read more

It's not every day you can climb out of bed and lounge on a floating inflatable or have breakfast al fresco by the swimming pool. But this is your holiday so you deserve something a bit more special. Book a holiday with an outdoor pool and keep the kids entertained with no effort, or take the two of you off to float in the sunlight with no-one else around. With a selection of both shared and private swimming pools available, you can give yourself a holiday to remember. View all of our holiday cottages with a swimming pool and choose your favourite property. At Classic Cottages, we handpick all of our self-catering cottages onto our books, so you can enjoy the finest accommodation around.

15 luxury self-catering cottages with outdoor pools

We are no longer accepting new bookings for holidays arriving before the 4th June. COVID-19

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £353 *

2 bedroom, dog friendly house with a pool near Perranporth, Cornwall


Nanteague House is semi-detached with its own south-facing sun-trap patio to the front, the perfect place for evening drinks as it overlooks the central courtyard and heated swimmi...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £353 *

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £354

1 bedroom, dog friendly cottage with an outdoor pool Perranporth, Cornwall.


Nanteague Cottage is a spacious one bedroom cottage, ideal for couples, and shares a heated swimming pool with Nanteague House (392) (heated by an air source heat pump and availabl...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £354

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

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £728 *

4 bedroom, rural self catering cottage in Cadgwith, West Cornwall.


This spectacular holiday home, located in the heart of the Lizard peninsula, is perfectly proportioned for a large family group or friends. Situated a short drive from one of t...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £728 *

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £376

3 bedroom, dog friendly holiday cottage and a pool in Croyde


Close to some of north Devon’s best surfing beaches, Orchard Dene is in the heart of the lovely village of Georgeham, with two good pubs and a shop within walking distance. The san...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £376

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £514

2 bedroom self catering apartment near the beach in Seaview.


Apt 1 Springfield Court is a luxurious, ground floor apartment, set in an exclusive development in the picturesque village of Seaview. It would suit a small family or a couple in n...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £514

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £550

2 bedroom self catering apartment with sea views in Seaview, Isle of Wight


This stunning building is set back from the Seaview Duver accessed by an impressive driveway; as you enter through the grand set of gates and make your way up to the Penthouse you ...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £550

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £765

2 bedroom thatched, dog friendly cottage with sea views and a hot tub in Sennen.


Your hot tub and heated open air swimming pool await you in your private sanctuary set above the white sands and azure blue seas which are Sennen Cove. Reputed to be the most we...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £765

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £510

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


With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £510

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £621

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


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

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £621

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £800

3 bedroom self catering cottage in a rural setting near Ventnor, Isle of Wight


Set in the grounds of the impressive Pyle Manor, this newly refurbished cottage offers a wonderful base on the Isle of Wight with the shared use of an outdoor unheated swimming poo...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £800

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