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.

19 luxury self-catering cottages with outdoor pools

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £328

1 bedroom, dog friendly cottage with sea views at Lands End, Cornwall.


This retreat has so much to offer…including a shared outdoor heated swimming pool (available from the beginning of May to the end of September) and a shared games-room/gym, as well...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £328

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

7 nights from £345 *

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 £345 *

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

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

7 nights from £347

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 £347

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

7 nights from £714 *

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 £714 *

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  • 15% off

    20 Dec 2019 - 27 Dec 2019

    £1976.25 £1679.60

  • 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
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £436

2 bedroom, dog friendly cottage near the beach in Sennen with a pool.


Immaculate and furnished to a very high standard, this first (or last) holiday cottage in England, is a contemporary retreat. It has a wood-burner, a large garden, a games-room/gym...

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

7 nights from £436

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

7 nights from £458

2 bedroom self catering apartment near the beach in Seaview.


A ground floor apartment set within a gated development, 2 Springfield Court enjoys use of eight acres of shared grounds, a heated outdoor swimming pool and tennis court. It would...

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

7 nights from £458

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

7 nights from £480

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 £480

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

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

7 nights from £495

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 £495

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

7 nights from £527

2 bedroom, cottage with sea views, hot tub and pool in Sennen


Definitely the first (or last) hot tub and outdoor swimming pool in the country! This immaculate retreat is all on one level making it perfect for guests of all ages. Your own priv...

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

7 nights from £527

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