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 accommodation 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.

16 luxury self-catering cottages with outdoor pools

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £295

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 £295

View
  • 10% off

    25 Jan 2019 - 1 Feb 2019

    £327.77 £295.20

  • 10% off

    8 Feb 2019 - 15 Feb 2019

    £327.77 £295.20

  • 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. Standing detached at the edge of the central courtyard, it has a large patio sheltered by fencing to offer p...

  • 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 the m...

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

7 nights from £714 *

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

7 nights from £392

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) contemporary retreat has a wood-burner, use of the large outdoor heated swimming pool (available from the beg...

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

7 nights from £392

View
  • 10% off

    25 Jan 2019 - 1 Feb 2019

    £435.60 £392.40

  • 10% off

    1 Feb 2019 - 8 Feb 2019

    £435.60 £392.40

  • 10% off

    16 Feb 2019 - 23 Feb 2019

    £501.60 £451.80

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

7 nights from £396

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


Close to some of north Devon’s best sandy surfing beaches, Orchard Dene is in the heart of the lovely village of Georgeham, with two good pubs and a shop within walking distance. T...

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

7 nights from £396

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

7 nights from £458

2 bedroom self catering apartment near the beach in Seaview.


2 Springfield Court is an exclusive, ground floor apartment set within a gated development. Boasting eight acres of shared grounds, guests can enjoy use of the extensive grounds, h...

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

7 nights from £458

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

7 nights from £475

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 hot ...

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

7 nights from £475

View
  • 10% off

    25 Jan 2019 - 1 Feb 2019

    £527.43 £474.30

  • 10% off

    1 Feb 2019 - 8 Feb 2019

    £527.43 £474.30

  • 10% off

    8 Feb 2019 - 15 Feb 2019

    £527.43 £474.30

  • 10% off

    15 Feb 2019 - 22 Feb 2019

    £599.67 £540.00

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

  • 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

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

7 nights from £485

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


Bright and spacious, 10 Springfield Court is a second floor apartment set within eight acres of beautiful communal grounds. It would ideally suit a couple or small family. With...

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

7 nights from £485

Loading more