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

7 nights from £685

2 bedroom thatched, dog friendly cottage with sea views in Sennen.


Set above Sennen Cove and reputed to be the most westerly thatched cottage in Britain, No Place is a detached retreat with a heated outdoor pool (available from beginning of May to...

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

7 nights from £685

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

7 nights from £480

3 bedroom self catering apartment near the beach in Seaview.


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 £480

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

7 nights from £592

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 £592

  • 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 swimming pool. Locate...

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

7 nights from £800

View
  • 15% off

    29 Jun 2019 - 6 Jul 2019

    £1499.94 £1275.00

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

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1151

4 bedroom thatched, dog-friendly cottage near South Molton, Devon.


Hidden deep in the truly peaceful, unspoilt north Devon countryside, in the grounds of an historic castle, lies Affeton Barton; a 16th Century farmhouse, newly renovated to a very ...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1151

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £950

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


Dip your toes into the gorgeous swimming pool (available from May to the end of September) in this beautifully presented and very spacious house just a few minutes walk from Seagro...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £950

View
  • 15% off

    29 Jun 2019 - 6 Jul 2019

    £1400.07 £1190.06

  • 10% off

    13 Jul 2019 - 20 Jul 2019

    £1799.91 £1619.92

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £2095

4 bedroom cottage with sea views near Bigbury-on-Sea, South Devon.


Sunnynook is a true beachside retreat, boasting the most incredible, unrivalled sea and beach views over Bigbury-on-Sea, Bantham and Burgh Island. This wonderful home also has a fa...

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £2095

  • Sleeps 7 + 2 cots in 2 properties
  • Changeover Sat

7 nights from £693 *


Nanteague Farm spreads over 130 acres with a beautifully landscaped coarse fishing lake set in the centre, stocked with carp, rudd, perch, roach and bream. With a heated outdoor sw...

  • Sleeps 7 + 2 cots in 2 properties
  • Changeover Sat

7 nights from £693 *

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

7 nights from £963


These are the first and last holiday cottages in England! Just a stone's throw from Land's End with its dramatic cliffs, coastal paths and below, the crashing Atlantic Ocean. Mont...

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

7 nights from £963