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.

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.

28 luxury self-catering cottages with outdoor pools

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. The apartment boasts a private terrace overlo...

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

Price per week £470 - £1060

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


10 Springfield Court is a wonderful, second floor apartment set within eight acres of communal grounds. The property also benefits from the shared use of an outdoor heated swimming...

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

Price per week £475 - £1060

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
  • Regret no pets
  • Changeover Sat

Price per week £485 - £1050

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


The hot tub, private terrace and sea views make this a perfect retreat at any time of the year. With the shared use of an outdoor heated swimming pool (available from the begin...

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

Price per week £517 - £1445

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

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 Fri

Price per week £672 - £1679

2 bedroom, dog friendly apartment with sea views in Mullion.


With uninterrupted views of the most picturesque storybook fishing harbour in Cornwall, this fabulous first floor apartment with a private balcony sits in an enviable position righ...

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

Price per week £780 - £2149

2 bedroom, dog friendly apartment with sea views in Mullion.


Captivating is just one word to describe the views from this fabulous first floor apartment located in the heart of Mullion Cove with its quaint cobbled slipway; this magical place...

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

Price per week £780 - £2149

3 bedroom self catering apartment near the beach in Seaview.


A ground floor apartment housed within an exclusive development, you'll feel an air of grandeur to a holiday at 3 Springfield Court with an impressive driveway just off the Seaview...

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

Price per week £470 - £1082

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

Price per week £580 - £1474

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


A gorgeous Victorian three bedroom house on the outskirts of Shanklin with a lovely secluded garden and a private swimming pool. Beautifully decorated throughout, the Owner has tak...

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

Price per week £706 - £1595

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Loading more