Holiday Cottages with Outdoor Pools

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.

20 luxury self-catering cottages with outdoor pools

3 Springfield Court is a 3 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £680

3 Springfield Court

3547

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
  • No pets
  • Changeover Sat

7 nights from £680

The Drey is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight
  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £780

The Drey

5139

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


Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...

  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £780

Shore House is a 3 bedroom self catering cottage with sea views in Seaview, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1118

Shore House

3778

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


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

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1118

Appledore is a 4 bedroom, dog friendly apartment with sea views near Braunton.
  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

From £458 per night

Appledore

5541

4 bedroom, dog friendly apartment with sea views near Braunton.


Sitting on the clifftop, with breathtaking views of the golden sands of Saunton and over the Atlantic Ocean, a dreamy coastal escape awaits at Appledore. Sleeping seven and dog-...

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

From £458 per night

Channel View is a 4 bedroom, rural self catering cottage in Cadgwith, West Cornwall.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1355

Channel View

3722

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
  • No pets
  • Changeover Fri

7 nights from £1355

Beach House is a 4 bedroom self catering cottage with river views near Pembroke.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £4038

Beach House

5197

4 bedroom self catering cottage with river views near Pembroke.


Welcome to Beach House, a very special getaway hidden within the timeless beauty of Pembrokeshire National Park. The secluded location is nothing short of idyllic; nestled into the...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £4038

The Penthouse is a 4 bedroom apartment with sea views near Braunton, North Devon.
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

From £870 per night

The Penthouse

5536

4 bedroom apartment with sea views near Braunton, North Devon.


Perfectly situated overlooking the beautiful beach at Saunton Sands on the dramatic north Devon coast, The Penthouse is the ultimate five star luxury retreat offering stylish open ...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

From £870 per night

Little Forelands is a 5 bedroom self catering cottage with sea views in Bembridge, Isle of Wight
  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £2397

Little Forelands

4474

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


This absolutely lovely family home in Bembridge, on the east coast of the Isle of Wight, has a large garden and stunning sea views. With a gated entrance Little Forelands is privat...

  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £2397

Sunnynook is a 4 bedroom cottage with sea views in Bigbury-on-Sea, South Devon.
  • Sleeps 10 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £2857

Sunnynook

4157

4 bedroom cottage with sea views in 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
  • No pets
  • Changeover Fri

7 nights from £2857

Dominey's Yard

  • Sleeps 18 + 4 cots in 4 properties
  • Changeover Fri

7 nights from £2018

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