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
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.14 luxury self-catering cottages with outdoor pools
7 nights from £530
Darling Chestnut
60091 bedroom self catering cottage near Helford, West Cornwall.
Resting under the ancient chestnut tree, not far from the oak-lined banks of the Helford, this beautifully converted detached barn has been curated into a dreamy retreat for two lu...
7 nights from £530
7 nights from £977 *
Rydon
55053 bedroom, dog friendly cottage near Bovey Tracey, South Devon.
Introducing Rydon, a 15th Century barn which has been restored and crafted into this most luxurious and comfortable retreat. This 'once upon a time' flower store has been architect...
7 nights from £977 *
7 nights from £1230 *
Marnylunn
47174 bedroom, dog friendly cottage with sea views near Helford.
A luxurious residence with far reaching sea views offering a real home-from-home any time of year, and in the idyllic and tranquil setting of Gillan Creek, Marnylunn means 'mariner...
7 nights from £1230 *
7 nights from £659
Strawberry Hole Barn
58142 bedroom thatched, dog friendly self catering cottage near Rye.
Escape to this gorgeous thatched barn, sat in the grounds of the owners' double oast house, within walking distance of Great Dixter House and Gardens. This spacious property offers...
7 nights from £659
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7 nights from £713
Swallows' Nest
60072 bedroom self catering cottage near Helford, West Cornwall.
Resting in a secluded corner of rural Cornwall yet perfectly placed to explore the gentle waters of the Helford River, Swallows' Nest is a soulful and quietly luxurious barn conver...
7 nights from £713
7 nights from £737
Apt 1 Springfield Court
35752 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...
7 nights from £737
7 nights from £850
Starry Skies
60082 bedroom self catering cottage near Helford, West Cornwall.
Hidden away near the serene waters of the Helford River lies this thoughtfully renovated barn conversion and wild spa, where every detail has been crafted with care. From the soft-...
7 nights from £850
7 nights from £1175 *
Channel View
37224 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...
7 nights from £1175 *
7 nights from £1361 *
Capella
59314 bedroom holiday cottage with sea views in Croyde, North Devon.
Welcome to Capella! With its own swimming pool, hot tub and cinema, this gorgeous escape is the perfect getaway for larger family gatherings or a catch up with friends. Nestled...
7 nights from £1361 *
7 nights from £780
The Drey
51393 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 ...
7 nights from £780
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
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.
