Holiday rentals with a pool in Chesil Beach

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Top-rated rentals with a pool in Chesil Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
An expansive wooden deck is featured, with a modern round fire pit positioned among lush greenery and vibrant flowers. Large glass doors allow views into the interior space, which is visible beyond the deck. The natural landscape extends in the background under a clear sky.
Shepherd’s hut in Lyme Regis
4.99 out of 5 average rating, 131 reviews

Headland Hideaway Shepherd's Hut in Lyme Regis

SHEPHERDS HUT An opulent hideaway retreat nestled on the Lyme Bay headland with uninterrupted ocean views, perfect for romantics & family adventurers. With an expansive sundeck, fire pit & swimming pool & endless expanse of garden. Embark on the most charming private adventure from bedroom shepherd's hut & adjacent shower room to the architectural wonder of the glass framed kitchen, diner & sitting room with freestanding log burner & stylish interior. Sit and wonder at the expanse of ocean views

Guest favourite
A gravel driveway leads to a charming white house surrounded by lush greenery. The property features a two-story structure and an annexe, both set within spacious grounds. Noticeable are the well-maintained gardens and outdoor seating areas, perfect for gatherings.
Home in Somerset
4.91 out of 5 average rating, 262 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

Group Gatherings Host your own event Exclusive use 10-16 guests Min 2 off peak Jacuzzi All year Outdoor Pool (heated in summer; cold in winter!) Sun Deck Garden Kitchen/Bar Games room: Music/Karaoke system Wood burner TV Communal eating space, shower/wc Escape Room Somerset Evening -pulled pork cider tasting welly wanging Large peaceful grounds BBQ Fire Pit Annexe (sole use) kitchen lounge bathroom 2 bedrooms 2 sofa beds House (part use): 4 bedrooms 3 bathrooms Glamping Trailer

Top guest favourite
An aerial view showcases the neighborhood surrounding the property, with the sparkling sea visible in the distance. Nearby sandy beaches and the West Bay Harbour are highlighted. A series of homes are visible with well-maintained gardens and driveways, demonstrating the calm coastal environment.
Home in West Bay
5 out of 5 average rating, 12 reviews

Luxury House 100m to beach - sleeps 8 Pool+Hot Tub

This stylish place to stay is perfect for family trips. A short stroll to the beaches and harbour at West Bay makes the house the perfect location for a beach holiday. The South West Coast Path and Jurassic Coast are just 25 metres from the door. A heated swim spa and separate hot tub are among the many facilities at the house. Ample private parking includes 2 EV Chargers. Spectacular views across Lyme Bay to Portland. Beautiful bathrooms and Showers. Luxury Kitchen. Wonderful terraces and BBQ.

Guest favourite
The interior features two twin beds with colorful bedding arranged against wooden walls. A dining table is set with two glasses of red wine, a bottle, and a small vase of flowers. A window offers views of the surrounding greenery.
Shepherd’s hut in Dorset
4.89 out of 5 average rating, 192 reviews

Everdene shepherd's hut

Lovely views of the Blackmore Vale (amazing sunsets weather permitting!) Our huts are in a secluded area of the farm. Kingsize bed/twin beds opposite ends with curtains for privacy. Woodburner, hot/cold running water, fridge, hob, microwave, wardrobe. Picnic bench & fire pit outside. Wonderful walks, only 10 minutes on foot to village shop and pub. Great for families. Short walk to luxury wetrooms, w/m, drier. Fishing on farm. Indoor exercise pool payable locally. (Subject to availability)

Superhost
An inviting outdoor dining area is nestled beside a serene swimming pool. A glass table is set with plates and cutlery, surrounded by comfortable seating adorned with patterned cushions. Lush greenery and flowering plants create a relaxing atmosphere.
Home in Dorset
4.93 out of 5 average rating, 14 reviews

East Creek + beach side + pool, dog Ringstead Bay

East Creek in Ringstead is newly refurbished with a brand new kitchen, lounge and bathroom. This house sleeps 10, has fast broadband and has fantastic views. Step onto your expansive deck, where panoramic views of the azure sea stretch endlessly before you. This is the ultimate vantage point for coastal bliss. Your own private pool awaits, inviting you to cool off in style or soak up the sun in absolute privacy. Swimming pool open May to end of September, for 2025 trailing end of October.

Superhost
An indoor pool is surrounded by sleek gray tiling and illuminated by recessed lighting. The pool's inviting turquoise water reflects the ceiling lights. A cozy seating area with cushions is visible in the corner, providing a relaxed atmosphere.
Cottage in Osmington
4.86 out of 5 average rating, 153 reviews

A luxury unique home spa - White Stones Retreats.

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

Guest favourite
A rectangular freshwater pool is framed by a wooden deck, surrounded by a landscaped garden. Lush greenery and rolling hills are visible in the background, offering a serene and expansive view of the countryside.
Bungalow in Charmouth
4.94 out of 5 average rating, 221 reviews

Secluded hideaway, heated pool, walks, fossils

The Annex is bright, comfortable and cosy with a wood burner for winter. The public footpath crossing our garden next to the river Char links with many others - great for dog walkers. We are close to Charmouth beach and Lyme Regis – renowned for their fossil treasures. Love swimming? our freshwater pool is generally heated to a very cosy 29 - 30 degrees (warm bath temperature) and can be used from April to October With advance notice, the twin beds can be connected to form a king size bed

Top guest favourite
A charming outdoor view showcases a wooden railway carriage and adjacent structure surrounded by a lush green lawn. Sunlight illuminates the inviting patio area with seating, while wattle fencing adds a natural touch to the landscape.
Train in Axminster
4.99 out of 5 average rating, 285 reviews

Clover Carriage with pool, sauna and outdoor bath

Nestled into our working farm, this lovingly restored railway carriage is the perfect spot for a romantic stay away. The views are out of this world and all viewable from the large glass doors so you can stay tucked up in bed or on the sofa in front of the fire, with great wifi, free access to our beautiful heate pool & sauna (located in the pool house), beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and a romantic outdoor bath

Top guest favourite
A green yurt is nestled among lush grass and trees, with a spacious wooden terrace visible nearby. The landscape features rolling hills in the background, under a bright blue sky illuminated by rays of sunshine. The area offers a serene rural setting.
Yurt in Colyton
4.98 out of 5 average rating, 175 reviews

Buzzard Yurt - A unique eco holiday in East Devon

Unique and comfortable yurt (sleeps 5+), large terrace, stunning views - also you could check out Kingfisher yurt (bigger kitchen) by the swimming pond. Private kitchen, chill-out cabin, shower, rustic flushing loo, compost loo with a view, campfire area. Wild swimming pond (fenced) Bookable woodfired hot tub. Dog friendly, footpaths. Kid heaven! Late check-out negotiable. By booking you take full responsibility for the safety of your group. Check-in form /waiver on arrival please.

Guest favourite
A spacious corner sofa is adorned with colorful cushions in yellow, gray, and blue. A cozy navy blanket drapes over the side. A wooden coffee table holds a selection of brochures, with natural light filtering through sheer curtains at the nearby window.
Home in Preston Road
4.85 out of 5 average rating, 118 reviews

Spacious Caravan near sea Weymouth Bay Haven

Our holiday home is spacious with a well equipped kitchen. Located 12-15min flat walk (buggy friendly) from the seaside. The Haven park offers a swimming pool, live entertainment and play areas for kids until 14th November (access to indoor complex is an additional fee on a first come first serve basis) We are opposite the activity field. One car parking space next to the caravan.. CHANGEOVER DAYS ARE MONDAY OR FRIDAY. Please contact us to make a shorter booking or with any questions.

Guest favourite
The entrance of the cottage is framed by vibrant greenery and blooming flowers. A wooden deck leads to a welcoming door, which is complemented by a classic lantern. A decorative sailboat can be seen through the window, adding a touch of charm to the exterior.
Cottage in Charmouth
4.89 out of 5 average rating, 152 reviews

Daisy Cottage on the Jurassic Coast

A cosy and stylish, dog-friendly cottage, set amid the beautiful fields and woodlands of the Fernhill Estate with easy walking access to the coastal village of Charmouth and only 2 miles to Lyme Regis. The South West Coastal Path runs opposite our front door and our guests have seasonal access to a heated outdoor pool. Our cottage sleeps four and is furnished and equipped to a very high standard with everything you need for a relaxing holiday on the Jurassic Coast in West Dorset.

Superhost
The exterior of The Duck House is depicted, showcasing a charming two-story chalet surrounded by lush greenery. The light yellow walls complement the natural landscape, while windows reflect the tranquil sky. The well-maintained lawn offers open space for relaxation and play.
Chalet in Whitchurch Canonicorum
4.88 out of 5 average rating, 226 reviews

The Duck House. A child/dog friendly rural chalet

The Duck House is a lovely child/dog friendly chalet nestling in the orchard at Plenty Cottage. Quiet and peaceful it's the perfect retreat for a family - and dogs are especially welcome! Open plan living it’s a comfortable and home from home. A wonderful rambling garden, summerhouse, BBQ and a (free) heated swimming pool (1st April - 31st Sept). The mantra is 'No Stress'. Ample parking, dog/child friendly pub 7 mins walk away. Wonderful NT beaches just five min drive.

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