Vacation rentals with a pool in Chesil Beach

Find and book unique homes with a pool on Airbnb

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 favorite

Shepherd’s hut in Lyme Regis

4.99 out of 5 average rating, 105 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 favorite

Home in Somerset

4.92 out of 5 average rating, 238 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

Group Gatherings Host your own event Exclusive use 10-16 guests (6-16 winter) 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 -pork roast 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

Superhost

Home in Osmington

4.88 out of 5 average rating, 82 reviews

Large coastal cottage with spa and private pool

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 favorite

Barn in Long Sutton

4.87 out of 5 average rating, 312 reviews

Somerset Threshing Barn w/ Pool, Hot Tub & Sauna

Discover the Threshing Barn, an ideal spot for family or group gatherings. Enjoy the spacious double-height kitchen and the cozy lounge with woodburner. Unwind in the covered hot tub and sauna, take a dip in the heated pool (open May to Sept) or play table tennis, pool, and table football. Explore nearby footpaths leading to three excellent pubs. We can help organise catering, pampering, and a wide range of activities, from archery and shooting to cider tasting, both on-site and off-site.

Guest favorite

Guesthouse in Iwerne Minster

4.97 out of 5 average rating, 61 reviews

One bed Lodge in AONB Dorset with shared pool area

Fully refurbished ,Brook Lodge sits in the grounds of the main house in the village of Iwerne Minster. One bedroom , king sized bed. Bathroom with free standing bath and separate walk in shower. Open plan living area downstairs with sofa , dining area for 4, new fitted kitchen ,separate cloakroom and entrance hall. Small outdoor semi private seating area.Free WiFi .TV. Welcome pack. NB Outdoor heated pool OPEN beginning JUNE to SEPTEMBER ONLY .NB Pool use is shared with property owners.

Superhost

Cabin in Dorset

4.88 out of 5 average rating, 16 reviews

Bay View Holiday Home With Sea Views

Spacious two bedroom holiday home with a Balcony/Sun deck. Situated on a wide sunny plot in the most desirable Bay Hollow which has a splendid sea views over the bay at the award winning "Rockley Park" in Dorset.. The holiday home is 'Platinum' graded and benefits from central heating and double glazing. It is a short walk from the amenities and 150yds walk to the lovely sandy beach, with cafe and water sports. Haven passes are available at an extra cost for swimming and entertainment.

Guest favorite

Home in Harpford

5 out of 5 average rating, 6 reviews

The Pool House

Set within the grounds of our old rectory, The Pool House provides a wonderful retreat for those looking to escape to the country whilst being a short drive from the seaside town of Sidmouth and nearby city of Exeter. The Pool House has been renovated to a high specification providing spacious contemporary accommodation with use of heated outdoor swimming pool (mid May to mid September) during the day, and exclusive use of the courtyard in the evening. We also provide fast WiFi.

Top guest favorite

Home in Lyme Regis

5 out of 5 average rating, 24 reviews

Your Own Private Indoor Pool. Rural Seaside

Up to 30% discount on Mon-Fri bookings in May and June 2025. Coombehayes Barn. Beautifully appointed, self-contained, spacious. A mile from the sea. Super warm, private indoor pool - for your exclusive use. Perfect for relaxed family/friends get-togethers and celebrations. Tranquil yet convenient location. Lyme Regis, Jurassic Coastline. Beaches, footpaths, fossils. Lots for kids to do: PS5, table football, table tennis. Large, safe, enclosed garden. Super fast wifi.

Top guest favorite

Cottage in Dorset

4.98 out of 5 average rating, 347 reviews

The Condo (Indoor Pool available May- end Sept)

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Guest favorite

Condo in Willand

4.98 out of 5 average rating, 90 reviews

Luxury Apartment with pool,indoor heated.

Pitfield Apartment is in a lovely old Village, inbetween Exeter and Taunton with easy access to the M5. Lots of activities nearby, some within walking distance, others a short drive away. See location for list. Also close to the Grand Western Canal, which provides a great place to cycle, walk or canoe. Blackdown Hills and coast is only a 35 minute drive away. Great place to enjoy beaches and moors. Continental breakfast provided.

Top guest favorite

Home in Bournemouth

4.97 out of 5 average rating, 72 reviews

Incredible sea views and heated outdoor pool

“With its incredible sea views, contemporary open-plan living and heated outdoor pool, this Airbnb is like something out of a Hollywood film” according to Good Housekeeping May 2024. The designer garden with hard and soft landscaping features a heated private endless pool (available April to December) and amazing sea views that draw you to the cliff top deck. Powerboat charter available on prior request.

Guest favorite

Bungalow in Saint Leonards

4.87 out of 5 average rating, 55 reviews

Forest views in secluded location, swimming pools

Beautiful forest views! Family holiday home on Oakdene Forest Park, situated in a peaceful location directly overlooking the forest. Minutes from The New Forest & Dorset beaches - perfect for a family holiday. The park has a leisure complex which includes pools, sauna, jacuzzi, steam room & gym as well as entertainments, bars/restaurant & kids activities.

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What guests are saying

Cottage Farmstay Pool Dairy

5 out of 5 average rating, 36 reviews1 week ago

Kathryn is a fantastic host. Friendly, but left us to our holiday. The Dairy cottage is small but has everything you need. The views are beautiful and it is very quiet. There is a great games room, which is fully equipped and we all enjoyed that. Lovely swimming pool and tennis court too. Easy to get to local beaches and a huge tesco nearby for supplies. Highly recommend.

Cottage in Colyton

What guests are saying

Stunning Static/Mobile Home.

5 out of 5 average rating, 26 reviews1 week ago

What an amazing stay 😍😍😍 place was as same as discribtion and images. Surround was soo good ,quite and peaceful. One word for host Liz ‘superstar’ , got quick response for all text.very friendly and polite. I will visit this place again ❤️❤️ just in live with the comfort of this caravan . Very cozy, clear and beautufuly decorated . 10/10 rating for this place ❤️❤️❤️

Holiday park in Saint Leonards

What guests are saying

Large Airy Barn conversion, 5 bedrooms, Jurassic

4.9 out of 5 average rating, 52 reviews4 months ago

Lovely barn, great for a big group (we were 7 adults, 2 kids). We were in there for Christmas and the place had a lovely homely feel to it, great for the festive season. Super warm, no issues there at all. Not perfect for little kids running around (hard times floors, mini steps, very hot AGA in the kitchen etc), a few issues with low water pressure in some of the bathrooms, but otherwise spot on. Would definitely recommend, thanks for a top stay.

Home in Charmouth

What guests are saying

My Way - 3 bedroom, near beach, brilliant site

4.85 out of 5 average rating, 27 reviews2 weeks ago

Myself, husband and 6 year old had a fabulous 4 nights at Katy and Ray's place, vist8ng from London for the easter holidays . It was a great base to explore the area, so close to the beautiful beaches on the Studland we loved being onky a 5 minute drive away from the beaches. Also explored the Blue Pool, and rode on the steam trains from Swange to Norden. If driving head to reception to get a map as we did find it tricky find in a car where the carvan was. You can park you car on the grass outside it, as we asked reception but does require some manoeuvring driving between the other caravans. However super convenient to have your car close to unload from. there's also a bus stop right outside the complex. We used the indoor pool on site, easy to book, and the pool itself was a good size for our 6 year old to splash and swim about in. A great addition for a less sunny day. A great value place, cosy, clean and with games for kids, felt like a home away from home. We'd stay again!

Cabin in Dorset

What guests are saying

Wayside Luxury House Indoor heated Pool & Hot Tub

5 out of 5 average rating, 7 reviews1 week ago

This was the perfect place for a family celebration. We felt totally spoilt with all the wonderful amenities in this luxury property. The pool was very popular (especially the kids) and the bbq lodge was so much fun. The owners were very helpful, everything was beautifully done and there was everything we needed. We had the best time and would absolutely love to come again. We would highly recommend to anyone looking for a real treat. Thank you so much.

Vacation home in Blackborough

What guests are saying

Our Plaice by the Sea

4.97 out of 5 average rating, 35 reviews5 days ago

We loved our stay at Our Plaice by the sea. Great location and caravan was immaculate and in a superb position on the holiday site. Lovely walks and on site amenities. Cindy was such a lovely host, very attentive and extremely helpful. We were extremely pleased and had an amazing time! Thanks Cindy. Definitely recommend to family and friends and would love to stay again.

Chalet in Dorset

What guests are saying

Large Caravan # 6-8 Berth # Pool & Gym On Site

4.8 out of 5 average rating, 93 reviews6 months ago

Anne's lovely caravan provided an ideal base for our mini-break. Anne is very friendly and was helpful answering my questions beforehand and responding to a minor issue during our stay. The caravan was clean, well maintained and comfortable. The blue sky and sunshine in October was an added bonus!

Camper/RV in Dorset

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