Vacation rentals with a pool in Weymouth and Portland District

Shepherd’s hut in Lyme Regis

A wooden swimming pool is positioned next to a neatly maintained lawn area. A ladder leads from the grassy ground to the pool's edge, while a modern wooden structure is visible in the background, framed by greenery and a clear blue sky.

4.99 out of 5 average rating, 105 reviews

Headland Hideaway Shepherd's Hut in Lyme Regis

JoRating, 5 stars1 day ago

Simply perfect! I'd like to say our stay was terrible so no-one else finds this fantastic hide-away but I can't. As soon as we stepped inside, we immediately relaxed. The decor and view create a peaceful environment that we all enjoyed. The pool and fire-pit were the kids favourite. Easy walk into Lyme Regis with lots of independent shops, fossil hunting and restaurants. Mike has been brilliant - communication has been excellent. We were all super sad to leave! Hopefully we will get back there soon.

4.92 out of 5 average rating, 238 reviews

An outdoor pool is surrounded by a wooden deck, featuring lounge chairs and umbrellas for shade. A colorful inflatable floats on the water, while lush greenery provides privacy along the perimeter.

Home in Somerset

Country House - Pool Jacuzzi Escape Room Karaoke

HannahRating, 5 stars2 weeks ago

Just come back from Mistletoe Farm after celebrating a Hen weekend there. We all could not fault the hosts, they were incredible & always checking if we needed anything, so helpful throughout the whole stay. Mistletoe Farm is beautiful & so peaceful. Plenty to do within the property. We all especially loved the pool/hot tub & also the karaoke machine was a big hit. It really is the perfect place either for celebrating a special occasion or a family weekend. We all enjoyed our stay & said it is a place we would love to go back to. Thank you again to the amazing hosts. Would highly recommend this air b&b 😊

Guesthouse in Iwerne Minster

A shared outdoor heated pool is framed by a spacious brick patio, with sun loungers positioned nearby. Lush greenery surrounds the pool area, enhancing the private ambiance. A red-brick building with multiple windows is visible in the background alongside a thatched-roof house.

4.97 out of 5 average rating, 61 reviews

One bed Lodge in AONB Dorset with shared pool area

MatthewRating, 5 stars3 weeks ago

Brook Lodge was a lovely relaxing stay in a quiet little village. Debs was an excellent host, communicated well, and provided a handbook with recommendations of places to visit in the village and the surrounding area. The lodge was really clean, well decorated and we thoroughly enjoyed our two night stay and will be visiting again in the future. Thank you Debs

5 out of 5 average rating, 16 reviews

Home in Southbourne

Perfect family house, heated pool, close to beach

SusanRating, 5 stars8 months ago

My family and I have just returned from a 4 night stay at The Oaks and we all wished we could have stayed longer. The house is well equipped, clean and tidy. There was plenty of room for 7 adults and 1 infant. The bedrooms were comfortable with fresh linen. I particularly booked this accommodation for the outside pool and this didn't disappoint. A perfect size pool for us and we enjoyed sitting around the garden and pool area. Beautiful Sobo beach is walking distance from the house and there are many good places to eat and drink nearby. We enjoyed a birthday celebration lunch at The Captains club restaurant which we would highly recommend, great food and attentive staff. A big thank you to Maggie And Peter for a great airbnb property.

5 out of 5 average rating, 24 reviews

An indoor swimming pool is contained within a sunlit structure, featuring a glass-paneled roof and surrounded by wooden beams. Comfortable wicker chairs are placed along one side, while the vibrant blue water invites relaxation and enjoyment.

Home in Lyme Regis

Your Own Private Indoor Pool. Rural Seaside

DebbieRating, 5 stars2 months ago

Beautiful property in a lovely scenic country setting, but being only a few minutes drive from the beach. Great indoor pool and a lovely garden. Property a lovely mix of old world country cottage, but with all the mod cons needed for everyday life. Everyone loved the holiday, from young to old and enjoyed watching tv together with a real fire on chilly evenings. Loved Uplyme and Lyme Regis.

4.98 out of 5 average rating, 348 reviews

Cottage in Dorset

The Condo (Indoor Pool available May- end Sept)

NasimaRating, 5 stars2 days ago

I had an absolutely wonderful stay at the condo! From the moment I arrived, everything exceeded my expectations. The space was spotless, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable and relaxing stay. The location was perfect — close to everything yet peaceful and quiet, offering the ideal retreat after a day of exploring. Communication with the host was seamless; they were incredibly responsive, kind, and made me feel truly welcome. I couldn’t have asked for a better experience and would highly recommend this condo to anyone looking for a perfect getaway. I can’t wait to return! thank you once again.

4.97 out of 5 average rating, 72 reviews

A spacious outdoor area is seen featuring a heated private pool, surrounded by modern landscaping. A large umbrella provides shade over comfortable seating, while lush greenery and a distant sea view enhance the tranquil atmosphere.

Home in Bournemouth

Incredible sea views and heated outdoor pool

PaulRating, 5 stars1 week ago

What a lovely place to stay, we’ve stayed at few beach front places on Airbnb and this one is certainly up there with our favourites. Such a lovely interior, nice touches everywhere. Really comfortable beds. Very peaceful and calm and stunning views from the garden to chill. The location to the beach within a few minutes walk is just superb. Andy and Rachel were just lovely throughout. We can’t wait to book again. And a welcome basket was a nice surprise.

Bungalow in Saint Leonards

A leisure pool area is depicted with children playing in the water, featuring a shallow section and a water fountain. Surrounding loungers are arranged along the poolside, with a red-roofed building visible in the background. The scene conveys a vibrant, family-friendly atmosphere.

4.87 out of 5 average rating, 55 reviews

Forest views in secluded location, swimming pools

EdwardRating, 5 stars7 months ago

We’d just finished a 2 night stay at this park and wanted to be extend it because our little boy was having such a great time. Jamie’s place was absolutely perfect! It’s in a nice and quiet area of the park with the decking area overlooking the woods which was lovely to wake up to. Our son loved watching the squirrels feeding off the peanuts he’d left out there for them. Jamie provides these for guests and it’s a really nice touch and a great way to keep youngsters entertained. The caravan is spotlessly clean, cosy, modern and comfortable and also very well equipped. This made our stay even more enjoyable and made life easier for 2 exhausted parents! The two nights before our booking were in a similar layout caravan elsewhere on the park however, the double bed was nowhere near as comfortable as what’s in this one. If you like a good nights sleep then you’ll certainly get that here! The main club house is only a short walk away from the van. 10/10 from us!

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Weymouth and Portland District rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 22 reviews

An indoor swimming pool is illuminated by natural light from large windows, showcasing a serene turquoise water surface. The high ceiling is framed by steel beams, and the surrounding brick walls add warmth to the space.

Home in Blandford Forum

Launceston Farmhouse with swimming pool & sauna

ElizabethRating, 5 stars9 months ago

Gorgeous, well equipped house in peaceful surroundings. We wanted somewhere that we could unwind as a family after a busy few months with work and exams and this was perfect. Access to the pool was the cherry on the cake. Catherine and Sarah were great hosts.

4.84 out of 5 average rating, 112 reviews

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

Spacious Caravan near sea Weymouth Bay Haven

SuzanneRating, 5 stars3 months ago

This is our second time staying in this lovely caravan. It’s always pristine and lovely. I always felt like a home away from home there. The bedrooms are a good size and the extra full bathroom is a definite plus! I’d highly recommend staying here.

5 out of 5 average rating, 33 reviews

Home in Crossways

Stunning Home with Roof Terrace at Silverlake

BarbaraRating, 5 stars3 weeks ago

The accommodation was spotlessly clean beautifully decorated, with luxuriously comfortable beds to sleep in, large fluffy thick towels. Kitchen equipment had everything Rhian’s accommodation is pure luxury.

5 out of 5 average rating, 26 reviews

A tranquil country retreat is set amidst lush greenery, with a historic flint stone house complemented by a modern extension. An organic swimming pond, surrounded by vibrant foliage and wildflowers, reflects the clear blue sky, creating a serene outdoor environment.

Home in Branscombe

Idyllic country house, organic swim pond, hot tub

DeborahRating, 5 stars1 week ago

We had the most amazing stay at Hill MIll. The house stands in the most beautiful grounds and is the most peaceful and calm setting we've ever stayed in. When we first arrived we just stood outside admiring the surroundings for almost 20 minutes before we even stepped inside. We had everything we needed and more. Our grandsons ages 2, 4, 5, 12, & 13 loved it. The natural swimming pond was so refreshing for a morning dip it certainly woke us all up!! You could walk directly from the house into Branscombe and on route stop for a drink at the Masons Arms (a beautiful pub) and then continue to join the coastal path to Beer. We would love to return and bring some other friends with us as we haven't stopped talking about it since we got back. Thank you Ian for being such a responsive and helpful host. See you again soon!!

4.94 out of 5 average rating, 49 reviews

A charming entrance gate opens to the beautifully landscaped property. The stone building showcases traditional architecture, featuring large windows that reflect natural light. Lush greenery surrounds the gate and leads towards the conservatory, creating an inviting outdoor space.

Home in Crewkerne

Perfect Country Home. Plenty of outdoor terraces

JulesRating, 5 stars1 month ago

We had a gorgeous stay! The place itself is stunning and the furnishings extremely tasteful and comfortable. I would happily go back. Very much an elegant home from home!

4.97 out of 5 average rating, 31 reviews

An indoor swimming pool features crystal-clear water, with a vibrant blue water slide visible nearby. The spacious area is enhanced by natural light streaming through large windows. A playful pattern of yellow inflatables lines one side of the pool, adding a touch of fun.

Home in Saint Leonards

Pinto Holiday Home Oakdene Forest Park Passes Inc!

NirvanaRating, 5 stars1 day ago

Sally was so lovely the place was so nice, comfy and clean she really thought about the little things! location was fantastic! lots to do we can't wait to go back.!

5 out of 5 average rating, 3 reviews

A spacious outdoor pool is set within a well-maintained garden, surrounded by lush greenery and flowering shrubs. The clear blue water reflects the sky, while a stone bench offers a resting spot alongside the pool. The area is open and inviting, promising relaxation.

Home in Buckland Newton

Poacher's Cottage

AliceRating, 5 stars10 months ago

Our stay at Poachers cottage was really wonderful and exactly what we had wanted. The grounds are absolutely beautiful and the cottage was so thoughtfully and beautifully done. The facilities were incredible and we were very lucky to have the pool to ourselves with beautiful weather when we stayed. There was loads for our toddler to do and Adele had any bits we might need for him. I am pretty heavily pregnant and between the pool and the very comfortable beds I had a wonderfully relaxing stay and anytime I needed something, somehow it was already there in the cupboard or in the bedroom. We couldn’t have asked for more. Home made cake and local bits when we arrived and all. Honestly I’ve been so torn on whether to keep this place all to myself but I couldn’t help but rave about my holiday when I got home and have had 3 friends ask for the link to go and stay!

4.84 out of 5 average rating, 62 reviews

The outdoor swimming pool, surrounded by a wooden deck, is visually striking against a backdrop of rolling hills. Lounge chairs are arranged invitingly, while greenery and flowering plants frame the area, creating a pleasant space for relaxation.

Home in Chideock

Escape from it all at the Doghouse!

MeridithRating, 5 stars4 months ago

Fabulous country home walking distance to beach, pub and great hiking paths. Very cozy & warm. Our family loved our 3 nights and wished it was longer!

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Condo rentals with a pool

A modern three-story building features a combination of white and stone façades, with multiple large windows on each floor. A landscaped area with greenery is visible in the foreground, along with a gated entrance. The setting is enhanced by a blue sky dotted with clouds.

4.86 out of 5 average rating, 22 reviews

Apartment 12

DonnaRating, 5 stars19 months ago

The apartment was fabulous! Well located, clean throughout and everything you need for a home from home experience. Laura was a fantastic host, very responsive and made checking in very straightforward and simple. Thank you for a lovely stay 😊

The modern building showcases a three-story design with a light-colored facade and large windows. A balcony extends from the upper level, while landscaping with greenery frames the entrance. The property is situated near a paved road, under a clear blue sky with white clouds.

4.83 out of 5 average rating, 23 reviews

The Palms, Apartment 15

TimRating, 5 stars33 months ago

Had a great stay at the apartment. Place was clean and had everything you’d need for your stay Excellent location for access to shops, restaurants and beach.

An indoor pool area is enclosed by large glass windows, allowing natural light to illuminate the clear water. Lush green plants are positioned around the pool, enhancing the calming atmosphere. A glimpse of the outdoor pool and landscaped gardens can be seen through the windows.

5 out of 5 average rating, 3 reviews

Bournemouth Seafront, Summer Timeshare apartment

SvetlanaRating, 5 stars20 months ago

We spent 6 days in an excellent accommodation and the facilities in the hotel were great. Our host was very helpful and supportive if we had any questions. We would definitely highly recommend this apartment.

A modern three-story building is depicted with a mix of white and light stone exteriors. Multiple large windows allow natural light, and a balcony is visible on the upper floor. Lush greenery enhances the entrance, complemented by decorative fencing along the sidewalk.

4.9 out of 5 average rating, 31 reviews

The Palms Apartment 16 with Balcony

VladyslavRating, 5 stars8 months ago

Absolutely brilliant please. Great host. Reasonable price!

4.82 out of 5 average rating, 33 reviews

An aerial view of the apartment building is shown, with the sea visible in the distance. Surrounding residential buildings and roads are clearly depicted. A green area with trees is present in front of the building, along with parked cars lining the street.

Condo in Southbourne

2-BR Penthouse Apt. close to Beach with Pool*.

JulieRating, 5 stars1 week ago

Had a wonderful stay in this spacious apartment. The place is very well equipped with everything you could need. Huge shower, very comfy beds and a balcony. Short walk to beach, shops and lot's of great restaurants and bars. Friendly, helpful hosts. Can't wait to come back. Thank you so much!

A modern, three-story building is shown with a mix of white and beige façades. Large windows allow natural light, and a central entrance is framed by a small balcony. A manicured garden with palm plants is situated in front, separated by a decorative fence.

4.94 out of 5 average rating, 18 reviews

The Palms Studio 6

NouriattRating, 5 stars7 months ago

My parents had an amazing one-month stay at Laura’s Airbnb! The apartment was exactly as described. Clean, comfortable, and well-equipped. The location was perfect, close to local shops, restaurants, and public transportation, which made exploring the area so easy. Laura was incredibly welcoming, quick to respond to any questions. I would highly recommend staying here to anyone looking for a pleasant and hassle-free experience! Thank you, Laura