Vacation rentals with a pool in Weymouth

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Weymouth

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

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Superhost

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.

Shepherd’s hut in Lyme Regis

4.99 out of 5 average rating, 104 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

Superhost

An open living area features a comfortable sofa facing a rustic wooden dining table with colorful chairs. A vintage red refrigerator adds a pop of color, while wooden accents and paneling create a warm ambiance. Natural light filters through the windows, illuminating the space.

Holiday park in Hampshire

4.91 out of 5 average rating, 54 reviews

Lovely dog friendly leafy lodge

Centrally located, unique lodge with amazing facilities and a beautiful tranquil setting. Perfect for those looking for that extra bit of space, a bit of added luxury or if there is a group of you, then look no further. free standing furniture, New York loft style décor and panoramic glass sliding doors creating a nature on the-inside vibe. The main bedroom features a stand-alone, roll-top bathtub (hidden Tv) and an en-suite. The second bedroom is a twin room with comfy beds lots of storage.

Superhost

An indoor heated swimming pool is framed by rustic brick walls and wooden beams. Large windows allow natural light to flood the space, highlighting the serene water surface. A built-in seating area lines one side of the pool, enhancing the inviting atmosphere.

Home in Somerset

4.87 out of 5 average rating, 100 reviews

Cosy barn conversion with connecting indoor pool

Pennard Hill Farm is a family farm with breathtaking views over the Mendip Hills. Our holiday cottages are very individual and have bags of character and charm. The Haybarn is a beautiful barn conversation next to the indoor heated swimming pool, across the courtyard from the main farm house. There is plenty to see and do nearby such as Longleat Safari Park, Hauser & Worth Art Gallery, exploring the local towns of Wells, Frome and Glastonbury and enjoying long walks right on the doorstep.

Superhost

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.

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

Home in East Southbourne

5 out of 5 average rating, 16 reviews

Perfect family house, heated pool, close to beach

Our much-loved home works so well for family guest groups with occasional availability throughout the year. Its 7 mins walk to the lovely sandy beaches of Southbourne. You will find some great bars and restaurants nearby & can explore historic Christchurch and the beautiful seaside resorts around Bournemouth and Dorset. This listing is part use of the house (owners rooms locked), but you will have the place to yourselves.The outdoor heated pool is open from early April until September.

Superhost

A view of a tranquil bay is presented, featuring a clear blue sky dotted with fluffy clouds. Soft sunlight glimmers on the water's surface, while hills can be seen in the distance, creating a serene backdrop between the two buildings.

Cabin in Dorset

4.87 out of 5 average rating, 15 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.

Superhost

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

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.

Superhost

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!

Superhost

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 Westbourne

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.

Superhost

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.

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.

Superhost

An indoor pool stretches across the room, showcasing crystal-clear water and a tiled surround. Natural light filters in through large windows, illuminating the wooden ceiling beams and creating an open, airy feel. The area is designed for relaxation and leisure, with a serene view of the countryside.

Home in Stockland

5 out of 5 average rating, 21 reviews

Rural idyll with exclusive private indoor pool

Modern house extending to 180 sqm with indoor pool (10m x 5m) for exclusive private use by guests, terrace and garden. Studio, bedroom, kitchen, bathroom and laundry room with plenty of space to relax. Fantastic views over unspoilt countryside with plenty of walking possibilities and a village pub/restaurant in nearby Stockland.

Superhost

A spacious living area features a vaulted ceiling and is illuminated by recessed lighting. Comfortable sofas are arranged near a coffee table, with a television set displayed on a wooden shelf. Large glass doors open to a private outdoor space, enhancing natural light.

Chalet in Fordingbridge

4.85 out of 5 average rating, 131 reviews

New Forest lodge - 194 NO PETS

Stunning lodge located in a really private section of the park. Hot tub is included in the cost. Refurbishment plans - All new Parquet flooring and new carpets throughout from Oct 2024!!! Disposable BBQ’s are only allowed if used with a bbq holder that the park provide for free. NO DOGS - sorry it’s a pet free lodge.