Vacation rentals with a pool in Weymouth and Portland District

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Top-rated rentals with a pool in Weymouth and Portland District

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

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Top guest favorite

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, 106 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

Top guest favorite

The exterior of the caravan is presented, featuring pale blue cladding and a spacious covered decking area with white railings. Large windows allow for ample natural light, and a clear blue sky adds to the seaside charm. The surrounding area includes lush greenery.

Chalet in Dorset

4.97 out of 5 average rating, 36 reviews

Our Plaice by the Sea

'Our Plaice by the Sea' is a 2 bedroom caravan, on the flagship Littlesea Haven holiday park. Our Plaice feels like a home from home, reminding us of a beach hut with its pale- blue cladding, decking out front and stunning views of Chesil Beach; it stands out, giving a relaxed seaside vibe. There’s plenty to do on-site with an indoor and outdoor pool, adventure golf, arcade, day and night entertainment (Haven passes to be purchased) fabulous coastal path walks and near to the Jurassic coastline.

Guest favorite

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

4.91 out of 5 average rating, 239 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

A private hot tub rests on a stone patio, with bubbling water inviting relaxation. Nearby, wooden outdoor seating is positioned alongside a small table, suggesting a serene spot for enjoyment. Lush greenery and trees frame the scene, enhancing the tranquil outdoor setting.

Cottage in Woolland

4.86 out of 5 average rating, 7 reviews

Escape to the country! hot tub retreat for 7

Welcome to The Victorian Barn Countryside Estate & Farm in Dorset. Set in 65 acres of lush green parkland The Victorian Barn Estate offers the perfect retreat for your Dorset escape. Explore the rural footpaths and fishing lakes, take a dip in the warm indoor pool, enjoy your bubbly private hot tub, have fun with the kids in the games rooms and outdoor play area or simply relax in your comfortable accommodation. Perfect for any occasion and within easy drive of the historic Jurassic Coast.

Superhost

A spacious living area features large windows allowing natural light to fill the room. A light-colored sofa and coffee table are positioned centrally, complemented by decorative pillows. A wall-mounted television is visible, creating a cozy entertainment space. The outdoor terrace can be glimpsed through the sliding glass doors.

Camper/RV in Furzehill

4.92 out of 5 average rating, 13 reviews

Wilksworth Holiday Park - 2 Bed - Pool Access

Escape to our charming 2 bedroom home nestled in the serene Wilksworth Holiday Park near Dorset’s picturesque countryside and stunning golden beaches. Perfect for families or couples, our home offers a cozy retreat with modern amenities. Enjoy shared access to a refreshing pool, perfect for unwinding after a day of exploration. Discover nearby scenic trails, quaint villages, and breathtaking coastal views. Your ideal getaway awaits, combining relaxation and adventure in a beautiful setting.

Guest favorite

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

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

4.88 out of 5 average rating, 17 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.

Top guest favorite

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.

Guest favorite

Barn in Long Sutton

4.93 out of 5 average rating, 175 reviews

Steam Room, Sauna, Hot Tub and Heated Pool

Enjoy a little luxury at The Pictureworks, a stylish industrial loft designed for celebrations, holidays, and friend getaways. The property is well-appointed with all you need for an exceptional getaway. Enjoy your private spa with hot tub, steam room, and sauna, along with two heated pools, one exclusively for you. Dine in style at the huge tables, both indoor and outdoor. Open the large bi-fold doors (45ft in total) for a seamless blend of indoor/outdoor.

Top guest favorite

Cottage in Dorset

4.98 out of 5 average rating, 348 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!

Top guest favorite

An outdoor swimming pool is visible, featuring clear turquoise water under a sunny sky. Surrounding fencing provides a boundary, and expansive views of the countryside can be seen in the background. The pool area includes a stone patio for lounging.

Home in Margaret Marsh

5 out of 5 average rating, 29 reviews

Charming thatched farmhouse, heated pool & cottage

Lose yourself in the peaceful hideaway in the middle of nature, yet only 10 minutes from the ever popular town of Shaftesbury, and less than an hour to the beach. Wonderful grounds and expansive open views in the great British countryside. Main house + cottage. Pool is outdoors and will be available from the end of April until end of September.

Guest favorite

An enclosed swimming pool features a clear protective cover, allowing for year-round enjoyment. The pool area is surrounded by light-colored tiles, and colorful pool floats are visible on the water. Lush greenery is seen in the background, enhancing the tranquil setting.

Home in Dorset

4.84 out of 5 average rating, 57 reviews

Spacious Group Stay | Pool • Hot Tub • Sleeps 7

Rivendell Park: Luxurious 4-bed retreat sleeping 7. Perfect all year-round - even for Christmas & New Year! Features en-suite rooms, a spacious conservatory lounge with wood burner, semi-commercial kitchen, and private terrace. Enjoy shared access to a heated pool, hot tub, and a lively summer terrace bar — ideal for families or group getaways.