Vacation rentals with a pool in Weymouth and Portland District

Find and book unique homes with a pool on Airbnb

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, 107 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

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.

Guest favorite

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.

Guest favorite

A modern lodge is surrounded by greenery, featuring a heated swimming pool to the side. Bi-fold doors reveal a spacious dining area with outdoor seating under white umbrellas. The structure showcases a wooden façade and large windows, providing a bright and open atmosphere.

Home in Long Sutton

4.89 out of 5 average rating, 253 reviews

Heated Pool, Hot Tub, Sauna, Games - Upton Bourn

Welcome to Upton Bourn Lodge, where unforgettable memories await for families and friends celebrating, or reuniting. Enjoy meals in the spacious double height dining room with seating for all. Take a dip in your heated pool, relax in the hot tub and sauna, and enjoy various games like table tennis, football, and pool. Explore nearby footpaths to visit three pubs offering superb food, beer, and cider. Catering, pampering or a host of on and offsite activities available to guests.

Top guest favorite

Home in Lyme Regis

5 out of 5 average rating, 24 reviews

Your Own Private Indoor Pool. Rural Seaside

OFFER 4 NIGHTS FOR THE PRICE OF 3! 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, 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

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

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

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 swimming pool is enclosed within a clear canopy, allowing natural light to flood the space. The pool features a serene turquoise color, with inflatable pool toys floating on the surface. Surrounding loungers offer a comfortable area for relaxation.

Apartment in Horton

4.8 out of 5 average rating, 49 reviews

Peaceful 2-Bed Escape | Hot Tub • Pool • Sauna

Rivendell park: Stylish 2-bedroom flat with private entrance, set within a peaceful holiday park. This bright, self-contained space is perfect for a relaxing escape from everyday life. Guests enjoy shared access to the seasonal heated pool, large hot tub, sauna and beautifully maintained gardens — ideal for unwinding or exploring the outdoors.