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Holiday 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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Guest favourite
A gravel driveway leads to a charming white house surrounded by lush greenery. The property features a two-story structure and an annexe, both set within spacious grounds. Noticeable are the well-maintained gardens and outdoor seating areas, perfect for gatherings.
Home in Somerset
4.91 out of 5 average rating, 278 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

Group Gatherings Host your own event Exclusive use 10-16 guests Min 2 off peak 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 -pulled pork 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

Guest favourite
A rustic Acorn Hut, clad in green, is surrounded by lush foliage and blooming flowers. A hot tub sits on a wooden deck, while a wood burner is positioned nearby, enhancing the natural setting. The entrance to the hut is inviting, framed by greenery.
Shepherd’s hut in Ashley Heath
4.95 out of 5 average rating, 455 reviews

Shepherd's Hut (wood-fired hot tub/sauna optional)

Get away from it all and create romantic memorable moments in your rustic Acorn Hut. Step outside and be enveloped by nature and enjoy sitting in front of a fire pit or have a BBQ or a relaxing hot tub (EXTRA CHARGE). Acorn Hut has everything you need to stay comfortably and is particularly suited for nature lovers. Its small Hobbit wood burner will keep you snug and warm on a cold evening. Toilet/shower. Other cabins on site/ Horton Road which can be noisy at times. Hut is not fully fenced in.

Superhost
The interior features two twin beds with colorful bedding arranged against wooden walls. A dining table is set with two glasses of red wine, a bottle, and a small vase of flowers. A window offers views of the surrounding greenery.
Shepherd’s hut in Dorset
4.89 out of 5 average rating, 198 reviews

Everdene shepherd's hut

Lovely views of the Blackmore Vale (amazing sunsets weather permitting!) Our huts are in a secluded area of the farm. Kingsize bed/twin beds opposite ends with curtains for privacy. Woodburner, hot/cold running water, fridge, hob, microwave, wardrobe. Picnic bench & fire pit outside. Wonderful walks, only 10 minutes on foot to village shop and pub. Great for families. Short walk to luxury wetrooms, w/m, drier. Fishing on farm. Indoor exercise pool payable locally. (Subject to availability)

Guest favourite
A serene outdoor seating area is highlighted, featuring two wicker armchairs with soft cushions and a glass-topped table. Beyond, the tranquil Fleet Lagoon reflects sunlight, providing picturesque views, while colorful flowers add a touch of warmth to the setting.
Chalet in Weymouth
4.95 out of 5 average rating, 235 reviews

Summer Lodge

The Summer Lodge boasts uninterrupted views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the South West Coast Path (Jurassic Coast). Located just one mile from the Isle of Portland, the home of the 2012 Olympic sailing events and a short drive from Weymouth town centre and harbour, our stunning holiday home is perfectly situated for anyone wanting a coastal escape. Our sea view lodge sleeps 6 people. There are 2 double bedrooms and a small double sofa bed.

Top guest favourite
A green yurt is nestled among lush grass and trees, with a spacious wooden terrace visible nearby. The landscape features rolling hills in the background, under a bright blue sky illuminated by rays of sunshine. The area offers a serene rural setting.
Yurt in Colyton
4.98 out of 5 average rating, 194 reviews

Buzzard Yurt - A unique eco holiday in East Devon

Unique and comfortable yurt (sleeps 5+), large terrace, stunning views - also you could check out Kingfisher yurt (bigger kitchen) by the swimming pond. Private kitchen, chill-out cabin, shower, rustic flushing loo, compost loo with a view, campfire area. Wild swimming pond (fenced) Hot tub (can be advance booked by EITHER Kingfisher or Buzzard yurt). Dog friendly, footpaths. Kid heaven! By booking you take responsibility for safety of your group. Check-in form /waiver on arrival please.

Top guest favourite
Cottage in Combe Saint Nicholas
5 out of 5 average rating, 21 reviews

Big 3 bed cottage with wild swimming & woodburner

The Stables at Combe Head House are nestled within the private grounds, tucked away from the road. Enjoy our meticulously renovated three-bedroom converted stables. Decorated with a curated selection of vintage furniture, this enchanting space offers a unique blend of old-world charm and modern comfort. Plenty of parking right outside on a large private driveway. Escape the hustle everyday life and immerse yourself in the timeless beauty of our historic stables. Time to relax and recharge…

Superhost
An indoor pool is surrounded by sleek gray tiling and illuminated by recessed lighting. The pool's inviting turquoise water reflects the ceiling lights. A cozy seating area with cushions is visible in the corner, providing a relaxed atmosphere.
Cottage in Osmington
4.85 out of 5 average rating, 190 reviews

A luxury unique home spa - White Stones Retreats.

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.

Top guest favourite
A modern caravan is positioned on a spacious grassy plot. It features a large deck with white railing and a series of windows providing ample natural light. The exterior is clad in light-colored panels, and nearby caravans are visible in the background.
Chalet in Dorset
4.94 out of 5 average rating, 111 reviews

A luxurious modern 3-bedroom Swift Bordeaux

A luxurious modern 3-bedroom Swift Bordeaux Silver Prestige. This fabulous caravan is situated at Haven Littlesea Holiday Park in Weymouth in a spacious plot with views of the Fleet Lagoon and Chesil Beach. Sleeps up to 6 people. 1.5 bathrooms Linen and towels supplied. Parking spaces for 2 cars. Outside decking and seating area. Onsite restaurant, laundrette and local shop. For use of swimming pool, entertainment venue and booking activities you can purchase Play Passes from Haven

Guest favourite
A modern static holiday home with a white exterior is shown, featuring large windows that allow natural light. A spacious deck with a white railing provides access, while well-maintained greenery surrounds the entrance, creating a welcoming outdoor space.
Chalet in Dorset
4.81 out of 5 average rating, 57 reviews

Luxurious holiday home at Weymouth Bay

2015 Luxurious Willerby Chambery static holiday home. Located in a quiet corner on Havens Weymouth Bay Holiday Park. Sleeps 4/up to 6 if using sofa bed. 2 Bedrooms. Sorry no pets.The main bedroom en suite toilet and sink and 24” smart tv/ dvd. 1 x twin bedroom and a pull out sofa bed in lounge. 43” smart tv player in lounge. Wi-fi , Bluetooth speakers in ceiling. Full size fridge/freezer, microwave, full size cooker. Central heating and double glazing. Patio doors, decking.Allocated parking

Guest favourite
A charming barn conversion features natural stone walls and large windows that invite ample sunlight. The surrounding landscape includes lush greenery and a clear blue sky, creating a serene rural atmosphere. The driveway leads to the entrance, providing easy access to the property.
Cottage in Dorset
4.79 out of 5 average rating, 199 reviews

Stunning Barn conversion with heated swimming pool

Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

Top guest favourite
A renovated railway carriage features a wooden deck, framed by lush grass and potted plants. Outdoor seating arrangements include a circular table and two chairs, contributing to a welcoming atmosphere. Large glass doors open up to a bright interior, framed by decorative flower pots.
Train in Axminster
4.99 out of 5 average rating, 348 reviews

Foxglove Carriage with pool, sauna & outdoor bath

Nestled into our working farm, this lovingly restored railway carriage is the perfect spot for a romantic stay away. The views are out of this world and all viewable from the large glass doors so you can stay tucked up in bed or on the sofa in front of the fire, with great wifi, free access to our beautiful heated pool and sauna in the pool house, beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and romantic outdoor bath.

Top guest favourite
The image captures a log cabin with a green grass roof adorned with seasonal bluebells. A chimney emits smoke, indicating warmth within. A wooden hot tub is positioned on the deck, surrounded by trees and nature, inviting a serene outdoor experience.
Cabin in Ringwood
4.94 out of 5 average rating, 304 reviews

Piilopirtti - a traditional Finnish log cabin

Spend your days in a traditional Finnish log cabin with a grass roof. Step outside and be enveloped by rhododendrons and enjoy sitting in front of a fire pit or a BBQ amongst trees and nature. The main room is for sleeping and living with a super-king size bed, table, TV, 2 easy chairs. The cabin has a fully equipped kitchen and a bathroom. Cabin is not fenced in. Adjacent to Ringwood Forest where you will find a cycle trail, Moors Valley Country Park, a golf course and a lake.

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