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

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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, 118 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

A wooden deck features a neutral-toned table surrounded by matching chairs, providing a seating area with panoramic views of Swanage Bay. The coastline can be seen in the distance, framed by lush greenery and a clear blue sky.

Chalet in Dorset

4.93 out of 5 average rating, 275 reviews

Breathtaking sea views from this light, cosy lodge

Seascape is a bright, airy lodge down its own drive at the edge of Swanage Bay View. Adjoining Townsend Nature Reserve it enjoys utter tranquillity and spectacular views over the bay, as seen on 'A Place in the Sun'. With its tasteful modern furnishings, central heating and double glazing, Seascape is a cosy winter retreat, while in Spring and Summer use of a 1903 beach hut on a private beach is included. In addition, guests enjoy the amenities of SBV - all within a 15 min walk of the seafront!

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, 185 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)

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

4.87 out of 5 average rating, 136 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.

Guest favorite

A rectangular freshwater pool is framed by a wooden deck, surrounded by a landscaped garden. Lush greenery and rolling hills are visible in the background, offering a serene and expansive view of the countryside.

Bungalow in Charmouth

4.94 out of 5 average rating, 210 reviews

Secluded hideaway, heated pool, walks, fossils

The Annex is bright, comfortable and cosy with a wood burner for winter. The public footpath crossing our garden next to the river Char links with many others - great for dog walkers. We are close to Charmouth beach and Lyme Regis – renowned for their fossil treasures. Love swimming? our freshwater pool is generally heated to a very cosy 29 - 30 degrees (warm bath temperature) and can be used from April to October With advance notice, the twin beds can be connected to form a king size bed

Top guest favorite

An outdoor space is featured, showcasing a heated swimming pool surrounded by a wooden deck. Two lounge chairs are positioned nearby, along with a dining table. The backdrop includes lush greenery, emphasizing a natural environment. An outdoor grill is also present, offering additional amenities.

Guest suite in Dorset

4.95 out of 5 average rating, 131 reviews

Great for visiting Dorset - woodland walk to beach

Situated in the heart of Branksome Park in Poole this newly built annexe is within walking distance of Branksome Chine, Bournemouth and Sandbanks beaches. Nearest restaurants and bars are 15 minutes walk at Penn Hill and Westbourne. The property is located 2 miles from Bournemouth with regular buses close-by. Branksome railway station is 0.75 mile distance. Further afield the accommodation makes a great hub to explore the wider area including the Jurassic Coast, New Forest and Studland.

Guest favorite

A sandy beach stretches along the coastline, meeting the calm blue waters. The shoreline features pebbles and patches of seaweed, with gentle waves visible. Clear skies and scattered clouds enhance the serene atmosphere, while distant land is observable along the horizon.

Tiny home in Dorset

4.87 out of 5 average rating, 100 reviews

Get-a-Wey a static caravan at Haven Weymouth Bay

SUPERB ' 2020' edition ABI New Horizon. Sleeps up to 8 people. 1 double, 2 twin bedrooms (pull-out double sofa bed in lounge), shower/toilet, separate toilet, kitchen and lounge area. Located in a quiet area of the park and a short walk to nearby Bowleaze Cove. Note; This is caravan ONLY, a Haven pass may be required to access some areas of the park, including swimming pools. Prices for passes can be found on Haven website. WiFi is available throughout the caravan and main buildings

Guest favorite

A serene king bedroom features a beautifully styled headboard with a floral pattern, accompanied by two bedside lamps casting a warm glow. Crisp linens are arranged neatly on the spacious bed, with decorative towels folded on the coverlet, adding a touch of elegance to the space.

Chalet in Weymouth

4.97 out of 5 average rating, 253 reviews

The Fleet Retreat

Our luxurious accommodation, ‘The Fleet Retreat’ boasts views of the Fleet Lagoon, a stunning nature reserve nestled between world famous Chesil beach and the South West Coast Path. It is situated just 1 mile from Portland and 2 miles from Weymouth town centre Our luxurious accommodation is in close proximity to an abundance of beaches, walks and activities. It is perfect for couples wanting to while away a lazy weekend or for families wanting to explore all that Dorset has to offer.

Guest favorite

The spacious outdoor dining area is highlighted by a large table surrounded by light green chairs. An umbrella provides shade, and the path leads towards a modern house with large glass windows reflecting the garden's greenery.

Home in Long Sutton

4.9 out of 5 average rating, 263 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

A heated outdoor swimming pool is surrounded by paved decking, showcasing vibrant blue water under a clear sky. Lounge chairs are positioned nearby for relaxation, and a gazebo is visible in the background, adding to the tranquil outdoor setting.

Train in Axminster

4.99 out of 5 average rating, 287 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.

Superhost

The image displays a heated swimming pool enclosed within a clear poly tunnel. The water is calm and reflects the overhead light, creating a serene atmosphere. Poolside tiles extend along the edges, and a rolled-up cover can be seen at one end.

Apartment in Whitchurch Canonicorum

4.92 out of 5 average rating, 272 reviews

The Duck Wing, quirky dog friendly apartment

The Duck Wing is a quirky, self contained apartment on the first floor within Plenty Cottage. It's beautifully appointed for a relaxed, carefree stay in a wonderfully rural environment. Nothing is too much trouble. It sleeps two in double bed in a pretty bedroom and has a double sofa bed too. Own bathroom/shower, a separate WC and a warm spacious living area. The pub is 7 mins walk away and the beaches a 5 mins drive. The private, heated swimming is available 1st April - 31 Sept

Top guest favorite

An indoor swimming pool is featured, surrounded by large windows allowing natural light. The ceiling beams reveal a spacious, airy atmosphere. Two red chairs are positioned nearby, and a shallow end is visible with steps leading into the water. A blue cover rests along one side of the pool.

Cottage in Dorset

4.98 out of 5 average rating, 360 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!