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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Guest favorite

An expansive wooden deck is featured, with a modern round fire pit positioned among lush greenery and vibrant flowers. Large glass doors allow views into the interior space, which is visible beyond the deck. The natural landscape extends in the background under a clear sky.

Shepherd’s hut

4.99 out of 5 average rating, 127 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 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

4.96 out of 5 average rating, 402 reviews

Cosy Shepherd's Hut with wood-fired hot tub

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 are only a few meters away. One photo shows its location to other cabins / Horton Road.

Top guest favorite

Yurt

4.99 out of 5 average rating, 119 reviews

Kingfisher yurt, A unique eco holiday in Devon

Unique yurt (sleeps 5+) surrounded by oak trees, next to the wild swimming pond (shared /gated.) Also check out Buzzard yurt with its terrace / views Private large, rustic, open plan kitchen (+ games, maps and books), shower, compost loo and fire pit. The shared games/music cabin adjoins your kitchen. Dog friendly. Use of our 26 acre rewilding woodland a 45 minute hike away. Bookable hot tub. The safety of your group is your responsibility. Check-in form /waiver to sign on arrival please.

Guest favorite

An open-plan living area is shown, featuring a spacious L-shaped sofa with decorative cushions. A coffee table is positioned in front, complemented by a wall-mounted TV. The kitchen area is visible in the background, illuminated by modern lighting and hidden appliances.

Vacation home

4.94 out of 5 average rating, 139 reviews

Family friendly & comfortable 2 Bed Holiday Home

Family friendly 2-bed holiday home (sleeps 6), centrally heated & double glazed throughout. Located in a quiet cul-de-sac close to all park amenities & adjoining beach. Price includes Wi-Fi. Open plan living space with large L shaped sofa/bed, 43" TV, & fully equipped integrated kitchen. Family shower room, & an en-suite to the Master bedroom, which also has a fitted double wardrobe, 32” TV & king-size bed. The twin bedroom has two single beds. The patio doors lead to a wraparound veranda.

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

4.94 out of 5 average rating, 219 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

A charming outdoor view showcases a wooden railway carriage and adjacent structure surrounded by a lush green lawn. Sunlight illuminates the inviting patio area with seating, while wattle fencing adds a natural touch to the landscape.

Train

4.99 out of 5 average rating, 281 reviews

Clover Carriage with pool, sauna and 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 heate pool & sauna (located in the pool house), beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and a romantic outdoor bath

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

4.93 out of 5 average rating, 282 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 cosy in winter, while outside, the large deck offers a panoramic view all the way to Corfe Castle. In addition, guests enjoy the amenities of SBV - all within a 15 min walk of the seafront!

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

4.87 out of 5 average rating, 102 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 spacious corner sofa is adorned with colorful cushions in yellow, gray, and blue. A cozy navy blanket drapes over the side. A wooden coffee table holds a selection of brochures, with natural light filtering through sheer curtains at the nearby window.

Home

4.85 out of 5 average rating, 117 reviews

Spacious Caravan near sea Weymouth Bay Haven

Our holiday home is spacious with a well equipped kitchen. Located 12-15min flat walk (buggy friendly) from the seaside. The Haven park offers a swimming pool, live entertainment and play areas for kids until 14th November (access to indoor complex is an additional fee on a first come first serve basis) We are opposite the activity field. One car parking space next to the caravan.. CHANGEOVER DAYS ARE MONDAY OR FRIDAY. Please contact us to make a shorter booking or with any questions.

Guest favorite

Cottage

4.89 out of 5 average rating, 147 reviews

Daisy Cottage on the Jurassic Coast

A cosy and stylish, dog-friendly cottage, set amid the beautiful fields and woodlands of the Fernhill Estate with easy walking access to the coastal village of Charmouth and only 2 miles to Lyme Regis. The South West Coastal Path runs opposite our front door and our guests have seasonal access to a heated outdoor pool. Our cottage sleeps four and is furnished and equipped to a very high standard with everything you need for a relaxing holiday on the Jurassic Coast in West Dorset.

Top guest favorite

Cabin

4.94 out of 5 average rating, 264 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.

Superhost

Chalet

4.88 out of 5 average rating, 225 reviews

The Duck House. A child/dog friendly rural chalet

The Duck House is a lovely child/dog friendly chalet nestling in the orchard at Plenty Cottage. Quiet and peaceful it's the perfect retreat for a family - and dogs are especially welcome! Open plan living it’s a comfortable and home from home. A wonderful rambling garden, summerhouse, BBQ and a (free) heated swimming pool (1st April - 31st Sept). The mantra is 'No Stress'. Ample parking, dog/child friendly pub 7 mins walk away. Wonderful NT beaches just five min drive.