Holiday rentals with a pool in Weymouth

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Top-rated rentals with a pool in Weymouth

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

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Top guest favourite
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 in Lyme Regis
4.99 out of 5 average rating, 131 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 favourite
Barn in Dinton
5 out of 5 average rating, 151 reviews

Unique, romantic luxury countryside retreat

Unique luxury cottage for two, an ancient dovecote with a fabulous swimming pool. Beautifully furnished, romantic and spacious, in gorgeous peaceful countryside, the thick stone walls make it warm and cosy in winter, cool in summer as well as quiet and private. Upstairs there is a very comfortable super kingsize bed, a rolltop bath, a huge velvet sofa and a 50" TV. Downstairs is a shower room, kitchen and large dining area. Lovely walks from the door and close to Salisbury, Longleat & Stonehenge

Top 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
4.96 out of 5 average rating, 414 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.

Guest favourite
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, 192 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
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
4.86 out of 5 average rating, 153 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 favourite
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, 221 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 favourite
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 in Axminster
4.99 out of 5 average rating, 285 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 favourite
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, 288 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 favourite
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 in Overcombe
4.85 out of 5 average rating, 118 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.

Top guest favourite
A secluded yurt is nestled among trees beside a tranquil, reflective swimming pond. Wooden decks are visible along the water's edge, while the surroundings are adorned with greenery, showcasing the serenity of the natural setting.
Yurt in Colyford
4.98 out of 5 average rating, 127 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. Bookable (ASAP) hot tub. The safety of your group is your responsibility. Check-in form /waiver to sign on arrival please.

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, 274 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.

Top guest favourite
A large heart-shaped sculpture is positioned on a circular wooden platform, surrounded by natural vegetation. The backdrop features rolling hills under a sky with varying cloud coverage, enhancing the scenic view of the surrounding landscape.
Holiday park in Hampshire
4.99 out of 5 average rating, 171 reviews

Sandy Balls Holiday Village New Forest Hampshire

Spacious and well equipped holiday home located in a quiet spot at Sandy Balls Holiday Village. Bed linen & WIFI are included. Facilities: Indoor/outdoor pools, gym, jacuzzi, 2 adventure play areas, soft play, arcade, restaurants, Starbucks coffee shop and a village store. Enjoy evening entertainment and family activities, bike hire & alpaca walks. Sandy Balls is the perfect location for exploring the New Forest and surrounding areas. Paulton’s Park is 25 minutes away.

Popular amenities for Weymouth rentals with a pool

Quick stats about holiday rentals with a pool in Weymouth

  • Total holiday rentals

    Explore 60 holiday rentals in Weymouth

  • Nightly prices starting at

    Weymouth holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,480 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    50 of Weymouth holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Weymouth rentals

  • 4.8 Average rating

    Weymouth stays are highly rated by guests – averaging 4.8 out of 5!

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