Holiday rentals with a pool in Weymouth

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Weymouth

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

%{current} / %{total}1 / 1
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 Uplyme
4.99 out of 5 average rating, 133 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, 159 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
4.95 out of 5 average rating, 439 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 favourite
A wooden deck area is furnished with two comfortable chairs and a small table adorned with refreshments. A canopy provides shade, and vibrant flowers are seen hanging nearby, adding a touch of color to the natural surroundings of trees and greenery.
Cabin in Ringwood
4.96 out of 5 average rating, 295 reviews

Cosy Wooden Cabin by the Woods

Spend your days in a cosy timber-framed cabin enveloped by rhododendrons. With a wood-burning stove, a garden and terraces you'll be sure to have what you need for a relaxing stay. Head out of the garden gate and you’ll enter Ringwood Forest with a cycle trail, Moors Valley Country Park, a golf course and a lake. A 5min drive will take you to the historic market town of Ringwood. Go east and you’ll hit the beautiful New Forest National Park or head south to the sandy beaches of Bournemouth.

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 Hilton
4.89 out of 5 average rating, 194 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, 222 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.

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, 174 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 tranquil view of the hut by a calm lake, surrounded by lush greenery and tall grasses. The serene water reflects the clear sky and distant trees, creating a peaceful atmosphere. The wooden fence encloses the property, highlighting the retreat's seclusion.
Shepherd’s hut in Plaitford
4.96 out of 5 average rating, 377 reviews

Shepherds Pye - Lakeside Retreat In The New Forest

Shepherd's Pye is a unique, 1920's Railway Carriage. Rescued from a local farm as a neglected frame, it has been lovingly restored by ourselves into a cosy, modern retreat on the edge of the New Forest. The hut is set in a secluded, private spot on our farm overlooking a lake. It is self contained and finished to a high standard; including a comfy double bed, heating, mains electrics and a fully equipped kitchen and en-suite bathroom, supplying all you need for rural yet comfortable stay.

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, 295 reviews

Breathtaking sea views from this light, cosy lodge

Seascape is a bright, airy lodge tucked away 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 in warmer weather, 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!

Top Guest favourite
Train in Hawkchurch
4.99 out of 5 average rating, 304 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 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, 193 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
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 Warmwell
4.98 out of 5 average rating, 378 reviews

Private use of 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!

Popular amenities for Weymouth rentals with a pool

Quick stats about holiday rentals with a pool in Weymouth

  • Total holiday rentals

    Explore 50 holiday rentals in Weymouth

  • Nightly prices starting at

    Weymouth holiday rentals start at $71 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,320 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Weymouth holiday rentals include Wi-Fi 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!

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Dorset
  5. Weymouth
  6. Rentals with pools