
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.

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

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

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.

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.

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)

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.

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.

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.

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!

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

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

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
House rentals with a pool

Coastal, New Forest 3 Bed Home Facilities Included

Spacious Caravan near sea Weymouth Bay Haven

Stunning Home with Roof Terrace at Silverlake

Heated Pool, Hot Tub, Sauna, Games - Upton Bourn

Country House - Pool Jacuzzi Escape Room Karaoke

Gardener's Cottage

The Beach House Bournemouth

Wimborne luxury dog friendly lodge with pool
Condo rentals with a pool

Seascape Apartment

Holiday apartment own heated indoor pool & sauna

Flat 10 Pelican House

Bournemouth 2 Bedroom Apartment 22

The Palms, Apartment 2

2-BR Penthouse Apt. close to Beach with Pool*.

The Palms, Apartment 19

The Palms Studio 6
Other holiday rentals with a pool

The Woodlark Lodge with Harbour Views

Modern Spacious Holiday Home With Sea Views

A luxurious modern 3-bedroom Swift Bordeaux

Big 3 bed cottage with wild swimming & woodburner

Charming cottage with pool in the New Forest

Kingfisher Lodge with Sea Views

Pet Friendly Holiday Home by Ally Cat Breaks

Our Plaice by the Sea
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!
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- New Forest National Park
- Paultons Park Home of Peppa Pig World
- Weymouth Beach
- Stonehenge
- Boscombe Beach
- Bournemouth Beach
- Brixham Harbour
- Lyme Regis Beach
- Bournemouth International Centre
- The Tank Museum
- Kimmeridge Bay
- Southbourne Beach
- Torquay Beach
- Highcliffe Beach
- Beer Beach
- Crealy Theme Park & Resort
- Preston Sands
- Mudeford Quay
- Mudeford Sandbank
- Shorefield Country Park
- Longleat Safari Park
- West Bay Beach
- Charmouth Beach
- Man O'War Beach




