
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

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.

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.

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

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

Buzzard Yurt - A unique eco holiday in East Devon
Unique and comfortable yurt (sleeps 5+), large terrace, stunning views - also you could check out Kingfisher yurt (bigger kitchen) by the swimming pond. Private kitchen, chill-out cabin, shower, rustic flushing loo, compost loo with a view, campfire area. Wild swimming pond (fenced) Bookable woodfired hot tub. Dog friendly, footpaths. Kid heaven! Late check-out negotiable. By booking you take full responsibility for the safety of your group. Check-in form /waiver on arrival please.

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!

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

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.

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.
Popular amenities for Weymouth rentals with a pool
House rentals with a pool

Huge country house - wood burners - sleeps 4/10

Charming & cosy thatched farmhouse with fireplace

Country House - Pool Jacuzzi Escape Room Karaoke

5* Luxury dog friendly lodge @ Hoburne Bashley

Large Airy Barn conversion, 5 bedrooms, Jurassic

Pet friendly 2 bed holiday home

Flint Cottage for two with indoor pool & sauna

Peaceful West Dorset location
Apartment rentals with a pool

Seascape Apartment

Holiday apartment own heated indoor pool & sauna

Flat 10 Pelican House

The Palms Apartment 16 with Balcony

The Palms, Apartment 2

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

The Palms Studio 6

The Palms, Apartment 19
Other holiday rentals with a pool

Luxurious holiday home at Weymouth Bay

Bay View Holiday Home With Sea Views

Cosy caravan in private woodland setting

One bed Lodge in AONB Dorset with shared pool area

Amazing Lodge, edge of Forest with giant deck

Charming cottage with pool in the New Forest

Kingfisher Lodge with Sea Views

Dorset Coastal Holiday Home
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 £37 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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- New Forest National Park
- Paultons Park Home of Peppa Pig World
- Weymouth Beach
- Stonehenge
- Boscombe Beach
- Kimmeridge Bay
- Bournemouth Beach
- Highcliffe Beach
- The Tank Museum
- Southbourne Beach
- Poole Quay
- Crealy Theme Park & Resort
- Preston Sands
- Sandy Bay Beach Blue Flag Winner 2019
- Mudeford Sandbank
- Beer Beach
- Man O'War Beach
- Charmouth Beach
- Torre Abbey
- Oddicombe Beach
- Oake Manor Golf Club
- Hurst Castle
- Compton Beach
- The Needles Old Battery & New Battery




