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

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

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Guest favorite

Home in Somerset

4.92 out of 5 average rating, 227 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

Group Gatherings Host your own event Exclusive use 10-16 guests (6-16 winter) Jacuzzi (all year) Outdoor Pool (heated in summer; cold water in winter!) Sun Deck Garden Kitchen/Bar Games room: Music/Karaoke system, Wood burner, TV, Communal eating space, shower/wc Escape Room Traditional Somerset Evening with cider tasting and welly wanging Large peaceful grounds BBQ Fire Pit Annexe: kitchen lounge wet room 2 bedrooms 2 sofa beds House: 4 bedrooms 3 bathrooms Bell Tent 3-4 beds

Guest favorite

Shepherd’s hut in Dorset

4.89 out of 5 average rating, 173 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 favorite

Chalet in Weymouth

4.95 out of 5 average rating, 189 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.

Superhost

Cottage in Osmington

4.86 out of 5 average rating, 113 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.

Superhost

Chalet in Dorset

4.84 out of 5 average rating, 107 reviews

2021 Deluxe 2 Bedroom Caravan Sleeps 6 with WI-FI

Modern and spacious 2021 ABI Coworth 6 berth caravan. Situated just 2 miles from Weymouth town centre and beach, and 5 miles from Portland, in a great family friendly location at Littlesea Haven Holiday Park in Weymouth. Right on the Jurassic coast with multiple nearby beaches, coastal walks, Weymouth marina, water-sports and many nice places to dine. The caravan is fully furnished and fully equipped with all the usual home comforts, as well as free parking outside, and outside dining area.

Guest favorite

Bungalow in Charmouth

4.95 out of 5 average rating, 195 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

Guest favorite

Train in Axminster

4.99 out of 5 average rating, 230 reviews

Clover Carriage, sauna, underfloor heat, log fire

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 sauna in the pool house (pool closed for winter!), beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights. It's a winter dream.

Superhost

Home in Preston Road

4.84 out of 5 average rating, 111 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.

Superhost

Cottage in Dorset

4.75 out of 5 average rating, 162 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

Guest favorite

Rental unit in Whitchurch Canonicorum

4.94 out of 5 average rating, 256 reviews

The Duck Wing, quirky dog friendly apartment

The Duck Wing is a quirky, self contained apartment on the first floor within Plenty Cottage. It's beautifully appointed for a relaxed, carefree stay in a wonderfully rural environment. Nothing is too much trouble. It sleeps two in double bed in a pretty bedroom and has a double sofa bed too. Own bathroom/shower, a separate WC and a warm spacious living area. The pub is 7 mins walk away and the beaches a 5 mins drive. The private, heated swimming is available 1st April - 31 Sept

Guest favorite

Cottage in Charmouth

4.9 out of 5 average rating, 110 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.

Guest favorite

Home in Dorset

4.96 out of 5 average rating, 217 reviews

Cosy Chesil Beach Getaway - Weymouth

Welcome to our beautiful static caravan, situated on the 5* award wining Chesil Beach Holiday Park. You can enjoy views across Chesil beach towards to the Isle of Portland. Ideal for making the most of all that Weymouth has to offer, as well as Portland and the Jurassic Coast. It is also perfectly located for walking the infamous South West Coast Path, which runs along the bottom end of the site. ** PLEASE NOTE, WE DON'T PROVIDED BED LINEN** One dog per booking welcome.