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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Superhost

Chalet in Dorset

4.94 out of 5 average rating, 230 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 a cosy winter retreat, while in Spring and Summer use of a 1903 beach hut on a private beach is included. In addition, guests enjoy the amenities of SBV - all within a 15 min walk of the seafront!

Feb 18 – 25

$160 per night

Guest favorite

Yurt in Colyton

4.98 out of 5 average rating, 126 reviews

Buzzard Yurt - A unique eco holiday in East Devon

Unique and comfortable yurt (sleeps 5) with large terrace and stunning views of Devon Exclusive use of a separate kitchen, hut, shower, compost loo and campfire area. Homegrown produce available from our organic smallholding Wild swimming in our natural swimming pond. Woodfired hot tub available (£50 a day) Dog friendly with great footpaths straight from the field. Use of our 26 acre rewilding woodland a 30 minute hike away, forest school activities, games, maps and books. Kid heaven!

Mar 16 – 23

$107 per night

Guest favorite

Home in Somerset

4.91 out of 5 average rating, 208 reviews

Country House - Jacuzzi Pool 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

Jan 17 – 24

$64 per night

Guest favorite

Bungalow in Dorset

4.96 out of 5 average rating, 193 reviews

Cosy Chesil Beach Getaway

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. One dog per booking welcome. **PLEASE NOTE : BED LINEN PROVIDED FOR AN ADDITIONAL CHARGE**

Jan 24 – 31

$190 per night

Guest favorite

Bungalow in Charmouth

4.94 out of 5 average rating, 180 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

Oct 7 – 14

$201 per night

Guest favorite

Train in Axminster

4.99 out of 5 average rating, 189 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.

Sep 19 – 26

$107 per night

Superhost

Home in Preston Road

4.83 out of 5 average rating, 109 reviews

Haven Weymouth Bay Holiday Park

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.

Oct 21 – 28

$140 per night

Superhost

Home in Dorset

4.81 out of 5 average rating, 119 reviews

Deluxe caravan & decking Littlesea Haven Resort

12ft wide caravan. 2 bedroom sleeps up to 6. Spacious open plan lounge/kitchen/dinning area. L shape sofa with separate eating area. Modern style kitchen. Fridge and microwave Ample double bedroom. 2 double wardrobes and dressing table, with a large mirror. own WC and basin. twin bedroom with single wardrobe. Gas fire in lounge, fan heaters in the bedrooms. Gas, water and electricity included Shower room & WC 52 inch TV in the lounge Decking, outside table and chairs, free Wifi

Oct 7 – 14

$78 per night

Guest favorite

Apartment in Whitchurch Canonicorum

4.94 out of 5 average rating, 235 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

Apr 21 – 28

$113 per night

Guest favorite

Chalet in Weymouth

4.93 out of 5 average rating, 121 reviews

Bowleaze Cove with a view

Modern, 3 bed static in an elevated position on the beautifully kept Bowleaze Cove Holiday Park & Spa on the Jurassic Coast! 1 double, 2 twins & sofabed.2 bathrooms,1 with power shower.Large gated deck area with seating & sea views.Parking for 2 cars. Site facilities: spa/gym/restaurant/sports bar/soft-play/kids park/pool (indoor & outdoor). Prices include park passes. Sorry no single sex groups or dogs. For off peak bookings, contact us directly to discuss flexible stays.

Sep 9 – 16

$149 per night

Superhost

Guesthouse in Swanage

4.86 out of 5 average rating, 143 reviews

Swanage Sands Vegetarian/Vegan Studio

The Sands Studio with its view of the sea stands in the garden of an Edwardian seaside home; situated opposite a short 100 yard footpath straight onto the beach. The room is available on a vegetarian self-catering basis. We are very grateful to our guests for respecting that this is part of a no meat no fish home! The Sands Studio is en-suite, with wifi, 100% cotton linen and towels, kingsize bed, chair bed and a cot or air-bed, television, dvd player, and kitchenette.

Feb 25 – Mar 4

$117 per night

Guest favorite

Cottage in Dorset

4.98 out of 5 average rating, 314 reviews

The Condo (Indoor Pool available May-Oct only)

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!

Mar 23 – 30

$113 per night