Vacation rentals with a pool in Weymouth and Portland District

Find and book unique homes with a pool on Airbnb

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

Cabin in Ringwood

4.96 out of 5 average rating, 208 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.

Mar 19 – 26

R2,890 ZAR per night

Guest favorite

Shepherd’s hut in Ashley Heath

4.96 out of 5 average rating, 245 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.

Jan 12 – 19

R1,980 ZAR per night

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 8 – 15

R3,430 ZAR 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**

May 9 – 16

R4,148 ZAR per night

Guest favorite

Bungalow in Charmouth

4.94 out of 5 average rating, 179 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

Nov 18 – 25

R4,109 ZAR per night

Guest favorite

Train in Axminster

4.99 out of 5 average rating, 186 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.

Feb 17 – 24

R2,101 ZAR per night

Superhost

Home in Preston Road

4.83 out of 5 average rating, 108 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.

Aug 2 – 9

R3,868 ZAR per night

Guest favorite

Shepherd’s hut in Churchstanton

4.97 out of 5 average rating, 169 reviews

Secluded Stargazing Romantic Shepherds hut&hot tub

Shepherds hut on the Blackdown hills on the rural Somerset/Devon border over looking countryside in secluded spot, own Wood fired hot tub with views of farmland and animals. Wood burning stove in hut with fire pit outside. Private parking, bicycles available to borrow to explore the surrounding AONB. 1mile from village with pub and shop. Hut includes large shower, toilet and heated towel rail. Kitchen area has fridge, Belfast sink, and induction hob. Great for stargazing and relaxing.

Jun 14 – 21

R2,322 ZAR 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 22 – 29

R1,719 ZAR 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 13 – 20

R2,497 ZAR per night

Guest favorite

Chalet in Weymouth

4.93 out of 5 average rating, 120 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.

Aug 31 – Sep 7

R3,072 ZAR per night

Superhost

Guesthouse in Swanage

4.86 out of 5 average rating, 142 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.

Sep 11 – 18

R2,590 ZAR per night