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Vacation rentals with a pool in Weymouth

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Weymouth

  • Total vacation rentals

    Explore 50 vacation rentals in Weymouth

  • Nightly prices starting at

    Weymouth vacation rentals start at G$14,648 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,300 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Weymouth vacation 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!

Top-rated rentals with a pool in Weymouth

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

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Top guest favorite
The exterior of a timber-framed cottage is showcased, featuring a vibrant flower mural on the side. A wooden door and window provide character, while greenery and blooming flowers surround the structure, set against a backdrop of towering trees.
Cabin in Ringwood
4.94 out of 5 average rating, 105 reviews

Rose Cottage (wood-fired hot tub/sauna - optional)

Rose Cottage is a timber-framed building with a lovely, high ceiling living/dining area and a wood burner. The cottage has a fully equipped kitchen, washing machine, dishwasher. Downstairs: 1 bedroom with a king-size bed, one small room with a bunk bed. Upstairs: A step ladder leads up to the attic room with one double and two single beds. Downstairs are 2 bathrooms, each with a shower, toilet, sink. No Wifi. Garden fully fenced in! / check height if jumpy dogs Direct access to Ringwood Forest.

Guest favorite
A rustic Acorn Hut, clad in green, is surrounded by lush foliage and blooming flowers. A hot tub sits on a wooden deck, while a wood burner is positioned nearby, enhancing the natural setting. The entrance to the hut is inviting, framed by greenery.
Shepherd’s hut in Ashley Heath
4.95 out of 5 average rating, 464 reviews

Shepherd's Hut (wood-fired hot tub/sauna optional)

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. Other cabins on site/ Horton Road which can be noisy at times. Hut is not fully fenced in.

Superhost
The interior features two twin beds with colorful bedding arranged against wooden walls. A dining table is set with two glasses of red wine, a bottle, and a small vase of flowers. A window offers views of the surrounding greenery.
Shepherd’s hut in Dorset
4.89 out of 5 average rating, 202 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
A serene outdoor seating area is highlighted, featuring two wicker armchairs with soft cushions and a glass-topped table. Beyond, the tranquil Fleet Lagoon reflects sunlight, providing picturesque views, while colorful flowers add a touch of warmth to the setting.
Chalet in Weymouth
4.95 out of 5 average rating, 240 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
An indoor pool is surrounded by sleek gray tiling and illuminated by recessed lighting. The pool's inviting turquoise water reflects the ceiling lights. A cozy seating area with cushions is visible in the corner, providing a relaxed atmosphere.
Cottage in Osmington
4.86 out of 5 average rating, 195 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.

Top guest favorite
A modern caravan is positioned on a spacious grassy plot. It features a large deck with white railing and a series of windows providing ample natural light. The exterior is clad in light-colored panels, and nearby caravans are visible in the background.
Chalet in Dorset
4.94 out of 5 average rating, 114 reviews

A luxurious modern 3-bedroom Swift Bordeaux

A luxurious modern 3-bedroom Swift Bordeaux Silver Prestige. This fabulous caravan is situated at Haven Littlesea Holiday Park in Weymouth in a spacious plot with views of the Fleet Lagoon and Chesil Beach. Sleeps up to 6 people. 1.5 bathrooms Linen and towels supplied. Parking spaces for 2 cars. Outside decking and seating area. Onsite restaurant, laundrette and local shop. For use of swimming pool, entertainment venue and booking activities you can purchase Play Passes from Haven

Guest favorite
A wooden deck features a neutral-toned table surrounded by matching chairs, providing a seating area with panoramic views of Swanage Bay. The coastline can be seen in the distance, framed by lush greenery and a clear blue sky.
Chalet in Dorset
4.94 out of 5 average rating, 309 reviews

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!

Top guest favorite
Train in Axminster
4.99 out of 5 average rating, 322 reviews

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

Guest favorite
A spacious corner sofa is adorned with colorful cushions in yellow, gray, and blue. A cozy navy blanket drapes over the side. A wooden coffee table holds a selection of brochures, with natural light filtering through sheer curtains at the nearby window.
Home in Weymouth
4.85 out of 5 average rating, 122 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.

Guest favorite
A charming barn conversion features natural stone walls and large windows that invite ample sunlight. The surrounding landscape includes lush greenery and a clear blue sky, creating a serene rural atmosphere. The driveway leads to the entrance, providing easy access to the property.
Cottage in Dorset
4.79 out of 5 average rating, 199 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

Top guest favorite
A bright living area contains large windows with sheer curtains, allowing natural light to fill the space. A comfortable sofa is positioned against the wall, and a wooden dining table with soft chairs is visible. Shelving units feature decorative accents and a television.
Home in Weymouth
4.97 out of 5 average rating, 285 reviews

Cosy Chesil Beach Getaway - Weymouth *no fees!*

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 PROVIDE BED LINEN** One dog per booking welcome.

Guest favorite
An indoor swimming pool is featured, surrounded by large windows allowing natural light. The ceiling beams reveal a spacious, airy atmosphere. Two red chairs are positioned nearby, and a shallow end is visible with steps leading into the water. A blue cover rests along one side of the pool.
Cottage in Dorset
4.97 out of 5 average rating, 393 reviews

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

When is the best time to visit Weymouth?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,249 GYDG$28,249 GYDG$24,901 GYDG$27,412 GYDG$30,132 GYDG$28,249 GYDG$36,619 GYDG$40,386 GYDG$26,366 GYDG$26,575 GYDG$22,390 GYDG$21,553 GYD
Avg. temp7°C7°C8°C9°C12°C15°C17°C17°C16°C13°C10°C8°C

Destinations to explore

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