Holiday rentals with a pool in Weymouth

Find and book unique homes with a pool on Airbnb

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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Guest favourite

Barn in Dinton

5 out of 5 average rating, 110 reviews

Unique, romantic luxury retreat with swimming pool

Beautifully furnished, romantic and spacious ancient dovecote in a gorgeous peaceful countryside setting, the thick stone walls make it warm and cosy in winter, cool in summer as well as quiet and private. Private swimming pool available, heated in summer. Upstairs there is a luxurious super kingsize bed, a rolltop bath, a huge velvet sofa and a 50" TV and downstairs is a shower room, kitchen and large dining area. Lovely walks from the door and close to Salisbury, Longleat, Stonehenge and Bath

Guest favourite

Shepherd’s hut in Ashley Heath

4.95 out of 5 average rating, 315 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.

Superhost

Chalet in Dorset

4.93 out of 5 average rating, 250 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!

Guest favourite

Holiday park in Hampshire

4.99 out of 5 average rating, 138 reviews

Sandy Balls New Forest Holiday Village

A spacious, well equipped holiday home situated in a quiet location at Sandy Balls Holiday Village. Guest passes, bed linen & free WIFI are included. Indoor/outdoor pools, gym, jacuzzi and spa, children’s adventure play areas, soft play, arcade, restaurants, coffee shop and a village store. Enjoy evening entertainment and family activities including bike hire and alpaca walks. Sandy Balls the perfect location for exploring the New Forest and surrounding areas. Paulton’s Park is 20 minutes away

Guest favourite

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 favourite

Shepherd’s hut in Plaitford

4.96 out of 5 average rating, 333 reviews

Shepherds Pye - Lakeside Retreat In The New Forest

Shepherd's Pye is a unique, 1920's Railway Carriage. Rescued from a local farm as a neglected frame, it has been lovingly restored by ourselves into a cosy, modern retreat on the edge of the New Forest. The hut is set in a secluded, private spot on our farm overlooking a lake. It is self contained and finished to a high standard; including a comfy double bed, heating, mains electrics and a fully equipped kitchen and en-suite bathroom, supplying all you need for rural yet comfortable stay.

Guest favourite

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 favourite

Train in Axminster

4.99 out of 5 average rating, 231 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.

Guest favourite

Cottage in Charmouth

4.9 out of 5 average rating, 113 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.