Holiday rentals with a pool in Weymouth

4.89 out of 5 average rating, 46 reviews

Holiday park

Lovely dog friendly leafy lodge

Centrally located, unique lodge with amazing facilities and a beautiful tranquil setting. Perfect for those looking for that extra bit of space, a bit of added luxury or if there is a group of you, then look no further. free standing furniture, New York loft style décor and panoramic glass sliding doors creating a nature on the-inside vibe. The main bedroom features a stand-alone, roll-top bathtub (hidden Tv) and an en-suite. The second bedroom is a twin room with comfy beds lots of storage.

4.88 out of 5 average rating, 74 reviews

Large coastal cottage with spa and private pool

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.

4.86 out of 5 average rating, 306 reviews

Barn

Somerset Threshing Barn w/ Pool, Hot Tub & Sauna

Discover the Threshing Barn, an ideal spot for family or group gatherings. Enjoy the spacious double-height kitchen and the cozy lounge with woodburner. Unwind in the covered hot tub and sauna, take a dip in the heated pool (open May to Sept) or play table tennis, pool, and table football. Explore nearby footpaths leading to three excellent pubs. We can help organise catering, pampering, and a wide range of activities, from archery and shooting to cider tasting, both on-site and off-site.

4.92 out of 5 average rating, 12 reviews

Campervan/Motorhome

Wilksworth Holiday Park - 2 Bed - Pool Access

Escape to our charming 2 bedroom home nestled in the serene Wilksworth Holiday Park near Dorset’s picturesque countryside and stunning golden beaches. Perfect for families or couples, our home offers a cozy retreat with modern amenities. Enjoy shared access to a refreshing pool, perfect for unwinding after a day of exploration. Discover nearby scenic trails, quaint villages, and breathtaking coastal views. Your ideal getaway awaits, combining relaxation and adventure in a beautiful setting.

4.84 out of 5 average rating, 55 reviews

Large peaceful home very near the sea with pool.

A delightful property at the edge of a quiet village. Wonderful walking through the vale, to the sea, or on the national trust land along the coast, all from your front door or a 5 minute drive to the sea. (Please note Xmas and New Year are 4 night minimum) Comprising of a house and two straw bale chalets with 11 bedrooms, 5 doubles ( 1 with a single bed and cot as well) , 4 singles and 2 twins. There are 3 kitchens, 4 bathrooms and a heated indoor pool. The village pub is a short walk.

4.97 out of 5 average rating, 58 reviews

Guest house

One bed Lodge in AONB Dorset with shared pool area

Fully refurbished ,Brook Lodge sits in the grounds of the main house in the village of Iwerne Minster. One bedroom , king sized bed. Bathroom with free standing bath and separate walk in shower. Open plan living area downstairs with sofa , dining area for 4, new fitted kitchen ,separate cloakroom and entrance hall. Small outdoor semi private seating area.Free WiFi .TV. Welcome pack. NB Outdoor heated pool OPEN beginning JUNE to SEPTEMBER ONLY .NB Pool use is shared with property owners.

5 out of 5 average rating, 16 reviews

Perfect family house, heated pool, close to beach

Our much-loved home works so well for family guest groups with occasional availability throughout the year. Its 7 mins walk to the lovely sandy beaches of Southbourne. You will find some great bars and restaurants nearby & can explore historic Christchurch and the beautiful seaside resorts around Bournemouth and Dorset. This listing is part use of the house (owners rooms locked), but you will have the place to yourselves.The outdoor heated pool is open from early April until September.

5 out of 5 average rating, 23 reviews

Your Own Private Indoor Pool. Rural Seaside

Midweek breaks available in 2025. Book 3 nights, get 4th free. Mon-Fri. Coombehayes Barn. Beautifully appointed, self-contained, spacious. A mile from the sea. Super warm, private indoor pool - for your exclusive use. Perfect for relaxed family/friends get-togethers and celebrations. Tranquil yet convenient location. Lyme Regis, Jurassic Coastline. Beaches, footpaths, fossils. Lots for kids to do: PS5, table football, table tennis. Large, safe, enclosed garden. Super fast wifi.

4.98 out of 5 average rating, 343 reviews

Cottage

The Condo (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!

4.97 out of 5 average rating, 69 reviews

Incredible sea views and heated outdoor pool

“With its incredible sea views, contemporary open-plan living and heated outdoor pool, this Airbnb is like something out of a Hollywood film” according to Good Housekeeping May 2024. The designer garden with hard and soft landscaping features a heated private endless pool (available April to December) and amazing sea views that draw you to the cliff top deck. Powerboat charter available on prior request.

4.87 out of 5 average rating, 55 reviews

Bungalow

Forest views in secluded location, swimming pools

Beautiful forest views! Family holiday home on Oakdene Forest Park, situated in a peaceful location directly overlooking the forest. Minutes from The New Forest & Dorset beaches - perfect for a family holiday. The park has a leisure complex which includes pools, sauna, jacuzzi, steam room & gym as well as entertainments, bars/restaurant & kids activities.