Holiday 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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Top guest favourite

Shepherd’s hut in Lyme Regis

4.99 out of 5 average rating, 107 reviews

Headland Hideaway Shepherd's Hut in Lyme Regis

SHEPHERDS HUT An opulent hideaway retreat nestled on the Lyme Bay headland with uninterrupted ocean views, perfect for romantics & family adventurers. With an expansive sundeck, fire pit & swimming pool & endless expanse of garden. Embark on the most charming private adventure from bedroom shepherd's hut & adjacent shower room to the architectural wonder of the glass framed kitchen, diner & sitting room with freestanding log burner & stylish interior. Sit and wonder at the expanse of ocean views

Guest favourite

Holiday park in Hampshire

4.91 out of 5 average rating, 56 reviews

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.

Guest favourite

Home in Somerset

4.91 out of 5 average rating, 240 reviews

Country House - Pool Jacuzzi 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 in winter!) Sun Deck Garden Kitchen/Bar Games room: Music/Karaoke system Wood burner TV Communal eating space, shower/wc Escape Room Somerset Evening -pork roast cider tasting welly wanging Large peaceful grounds BBQ Fire Pit Annexe (sole use): kitchen lounge bathroom 2 bedrooms 2 sofa beds House (part use): 4 bedrooms 3 bathrooms Glamping Trailer

Guest favourite

Guest house in Iwerne Minster

4.97 out of 5 average rating, 61 reviews

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.

Top guest favourite

Home in Southbourne

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.

Guest favourite

Cabin in Dorset

4.88 out of 5 average rating, 17 reviews

Bay View Holiday Home With Sea Views

Spacious two bedroom holiday home with a Balcony/Sun deck. Situated on a wide sunny plot in the most desirable Bay Hollow which has a splendid sea views over the bay at the award winning "Rockley Park" in Dorset.. The holiday home is 'Platinum' graded and benefits from central heating and double glazing. It is a short walk from the amenities and 150yds walk to the lovely sandy beach, with cafe and water sports. Haven passes are available at an extra cost for swimming and entertainment.

Guest favourite

Home in Long Sutton

4.89 out of 5 average rating, 253 reviews

Heated Pool, Hot Tub, Sauna, Games - Upton Bourn

Welcome to Upton Bourn Lodge, where unforgettable memories await for families and friends celebrating, or reuniting. Enjoy meals in the spacious double height dining room with seating for all. Take a dip in your heated pool, relax in the hot tub and sauna, and enjoy various games like table tennis, football, and pool. Explore nearby footpaths to visit three pubs offering superb food, beer, and cider. Catering, pampering or a host of on and offsite activities available to guests.

Top guest favourite

Home in Lyme Regis

5 out of 5 average rating, 24 reviews

Your Own Private Indoor Pool. Rural Seaside

OFFER 4 NIGHTS FOR THE PRICE OF 3! Mon-Fri bookings in May and June 2025. 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.

Top guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 349 reviews

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!

Top guest favourite

Home in Bournemouth

4.97 out of 5 average rating, 72 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.

Guest favourite

Bungalow in Saint Leonards

4.87 out of 5 average rating, 55 reviews

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.

Superhost

Flat in Horton

4.8 out of 5 average rating, 49 reviews

Peaceful 2-Bed Escape | Hot Tub • Pool • Sauna

Rivendell park: Stylish 2-bedroom flat with private entrance, set within a peaceful holiday park. This bright, self-contained space is perfect for a relaxing escape from everyday life. Guests enjoy shared access to the seasonal heated pool, large hot tub, sauna and beautifully maintained gardens — ideal for unwinding or exploring the outdoors.