Family-friendly holiday rentals in Weymouth and Portland District

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Weymouth and Portland District family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Cabin in Forton
4.89 out of 5 average rating, 159 reviews

Woodpecker Lodge - Log Cabin with Private Hot Tub

DianaRating, 5 stars3 weeks ago
We had a lovely week at Alpine Grove touring park. Clear communication from Keith. The space was very clean and had all facilities needed for our stay. Our toddler also really enjoyed the swimming pool! Would definitely stay again. Loved it
Top guest favourite
Shepherd’s hut in Ilminster
5 out of 5 average rating, 232 reviews

Romantic Shepherds Hut & Wood-fired Hot Tub

KerryRating, 5 stars1 week ago
What a beautiful little place! Fiona is a lovely host and the place is beautiful with everything you need. Much needed reset for my husband and I. Thank you! 😊
Guest favourite
Home in Somerset
4.91 out of 5 average rating, 244 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

ClaireRating, 5 stars2 weeks ago
We stayed here for a family holiday, 4 adults and 6 children aged 11-15 and we all had a lovely time. There is lots to do at Mistletoe Farm; the pool and hot tub were great, the games room/ garden kitchen area was perfect for us to all get together to eat, play darts or do karaoke and the escape room was a big hit with the kids. We also enjoyed an evening around the fire pit toasting marshmallows. It’s set in beautiful surroundings and we enjoyed walks to the local pub for dinner and also to the reservoir. Lyme Regis was close enough for a day out too. The accommodation was clean and tidy and well equipped and the teenagers enjoyed having a glamping pod to themselves for a bit of independence. Paul and Sandra were excellent hosts, super friendly, welcoming and helpful, they leave you to enjoy your holiday but somehow always manage to be there when you need them! Highly recommend.
Guest favourite
Barn in Long Sutton
4.87 out of 5 average rating, 317 reviews

Somerset Threshing Barn w/ Pool, Hot Tub & Sauna

LamineRating, 5 stars2 days ago
We've just returned from another wonderful stay at this property in Long Sutton. As returning guests, we were delighted to find it just as perfect as we remembered. The location is stunning, offering peace and tranquility, and the property itself is immaculate. This time, we particularly enjoyed the pool and sauna – a real treat! We can't wait to return. Many thanks to George and Gill for the amazing hospitality.
Guest favourite
Home in Hamworthy Poole
4.97 out of 5 average rating, 384 reviews

Poole Harbour View,Top Location Opp Hot-tub /Sauna

SarahRating, 5 stars2 weeks ago
Amazing place! Perfect location for a family holiday. The house has absolutely everything you need and more. We really enjoyed sea kayaking and paddle boarding with all Daves's kit. The sea is so close you can carry everything down to the shore. We really loved the hot tub and sauna and bbq area. The games room was a great space for the kids to hang out and play as well as the adults. We couldn't have wanted more. We'd wholeheartedly recommend this amazing house.
Guest favourite
Cottage in Dinnington
4.95 out of 5 average rating, 523 reviews

The Cottage, Parsonage Farmhouse with hot tub

HarrietRating, 5 stars1 week ago
We had a really lovely stay here this week. The garden is beautiful, so peaceful and we even saw a woodpecker hopping around the grass one afternoon. Our daughter adored the trampoline and climbing frame, we also really enjoyed relaxing in the hot tub each day after exploring. We did day trips to Lyme Regis, Beer and Forde Abbey & Gardens. A perfect, peaceful spot to spend a few days, thank you.
Guest favourite
Home in Wimborne Saint Giles
4.94 out of 5 average rating, 154 reviews

Charming Country Cottage

CarolineRating, 5 stars1 month ago
Definitely recommend Sam’s beautiful house. Immaculately kept garden with hot tub and huge trampoline which kept the children busy. All rooms with clean and had everything that we needed. Beds very comfortable and bathrooms were clean and showers etc all in good order. Thank you!
Guest favourite
Hut in Dorset
4.95 out of 5 average rating, 111 reviews

Astronomer Shepherd's hut

CeraRating, 5 stars1 week ago
Had a lovely stay in this beautiful hut. Unfortunately we had cloudy skies so didn’t get to stargaze. Loved our animal neighbours and the visits from the ducks. The BBQ and facilities were great we enjoyed cooking and eating al fresco all weekend. Walked to Winyard Gap for a pub lunch. All in all a lovely relaxing weekend.

Family- and pet-friendly home rentals

Guest favourite
Religious building in East Stoke
4.91 out of 5 average rating, 118 reviews

Amazing converted church -Dorset’s Jurassic Coast

KateRating, 5 stars1 week ago
What a lovely surprise for we history buffs to find ourselves in an historic church and graveyard. Once inside, delighted at the little touches on theme, eg welcome goodies greatly appreciated. On our long trip, the most comfortable beds and pillows yet. Also compared to many AirBNBs, Gordon’s place had good kitchen facilities eg plenty of cups, plates and cutlery etc.
Superhost
Cottage in Bridport
4.9 out of 5 average rating, 122 reviews

5* Cottage on Chesil Beach Dorset Jurassic Coast

LisaRating, 5 stars3 months ago
Wow, what a stunning location. It's every bit as beautiful as in the photos. We watched glorious sunsets from the terrace and enjoyed walks on the beach. I enjoyed looking around the immaculately kept gardens and could have watched the colourful koi in the pond for hours, plus the two cute horses in the field. Andrew's directions to the house are spot-on, please don't trust your satnav or you risk being taken down some very narrow lanes with grass growing in the middle and no passing places. Ask me how I know. There is no mobile reception at the house, as you would expect given the location, but the wifi is very good. Beds and bedding super comfortable.
Superhost
Home in Dorset
4.86 out of 5 average rating, 129 reviews

Modern Olympic eco-house Dorset by the sea

AdamRating, 5 stars2 months ago
I had a fantastic stay at this Airbnb. The house was clean, comfortable, and exactly as described – the perfect home base for our trip. Our host, Paul, was incredibly friendly and accommodating, and he went out of his way to make sure everything was just right. He also gave us loads of great suggestions for local activities and places to check out, which really helped us make the most of our time in the area. Communication was easy and quick, and I felt genuinely welcomed from the moment I arrived. Couldn’t have asked for a better host or a better experience. Thanks again, Paul – we’d love to come back!
Guest favourite
Guest suite in Cattistock
4.91 out of 5 average rating, 406 reviews

Willow Annexe

JanetRating, 5 stars3 weeks ago
Such an amazing place in a beautiful tranquil village location. Sally's place is so well equipped that you could live there. We used the local shop and pub at Sally's recommendation which were both great and would revisit the idea area again. Sally was quick to respond when I had to message her. We found Sally and Bob to be excellent hosts. Thank you to both.
Superhost
Guest suite in Morcombelake
4.91 out of 5 average rating, 443 reviews

Modern studio, hillside garden with amazing views

RichardRating, 5 stars3 weeks ago
Great location within easy walking distance of south coast path to visit Seatown and Charmouth. Spotlessly clean and well equipped. Ideal for a short break. Louise very kindly provided lots of local recommendations too.
Superhost
Home in Bishop's Caundle
4.76 out of 5 average rating, 544 reviews

Ryalls Stud Cottage

AngieRating, 5 stars1 day ago
Lovely little cottage. Was very quiet and private. Had everything you needed. Great base for exploring Sherborne and surrounding areas.
Guest favourite
Guest suite in Duntish
4.9 out of 5 average rating, 465 reviews

Duntish Studio

TonyRating, 5 stars1 week ago
Everything catered for, comfortable and relaxing stay, helpful and friendly host and a generous welcome pack.
Top guest favourite
Bungalow in Dorset
4.95 out of 5 average rating, 174 reviews

Dairy House Self Catering Annexe

Nicholas PaulRating, 5 stars1 month ago
We've just spent two great nights at the Dairy House. It's a lovely place set in beautiful surroundings. Great if you've got a dog. The place was really clean and tidy, the beds are very comfortable and the hosts really helpful and welcoming. I would thoroughly recommend staying here if you're looking for somewhere in the area.

Family-friendly home rentals with a pool

Guest favourite
Cottage in East Coker
4.94 out of 5 average rating, 34 reviews

The Cottage at Flo’s Cottages with Indoor Pool

RebeccaRating, 5 stars9 months ago
This was a perfect place to stay for our family of four. Our daughters especially enjoyed the swimming pool. The cottage was clean, with beautiful surroundings and had everything we needed. It was also really lovely to be able to book my Dad into the ‘Little Stable’, which is a smaller, 2 person dwelling available to book. Fiona is a fantastic host and responded quickly to any queries. We would definitely recommend this to our family and friends.
Guest favourite
Chalet in Dorset
4.94 out of 5 average rating, 268 reviews

Breathtaking sea views from this light, cosy lodge

JaneRating, 5 stars1 week ago
Our second visit to this super property. Spotlessly clean throughout with everything you could need for your time away. The weather was great whilst we were staying so we were able to make good use of the decking overlooking Swanage Bay. Judith was very quick to respond when we had a question and she also recommended plenty of places for us to visit. Milk tea coffee and Dorset biscuits were left for us when we arrived which was a welcome treat when we arrived. Many thanks Judith and we will look forward to returning again next year.
Superhost
Home in Preston Road
4.84 out of 5 average rating, 113 reviews

Spacious Caravan near sea Weymouth Bay Haven

SuzanneRating, 5 stars5 months ago
This is our second time staying in this lovely caravan. It’s always pristine and lovely. I always felt like a home away from home there. The bedrooms are a good size and the extra full bathroom is a definite plus! I’d highly recommend staying here.
Top guest favourite
Home in Lyme Regis
5 out of 5 average rating, 24 reviews

Your Own Private Indoor Pool. Rural Seaside

DebbieRating, 5 stars3 months ago
Beautiful property in a lovely scenic country setting, but being only a few minutes drive from the beach. Great indoor pool and a lovely garden. Property a lovely mix of old world country cottage, but with all the mod cons needed for everyday life. Everyone loved the holiday, from young to old and enjoyed watching tv together with a real fire on chilly evenings. Loved Uplyme and Lyme Regis.
Guest favourite
Home in Blandford Forum
4.98 out of 5 average rating, 55 reviews

Flint Cottage for two with indoor pool & sauna

Noelle And SamRating, 5 stars3 months ago
We had a blissful few days at Flint cottage. Wonderful kitchen to cook in, and multiple fabulous farm shops nearby. We ordered a heat and eat pie and a DIY breakfast pack for our first night, which made the start of the holiday so much more chilled out. The outdoor bath was also really special. We were so comfortable throughout we just relaxed completely. Can’t wait to come back!
Superhost
Barn in Eype
4.66 out of 5 average rating, 68 reviews

Cosy barn annex. 10 min walk to beach, heated pool

CharlesRating, 5 stars2 weeks ago
We had a lovely stay at the annex. Very relaxing and secluded and great walk to the beach. Hosts were helpful and beautiful flowers in every room lovely touch x
Guest favourite
Flat in Whitchurch Canonicorum
4.94 out of 5 average rating, 263 reviews

The Duck Wing, quirky dog friendly apartment

TamarRating, 5 stars3 weeks ago
beautiful swimming pool!! thank you so much for letting us enjoy it. xx
Guest favourite
Cottage in Sherborne
4.91 out of 5 average rating, 419 reviews

Secret Rural Retreat

AprilRating, 5 stars2 weeks ago
The magical barn ✨ We had a wonderful stay at the Gate Barn. The location is simply beautiful - within the grounds of a gorgeous home. The barn was spotlessly clean and well equipped. The kids loved their bedroom and slept so well - enhanced by exploring the grounds and expenditure energy on the trampoline and swing. Sadly the pool was being cleaned (maybe check availability) but regardless we had a wonderful stay. The Wilde Story did lovely pizzas and The Mitre pub is having an amazing garden renovation. We will definitely be back ❤️

Destinations to explore