Family-friendly vacation rentals in Isle of Portland

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Popular amenities for Isle of Portland family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A solid wood cabin is nestled among lush greenery and vibrant flowering shrubs. Tall trees surround the cabin, providing a sense of seclusion while allowing natural light to filter through the leaves. A warm, inviting entrance with a lantern enhances the rustic charm.
Cabin in Forton
4.89 out of 5 average rating, 157 reviews

Woodpecker Lodge - Log Cabin with Private Hot Tub

JackRating, 5 stars1 month ago
Me and my partner have just finished our stay with alpine grove and would highly recommend visiting. We stayed in the woodpecker lodge and from the log burner to the hot tub everything about this lodge was perfect, Kieth and Serena service is amazing and we can’t wait to visit again soon. Thank you again for such an amazing stay.
Top guest favorite
A wooden hot tub sits in the foreground, with a charming Shepherd's Hut visible in the background. The hut features light blue doors and a large window, surrounded by manicured grass and blossoming trees. Outdoor seating is placed throughout the garden, providing a serene atmosphere.
Shepherd’s hut in Ilminster
5 out of 5 average rating, 228 reviews

Romantic Shepherds Hut & Wood-fired Hot Tub

EmmaRating, 5 stars1 week ago
We had a lovely 2 night stay at the hut. Fiona was a really great host who came out to us even though it was late and raining! The hut was super warm on arrival and it has an internal heater and towel rail which is nice. It was also nice to be welcomed with some baked goods which we enjoyed the next morning. The bed was super comfy and we slept really well. The hot tub was nice to relax in… you get all the stuff provided for it which is good and on previous experiences this isn’t always the case. We used the Fire pit and you get some cushions to use which are under the bed and extra blankets which again is really nice. It’s exceptionally well thought out and the lord of added extras make it really nice. Would deffo return
Guest favorite
A private outdoor hot tub is set on a wooden decking area, surrounded by lush greenery and rustic wooden walls. Bubbles rise from the water, creating a relaxing ambiance. The hot tub is covered with a protective lid that is partially raised.
Home in Somerset
4.92 out of 5 average rating, 238 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

HannahRating, 5 stars2 weeks ago
Just come back from Mistletoe Farm after celebrating a Hen weekend there. We all could not fault the hosts, they were incredible & always checking if we needed anything, so helpful throughout the whole stay. Mistletoe Farm is beautiful & so peaceful. Plenty to do within the property. We all especially loved the pool/hot tub & also the karaoke machine was a big hit. It really is the perfect place either for celebrating a special occasion or a family weekend. We all enjoyed our stay & said it is a place we would love to go back to. Thank you again to the amazing hosts. Would highly recommend this air b&b 😊
Guest favorite
An Edwardian farmhouse is presented, featuring a combination of red brick and serene landscaping. Large windows on the porch allow natural light to enter, while a sloped roof is adorned with solar panels. Lush greenery surrounds the building, highlighting its rustic charm.
Home in Toller Porcorum
4.94 out of 5 average rating, 67 reviews

Frogmore House near Jurassic Coast with hot tub

BeckyRating, 5 stars7 months ago
What an utterly beautiful place to stay with friends. We couldn’t have asked for a better stay than what we had at Frogmore House. Rosemary was such a great host and made sure our stay was perfect. Loads of little touches that made us feel right at home. There was everything you needed from coal to dishwasher tablets and even some fizz in the fridge!! Such a memorable weekend! Thank you again Rosemary, your house is wonderful. We would definitely stay again and recommend to others 🌟
Guest favorite
A hot tub is situated in a shaded area under a large umbrella, surrounded by greenery. In the background, a wooden play structure, a trampoline, and swings are visible, adding to the outdoor space designed for relaxation and entertainment.
Home in Wimborne Saint Giles
4.94 out of 5 average rating, 153 reviews

Charming Country Cottage

JeffRating, 5 stars1 week ago
We chose a long weekend the week before Easter. The house and the location matched our expectations and needs. Allan’s meet and greet on arrival was a warm welcome and informative. Brook House is a lovely home and we had a great stay. The spacious kitchen, bedrooms downstairs, wood burner and hot tub are real highlights. We enjoyed a BBQ and a Sunday Roast during our stay. The outdoor patio lights work very well to enjoy the garden in the evenings. The house is wonderfully located to explore the south coast and nearby attractions. We enjoyed a walk to the local club for drinks and live music. (Only available Fridays) on the first evening. We did a day trip to Brownsea Island which was fun. Moors Valley Country Park and Forest nearby offers a lot of options for a family Sunday outing. Our only fault was not staying a few more days!
Guest favorite
A wood-fired hot tub is illuminated with soft blue light, surrounded by a serene outdoor landscape at dusk. A quiet horizon is visible in the background, enhancing the sense of tranquility. The metal flue of the hot tub adds a rustic touch to the setting.
Hut in Dorset
4.95 out of 5 average rating, 108 reviews

Astronomer Shepherd's hut

LunaRating, 5 stars1 week ago
My partner and I had a gorgeous stay at the shepherds hut - it’s super cosy and in a beautiful spot! The hot tub was so lovely with wonderful views and the hosts have still managed to keep the area private. It was also wonderful to see all the lambs and ducks come to visit us each day! Tracy and James were fab hosts and we would definitely come back in the future!
Guest favorite
A comfortable sitting area features a light-colored sofa adorned with various cushions, complemented by a small side table with a lamp. A potted plant adds a touch of greenery beside the television. Natural light enters through nearby windows, enhancing the cozy atmosphere.
Home in Alton Pancras
4.96 out of 5 average rating, 89 reviews

Little Coombe, a luxury rural cottage with Hot tub

AlisonRating, 5 stars2 months ago
Beautiful place, exactly as described, comfortable and warm and everything we needed for a relaxing long weekend.
Superhost
A spacious kitchen and dining area is showcased, featuring a wooden table surrounded by six chairs. Sleek cabinetry complements the modern appliances, and natural light filters in through two windows, enhancing the open layout.
Chalet in Pibsbury
4.85 out of 5 average rating, 469 reviews

Off grid chalet . HOT TUB & SAUNA. Kid friendly.

JessicaRating, 5 stars2 months ago
The place was amazing!! Very private, great responses from Kevin and his daughter Jasmine they were very friendly. Bed was super comfy and lots of storage if you are planning to stay for a week/longer. We will definitely be coming again. The hot tub was a bonus and explained very clearly how to use it! Super flexible check in time!

Family- and pet-friendly home rentals

Guest favorite
A charming stone cottage is visible surrounded by well-maintained greenery and an expansive lawn. The building features multiple windows framed by shrubs and is complemented by a wooden fence. A large tree and planted pots enhance the outdoor space.
Cottage in Dorset
4.89 out of 5 average rating, 193 reviews

Admiral's Cottage nr Bridport and Beaminster

GemmaRating, 5 stars2 weeks ago
Perfect holiday accommodation & location. Warm, friendly and extremely thoughtful hosts. Spotlessly clean and extremely well-appointed cottage, with lovely welcome treats for us and our dog. Very peaceful, rural location with lovely animals & games room on site for children and easy access to the Dorset coast. Literally the best cottage we’ve stayed in.
Guest favorite
The Pink House is visible in the distance, framed by branches of trees against a backdrop of rolling hills and soft clouds. The surrounding landscape features open grassland, contributing to the serene rural setting.
Cottage in East Lulworth
4.83 out of 5 average rating, 104 reviews

The Pink House at Lulworth, Dorset

SusanRating, 5 stars7 months ago
We had a brilliant stay at the Pink House! The house itself was beautifully decorated and was warm and inviting - we felt really at home here. Deborah was very friendly and responsive in her communication and sent us lots of local recommendations of things to do and places to visit. The garden was really private and we loved the built in BBQ and home-grown tomatoes and cucumbers, and the welcome basket that we're waiting for us when we arrived. The Pink House is in a great location with walks right from the front door and only 15-30 mins drive to the various beaches. We had a wonderful stay and wished we booked for longer - we'll definitely be back again!
Guest favorite
A group of charming buildings in various colors are displayed together, showcasing a blend of architectural styles. The blue and pink facades are accented by greenery and festive bunting, creating a vibrant and inviting streetscape near the waterfront.
Apartment in Lyme Regis
4.9 out of 5 average rating, 441 reviews

Blue Horizons seaside flat in town centre

RachelRating, 5 stars2 weeks ago
Another great stay at Blue Horizons, great central location, clean apartment and easy to park up in Charmouth Road car park and walk down.
Guest favorite
A charming stone cottage is partially visible among tall green plants and fencing. The structure features a sloping roof with prominent gabled windows and wooden accents. Soft clouds drift across a blue sky, highlighting the rural setting.
Cottage in Chideock
4.87 out of 5 average rating, 213 reviews

Idyllic views, quiet,cosy, Jurassic coast cottage

SophieRating, 5 stars2 weeks ago
Really beautiful cottage. The pictures dont do it justice and the location is stunning with plenty to do in the local and surrounding area. There were 4 adults and one child in our group and the cottage was spacious enough for us all. The facilities were excellent and Debra had thought of everything we could possibly need. Extremely comfortable bed and wonderful fresh linen too! The 10-15min walk to the beach and seafront pub was wonderful and we climbed the Golden Cap from the cottage on a sunny clear day. Thanks for having us!!
Superhost
Townhouse in Dorset
4.87 out of 5 average rating, 138 reviews

Historic Seaman Chaplaincy, Seaview all rooms

ChloeRating, 5 stars2 months ago
Great stay in a beautifully restored old building with big comfy beds. 5 minutes walk from the beach and a pub serving delicious food (worth booking ahead). Very friendly volunteers at the nearby DD centre/war museum, well worth a visit to see the history of the Isle of Portland and fun for the children, they get to climb inside a tank!
Guest favorite
A spacious living area features a striped sofa and a plush red couch, complemented by a rocking chair. Light enters through large doors that lead to the deck area. A fireplace adds a classic touch, while artwork adorns the walls.
Home in Swanage
4.84 out of 5 average rating, 141 reviews

200m walk to beach, town & SW Coastal path

MartinRating, 5 stars1 week ago
Slight concern about parking but easy to unload by front door. Then spaces to park on Durlston Road and in evening there were spaces by front door :-)) moved cars down did not need to move them again so easy departure.
Top guest favorite
The Dairy House Annexe is set within a serene landscape, surrounded by greenery. The property features a spacious exterior with a combination of buildings, parking areas, and well-maintained gardens. Adjacent fields contribute to the tranquil atmosphere, providing a relaxing environment for visitors.
Bungalow in Dorset
4.95 out of 5 average rating, 171 reviews

Dairy House Self Catering Annexe

SaraRating, 5 stars2 weeks ago
Bliss! If you're thinking of booking, go for it (and then add one more night - our only regret was not staying longer to soak in the beautiful, peaceful surroundings). Wonderful, friendly hosts and a lovely warm, welcoming home. We felt right at home and would love to stay again.
Guest favorite
A scenic view of the farm encompasses rolling green hills under a clear blue sky, with a mix of traditional farm buildings and well-maintained grounds. The landscape features patches of trees and open fields, contributing to a serene rural atmosphere.
Tiny home in Dorset
4.9 out of 5 average rating, 245 reviews

North End Farm, Old Cricket Pavilion

DrewRating, 5 stars1 week ago
Eddie and family gave us a beautiful and peaceful retreat to return to every night after our days of adventure. Close to all amenities, but secluded enough that you can retreat from the hustle and bustle of the everyday should you need to. If you want to wake in the morning to fantastic vistas, the crystal sound of a the dawn chorus and an abundance of fresh breathable air, then Eddie and the family are more than happy to allow you into there little piece of heaven. The pavilion has all that one needs for a more than comfortable and peaceful stay. One of the best holidays A big thank you to Eddie and family for a warm welcome, a real home from home🙏

Family-friendly home rentals with a pool

Top guest favorite
The open-plan living area features comfortable seating options, including a gray sofa and vibrant accent chairs. A dining table with colorful chairs is positioned near the modern kitchen, while a log burner and bookshelves add functionality and warmth. Natural light enters through windows, enhancing the spacious feel.
Cottage in Dorset
4.98 out of 5 average rating, 347 reviews

The Condo (Indoor Pool available May- end Sept)

NasimaRating, 5 stars1 day ago
I had an absolutely wonderful stay at the condo! From the moment I arrived, everything exceeded my expectations. The space was spotless, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable and relaxing stay. The location was perfect — close to everything yet peaceful and quiet, offering the ideal retreat after a day of exploring. Communication with the host was seamless; they were incredibly responsive, kind, and made me feel truly welcome. I couldn’t have asked for a better experience and would highly recommend this condo to anyone looking for a perfect getaway. I can’t wait to return! thank you once again.
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
4.93 out of 5 average rating, 259 reviews

Breathtaking sea views from this light, cosy lodge

JodiRating, 5 stars2 weeks ago
What a diamond of a place you have here Judith! On top of holiday park overlooking the most stunning view of Swanage bay and surrounding countryside, almost 360 degrees!! The interior is very tastefully decorated and so comfortable. The beds were dressed with hotel quality, pure white cotton which gave an extra luxury feeling. Lots of table top games for all ages which would have been useful on rainy days but we were so lucky to have had brilliant sunshine throughout our stay! Just minutes drive from everywhere. Got to do the steami railway experience from Swanage. Kimmeridge fossil museum to see the largest ever intact fossil ever excavated! Favourite pub with outdoor views in Worth Matravers, The Square and Compass. Home made ciders, good beers and fab sausage rolls! Favourite fish restaurant, The Pier Head in Swanage. All in all, a fantastic place to stay and thanks to Judith a wonderful 5 star experience!
Superhost
A child plays on a rope swing, grasping the handle while suspended above a green, grassy area. A parent stands nearby, watching with a supportive demeanor. Surrounding structures include climbing elements and a slide, providing a playful environment.
Home in Preston Road
4.84 out of 5 average rating, 112 reviews

Spacious Caravan near sea Weymouth Bay Haven

SuzanneRating, 5 stars3 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 favorite
Home in Lyme Regis
5 out of 5 average rating, 24 reviews

Your Own Private Indoor Pool. Rural Seaside

DebbieRating, 5 stars1 month 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.
Superhost
Chalet in Whitchurch Canonicorum
4.88 out of 5 average rating, 209 reviews

The Duck House. A child/dog friendly rural chalet

LaniRating, 5 stars6 days ago
We chose Jo's place as it was close to Charmouth (11 mins) and Lyme Regis (14 mins by car). Our 6 year old son wanted to go fossil hunting. We arrived at Jo's cottage and she was there to greet us. She is very friendly and welcoming as well as her lovely dog Ruby. Jo also provided us with a travel cot and a changing mat for our 3 month old baby boy too, which was helpful. Jo provided us with a wheel barrow to carry our belongings to the Duck House as it was a little walk round the cottage. It's cosy and had all we needed. Our son liked the children's room he slept in and enjoyed the toys/games provided. My partner and my son did go in the swimming pool, however it was cold for our baby to go into. Jo did provide some bread, home made marmalade (that was lovely), butter, jam and milk. There was no hot water when we woke but when we contacted Jo she was straight on it and sorted it before we went out for the day. We enjoyed our stay - Thank you Jo.
Top guest favorite
A spacious deck overlooks the tranquil Fleet Lagoon, featuring a glass-topped table surrounded by four wicker chairs. A cushioned seating area is positioned nearby, inviting relaxation under the expansive sky filled with scattered clouds.
Place to stay in Weymouth
4.94 out of 5 average rating, 246 reviews

Pebble Lodge

GreigRating, 5 stars3 days ago
Another amazing time spent with family and friends in such a beautiful location. It feels like home and right now with a bad back, and not much walking possible, this is such a lovely place just to sit and watch the view change.
Superhost
A cozy seating area is provided by a deep purple sofa adorned with four decorative cushions. Two small side tables in yellow and green display a cup, complementing the light-filled space with a small window. A patterned rug adds texture to the wooden floor.
Home in Weymouth
4.76 out of 5 average rating, 17 reviews

Beaumont Village 14 (BV14), Silverlake, Dorset

RichardRating, 5 stars5 months ago
Fantastic stay, the house was immaculate and the surroundings are stunning. The view of the lake was breath taking and the facilities were great. We used the gym, tennis courts, swimming pool and had a nice coffee in the cafe. We said we would all definitely stay again. Thank you, Rick
Guest favorite
Cottage in Sherborne
4.91 out of 5 average rating, 414 reviews

Secret Rural Retreat

TahsinaRating, 5 stars7 months ago
This was our second visit and we absolutely loved it. Wonderful location, brilliant pool and gardens, and Fiona is very helpful and communicative host. Thank you for our stay :)

Destinations to explore