Kid-friendly holiday rentals in Isle of Portland

We had a lovely stay at 2 Castle in Dorset. The property was full of charm, with a perfect blend of character and comfort. Everything was clean, well-maintained, and thoughtfully prepared. The kitchen was well-equipped, the beds were very comfortable, and we really appreciated the extra bed Peter put in for our little one. The location was fantastic—quiet and peaceful, yet close enough to explore the beautiful Dorset countryside and coast. Communication with Peter was smooth and responsive throughout, and check-in was easy. There was a little play area right opposite to the house and my little one enjoyed playing there. Overall, a wonderful spot for a relaxing getaway. We’d definitely stay here again and highly recommend it to others.

We had a wonderful time in Woodpeckers Rest at the Brookside Farm. The very vision of verdant peace. It was a great launching pad for adventures all along the Jurassic Coast and throughout Dorset. Thanks to Charlotte for being so communicative and welcoming!

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!

We had a very pleasant stay in Laura's lovely cottage, would happily book again.

Beautiful, light, airy and comfortable home in a perfect location for us. Everything you need in the kitchen for cooking with. V comfy bed! It was lovely and peaceful but just a quick drive to Hive Beach/Burton Bradstock/Bridport . 5 min walk down the road to a lovely local farm shop and The Parlour restaurant for good food and cider made on the farm. Alison was very friendly and gave some good recommendations in the welcome pack.

A fantastic home to rent. Everything one needed was included. It’s modern and decorated beautifully, with all amenities that you need for a stay. I totally recommend this rental. Jenn

Lovely house and very clean. Excellent sea views from the top bedroom (although steep stairs to get there!) On a very narrow quiet street, but could easily drop stuff off and then move the car to free car park just down the hill. Would recommend the Cove Inn, which is easily walkable and Billy’s, which is on the causeway as you approach Weymouth

Thanks so much to Barney and Imogen for an amazing stay. Their cottage is light and spacious and beautifully furnished with all of the comforts and luxuries of home. We loved all the thoughtful touches such as a shopping cart for trips to the local supermarket, phone chargers in every room, TV platforms already set up and lots of interesting books and board games. And we were pleasantly surprised by the outside space which, although quite small, was a lovely, quiet, sunny spot for morning coffee.

Great location, with amenities - and views across Charmouth to the sea - just as shown in photos. Just 10 minutes or so wander downhill to the sea and only half a mile from the village centre with a good (early until 9.00pm) convenience store, small bakery, pharmacy and pubs. Lots of coastal and inland walks within relatively short drives and easy access to Lyme Very responsive host.

Yes, all the 5 star reviews are true! Our stay at Joy’s place was absolutely incredible from start to finish. The apartment was spotless. Joy supplied some wonderful goodies, pastries, scrumptious bread, biscuits and fresh fruit and milk. Lots of information about the area. As the buses were so frequent we used them to visit some wonderful scenic places. Everything one would want for a short stay. The views are amazing with lots of lovely walks nearby which our little dog Mollie loved.

Graham and Linda were very responsive, superb and very kind. They were especially flexible with check in and check out times when we were delayed and running late. We had a brilliant weekend stay at their place which is in a wonderful location with stunning views of the harbour and very close to the beach and all of the beachfront restaurants, cafes and pubs. Thank you for helping make our trip to Weymouth a special one which we shall remember for a long time.

Sebastian’s flat is in a perfect location. I chose it as my husband can’t walk long distances and everything was really nearby. No need to use the car if you want a break from driving. Beautifully comfortable, with lots of extras provided. We’ll be back! Thank you x

Stayed in 2 of Marks apartments over the last couple of months, both have been spotlessly clean and and perfect on each stay. The location is fantastic right on the harbour and parking is just outside( free after 6pm👍🏻) . I would highly recommend a stay in either of the apartments and Mark and Caroline are great hosts! I look forward to coming back soon!

I told my four-year-old we had been invited by 2 queens to stay in their castle—and what queens they were! Such a friendly reception and what a wonderfully whimsical place. The location is fabulous: you can’t see another property, just rolling hills of sheep (the friendliest photobombing sheep I’ve ever come across!), chickens, cows, horses… and the dogs are such a sweet, quiet presence too. Beds are luxurious and the whole house is super cosy with a fab little private garden. A real gem! Would definitely return.

Just back from a wonderful stay at Terrys beachside studios apartment we had the most amazing few days,being so close to the beach was wonderful the views were breathtaking.Thank you Terry we will definitely be back.

A great place to relax. The host was very friendly and helpful. Gave us ideas of where to eat and what to do. The apartment is situated in a beautiful location, walking distance to the beach. It was very clean. Would highly recommend this place.

We had a great stay. The flat was as described and well set up for a toddler. There were even toys to play with.

We’ve just returned from a wonderful 6 nights in Anthony’s annexe and what a beautiful space to recharge. Set in a peaceful neighbourhood on the SW coast path there are plenty of options for exploring the area on foot or the open top buses. The accommodation was just as described, comfortable with all the amenities that you could need and the welcoming bottle of wine and milk was much appreciated. We wouldn’t hesitate to use the annexe again when next visiting the area

Really well-equipped home, great position. Light and airy, sweet courtyard.

We enjoyed staying in the apartment, which was comfortable and well equipped. The location meant it was an excellent base for exploring Weymouth and beyond. Anna was a very helpful and welcoming host.

beautiful flat, with everything you need for a stay in Weymouth. We would highly recommend this to anyone.

Thank you so much Karen and Ian for such a beautiful week. We would definitely love to stay again.

Great little hideaway in stumbling distance of a bustling high street with great pubs and restaurants. The accommodation is very comfortable and very well equipped.

We absolutely loved our stay at Carley’s apartment. All directions and instructions were spot on and easy to follow. The apartment was perfect and the view is stunning, and everything we needed was thought of by Carley, who was also super helpful and friendly. We’d definitely recommend to anyone!