Family-friendly holiday rentals in Isle of Portland

1888 Portland stone cottage

1888 Portland stone cottage, with many original features. Stone fireplace with log burner. Cosy 2 bedroom, 3 storey cottage located within easy walking distance of Easton Square, which has local amenities, including grocery stores, chemist, pubs and cafes. Small sunny aspect courtyard with bistro table and chairs. A perfect holiday location all year round, for either sun and relaxation, or enjoy activities like windsurfing, sailing, diving, rock climbing, fishing, walking and bird watching.

1 Bed home near Sailing academy Portland, Weymouth

The home is located in Portland near to a Port and 5 miles to Weymouth also 10 min walk to sailing academy The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks,rock climming, cycle routes It is a one bedroom apartment.There is a small Beach and it’s a short walk to shops,cafe's and restaurants.Includes an open plan kitchen,living room and en-suite bathroom with electric showerThere is a sofa bed on request Parking is nearby but free parking is available in the street

Islands Wrest (The Galleon Rm). Pet friendly.

Nautical galleon themed room with own entrance, kitchen & shower room this your own space within owner occupied property. Explore Portland, an Island that features breathtaking views, beautiful walks. Castles, 3 lighthouses. Chesil beach. a Museum, rock climbing, wildlife, water sports. History of smugglers & pirates explore Church Ope Cove. 20 min on bus to Weymouth for more seaside fun! Set centrally on the Jurassic coast. This is a real hidden gem. Not suitable for infants (Adults only)

Milly Moll Cottage, next to Church Ope Cove.

Julie and Matt welcome you to Milly Moll Cottage. A quirky C18th, grade 2 listed property full of character and charm, just next door to the Portland museum. Built of Portland stone with original fireplaces and a cozy lounge with a log burner, from here you can explore the Jurassic coast. It’s a 2 minute walk to Church Ope Cove, either passing under Rufus Castle arch or via the ruins of St Andrews church and is ideally placed for numerous outdoor pursuits. We hope you will enjoy your stay.

CLOUD 9 🦚 Homely & Happy 😊 Near the Beach 🌊🐟🌞

Welcome home, welcome to CLOUD9🌅 Vintage-modern velvet luxury in the historic heart of Fortuneswell on the Isle of Portland🌊 Renovated & designed with love by our family🧡 Living/dining room, kitchen, downstairs w/c, enclosed garden. Spacious shower room plus 3 themed bedrooms 🦚🌸 with sea views⛵️ Chesil beach, co-op local, fish & chips & friendly pubs all close-by🐟 😊 Super fast 100mb+ WiFi. Fully equipped kitchen. *If booking for 1-2 only, loft room will be locked shut.

Breeze - White Stones Studios

Come and enjoy unique contemporary eco-friendly accommodation set in peaceful and creative surroundings at the heart of Easton, Portland, on the tip of The Jurassic coast. Located to the rear of White Stones Art Cafe's secluded and tranquil gardens there are three holiday studios available, each sat nestled together in peaceful surroundings. Breeze is one of our three bespoke holiday studios, finished to a high standard and providing a contemporary holiday experience.

Maidenwell Cottage. Near Chesil Beach, Portland

Maidenwell Cottage is a Grade II listed period property on Portland, the southernmost point of the Jurassic Coast that has been refurbished to a high standard and designed to make you feel at home. Chesil Beach, local shops, cafes and pubs are all a within a short walking distance. Maidenwell Cottage is perfect for families and couples looking for a cosy seaside retreat and those looking for a place to relax following a day of walking, climbing and water sports.

Quirky 2 bed holiday home with hot tub and sauna.

Newly built 2 bedroom cottage with hot tub and sauna located in Easton on Portland in Dorset. This unique home is built in Portland stone and has a ground floor outdoor space with patio and outdoor oven area as well as having an upstairs outdoor mezzanine area with bi-folding doors. The main living space that includes a 90” television. All equipped with sky Q including sports. Both bedrooms have super king beds and are en-suite with showers and jacuzzi baths.

Studio Pod 2

Pod 2 has a modern, fully equipped kitchen, bathroom, sofa, TV and drop-down double sofa bed. You can sit in bed with a view of the sea or chill on the deck with a glass of wine on a sunny evening. Our Pods come with bed linen and towels included. -Fantastic elevated sea views from the top level of Park (The view is shown in the images) -Large decking with outside seating -Innovative pull-down double bed and fold away sofa -No pets

The Backhouse, Southwell, Portland

A characterful, rustic old stable which has been converted into a small self contained holiday let. The accommodation is comfortable and full of character and quirks. The property is 3 minutes walk from the Jurassic coast path and provides easy access for Climbers, Walkers, Birdwatchers and Watersports. we do have dogs living in our home who do have access to the garden

Character cottage close to beach

Spacious and beautiful house 5 min walk to Chesil Beach. Free superfast wi-fi, well equipped kitchen including dishwasher and a cosy log burner in living room. Scandi style décor. Netflix and smart TV. Right in heart of Fortuneswell, Portland with some shops, pubs and restaurants close by. 10-15 min drive from Weymouth.

Top To Bottom beautiful cottage heart of Easton

My place is close to great views, restaurants and dining. You’ll love my place because of the location, the people, the outdoors space, and the neighbourhood. My place is good for couples, families (with kids), big groups, and furry friends (pets).