Family-friendly vacation rentals in Weymouth and Portland District

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Top-rated family-friendly rentals in Weymouth and Portland District

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Superhost

An open-plan lounge area displays a wood-burning fireplace set against a rustic stone hearth, with shelves featuring decorative items. Two low sofas are arranged for seating, accompanied by a colorful accent chair. Natural light enters through a window, illuminating the soft area rug.

Cottage in Dorset

4.87 out of 5 average rating, 342 reviews

18th Century Coastal Cottage

This historic home features original stone floors, rustic wood beam ceilings, a wood-burning fireplace, modern finishes, a sauna, and a private back patio overlooking the beach. Breathe in the refreshing ocean air from this hillside retreat. I’m sorry I have a no pets policy at the cottage. This cottage has steep stairs, low ceilings, a very low rise bed and a low sofa as seen in the pictures. 60 Mallams was built in approximately 1760 and still has many rustic features throughout. The cottage has two levels, ground floor consists of open plan lounge leading to the kitchen then conservatory with shower room. Which opens out into courtyard garden with a terrace and sea views. 1st floor has the main bedroom with a super king size bed and separate bathroom with a free standing bath with room for two.. Private parking on driveway 24hr key access safe by the front door I can be contacted at any time throughout your stay. The property is located just a five minute walk from Chesil Beach. It is also close to a number of the town's local shops and cosy pubs. There’s plenty of coastal walks all around Portland The sailing club is close offering various water sports There is bus services to and from Weymouth. There are amazing coastal walks around Portland. Please be mindful of the rubbish I have food waste bins , glass only tubs and the larger of the wheelie bins (green) are recycling only ( cans paper and plastic) and the black bins are general rubbish.. please be careful with the rubbish because if it's all mixed up the bin men won't take it away...

Guest favorite

An open plan living space features a green sofa, wood-burning stove, and a dining table surrounded by wooden chairs. The exposed brick wall adds character, while a patterned rug anchors the seating area. Natural light enters through a window, creating a bright atmosphere.

Guest suite in Portesham

4.85 out of 5 average rating, 190 reviews

Modern living in a Traditional quaint village.

A self contained house attached to owners property. Access via secure garage and own door. Offering privacy in beautiful countryside at the edge of the village with pub/ cafe and shop. Open plan living space with TV/DVD player and log burner for the colder months. Dishwasher and washing machine in the property. 1 Bedroom with sloping ceiling with double or twin beds. Can also accommodate 1 baby (under 2 years to share bedroom). Bathroom with bath and shower. Own small garden with patio area.

Top guest favorite

The spacious living area features exposed wooden beams and a blend of modern and antique furnishings. A black sofa, yellow accent chair, and coffee table are positioned atop a light wood floor. Large glass doors provide natural light and views of the outdoor area.

Barn in Whitchurch Canonicorum

5 out of 5 average rating, 151 reviews

The Barn @ Lower Park Farm, Nr Lyme Regis

A luxury barn conversion set in an area of outstanding natural beauty. This property blends comfort and space with seductive and classy interiors situated in a converted milking parlour. The area is renowned for great walks, cycling and horse riding through the picture-perfect countryside of Marshwood Vale. The nearest beach 3 miles away, with Lyme Regis just 6 miles away. This property offers the best of both worlds in terms of scenery and pretty seaside towns. Ideal for Coastal Path walkers.

Guest favorite

A serene outdoor seating area is highlighted, featuring two wicker armchairs with soft cushions and a glass-topped table. Beyond, the tranquil Fleet Lagoon reflects sunlight, providing picturesque views, while colorful flowers add a touch of warmth to the setting.

Chalet in Weymouth

4.96 out of 5 average rating, 204 reviews

Summer Lodge

The Summer Lodge boasts uninterrupted views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the South West Coast Path (Jurassic Coast). Located just one mile from the Isle of Portland, the home of the 2012 Olympic sailing events and a short drive from Weymouth town centre and harbour, our stunning holiday home is perfectly situated for anyone wanting a coastal escape. Our sea view lodge sleeps 6 people. There are 2 double bedrooms and a small double sofa bed.

Superhost

A historic three-story stone house is framed by blooming flowers in the foreground. The structure features large windows and a welcoming entrance, set against a clear blue sky, showcasing its charm and inviting atmosphere.

Townhouse in Dorset

4.87 out of 5 average rating, 142 reviews

Historic Seaman Chaplaincy, Seaview all rooms

The Gift House Portland is a historic Seaman's Chaplaincy, 3 storey late Georgian stone house. All 4 spacious bedrooms have sea view & perfect for sunset watching. Dog friendly (1dog only) Locate in island village, 5-8 mins walk to pebble beach, 17th century pub, restaurants, good coffee, good chippy & grocery shop. Jurassic coast walks, sculpture park, Portland stone quarry, cycling, swimming, rock climbing, sea fishing, diving, kayak, sailing, paddling, windsurf & more are around.

Top guest favorite

A spacious bed is dressed in a bold plaid design, complemented by vibrant red throw pillows. A decorative heart-shaped cushion adds a charming touch. Natural light illuminates the room, highlighting the warm wooden flooring.

Guesthouse in Dorchester

4.97 out of 5 average rating, 317 reviews

Lovely, Quiet Studio Annex (with Netflix)

Self contained, self catering studio annex based in the county town of Dorchester. The annex is suitable for 2 adults (a z-bed can be supplied for 1 child under 12). The towns amenities are all within a short walking distance, including the new 'Brewery Square' development. Great base to explore Dorset's fabulous coast, countryside and walk in the footsteps of Thomas Hardy's Casterbridge. Motorbike friendly, high chair & travel cot available. Complimentary tea and coffee. Netflix TV.

Top guest favorite

A welcoming kitchen area features a wooden breakfast table with two chairs and fruit. Bifold doors open to a large terrace with outdoor furniture, showcasing views of the surrounding greenery and gardens.

Home in Wynford Eagle

4.94 out of 5 average rating, 218 reviews

Woodpeckers Rest - Alpacas-Gardens-Brook-Tennis

Nestled in an area of Outstanding Natural Beauty, Wynford Eagle is one of West Dorset's hidden gems. Woodpeckers Rest is a cosy studio retreat, a haven for peace and relaxation which opens out onto a large terrace with stunning views of the valley, 8 acres of grounds and gardens and beautiful alpacas. A great base to explore Dorset, situated just 15 minutes from the Jurassic coastline and all this incredible area has to offer. Please also see listing for airbnb.com/h/swallows-return

Top guest favorite

The exterior of the cottage is showcased, highlighting a charming wooden structure adorned with climbing foliage. A gravel driveway leads up to the entrance, framed by neatly arranged planters. A wooden fence enhances the privacy of the property, complemented by young trees.

Cottage in Bridport

5 out of 5 average rating, 215 reviews

Berry Farm Cottage

Berry Farm Cottage nestles in a private area of the grounds of Berry Farm, which dates back to the 16th century. It is located in the charming Conservation Village of Walditch, within walking distance of Bridport. The Cottage itself has 2 bedrooms and two bathrooms with an open-plan living space and is set away from the main house in its own private grounds, with 1,200sqm (0.3acres) of orchard garden, as well as an outside patio with table and chairs, with country views.

Top guest favorite

The spacious studio features a large bed with dark red and neutral bedding. A leather Chesterfield sofa is positioned across from a flat-screen TV. Soft lighting is provided by wall sconces, while a decorative rug adds texture to the tiled floor.

Apartment in Weymouth

4.91 out of 5 average rating, 651 reviews

Splendid Quiet Ground Floor Apartment Near the Sea

This gorgeous large studio apartment with separate entrance is contained within an historic Georgian house, minutes from the ocean. Peace and quiet are ensured by a large well tended front garden with off street parking. The accommodation has a spacious shared patio, giving way to an established secluded garden. The apartment boasts a stylish fully fitted kitchen and leather Chesterfield sofa, chairs and a large comfy bed . There is an EV charger in the garage 55p/KWH

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, 256 reviews

Pebble Lodge

Pebble Lodge is a stylish, modern and luxury home from home for four guests (plus one infant). Situated on the five star Chesil Beach Holiday Park, Pebble Lodge boasts an uninterrupted view of the Fleet Lagoon and Chesil Beach, infamous parts of the Jurassic Coast. Beautiful accommodation, finished with some personal touches really makes Pebble Lodge the perfect coastal escape in all seasons.

Top guest favorite

A vibrant scene along the waterfront features colorful buildings lining the quay, reflecting a charming coastal atmosphere. The illuminated sky above hints at dusk, and an ornate railing runs parallel to the water, adding a picturesque element to the view.

Condo in Dorset

4.95 out of 5 average rating, 330 reviews

Your hideaway on Weymouth harbourside!

Harbour Hideaway....light and airy basement apartment with own courtyard in fantastic harbourside location. Permit parking for 1 car and dogs welcome. Main sandy beach 5 mins away and town is just across the bridge. Friday changeovers preferred if weekly durations. Please note that there are two single beds in the bedroom and a drop down King Size bed in the lounge (not in a separate room) x

Top guest favorite

A spacious patio area features a circular dining table surrounded by six chairs, complemented by a large umbrella. Decorative planters with green plants add a touch of nature. Full height glass doors provide a view of the surroundings while inviting natural light.

Apartment in Weymouth

5 out of 5 average rating, 467 reviews

Apartment with panoramic sea views

We are situated 600 yards, through the nature reserve, from the beach and at the top of the hill with panoramic views over Weymouth bay, beach and nature reserve. 3 miles from the town With loads of parking available outside .You’ll love my place because of the location, the views. good for couples, solo adventurers, business travellers and small, well behaved dogs.