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Family-friendly vacation rentals in Isle of Portland

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Top-rated family-friendly rentals in Isle of Portland

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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.

4.88 out of 5 average rating, 344 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...

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.

4.85 out of 5 average rating, 192 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 bright sitting area features a gray sofa adorned with decorative cushions. Large skylights fill the space with natural light, while a wooden coffee table and a minimalist media console are visible. Views of greenery can be seen through the windows, enhancing the bright ambiance.

4.97 out of 5 average rating, 149 reviews

Stylish self-contained annexe in rural mid Dorset

A thoughtfully designed space for two in glorious, peaceful Dorset countryside. Located on the edge of the lovely village of Hilton, this is a perfect place to hunker down for a few days or to use as a base for exploring all the amazing places that Dorset has to offer, all within easy reach. We are a gentle half hour stroll from Milton Abbey which is set in a magnificent Capability Brown landscape. We are also an easy trip (approximately 20 miles) from the spectacular Jurassic coast.

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.

4.88 out of 5 average rating, 145 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.

4.97 out of 5 average rating, 318 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

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.

5 out of 5 average rating, 219 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.

4.91 out of 5 average rating, 654 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

The exterior of the cottage is shown with a charming garden filled with lush greenery and blooming flowers. A wooden table and chairs are positioned on a gravel path, leading to large glass doors that open into the inviting interior.

4.94 out of 5 average rating, 286 reviews

The Little House, Hooke, Nr Bridport, West Dorset

A perfect cottage for two. Come and relax and unwind in this hidden corner of West Dorset. Quiet and peaceful yet within easy reach of the coast and all the local attractions. Lovely private garden, fabulous walks and you can bring your dog too! BEAMINSTER (3 miles away) is enchanting, with fabulous shopping and food. Enjoy the fun of Bridport market, and then a walk by the sea. COME AND SEE THE SNOWDROPS ! THEY ARE AT THEIR BEST RIGHT NOW

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.

4.94 out of 5 average rating, 259 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.

4.96 out of 5 average rating, 334 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.

5 out of 5 average rating, 470 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.

An aerial view captures Bellamont House surrounded by rolling hills and vibrant autumn foliage. The light of dawn casts a warm glow over the property, emphasizing its spacious layout and serene setting within the Bride Valley landscape.

4.96 out of 5 average rating, 126 reviews

Elegant Wing of a Country House - Bride Valley

The West Wing is a beautiful self contained apartment of Bellamont House. It benefits from a smart, light and spacious atmosphere. It is well equipped with all the comforts of home. Bellamont is situated in the picturesque Bride Valley, a Designated Area of Outstanding Natural Beauty & is only 5 miles from the sea & the stunning World Heritage Jurassic Coast.

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Popular amenities for Isle of Portland family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior of Lanes End Cottage features traditional thatched roofing and charming brick detailing. Lush greenery is seen climbing the walls, complemented by a fenced front yard. A gravel pathway leads to the entrance, while a rustic barn is visible in the background.

5 out of 5 average rating, 3 reviews

Lanes End Cottage

A charming Edwardian farmhouse is prominently displayed, featuring a warm brick exterior and large windows. Solar panels are visible on the roof. A sunroom with glass walls is adorned with climbing greenery, blending harmoniously with the surrounding lush countryside.

4.93 out of 5 average rating, 70 reviews

Frogmore House near Jurassic Coast with hot tub

A contemporary house is visible from across the water, featuring large glass windows that reflect the surrounding greenery. The property is set within a grassy area, complemented by picnic tables and benches, with trees framing the home against a clear sky.

4.97 out of 5 average rating, 389 reviews

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

The open living area features exposed wooden beams and warm, natural tones. Comfortable seating arrangements include a white sofa and a wicker chair positioned around a wooden coffee table. Sunlight filters through large windows, illuminating the rustic charm of the space.

4.67 out of 5 average rating, 70 reviews

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

A charming shepherd's hut is situated among tall grass and wildflowers, framed by lush greenery. The wooden structure features a light blue door and large windows, offering glimpses of the serene surroundings. Steps lead up to the hut, enhancing the connection to nature.

4.96 out of 5 average rating, 113 reviews

Astronomer Shepherd's hut

The exterior of the cottage features a charming brick façade complemented by a slate roof. A hot tub is positioned near a patio set with a table and chairs under an umbrella, providing a space for outdoor dining. Lush greenery and fields are visible in the background.

4.98 out of 5 average rating, 205 reviews

Charming Brick Cottage with a Patio and Hot Tub

A cozy bedroom features a spacious bed with white linens and decorative pillows in green and geometric patterns. A light blanket is layered at the foot of the bed. Nightstands with soft lamps provide gentle illumination, complemented by a framed artwork on the wall.

4.96 out of 5 average rating, 94 reviews

Little Coombe, a luxury rural cottage with Hot tub

Water fountains gracefully stream from four jets in the hot tub, creating a soothing atmosphere. The clear water dances and glistens against the backdrop of a textured gray wall, enhancing the tranquil setting of the private courtyard garden.

4.86 out of 5 average rating, 112 reviews

Spa Cottage in Weymouth, Dorset

Family- and pet-friendly home rentals

A coastal view features a natural rock formation arching over a serene beach. The calm waters reflect the soft blue sky, while sandy stretches are dotted with a few visitors enjoying the shore. Distant islands are visible on the horizon.

4.85 out of 5 average rating, 224 reviews

Win Place

A wooden chalet features a charming entrance with double French doors and a small window, both framed by natural wood finishes. A welcome mat is positioned at the threshold, and a concrete path leads to the door. The surrounding area includes green plants and a quiet, rustic ambiance.

4.67 out of 5 average rating, 214 reviews

Self-catering Chalet with Parking

The exterior of a cedar-clad studio is visible amid lush greenery and blooming trees. A sloped roof is partially coated with moss, adding texture. Sunlight filters through the leaves, illuminating the surrounding area and highlighting the peaceful hillside setting.

4.9 out of 5 average rating, 450 reviews

Modern studio, hillside garden with amazing views

The entrance to The Old Bakery is framed by exposed brick walls and a small flowering garden. A potted rose and vibrant floral arrangements adorn the pathway, while a pair of light blue chairs invite relaxation. A sign marks the entrance to the apartment.

4.86 out of 5 average rating, 465 reviews

The Old Bakery

The cottage features a charming thatched roof and a front entrance framed by a well-kept garden, presenting various shrubs and flowering plants. A teal patio umbrella provides shade to a seating area, with large windows reflecting natural light. The exterior walls are painted in a soft white hue.

4.77 out of 5 average rating, 100 reviews

Warm and cosy, dog friendly, Character cottage

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.

4.88 out of 5 average rating, 224 reviews

Idyllic views, quiet,cosy, Jurassic coast cottage

The exterior of Duntish Studio is showcased, featuring a stone and brick facade with a pitched roof. Large windows allow natural light to enter. An entrance door with glass panels opens onto a paved area, surrounded by green trees and a quiet road with minimal traffic.

4.9 out of 5 average rating, 472 reviews

Duntish Studio

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.

4.9 out of 5 average rating, 255 reviews

North End Farm, Old Cricket Pavilion

Family-friendly home rentals with a pool

An outdoor terrace is depicted, featuring modern wicker furniture with plush cushions. A coffee table is centered among two armchairs, providing a comfortable space to enjoy views of the tranquil water. The surrounding railing frames the expansive coastal landscape under a sunny sky.

4.98 out of 5 average rating, 63 reviews

Harbour View Poole

Top guest favorite

A dining area is visible, featuring a wooden table set with plates and bowls. Large glass doors open towards the beach, allowing natural light to fill the space. In the background, the coastline extends into the horizon, with sandy shores meeting the sea.

4.97 out of 5 average rating, 39 reviews

Chesil Holiday Lodge, Weymouth *sea views*

Top guest favorite

An indoor swimming pool is featured, surrounded by large windows allowing natural light. The ceiling beams reveal a spacious, airy atmosphere. Two red chairs are positioned nearby, and a shallow end is visible with steps leading into the water. A blue cover rests along one side of the pool.

4.98 out of 5 average rating, 360 reviews

The Condo (Indoor Pool available May- end Sept)

A spacious corner sofa is adorned with colorful cushions in yellow, gray, and blue. A cozy navy blanket drapes over the side. A wooden coffee table holds a selection of brochures, with natural light filtering through sheer curtains at the nearby window.

4.84 out of 5 average rating, 114 reviews

Spacious Caravan near sea Weymouth Bay Haven

4.91 out of 5 average rating, 134 reviews

Bowleaze Cove with a view

The cottage features a charming brick exterior with a sloped slate roof. A tall chimney rises above the structure. Two entrances are framed by neatly trimmed plants, while the surrounding gravel area and green countryside create a welcoming atmosphere.

4.98 out of 5 average rating, 56 reviews

Flint Cottage for two with indoor pool & sauna

The image displays a heated swimming pool enclosed within a clear poly tunnel. The water is calm and reflects the overhead light, creating a serene atmosphere. Poolside tiles extend along the edges, and a rolled-up cover can be seen at one end.

4.92 out of 5 average rating, 270 reviews

The Duck Wing, quirky dog friendly apartment

A light-filled living area features large glass doors offering views of Poole Harbour. Comfortable seating includes a gray sofa and cushioned lounge chairs. A bookshelf and entertainment unit are positioned against the wall, while a dining table complements the modern décor.

4.85 out of 5 average rating, 13 reviews

Waratah unobstructed sea views Rockley Park, Poole

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