Family-friendly vacation rentals in Weymouth and Portland District

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

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Top guest favorite
An open plan kitchen and living area is showcased, featuring a modern kitchen island with three high bar stools. The living space includes a comfortable sofa accented with several cushions, while large windows allow natural light to fill the room.
Condo in Dorset
4.91 out of 5 average rating, 510 reviews

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

Guest favorite
A compact accommodation features a spacious bed with a neatly arranged blanket and a two-seater sofa. A mini kitchen area includes a kettle and sink. Natural light streams through a large window, highlighting the wood flooring and soft-toned walls.
Guesthouse in Southhill
4.84 out of 5 average rating, 292 reviews

Bright & Snug annexe with Parking in Weymouth

Welcome to our one bedroom self contained private accommodation with parking space in Weymouth. Consisting of a double bed, two seater sofa ( NOT suitable to sleep) , mini kitchen unit with sink, kettle & toaster, fridge, smart TV, chest of drawers, shower room. Weymouth town Centre, train station and Weymouth’s popular beach is a 20 minute walk through the RSPB nature reserve, where you will see swans, ducks & plenty of bird species. Pub, pharmacy & shop is only a 5 min stroll down the road

Guest favorite
A stylish living area features dark walls complementing a plush teal sofa with a decorative cushion. A small dining table and chairs are visible in the corner, with modern cabinetry and a kitchen area showcased in the background. Warm lighting enhances the inviting atmosphere.
Apartment in Dorset
4.79 out of 5 average rating, 167 reviews

The Snug - 2mins walk from the beach 🏝

Moments from Weymouth beach this lovely self catering apartment is perfectly located. Dorset is breathtaking with its Jurassic coast, explore popular spots like Lulworth cove or the isle of Portland or stay put and enjoy all that Weymouth’s bustling town, harbour and beaches have to offer. With great seafood, and a wonderful selection of restaurants within walking distance you won’t be at a loss of places to eat. Take a rib ride from the harbour and see if you can spot our resident dolphins.

Top guest favorite
A round porthole window features a serene view of calm waters reflecting the sky. A distant rocky shoreline with palm trees can be seen on the left side, framed by a textured wooden wall.
Bungalow in Dorset
4.95 out of 5 average rating, 196 reviews

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)

Top guest favorite
Condo in Dorset
4.97 out of 5 average rating, 202 reviews

Townhouse Flat

A lovely one bed first floor flat within family home. The flat sleeps 4, max 5 with z bed. The flat is self-contained, but is accessed via the family home front door, hallway and stairs. The flat is on the first floor of a period townhouse on Dorchester Road, and is close to local amenities (Tesco Express, pub, Post Office and chip shop). The beach is a 10 min walk away and the town centre is a 20 min walk. Free on street parking is available. See additional charges for Z bed hire.

Guest favorite
A large window presents a stunning view of the beach and sea, illuminated by natural light. The light curtains gently frame the window, while a television stands on a dresser nearby. The serene coastal scenery offers a glimpse of a sandy beach and distant hills.
Condo in Weymouth
4.91 out of 5 average rating, 462 reviews

Stunning Beachfront apartment overlooking the sea

A brand new apartment just 50 steps from the beach with free parking in the heart of Weymouth directly on the Esplanade with panoramic sea views of the award winning beach. Well equipped and nestled amongst shops and restaurants . Just minutes walk to bars , the harbour and train station. Fully fitted kitchen with family size fridge freezer, oven, microwave, toaster, kettle, cutlery, crockery, dishwasher, washing machine, flat screen TV's, Wifi, Hand, bath and beach towels provided.

Top guest favorite
The exterior of Sunnyside Lodge features a well-maintained brick facade adorned with vibrant flower planters. A paved driveway is visible, leading to the entrance, with clear space indicating off-road parking availability. The surrounding area includes privacy fencing and additional greenery.
Bungalow in Weymouth
4.97 out of 5 average rating, 337 reviews

Sunnyside Lodge

Sunnyside Lodge is a fully self-contained property with a private entrance and off-road parking located 1.4 miles from Weymouth town centre. The property has been converted to a holiday let, decorated to a crisp, clean and comfortable finish. The property comes with access to high speed WiFi, Sky Q and is fully fitted with fire alarms and a CO2 alarm. The location provides excellent transport links to surrounding local attractions including The Jurassic Coast - a World Heritage Site.

Guest favorite
A living room is presented with a navy blue feature wall and elegant chandeliers. A plush blue sofa and floral upholstered chairs provide seating around a central coffee table. A decorative mirror and artwork enhance the space, complemented by a non-working fireplace.
Apartment in Dorset
4.92 out of 5 average rating, 148 reviews

Esplanade: Beach front, Regency flat with parking

Alexandra House, Esplanade is on the seafront overlooking Weymouth’s glorious sandy beach and close to the bandstand, Pavilion theatre, harbour and town centre. This stunning Grade II listed property retains many of its original features and has a modern kitchen, new bathroom and free parking at the rear of the property for one car. This ground floor flat has been refurbished to a very high standard - step into luxury on the seafront and enjoy the uplifting view over Weymouth Bay.

Guest favorite
A row of elegant seaside buildings is highlighted, facing a calm stretch of beach. A clock tower stands prominently along the waterfront. Reflections are visible in the water, creating a peaceful scene under a partly cloudy sky.
Apartment in Dorset
4.89 out of 5 average rating, 119 reviews

Beach View Apartment

Whitesands apartments are situated on the seafront overlooking Weymouth’s glorious sandy beach and close to the Pavilion, harbour and town centre. Whilst retaining many of its original features, the property has been modernised to include fully fitted kitchens, central heating and new bathrooms. Refurbished and redecorated to a very high standard, Whitesands can now boast the interior quality that its imposing exterior has demanded.Enjoy the glorious view over Weymouth Bay.

Guest favorite
Apartment in Weymouth
4.89 out of 5 average rating, 450 reviews

Flat One The Beaches

***Flat one the Beaches is in a central position & can be noisy in the evenings especially at the weekends***Recently converted Grade II listed building on Weymouth seafront. The apartment is one of four located off a private inner courtyard on the first floor. well equipped apartment across the road from Weymouth’s award winning beach and nestled a stones throw away from Weymouth town with its great choice of harbour side restaurants and bars.

Top guest favorite
A bright and inviting area features a large window draped with sheer curtains, allowing natural light to flood in. A small wooden table with two chairs is positioned near the window, complemented by decorative items on the wall and a plant on the table.
Tiny home in Weymouth
4.9 out of 5 average rating, 243 reviews

Cosy Sail Loft on the harbour.

This special place is close to everything, making it easy to plan your visit. With your own parking space, own entrance, bedroom / lounge, own kitchen and Bathroom, you can be fully self sufficient or enjoy all the local pubs and restaurants on your door step. Literally right on the harbour front and only a minute away from the beach, this cosy property allows you to enjoy all of this seaside town within a few minutes.

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, 273 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.

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