
Family-friendly vacation rentals in Weymouth and Portland District
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Weymouth and Portland District
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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)

Seaside studio cabin minutes from 'secret' beach
Tucked away up an unmade track & five minutes walk from a 'secret' local beach; Cove Cabin is a compact, stylish, private space; perfect for a couple or two companions. On the doorstep of lesser known beaches & gardens but not far from Weymouth's bustling scenic harbour & golden sands. Ideal stop off whilst walking the SW Coast Path. The perfect area for watersports, wild swimming, walking, mooching around the harbour & locality, sampling the local seafood & eateries & just simply relaxing.

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.

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.

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.

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.

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.

The Hide in the treetops near weymouth town/beach
Open plan space: sleeps 2; king size bed; bed linen. Kitchen with induction hob; electric oven; microwave and fridge freezer; coffee machine; tea towels. Ensuite shower room; hand towels & Bath sheets. Beach Towels not provided so please remember to pack yours! Comfy sofa; dining table and 4 chairs. Large TV and wifi. No children of any age and no animals/pets allowed. Smoking strictly prohibited inside The Hide or on the grounds.

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.

Central, beach front apartment - with own balcony
Watch the sun rise and night fall over the bay from this charming, central Esplanade, Georgian first floor apartment with free parking permit. Looking directly onto Weymouth's award winning beach and just minutes from Weymouth's picturesque harbour and town. A comfortable, light and airy living space offering a large sea and beach view balcony with seating. Ideal for couples. Superfast Sky WiFi.

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.
Popular amenities for Weymouth and Portland District family-friendly rentals
Family-friendly home rentals with a hot tub

Cosy Shepherds Hut – Hot Tub, Pubs & Paws

Unique & Stunning Bespoke Thatched Shepherd's Huts

Townhouse, garden, hot tub, breakfast terrace.

Log Cabin/Hot Tub on Private Lake Jurassic Coast

Full use: hot tub/sauna/bbq/firepit/Netflix/Prime

Shepherd's Hut, with stunning views and hot tub

Bay View Luxury Stays - Southdown

The Annex @14
Family- and pet-friendly home rentals

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

A Charming Cottage, Just a Moment from the Beach

Stunning Barn conversion with heated swimming pool

Little Barn is a cosy dwelling in a remote valley

1888 Portland stone cottage

Joanne's Retreat - Cosy, Calming with Free Parking

Historic Seaman Chaplaincy, Seaview all rooms

Couples Luxury Retreat
Family-friendly home rentals with a pool

Secluded hideaway, heated pool, walks, fossils

Headland Hideaway Shepherd's Hut in Lyme Regis

The Condo (Indoor Pool available May- end Sept)

Family friendly & comfortable 2 Bed Holiday Home

6 Berth Caravan Poole Haven Holiday Free Beach Hut

Breathtaking sea views from this light, cosy lodge

Great for visiting Dorset - woodland walk to beach

The Duck Wing, quirky dog friendly apartment
Destinations to explore
- Durham Vacation rentals
- Paris Vacation rentals
- London Vacation rentals
- Picardie Vacation rentals
- Grand Paris Vacation rentals
- Thames River Vacation rentals
- South West Vacation rentals
- Inner London Vacation rentals
- Rivière Vacation rentals
- Brussels Vacation rentals
- Dublin Vacation rentals
- South London Vacation rentals
- Rentals with pools Weymouth and Portland District
- Rentals with an EV charger Weymouth and Portland District
- Waterfront rentals Weymouth and Portland District
- Chalet rentals Weymouth and Portland District
- Bed and breakfasts Weymouth and Portland District
- Townhouse rentals Weymouth and Portland District
- Cottage rentals Weymouth and Portland District
- Condo rentals Weymouth and Portland District
- Rentals with outdoor seating Weymouth and Portland District
- Apartment rentals Weymouth and Portland District
- RV rentals Weymouth and Portland District
- Rentals with beach access Weymouth and Portland District
- Rentals with lake access Weymouth and Portland District
- Guesthouse rentals Weymouth and Portland District
- Rentals with breakfast Weymouth and Portland District
- Tiny house rentals Weymouth and Portland District
- Rentals with a hot tub Weymouth and Portland District
- House rentals Weymouth and Portland District
- Rentals with a patio Weymouth and Portland District
- Rentals with a fire pit Weymouth and Portland District
- Rentals with a fireplace Weymouth and Portland District
- Rentals with a washer and dryer Weymouth and Portland District
- Beachfront rentals Weymouth and Portland District
- Pet-friendly rentals Weymouth and Portland District
- Hotel rooms Weymouth and Portland District
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- New Forest National Park
- Paultons Park Home of Peppa Pig World
- Stonehenge
- Weymouth Beach
- Boscombe Beach
- Bournemouth Beach
- Kimmeridge Bay
- Highcliffe Beach
- The Tank Museum
- Southbourne Beach
- Poole Quay
- Crealy Theme Park & Resort
- Preston Sands
- Mudeford Sandbank
- Beer Beach
- Man O'War Beach
- Charmouth Beach
- Rockley Park
- Torre Abbey
- Hurst Castle
- Compton Beach
- Tapnell Farm Park
- Palace House
- Farmer Palmer's Farm Park




