Family-friendly vacation rentals in City of Winchester

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Top-rated family-friendly rentals in City of Winchester

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

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Guest favorite

A spacious garden area is depicted, featuring a green slide attached to a wooden play structure. A tree stands nearby, providing shade, while a clothesline is visible on the left side, stretching across a neatly mowed lawn.

Home in West Wittering

4.98 out of 5 average rating, 144 reviews

West Wittering Village - short walk to beach.

A bright, relaxed family home in West Wittering village, a short walk from the famous sandy beach and the village pub. Suits an extended family group or 2 small families sharing. The amazing living space includes a large modern kitchen/family room, separate TV room and a large playroom with table tennis, pool table and lots of toys. A large garden surrounds the house and includes a shady eating area, a lovely south-facing sun deck, an hot shower, a fire pit and a play area with zip wire/ slide.

Guest favorite

An inviting entrance hall features a white door partially open to a garden view. A round mirror hangs on the wall beside a wooden console table, which holds decorative items. A potted plant stands beside the table, adding a touch of greenery to the space.

Home in Wiltshire

4.97 out of 5 average rating, 255 reviews

Glebe House, a beautiful country home

Beautiful Countryside Home. A gorgeous place to stay with family & friends. A beautifully proportioned and sunny 4 bedroom house with a stylish design. It has a stunning entrance hall, huge open plan kitchen and a utility room. Two bedrooms have their own ensuite. There is fantastic walking around, lovely pubs and great places nearby to visit including Salisbury, Stonehenge, Longleat Safari park, many historical sites and beaches within the hour. We can offer a hot tub subj to availability.

Guest favorite

A modern house features a unique curved roof, complemented by stone and plaster exterior walls. Large windows allow natural light to flood the interior, while a low stone wall outlines the property. The surrounding area presents a tranquil, residential street.

Home in Ventnor

4.96 out of 5 average rating, 105 reviews

Highlands - sleeps 8 - home from home

Our place is ideally situated in the heart of the Victorian town of Ventnor within walking distance of Ventnor park, the beach, the town centre, Steephill cove and and the Botanical Gardens. Despite this, it is in a quiet location and the house is light and airy with wonderful sea views. It is ideally suited to families with kids of all ages, couples and groups. You'll love the comfy beds, relaxed ambiance, mod cons, ample off-street parking and huge utility room to put all your beach gear.

Superhost

A spacious living and dining area is featured, showcasing a large sectional sofa with numerous cushions. A dining table is set with dishes and a bottle of wine, complemented by a floral centerpiece. Natural light enters through multiple windows, highlighting warm tones and elegant decor.

Guest suite in Ringwood

4.86 out of 5 average rating, 190 reviews

New Forest National Park, Manor House Wing for 9.

Gaddens Manor House Wing , 4 bedrooms 4 Bathrooms is the Whole West Wing of a 1920’s Arts and Craft Period House refurbished with modern facilities. The house is set in the New Forest National Park, with an amazing forest and garden location. The grounds, paddocks and woodland extend to 20 acres with great views from every room . The 4 bed-roomed , 4 Bath-roomed guesthouse wing, with its own entrance gates and front door, is the ideal location for your family and friends. Jayne & Chris

Superhost

A spacious bedroom is highlighted by a large, padded headboard and a patterned wall featuring yellow birds and foliage. Soft yellow curtains frame the window, and two bedside tables with lamps provide ample lighting. A plush white bed is styled with a neatly folded grey blanket.

Apartment in Freshwater

4.83 out of 5 average rating, 160 reviews

A very large homely seaside self catering flat.

Very close to the sheltered beach with beautiful sunsets, great views and lovely scenery. You’ll love our house because of the homely family atmosphere. We like to make your stay in our home feel like your home. We have a self catering flat with three bedrooms that can cater for up to 5 or a couple with up to three children plus a baby. We are situated near to bus routes and one of the ferry routes. The island is great for beaches, walking and mountain biking with numerous attractions.

Superhost

A cozy sitting area features soft blue carpets and a patterned area rug. A compact gray cabinet and a black armchair are visible, along with a wall adorned with various framed images. A television is mounted on the wall, contributing to the room's functionality.

Apartment in Poole

4.72 out of 5 average rating, 315 reviews

Sea-cret Summers-2 bed, sleeps six, great location

Property is seaside/beach theme, refurbishing and updating when no guests are booked, new king size bed, new sitting room and bedroom carpets. Stair basket for shoes at entrance. (semi detached so please respect neighbours) Warm welcome to families with children, get away for couples or retreat for someone on business, travel or work. Breakfast not provided but there are local shops and supermarkets close by and kitchen provided. Parking and own entrance. Please read house manual.

Superhost

The exterior of a charming thatched cottage is visible, featuring a distinctive roof, white walls, and dark wooden windows. A well-maintained garden with green bushes and flower accents enhances the entrance, while clear blue skies form a backdrop.

Cottage in Hampshire

4.85 out of 5 average rating, 163 reviews

New Forest cottage. Very close to Paulton’s Park.

Our delightful cottage provides the best of old world charm and modern convenience. It is a pretty 17th Century thatched cottage in a small village, furnished to a high standard with a lovely mature garden. We have a well equipped kitchen and cater for young children with 2 high chairs, travel cots & toys. Located in the New Forest National Park and not far to the coast, Paultons Park & other attractions. My place is good for couples, families with children and small groups.

Top guest favorite

The bedroom is furnished with two twin beds, dressed in nautical-themed linens. A wardrobe and bedside table are positioned beside each bed. A doorway leads to an adjoining bathroom, while natural light from the overhead light fixture brightens the space.

Apartment in Bournemouth

4.97 out of 5 average rating, 338 reviews

** Spotless** Beach House Apartment

Our spotlessly clean, fully equipped family apartment is situated just 8 minutes walk (approx 600 metres) from the beautiful beaches of Southbourne, Bournemouth. The local amenities are only a stone's throw away, which include coffee shops, conveniences stores, eateries and gift shops. There are regular buses to Bournemouth town centre. We welcome people of all backgrounds and our property is particularly suitable for families or couples wanting a quiet get-away by the sea.

Guest favorite

Home in Birdham

4.96 out of 5 average rating, 200 reviews

Beautiful Harbour Village House

Cornerstones is a large bright family holiday home with a south facing garden. A perfect location for boating, walking, beach activities and cycling. Convenient for Chichester, Goodwood and within walking distance of some lovely pubs and cafes. There are some beautiful walks from the house which include harbour footpaths. Local maps in the house. The log cabin is a great place for teens. Weekend bookings must include both Friday and Saturday.

Guest favorite

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.

Home in Hamworthy Poole

4.97 out of 5 average rating, 380 reviews

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

This spacious contemporary property in Poole Dorset has everything your family and friends need for a great stay,sleeps 12 people, great location for towns and sight seeing, beach and park across the road, over 200 5 Star reviews. EV Charger payable separately 0.70 per Kw. Kayaks and bikes included. Optional Hot Tub and Sauna, prices on request. Definitely not a party house, Strict quiet policy after 10pm, only Families allowed.

Top guest favorite

An open-plan living area is featured, showcasing a leather sofa and a contemporary rug. A dining table with two chairs sits next to a kitchenette adorned with modern appliances and exposed brick walls. Colorful wall art adds vibrancy to the space, illuminated by overhead lights.

Guesthouse in Fontwell

4.96 out of 5 average rating, 110 reviews

The Tack Room

The Tack Room - stylish self contained annexe with open plan living and kitchen, shower room with separate bedroom and secure parking within a gated driveway. Located 6 miles east of Chichester and Goodwood - easy access to both; close to Arundel, the South Downs National Park and perfectly situated to explore the beautiful countryside and beaches of the south coast. Fontwell racecourse is within easy walking distance.

Guest favorite

A contemporary living area is presented with a large grey sectional sofa featuring patterned cushions. A sleek television is positioned on a white media unit against a dark brick accent wall. Natural light flows through expansive windows, enhancing the airy feel of the space.

Home in East Wittering

4.94 out of 5 average rating, 210 reviews

Luxury family Witterings beach house with hot tub

Beautifully renovated, luxury accommodation just two minutes from the beach. The cafes and shops in East Wittering village are a short walk away, while the beautiful, sandy beach at West Wittering is a five minute drive / cycle or fabulous half hour walk. With large open plan living, a family friendly garden and an indulgent hot tub, the house is a perfect location for a large family / two family or friends get away.