Family-friendly holiday rentals in Hillway

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Hillway

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

1 of 1 pages1 / 1
Top Guest favourite
The shepherd's hut is set on a circular patio, featuring a dining table and comfortable chairs under a large parasol. Soft lighting is strung along the patio, and the grassy area leads to stepping stones, creating an inviting outdoor space with views of the surrounding countryside.
Shepherd’s hut in Bembridge
4.99 out of 5 average rating, 104 reviews

The Willow Shepherd's Hut, Isle of Wight

Welcome to The Willow at Hillway Huts, a shepherd's hut located on the outskirts of the village of Bembridge, Isle of Wight. A unique place to stay with views of the surrounding countryside, Bembridge airfield and our chickens. A short walk to Whitecliff Bay, the coastal path, local footpaths, a pub, bus stop and on the Round the Island cycle route. A cosy, comfortable living space with a kitchen, king sized bed, bathroom with large shower and private outside patio to relax and watch the sunset.

Top Guest favourite
A bright corner workspace features a small table with wooden legs and a minimalist design. Two potted plants are displayed on the table alongside stacked books. A comfortable chair is positioned nearby, with a cushioned window seat offering additional seating and natural light streaming in from large windows.
Barn in Wroxall
4.99 out of 5 average rating, 131 reviews

Idyllic, private & unique countryside holiday

Our Granary is a stylish, sustainable barn conversion set in idyllic countryside at the end of a quiet country lane, surrounded by a horseshoe of downs and near wonderful beaches. It truly is a picturesque spot, and all just 3 hours from London. The Granary has just been renovated from two agricultural buildings. With two comfy bedrooms, a large kitchen diner to inspire a great meal, a lounge with a wood burner and a huge window seat in which to gaze out at the garden, courtyard and the pool.

Top Guest favourite
A serene garden pond is surrounded by lush greenery and wildflowers, reflecting clear blue skies. A gazebo can be seen in the distance, complemented by wooden decking and seating that invites relaxation. Tall grasses frame the tranquil waters, creating a peaceful natural retreat.
Cottage in Nettlestone and Seaview
5 out of 5 average rating, 201 reviews

Pussy Mouse Rew, Idyllic Rural Cottage in 6 Acres

This accommodation has been specifically designed for couples looking for a tranquil break where quality and attention to detail are important factors. Ideal for romantic breaks or special occassions, surrounded by open countryside with an abundance of wildlife right outside your door. The quiet yet accessible location is a few minutes drive from various beaches perfect for cycling, walking, nature watching and exploring the IOW. See "Other details" for ferry discounts. EV charging at 40p KWH.

Top Guest favourite
A spacious bedroom is softly illuminated by two elegant lamps beside the bed. Neutral tones are complemented by soft bedding and decorative pillows. A window allows natural light to fill the room, and framed art pieces adorn the walls, enhancing the serene ambiance.
Guest suite in Bembridge
4.98 out of 5 average rating, 117 reviews

The Apple Store - peace and perfect sunsets

Tucked away from the village, neighbouring a historical windmill, The Apple Store is only a short walk to shops, pubs and beautiful beaches, Our quiet cosy annexe is the ideal spot from which to explore the Island. With its warm and intimate ambience, perfect sunsets with a glass in your hand, and enormous luxury bed for a great nights sleep, its a great place for couples to enjoy! ** Having made a booking we are able to refer you to our agent who offers significant ferry discounts **

Superhost
A sitting room is presented with a cozy gray sofa, complemented by a colorful area rug. Natural light filters through two windows, while a small table and an armchair add to the inviting space. Decorative elements include a mirror and potted plants along with wall-mounted features.
Home in Bembridge
4.82 out of 5 average rating, 142 reviews

Unique English Heritage Escape in *Bembridge* IOW

'The Annexe' forms part of the main residence built on the old parade ground of Steyne Wood Battery. The Battery was built on the eastern coastline of the Isle of Wight and became a scheduled monument in 2015, being one of the best surviving Victorian Batteries and, as such, all the bomb proof shelters, ammunition stores, gun positions and defensive structures in the surrounding grounds remain intact. The grounds around the property provide a peaceful escape in beautiful surrounds.

Top Guest favourite
Holiday home in Bembridge
5 out of 5 average rating, 103 reviews

Whitecliff Bay-IoW-Holiday Home-3 beds-parking

Whitecliff Bay Holiday Home- Relax with the whole family at this peaceful place to stay. Lots to do and see on the Isle of Wight. Very near the beach & Bembridge village. Beach, cycling, days out Whitecliff Bay Park Passes can be booked at a very reasonable cost, 3 weeks before travelling during peak season & collected on arrival at Guest Services. Reduced ferry travel is also available, subject to availability, please enquire regarding approximate cost as subject to change.

Guest favourite
A comfortable sitting area features a brown couch adorned with patterned cushions and a soft throw. A side table stands nearby, complemented by a lamp, while light streams in through the window, creating a cozy atmosphere.
Cottage in Bembridge
4.81 out of 5 average rating, 183 reviews

Coastal home ferry discount,family & dog friendly

Award winning cottage in seaside village. Ask about ferry discounts. Sleeps 4 adults and a baby. Your dog is welcome too. Park on the drive -big enough for a large 4x4 & forget the car. Walk to the sea in minutes, enjoy village life & chill. Tested by Tots award winning cottage 2021 voted best in the self catering category. VILLAGE CENTRE COMFY BEDS WIFI SMART TV COT, HIGH CHAIR, BABY BATH CHILD & DOG FRIENDLY SUNNY SECURE GARDEN with paving and astroturf

Top Guest favourite
A corner seating area features a wooden table and two folding chairs, positioned near expansive windows that provide unobstructed views of the sea. Soft natural light floods the space, highlighting the light-colored wood paneling and enhancing the coastal ambiance.
Apartment in Bracklesham Bay
4.95 out of 5 average rating, 190 reviews

Quirky & cool with amazing views to Isle of Wight

Quirky coastal property situated on the beach at Bracklesham Bay. This coastal inspired apartment is light and airy with dramatic sea views across to the Isle of Wight. Close to Chichester harbour and the South Downs and world renowned Goodwood, whether you’re a kite boarder or car enthusiast, this location has it all. Plenty of local restaurants and shops and with great fish and chips on your doorstep, you won’t have to venture far for that seaside experience.

Top Guest favourite
Tiny home in Isle of Wight
4.98 out of 5 average rating, 125 reviews

Luxury TinyHome • HotTub • Garden • Walk to Beach

Award-winning luxury tiny home with a private Jacuzzi® hot tub, just moments from Ryde's sandy beach. Perfect for romantic breaks, coastal walks and relaxed island stays, The Cabana offers your own private garden, underfloor heating, a super-comfy kingsize bed with premium linen, superfast fibre WiFi and Nespresso coffee machine - all within easy walking distance of shops, cafes and the vibrant seafront at Ryde, Isle of Wight. Exclusive ferry discounts included.

Top Guest favourite
The Watch House is viewed from a garden path lined with blooming flowers, leading down to the beach. The white exterior of the cottage is highlighted against a clear blue sky, while the tide is low, revealing a sandy shore.
Home in Lepe
4.98 out of 5 average rating, 146 reviews

Iconic Beach Front Stay | The Watch House, Lepe

A standout seafront landmark on Lepe Beach, The Watch House is a lovingly restored former lifeboat and coastguard station, once used to combat smuggling across the Solent. With original features, a modern kitchen, wood burner, cosy window seat over the water, and views to the Isle of Wight, it’s a guest favourite—“an iconic beachfront stay” and “perfect relaxing getaway.” Pet-friendly with parking for two, perfect for families, couples, or friends.

Top Guest favourite
Outdoor seating is provided on a patio area featuring a glass-top table and four grey chairs. An umbrella offers shade, while decorative bunting hangs above the window, contributing to a welcoming environment. The exterior is painted in soft blue tones.
Chalet in Sandown
4.9 out of 5 average rating, 141 reviews

2 bed chalet near the beach and tiger sanctuary

If you are looking for a tranquil accommodation then Sea La Vie @ Chalet 18 can offer you this. Set out in neutral colour schemes throughout with a touch of nautical thrown in. Tastefully of course. Sleeps four comfortably. The main bedroom has a double bed and the little room of the two has two single beds. There is a washing machine so no need to do all that washing once home!! Bedding and 2 towels are supplied per guest as is 2 tea towels

Guest favourite
A distant view of the chalk cliffs of Culver, situated next to the sparkling blue sea, is framed by rooftops and greenery. The clear sky enhances the scenic landscape, creating a serene atmosphere that reflects the coastal charm of the area.
Apartment in Sandown
4.9 out of 5 average rating, 126 reviews

Spacious apartment close to beach

UP TO 25% OFF RED FUNNEL FERRY TRAVEL FOR NEW BOOKINGS MADE & COMPLETED BY 14 SEPTEMBER 2026. Rosie's Place is a bright and airy 1st floor split level apartment in a quiet area with views of Sandown Bay and within walking distance of the beach and High St. It's well equipped & beautifully presented with its own lovely sunny garden, free wifi and private off road parking.

Popular amenities for Hillway family-friendly rentals