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Family-friendly holiday rentals in Drakenstein

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Drakenstein

  • Total holiday rentals

    Explore 590 holiday rentals in Drakenstein

  • Nightly prices starting at

    Drakenstein holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 13,330 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    350 properties feature pools

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

  • Wifi availability

    560 of Drakenstein holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Drakenstein rentals

  • 4.8 Average rating

    Drakenstein stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated family-friendly rentals in Drakenstein

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

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Top guest favourite
A charming white cottage is set against a clear blue sky, surrounded by greenery. Wooden windows and a pergola enhance the rustic design. A fence encloses the property, providing an inviting space for outdoor enjoyment.
Cottage in Wellington
4.96 out of 5 average rating, 154 reviews

Olifantskop Cottage - Cosy Farm Stay

Enjoy the best of the Cape Winelands in this cosy 2 bedroom (4 people) farm cottage. Situated between two big dams, the cottage offers beautiful views stretching as far as Table Mountain on a sunny day. We allow catch-and-release Bass fishing and you are welcome to take a stroll around the farm to see the cows and many calves that roams next to the dams. The farm is 75 km from Cape Town International Airport and 6 km outside Wellington - the closest town. We'd love to host you on our farm!

Guest favourite
A scenic view showcases Obiekwa Country House surrounded by a well-established indigenous garden. The property features a covered patio and swimming pool, with mountains providing a tranquil backdrop. The image captures the serene rural setting and proximity to vineyards.
Guest house in Riebeek-Kasteel
4.85 out of 5 average rating, 160 reviews

Obiekwa Country House

Obiekwa Country House is located in the picturesque, quaint village of Riebeek Kasteel; with its wine estates and gourmet restaurants. It is set in a quiet cul-de-sac and overlooking an adjoining vineyard. Although it is set in peaceful, rural surroundings, It is a fifteen minute walk to the village square. NO LOADSHEDDING A solar energy system is in place. Please note that advertised prices are for 2 persons sharing a bedroom. If 2 guests would like 2 bedrooms, please book for 3 people.

Superhost
Aerial view of a white house set amidst lush vineyards, surrounded by tall cypress trees. The landscape features distant mountains illuminated by soft sunlight, with rows of grapevines stretching across the foreground.
Home in Tulbagh
4.8 out of 5 average rating, 115 reviews

Huckleberry House

Huckleberry House is tucked away against the Witzenberg Mountains in the beautiful Tulbagh valley. It is surrounded by a vineyard, old Oaks and Wild Olive trees in a beautiful shady garden. The house is very spacious, newly renovated in a unique and tasteful style and is the perfect place to make special memories for family and friends. Each bedroom theme is influenced by a country (Bali, India and Japan) and there is a Kolkol hot-tub on the covered veranda. Furry friends are welcome :)

Superhost
A winding river flows through a rocky landscape, bordered by grass and low shrubbery. Rolling hills rise in the background, partially covered by clouds. Lush green plants are visible on both riverbanks, contributing to the natural serenity of the environment.
Cabin in Cape Winelands District Municipality
4.9 out of 5 average rating, 157 reviews

Bains Kloof log cabin on the riverbank #BainsBosch

#Bainsbosch A spacious tranquil rustic cabin on the banks of the Wit River at the base of Bains Kloof Pass. The cabin is surrounded by 2 hectares of fynbos and the Limietberg mountains. There is a full kitchen and 3 bedrooms. Mount Bain is a protected nature reserve . The Wit River flows down Bains Kloof. Guests can swim in pristine mountain water, hike into the surrounding mountains or visit several Wine estates nearby.". Backup power is provided for loadshedding.

Superhost
A panoramic view of the landscape reveals rolling hills and vineyards bathed in soft golden light at sunset. A solitary cabin is positioned on a hillside, framed by rugged rocks and greenery, with mountains rising in the background.
Cabin in Cape Winelands District Municipality
4.76 out of 5 average rating, 237 reviews

The Moongazing Cabin @ 9 Mount Bain

The Moongazing Cabin is a tranquil timber mountain cabin located on the 660ha Mount Bain Private Nature Reserve in the Bain's Kloof Valley overlooking the Waaihoek and Witzenberg Mountain Ranges. The area provides excellent choices for hiking, swimming, kloofing, birding, driving, wine tasting, seeing snow in winter or just relaxing. The cottage is equipped with gas stove, fridge and hot water and has a solar panel installation for charging electronic devices.

Top guest favourite
A quaint cottage is enveloped by lush vines, with a welcoming front porch featuring two chairs. The roof is made of metal, and wooden doors and windows complement the natural surroundings. Soft light accents the stone pathway leading to the entrance.
Cottage in Wellington
4.97 out of 5 average rating, 229 reviews

Vineyard Cottage at Bosman Wines

A serene, beautifully styled cottage with layered textures, soft neutral tones, and thoughtful finishes throughout. It features a cosy lounge, a well-appointed kitchen, and a dreamy en-suite bedroom designed for restful comfort. Set on the 8th generation Bosman Family Vineyards, the cottage offers sweeping vineyard views and an authentic sense of countryside living. A scenic 10-minute walk leads to the cellar, where a complimentary tasting awaits.

Guest favourite
A vintage wooden chair is positioned in a well-lit space, adorned with a purple pillow. A sign hanging from the chair's arm reads 'LIVING THE DREAM', adding a touch of character to the setup.
Loft in Riebeek-Kasteel
4.75 out of 5 average rating, 128 reviews

Little Oak Studio

Our little loft suite is nestled in a treelined garden above the garage. The gravel road in front of our property adds to the rural atmosphere guests will experience in the quaint village of Riebeek Kasteel. Our resident pet chickens may just produce a freerange egg for our visitors!! The Theron family are well traveled and love to welcome visitors to our home. We encourage you to engage with us and our animals or just relax among the trees!!

Top guest favourite
The exterior of the garden cottage is surrounded by lush greenery and colorful flowers. A covered entryway leads into the cottage, while two simple chairs are situated in the foreground, inviting relaxation. Smoke gently rises from a small fire pit, suggesting a cozy atmosphere.
Cottage in Riebeek-Kasteel
4.99 out of 5 average rating, 175 reviews

Fever Tree Cottage

Fever Tree Cottage is a secluded one bedroom garden cottage on a private property in Riebeeck Kasteel, a mere 50 meters from the town centre. The main property is on a dirt road, overlooks a farm dam and magnificent mountain views. The cottage is private, quiet and set in a lovely tranquil bird-filled garden. It is so close to town, that you can walk anywhere. Retreat to the quiet garden cottage after a day of shopping, eating and exploring.

Guest favourite
Home in Wolseley
4.94 out of 5 average rating, 123 reviews

Trendy private container home! Riverstone House.

Super trendy, double shipping container conversion. Modern, eco& stylish. Perfectly positioned on the dam for afternoon swims &amazing sunset views! Featuring SMEG gas stove, brass fixtures, and Victorian claw foot bath. 2 bedrooms, both ensuite. One with private outside shower. Enjoy a deep shaded patio with built in Bbq, inside and outside dining and lounge. Super cosy for winter with a wood burning closed combustion stove.

Guest favourite
A serene outdoor space features a sparkling pool surrounded by lush greenery. Sun loungers are positioned beside the water, while trees provide natural shade. The home is visible in the background, blending harmoniously with the tranquil garden setting.
Guest suite in Wellington
4.97 out of 5 average rating, 106 reviews

Beautiful country house set in lush garden

This stylish home located near the Wellington town center, schools, Huguenot College and CPUT, is hosted by Antoinette. It's the ideal spot for professional long stays, parents of students, wedding guests or explorers of the winelands looking for accommodation in the beautiful country town of Wellington, South Africa. [This property do have a back-up power system, therefor guests won't experience any loadshedding.]

Superhost
A cozy farm cottage is set against a backdrop of greenery and distant mountains. Tall cypress trees frame the entrance, while the patio features outdoor seating. The building is characterized by a sloped roof and large windows that invite natural light.
Cottage in Tulbagh
4.81 out of 5 average rating, 358 reviews

Hill Cottage

Nestled against the Witzenberg mountains just 9km outside the charming town of Tulbagh, is a cozy farm cottage called Hill Cottage. The farm offers a peaceful retreat where you can swim in the dam, hike amongst the proteas and enjoy the nature of the Cape. Only 90mins from Cape Town, it makes for the perfect romantic getaway to enjoy the natural beauty of one of the top rated small towns in South Africa!

Superhost
The exterior of Shepherd's Cottage features a charming white facade with rustic wooden shutters. A wooden deck surrounds a private plunge pool, while lounge chairs are positioned nearby. A outdoor dining table is situated to one side, amidst a grassy landscape and tall trees under a partly cloudy sky.
Farm stay in Cape Winelands District Municipality
4.85 out of 5 average rating, 110 reviews

Denneboom Shepherd's Cottage

In the early 1800s, Shepherd’s Cottage was the home of the herders who cared for the animals on this land. Loving restored to modern standards, the Shepherd’s Cottage is now a comfortable luxurious self-catering cottage with a massive indoor fireplace and outside firepit, two en-suite bedrooms, and its very own private plunge pool. The cottage have inverter and battery for loadshedding.

Popular amenities for Drakenstein family-friendly rentals

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