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Family-friendly holiday rentals in Drakenstein

Find and book unique family-friendly homes on Airbnb

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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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, 158 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.

Top guest favourite
A spacious outdoor deck features a wooden seating area with plush cushions, overlooking the ocean waves. A small round table holds potted plants, and the backdrop consists of rugged cliffs under a clear blue sky, creating a serene coastal environment.
Home in Misty Cliffs
4.99 out of 5 average rating, 167 reviews

Seaside Mountain Retreat in Misty Cliffs w/ Sauna

Seaside mountain retreat in exclusive Misty Cliffs nature reserve with endless views, pool and large fynbos garden with private path down to the beach. This architect designed wooden bungalow is perfect for exploring Cape Point and the Southern Peninsula or just switching off and relaxing in the verdant immersion of a conservation village. Featuring 2 large en-suite bedrooms as well as a cosy loft and additional bunkbeds for the kids. The house is just 45 minutes from Cape Town city centre.

Top guest favourite
The modern wood and glass home is set against a backdrop of cloudy blue skies. Large glass doors allow light into the living spaces, while the beachfront deck features outdoor seating and a dining area. Lush coastal vegetation surrounds the property.
Villa in Cape Town
4.99 out of 5 average rating, 180 reviews

Watersmeet On the beach at Klein Slangkop, Kommetjie

Modern wood and glass home with solar-heated pool on the beach in Klein Slangkop private security estate. Step from the front deck onto beautiful beach sand and direct access to some of the most pristine beaches in the Cape. Breathtaking views. Great surfing. Nature. Stunning sunsets. Situated on the west coast of the Peninsular 50 minutes to Cape Town City Center one way and 25 mins to Cape Point gate the other way. Noordhoek beach is to the right and Long Beach to the left of the house.

Top guest favourite
A rustic exterior view of a cottage features large wooden sliding doors surrounded by vibrant greenery. A stone path leads to the entrance, with well-maintained flower beds flanking the sides, complemented by a modern roof and solar panels overhead.
Cottage in Cape Winelands District Municipality
4.99 out of 5 average rating, 156 reviews

Heidi's Barn, Franschhoek

Situated on a small holding 5km outside Franschhoek, opposite the exquisite La Motte Wine Estate, Heidi’s Barn offers the perfect self-catering base from which to explore the Winelands. A fire pit, outdoor dining area and a large swimming pool (shared with one other cottage) are perfect for summertime relaxation while an indoor wood-burning fireplace and wooden floors throughout make for a cosy winter escape. The barn runs on mains power with solar back up for load shedding.

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, 228 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
Home in Wolseley
4.94 out of 5 average rating, 117 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 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, 352 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!

Top guest favourite
The cottage features a modern design with a sturdy grey exterior and a sloped roof. A covered porch with comfortable seating invites relaxation. Lush green grass surrounds the structure, complemented by neatly trimmed bushes. A warm sunset casts a gentle glow over the setting.
Farm stay in Stellenbosch
4.98 out of 5 average rating, 506 reviews

Romantic cottage with a pool AND an open air tub!

RiverStone Cottage lies at the foot of the majestic Simonsberg mountain with panoramic views in all directions. Whether you are relaxing under vast oaks or at the plunge pool and watching the sunset turn the mountains pink or are an early bird and watching the sun rise behind cheeky, pointed Botmanskop, there are moments aplenty to ooh and aah at the majesty that surrounds this very special place.

Guest favourite
The eco cabin is set against a backdrop of mountains, featuring a modern design with large glass panels that provide views of the natural surroundings. A wooden deck extends from the structure, leading towards a landscaped area with lush greenery and scattered rocks.
Cabin in Bain`s Kloof Pass
4.96 out of 5 average rating, 132 reviews

Bainskloof Mountain Eco Retreat - Black Pearl

Welcome to the Black Pearl! Discover a special place that boasts breathtaking mountain views from every room. This beautifully appointed cabin is equipped with all the amenities you could want and is thoughtfully designed to provide all the comforts you need for a rejuvenating getaway. Escape the ordinary and immerse yourself in the serenity of this remarkable destination.

Guest favourite
Home in Bain`s Kloof Pass
4.96 out of 5 average rating, 182 reviews

Magical Bainskloof Pass Getaway at Rocky Falls #1

Rocky Falls Cottage is an off-grid, spacious cottage offering ideal holiday accommodation. It is large enough for a family or group of friends, but it's still cosy enough for a couples getaway. Tucked away in the mountains of Bainskloof, Rocky Falls Cottage is set within a beautiful private nature reserve, offering peace, privacy, and natural surroundings.

Superhost
The cottage exterior features a covered patio with wooden beams, providing shade for relaxation. The plunge pool sits beside lounge chairs. Large windows and wooden shutters adorn the white-walled structure, while expansive green grass surrounds the area, leading to open vistas of the natural landscape.
Farm stay in Paarl
4.85 out of 5 average rating, 123 reviews

Denneboom Stable Cottage

The cottage offers the charm of reed ceilings and wooden shutters, and an authentic farm atmosphere with private swimming pool. The cottage is situated in a private game reserve and surrounded by Eland, Zebra, Wildebeest & Springbok. This cottage is equipped with solar panels, an inverter and batteries to assist with power during loadshedding.

Top guest favourite
A modern guesthouse is mirrored in the serene water of a pond, surrounded by green lawns and trees. The structure features a spacious terrace with outdoor seating, inviting relaxation and views of the clear blue sky and distant mountains.
Holiday home in Wolseley
4.98 out of 5 average rating, 152 reviews

Orchard Stay

We offer country living at its best. A self-catering guesthouse nestled between pear orchards, Orchard Stay offers you space and freedom inside and out. Comfort is a priority in this two bedroom farm house with both rooms having en-suite bathrooms and wow factor views of the orchards and Mostertshoek Mountain.

Popular amenities for Drakenstein family-friendly rentals

When is the best time to visit Drakenstein?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$205 SGD$205 SGD$194 SGD$160 SGD$159 SGD$158 SGD$158 SGD$156 SGD$163 SGD$170 SGD$176 SGD$214 SGD
Avg. temp22°C22°C21°C18°C15°C13°C13°C13°C15°C17°C19°C21°C

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 $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 12,750 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

    270 properties have a dedicated workspace

  • Wifi availability

    550 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!

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