Family-friendly vacation rentals in Drakenstein

4.96 out of 5 average rating, 154 reviews

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

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!

Guesthouse in Riebeek-Kasteel

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.

4.85 out of 5 average rating, 161 reviews

4.87 out of 5 average rating, 130 reviews

A sweeping view of the Hawequa Mountains is visible in the background, characterized by rugged peaks and lush greenery. The well-positioned accommodation features a spacious deck, while the surrounding landscape displays a blend of trees and natural terrain, providing a direct connection to nature.

Apartment in Wellington

Heuwels

Feast your eyes on the stunning mountain scenery and fill your senses with nature's beauty, smells and sounds in a home away from home. The self-catering unit is conveniently located for outdoor enthusiasts as it's surrounded by both mountain biking/hiking routes, wine farms and great local restaurants. An absolute paradise for birdwatchers. Also, an ideal breakaway far enough from city noises yet close enough to popular amenities. The unit also has its own lush green lawn to enjoy a picnic.

4.8 out of 5 average rating, 118 reviews

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

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 :)

Cottage in Cape Winelands District Municipality

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.

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.

4.99 out of 5 average rating, 183 reviews

Cabin in Cape Winelands District Municipality

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.

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.

4.9 out of 5 average rating, 158 reviews

Cabin in Cape Winelands District Municipality

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.

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.

4.76 out of 5 average rating, 238 reviews

5.0 out of 5 average rating, 105 reviews

A warm living area is highlighted by an exposed brick wall and wooden beams. A comfortable brown leather sofa is paired with a green chair, while a coffee table sits over the polished concrete floor. A small television is positioned across from the seating area, with a view of an adjacent bedroom.

Home in Stellenbosch

Farm house on Windon vineyard,Stellenbosch

This beautiful farm house has amazing views of the Stellenbosch mountain ranges .It has a very special indigenous garden and is beautifully decorated and equipped! It includes a full kitchen ,2 beautiful rooms and en suite bathrooms .There is a beautiful patio and braai area .It is a peaceful setting ,with access to walk and enjoy the farm including the zebra and springbuck ! You won’t be sorry you booked this magnificent spot ,you won’t ever want to leave !

4.97 out of 5 average rating, 230 reviews

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

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.

Cottage in Riebeek-Kasteel

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.

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.

4.99 out of 5 average rating, 179 reviews

Farm stay in Cape Winelands District Municipality

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.

Denneboom Shepherd's Cottage

In the early 1800s, Shepherd’s Cottage was the home of the sheepherders who cared for the animals on this land. Lovingly 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 is equipped with an inverter and battery backup for loadshedding.

4.85 out of 5 average rating, 111 reviews

4.81 out of 5 average rating, 361 reviews

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

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!

Popular amenities for Drakenstein family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Farm stay in Stellenbosch

Lakeside cabin with wood fired Hottub

4.98 out of 5 average rating, 307 reviews

Place to stay in Klapmuts SP

A large swimming pool is framed by a well-maintained lawn and garden. The white-walled house features multiple windows, providing views of the surrounding landscape. Sunlight reflects off the water, adding a serene quality to the outdoor space.

Mitre's Edge Pool House

4.89 out of 5 average rating, 140 reviews

4.98 out of 5 average rating, 100 reviews

A wooden cabin interior showcases a spacious bed dressed in crisp white linens, accented with a soft gray throw. Light filters through the windows, illuminating the natural wood paneling and furnishings, including a vintage wardrobe and stylish bedside lamps.

Cabin in Wolseley

Arum Lily Log Cabin

4.96 out of 5 average rating, 111 reviews

A spacious living area features large glass doors that open to a stunning ocean view. The room is furnished with a light-colored sectional sofa and a modern dining table. Art pieces decorate the walls, contributing to a bright, airy atmosphere.

Villa in Camps Bay

Azamara Luxury Villa - Camps Bay

Farm stay in Stellenbosch

A spacious deck features a wood-fired hot tub surrounded by wooden planters, complemented by comfortable outdoor chairs. Lush greenery fills the background, enhancing the tranquil setting. Sunlight illuminates the area, creating a warm atmosphere for relaxation.

Hidden gem in the heart of the winelands..

4.99 out of 5 average rating, 275 reviews

4.83 out of 5 average rating, 166 reviews

A cozy porch is framed by wooden beams, featuring potted plants positioned at regular intervals. The façade is complemented by two wooden doors and large windows, allowing natural light to enhance the inviting atmosphere of the cottage.

Cottage in Wolseley

Hoogwater Cottage

4.91 out of 5 average rating, 102 reviews

A private deck features a wood-fired hot tub, surrounded by wooden fencing and greenery. A view of distant hills and trees is visible beyond the deck, with sunlight filtering through at sunset, creating a tranquil outdoor setting.

Chalet in Wolseley

Steenbok Farm Cottages- Steenbok cottage,hot tub

Villa in Cape Winelands District Municipality

The aerial view reveals a spacious villa surrounded by lush greenery and vineyards, with mountains in the backdrop. A central swimming pool is framed by palm trees, enhancing the inviting outdoor space. Several separate structures can be seen on the property, contributing to a serene environment.

Pool Villa Stellenbosch CapeTown Hot Tub

4.83 out of 5 average rating, 115 reviews

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 271 reviews

Cottage

DeUitzicht Country cottage in winelands

4.78 out of 5 average rating, 138 reviews

A charming white cottage is framed by vibrant greenery, featuring large windows with wooden shutters. Flowering plants add to the natural beauty of the lawn, while a rustic wooden door lends a welcoming touch. A stone fire pit is visible in the yard, enhancing the outdoor experience.

Farm stay in Franschhoek

Orchards View - 4 pax

4.96 out of 5 average rating, 335 reviews

An open-plan living room is furnished with a comfortable couch and decorated with cushions. Large glass doors provide views of the outdoor area, which features a dining set on the stoep. Natural light enhances the airy ambiance, complemented by wooden beams on the ceiling.

Farm stay in Worcester

Vineyard House

Place to stay in Franschhoek

The historical cottage is framed by mature trees and features a welcoming façade. A white fence outlines the property, while a veranda with wooden beams is visible. The entrance is adorned with flower beds, adding a touch of greenery to the exterior.

La Vieille Cure

4.97 out of 5 average rating, 230 reviews

4.95 out of 5 average rating, 163 reviews

The outdoor space features a well-maintained lawn surrounded by lush greenery. In the background, a thatched-roof cottage is visible alongside a shaded gazebo. A jungle gym and slide are present, indicating a child-friendly environment, while a gentle slope leads towards a small pool area.

Home in Durbanville

Mieke's Cottage

4.87 out of 5 average rating, 127 reviews

Home in Franschhoek

Walk to Franschhoek Village • Pool • Mountain View

4.94 out of 5 average rating, 113 reviews

A spacious bedroom features a large bed with soft linens and light blue accents. The room is complemented by built-in cabinetry and a stylish red desk. Natural light filters through two windows, and a decorative chandelier enhances the ceiling's wood texture.

Home in Franschhoek

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

4.97 out of 5 average rating, 261 reviews

A spacious dining area is highlighted by a large wooden table surrounded by white chairs. Unique turquoise pendant lights hang above, drawing attention to a wall featuring nautical artwork. Light-colored wooden stairs lead to the upper levels, enhancing the open feel of the space.

Guesthouse in Camps Bay

Camps Bay Family Beach home with great views.

Family-friendly home rentals with a pool

Guest suite in Wellington

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.

Beautiful country house set in lush garden

4.97 out of 5 average rating, 106 reviews

4.96 out of 5 average rating, 175 reviews

Home in Franschhoek

Newly renovated, dreamy 3 bedroom house with Solar

Farm stay in Stellenbosch

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.

Romantic cottage with a pool AND an open air tub!

4.98 out of 5 average rating, 538 reviews

4.97 out of 5 average rating, 182 reviews

A modern outdoor seating area is visible beside a spacious pool, featuring a large umbrella for shade. The glass-fronted building showcases an inviting kitchen and dining space. Cozy seating arrangements with cushions are positioned around a wooden table, providing a relaxed atmosphere for gatherings.

Cottage in Koringberg

The Red House

Home in Cape Winelands District Municipality

A clear blue pool is framed by stone decking, reflecting the vibrant sky. Scenic mountains rise in the background, creating a serene landscape. Lush greenery lines the area, enhancing the natural beauty of the surroundings.

Rust du Stal

4.82 out of 5 average rating, 159 reviews

4.9 out of 5 average rating, 405 reviews

A scenic view is presented, featuring a vast green lawn framed by a large tree. The distant mountains rise prominently against a clear blue sky, offering a serene backdrop to the property.

Chalet in Franschhoek

La Provence Cottages | Ostrich Cottage

4.75 out of 5 average rating, 128 reviews

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

Little Oak Studio