Vacation rentals with a pool 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!

4.95 out of 5 average rating, 149 reviews

An aerial view captures the villa's spacious garden and the inviting pool area, framed by lush greenery. The surrounding landscape features majestic mountains and valleys, creating a serene backdrop. Solar panels on the roof contribute to the sustainable features of the home.

Villa in Franschhoek

VillaFortyTwo - quiet & spacious. Sleeps 4-10.

This hidden gem is situated in the centre of Franschhoek within walking distance of shops, market, galleries and superb restaurants. It's the ideal place to escape to, year-round, with family and friends. This lovely and very spacious solar-powered family home offers a large garden with magnificent views from the veranda, a 15m pool at the Poolhouse and enough fireplaces🔥🔥to keep you warm in winter. For outdoor sports & nature lovers, our "backyard" has abundant trails for hiking and cycling.

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

4.89 out of 5 average rating, 100 reviews

A spacious living area is characterized by large glass walls that provide panoramic views of the ocean. Comfortable seating is arranged around a central table, and natural light brightens the space. Elegant outdoor loungers are visible through the glass, inviting relaxation.

Villa in Camps Bay

360° Design Villa with sunset, whirlpool & privacy

With views for almost 360 degrees, there is a perfect blend of the high life together with tranquility as you move through the home. This stylish and spacious villa is situated high on the slopes of the Table Mountain Nature Reserve with its own garden gate leading straight into the reserve. The en-suite bedrooms are spacious and luxurious. The upper deck and lounge adjoin the kitchen have incredible views of the Twelve Apostles and Camp's Bay, the perfect place for sundowners in the jacuzzi !

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, 176 reviews

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

Nestled in the magnificent Slanghoek Valley. Surrounded by majestic mountains enchanted by peaceful surrounds, you will find Rust Du Stal. The valley offers adventures filled walks, horse riding and mountain bike trails. The valley can be visited throughout the year as each season reveals its own secret beauty. We offer comfortable, fully equipped, self-catering accommodations for your family. With outdoor and enclosed braai areas as well as Wi-Fi access and DSTV

4.82 out of 5 average rating, 159 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, 157 reviews

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.

4.94 out of 5 average rating, 123 reviews

Home in Wolseley

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.

4.92 out of 5 average rating, 120 reviews

The exterior of a chic coastal home is illuminated by dusk, showcasing a private pool reflecting the evening sky. The open-plan living area features large doors that connect to a spacious wooden deck, ideal for dining and relaxation, surrounded by tropical vegetation.

Home in Clifton

Bungalow 21 - Clifton 3rd by Steadfast Collection

Bungalow 21 feels like a hidden gem amongst Cape Town’s most prestigious coastline. Nestled above Clifton 3rd beach, the bungalow offers sweeping ocean views while you listen to the waves tumble in the bay. Within easy walking distance or a short drive to nearby shops, restaurants and bars, yet secluded enough to unwind to in peace, with its private swimming pool, which is a rare find within Clifton’s prestigious bungalows.

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

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.]

4.97 out of 5 average rating, 106 reviews

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

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, 110 reviews

Popular amenities for Drakenstein rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A rustic wooden table is set outdoors, featuring a loaf of bread, a selection of olives, and two glasses of white wine. A scenic backdrop of lush greenery and mountains is visible, creating an inviting atmosphere for outdoor dining.

5.0 out of 5 average rating, 122 reviews

Magnificent views / luxurious setting- Sérendipité

An open-plan living area features wooden beams and brick walls, with a spacious dining table surrounded by upholstered chairs. Natural light floods the space through large windows, highlighting the relaxed atmosphere. A staircase leads to a loft area, and a view of the pool can be seen outside.

4.92 out of 5 average rating, 156 reviews

Nooks Pied-a-Terre | Architecturally Stunning Home

A modern two-story house is showcased with a sunny blue sky overhead. Solar panels are installed on the roof, while landscaped gardens with various plants and greenery surround the property. A pathway leads up to the entrance, framed by neatly trimmed bushes.

4.96 out of 5 average rating, 141 reviews

Akademie House - your home from home

A modern white house is seen from the street, featuring multiple windows and a covered entrance. Lush greenery is visible alongside the property, while a mountain range with soft clouds is observed in the background, enhancing the serene setting.

4.93 out of 5 average rating, 214 reviews

The heart of Franschhoek

Home in Prince Alfred Hamlet

A scenic dirt road leads towards majestic mountains, framed by greenery. A group of children, accompanied by an adult, can be seen walking together down the path. The sky is partly cloudy, adding a touch of brightness to the landscape.

Spacious Elandsrivier Farmhouse

4.95 out of 5 average rating, 115 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.

4.94 out of 5 average rating, 112 reviews

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

4.89 out of 5 average rating, 111 reviews

Home in Stellenbosch

Bellevlei Estate | The Rock House

4.93 out of 5 average rating, 147 reviews

An expansive self-catering home is set against a mountain backdrop, featuring a well-kept lawn and a swimming pool. The architectural design incorporates natural wood elements, and light spills from large windows, indicating a bright, inviting interior.

Home in Stellenbosch

X Lanzerac - Luxurious 4 bedroom house with solar

Condo rentals with a pool

4.87 out of 5 average rating, 255 reviews

The spacious bedroom features a thatched roof with wooden beams, a large bed dressed in crisp linen, and a decorative throw. Natural light floods the room through large windows, illuminating a small desk and seating area. A cozy rug enhances the warm atmosphere.

Condo in Paarl

Shades of Africa - The Studio

4.92 out of 5 average rating, 182 reviews

A private plunge pool is set within a landscaped garden, surrounded by greenery. The water sparkles under sunlight, and the ocean can be seen in the background, enhancing the serene atmosphere of the space.

Condo in Camps Bay

Camps Bay The View Villa Gdn apt & Pvt Pool

4.83 out of 5 average rating, 123 reviews

Condo in Clifton

Oceanfront Luxury Penthouse - Clifton Sunset Views

Luxe

Condo in Camps Bay

Penthouse w/ Infinity Pool / Bar / BBQ / Balcony

4.89 out of 5 average rating, 132 reviews

4.91 out of 5 average rating, 167 reviews

Two cozy armchairs face a scenic view of the ocean at sunset. A small round table is positioned between the chairs on a textured rug, creating an inviting space for relaxation. The open door reveals a stunning coastal backdrop, enhancing the ambiance.

Condo in Lagoon Beach

Parker’s Park Lagoon

Condo in Cape Town City Centre

A modern living area features large glass windows providing expansive views of the surrounding landscape. A comfortable sofa adorned with cushions faces a sleek coffee table, while a decorative plant adds a touch of greenery. A flat-screen TV is mounted on a light wood console.

Perfect Views Of Table Mountain and Atlantic Ocean

4.93 out of 5 average rating, 254 reviews

4.91 out of 5 average rating, 149 reviews

A cozy lounge area is showcased with two gray sofas positioned around a wooden coffee table. Large glass windows provide an unobstructed view of the ocean, with the sun setting on the horizon. A small potted plant is placed on the table, complementing the serene atmosphere.

Condo in Lagoon Beach

Spectacular Beachfront Apartment

Condo in Cape Town City Centre

Signature Home @ Waterfront Canals

4.96 out of 5 average rating, 104 reviews

Home rentals with a private pool

Luxe

An Eco pool is set amidst a lush landscape, featuring a wooden deck with a pergola overhead. The water reflects the blue sky and surrounding greenery, creating a serene environment. Natural stone accents are visible along the pool's edges, enhancing the tranquil setting.

Villa in Oranjezicht

Solar-Powered Mountain Retreat with Natural Pool

4.92 out of 5 average rating, 183 reviews

Luxe

A bright bedroom features a spacious bed with neutral linens, complemented by decorative pillows. Floor-to-ceiling glass doors offer expansive views of the ocean, while sunlight streams in, radiating warmth. A small glass table is positioned to enhance the serene seaside ambiance.

Villa in Clifton

Opulent Clifton Beach House with Uninterrupted Sea Views.

4.97 out of 5 average rating, 198 reviews

Apartment in Tamboerskloof

An expansive terrace features a private splash pool with a wooden deck, overlooking stunning views of the mountains and cityscape. Floor-to-ceiling sliding doors connect the terrace to the modern interior, allowing for seamless outdoor access from the en-suite bedroom area.

Hillside Penthouse with Spectacular Table Mountain Views

4.99 out of 5 average rating, 335 reviews

4.95 out of 5 average rating, 109 reviews

A sunlit terrace features a wooden lounge chair with light fabric cushioning, positioned beside a small table. A bottle of champagne and two fluted glasses are placed on the table, with the ocean and palm trees visible in the background.

Home in Camps Bay

Villa Claybrook - Camps Bay

4.96 out of 5 average rating, 146 reviews

The backyard features a private salt-water pool surrounded by a stone terrace. Two sun loungers and a large umbrella provide shaded seating. Lush greenery frames the pool area, enhancing the tranquil setting beneath bright blue skies.

Home in Table Mountain

Table Mountain Home with Ocean View

4.96 out of 5 average rating, 182 reviews

A serene pool area is surrounded by lush greenery and tropical plants, offering a peaceful environment. The clear blue water of the pool reflects the surrounding foliage, while distinct seating areas are positioned along the pathway, providing inviting spaces for relaxation.

Villa in Green Point

Contemporary Farmhouse with Garden and Pool

4.95 out of 5 average rating, 134 reviews

The exterior of the bungalow features a solar-paneled roof, an infinity pool, and a spacious yard adorned with grass. Sun loungers and umbrellas are arranged by the pool, while a dining area is visible in the background, complemented by panoramic mountain views.

Bungalow in Clifton

Clifton Sunset - Superhost & Guest Favorite