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 !

4.91 out of 5 average rating, 121 reviews

Villa in Clifton

Private Villa & Heated Pool, Steps Away from Beach

Part of the YOLO Spaces Collection. Clifton is Cape Town’s jewel, no matter how many sunsets you have seen, it’s simply different here. The Private Villa is located near the promenade, in a wind free pocket, in the heart of energetic Clifton. Less than 2 minutes walking distance to the famous 4 Clifton Beaches. It is +/- 5 min drive from restaurants, shopping, entertainment & nightlife; 10 to 15 min drive to city centre; 25 to 30 min to the airport & is central to nearby tourist attractions.

4.87 out of 5 average rating, 317 reviews

A serene outdoor area is showcased with a rim flow pool surrounded by manicured grass and blooming lavender. A large umbrella provides shade over two loungers, while rolling hills and vineyards create a scenic backdrop under a clear blue sky.

Cottage in Franschhoek

Blueberry Hill Cottages - Lavender - Franschhoek

Lavender Cottage is a modern three bedroom self catering cottage with three bedrooms, main ensuite and the other two bedrooms share a full bathroom. There is a fully equipped kitchen with cooker, microwave and Nespresso coffee maker. The cottage has its own private terrace overlooking the large rim flow pool. The pool is situated on it's own large terrace and is shared with Olive cottage. We are ideal for guests who enjoy wine tours, the outdoors, hiking and biking plus horse riding.

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

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

Luxuriously appointed self-catering house near the manor house. Perfect for honeymooners and small families. Large swimming pool and Jacuzzi with splendid mountain and vineyard views. A big warm fireplace for the colder months! We offer, by appointment, complimentary cheese and wine pairings at our own boutique cellar. Please note: We will be discontinuing our breakfast offering as of April 2027. Any bookings made prior to then will still receive breakfast.

4.89 out of 5 average rating, 139 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.

Popular amenities for Drakenstein rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 172 reviews

Newly renovated, dreamy 3 bedroom house with Solar

4.98 out of 5 average rating, 145 reviews

Paloma Villa, Franschhoek | Pool & Fireplace

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

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

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

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

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

4.89 out of 5 average rating, 111 reviews

Home in Stellenbosch

Bellevlei Estate | The Rock House

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

Condo in Cape Town City Centre

Cape Town Calling | Stylish Stay | Rooftop Pool

4.82 out of 5 average rating, 136 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

4.89 out of 5 average rating, 132 reviews

Condo in Camps Bay

Penthouse w/ Infinity Pool / Bar / BBQ / Balcony

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

4.88 out of 5 average rating, 124 reviews

Condo in Camps Bay

Mountain View Penthouse | Secure 2BR, Views & Pool

Home rentals with a private pool

4.92 out of 5 average rating, 183 reviews

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

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

4.97 out of 5 average rating, 198 reviews

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.

4.95 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