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Holiday rentals with a pool in Drakenstein

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Drakenstein

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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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, 143 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.
Guesthouse in Riebeek-Kasteel
4.85 out of 5 average rating, 150 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
Home in Franschhoek
4.99 out of 5 average rating, 195 reviews

Mongoose Manor by Steadfast Collection

With the trifecta of privacy, location (on an equestrian estate) and dynamic design, this home ticks all the boxes for an idyllic stay in the winelands. Not only does it feature interiors by a top designer and breathtaking mountain and valley views, but full solar power and a location mere minutes from the town centre (as well as museums, galleries and wine estates) make it both distinguished and convenient. There is even a friendly water mongoose named Tilly who might drop by to visit.  

Guest favourite
A private pool reflects the clear sky, surrounded by a wooden deck and lush greenery. The two-story building is partially visible, featuring large windows that allow natural light. Outdoor seating is arranged under the shade of trees, creating a serene environment.
Guest suite in Courtrai
4.94 out of 5 average rating, 186 reviews

Aloe Suite surrounded by mountains

The Aloe Suite is nestled in the leafy neighbourhood of Courtrai in Southern Paarl. The double story space includes a kitchen, lounge and dining area on the lower level.Upstairs you’ll find a bedroom, en suite bathroom and a balcony overlooking the pool. Guests have a private entrance,patio and barbeque area and shared use of the pool . There is parking on the premises, TV (with netflix ) and Wi-Fi. Laundry can be arranged at a fee. Bed for a minor /child can be arranged on request too

Top Guest favourite
A secluded cottage features a stone base with white columns and a dark metal roof. Vines grow over the front porch, which includes two chairs and small tables. Lush green grass surrounds the entrance, enhancing the natural surroundings of vineyards and mountains.
Cottage in Wellington
4.97 out of 5 average rating, 219 reviews

Vineyard Cottage at Bosman Wines

Secluded cottage surrounded by vineyards and mountains with romantic, farm-style décor, open-plan kitchen, vineyard-covered front and back porch overlooking the beautiful Wellington wine valley. Fresh white linen bedding, private bathroom and a room with a view of the vineyards and the nursery vines. Small splash pool (cold water) in the backyard, private garage for parking, wine cellar on the farm, we include a complimentary wine tasting. Home to world renowned mountain bike trails.

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, 133 reviews

Heidi's Child, 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.

Guest favourite
A charming private stoep features two rattan chairs positioned beside a small table, inviting relaxation. Natural light filters in from the adjacent large doors, leading into the cottage. Lush greenery and a low garden wall offer a serene view of the surroundings.
Guesthouse in Paarl
4.87 out of 5 average rating, 236 reviews

Pepperpot Cottage in Paarl

Tranquil and serene, Pepperpot Cottage is a hidden gem situated in the historical centre of Paarl. The tiny 22 square meters is stylish and quaint with its own entrance and off street parking for one vehicle. It is completely private and guests are welcome to come and go at leisure. It has all the luxuries to make your stay relaxing and memorable with a lush view from the stoep across the garden, farm style pond and vegetable patch of our work in progress garden.

Top Guest favourite
Apartment in Camps Bay
4.98 out of 5 average rating, 283 reviews

Primaview, Camps Bay, Cape Town

Primaview is situated in beautiful Camps Bay, Cape Town. Offering comfortable accommodation, alongside an inviting pool and surrounded by panoramic views of mountains and sea. Camps Bay is a scenic residential area, close to the city, as well as the famous Clifton Beaches. There are shops and popular restaurants along the Camps Bay Promenade. The Table Mountain Cable Way is a few minutes drive away. Access to nearby hiking trails are within a few minutes walk.

Guest favourite
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
4.86 out of 5 average rating, 234 reviews

Shades of Africa - The Studio

Shades of Africa Guesthouse Paarl is a tranquil Cape Dutch styled house set amongst lush gardens offering a private studio apartment with views of surrounding mountains and famous Paarl Rock. Positioned on the Bergrivier within walking distance from the Paarl arboretum and central Paarl the 3rd oldest city in South Africa. Paarl is rich in culture and heritage offering a large variety of culinary experiences and wine farms to choose from.

Guest favourite
A modern double shipping container home is situated by a calm dam, showcasing large glass windows that reveal the interior. A wooden deck leads to the water, with a small boat ramp visible. Surroundings include dry, rocky terrain and distant mountains.
Home in Wolseley
4.94 out of 5 average rating, 110 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 Milnerton
4.98 out of 5 average rating, 104 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.]

Top Guest favourite
Home in Franschhoek
4.96 out of 5 average rating, 135 reviews

Newly renovated, dreamy 3 bedroom house with Solar

Enjoy a beautiful artistic home full of character and carefully curated interiors. Don’t worry about loadshedding with the solar and inverter system. All rooms have en-suite bathrooms. The main bedroom has a super king bed, the second room has a queen bed and the third room has a 3/4 bed as well as a bunk bed (2 singles) We really love catering to easy-going guests.

Popular amenities for Drakenstein rentals with a pool

When is the best time to visit Drakenstein?

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Avg. price$165 NZD$160 NZD$170 NZD$160 NZD$163 NZD$155 NZD$153 NZD$155 NZD$168 NZD$168 NZD$165 NZD$173 NZD
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Quick stats about holiday rentals with a pool in Drakenstein

  • Total holiday rentals

    Explore 740 holiday rentals in Drakenstein

  • Nightly prices starting at

    Drakenstein holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 14,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    340 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wi-Fi availability

    700 of Drakenstein holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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