Holiday rentals with a pool in Drakenstein

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!

Location · Family · Comfort

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.

Value · Location · Accuracy

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.

Family · Value · Cleanliness

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 !

Value · Location · Hospitality

Private Villa, Pool, Hot Tub 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.

Value · Location · Accuracy

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.

Location · Value · Air conditioning

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

Family · Location · Layout

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.

Family · Location · Access

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.

Value · Location · Bathroom

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.

Family · Value · Getting around

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.]

Family · Value · Quiet

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.

Value · Family · Biking