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Holiday rentals with a pool in Overberg District Municipality

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Top-rated rentals with a pool in Overberg District Municipality

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

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Top Guest favourite
A private boma area features a fire pit surrounded by colorful rock formations and shrubs. Two lounge chairs with striped cushions face a small table set with wine glasses, offering a scenic view of the distant mountains under a softly lit sky.
Guest suite in Sir Lowry's Pass
5 out of 5 average rating, 255 reviews

Intaba Studio Tranquil Getaway w/style & character

An ideal escape, our Studio is a private, self-catering garden unit located on the mountainside on a 300 Ha farm , with a pool (shared), & beaches closeby (15 min). Off the Grid - own power supply & fresh spring water extracted high in the mountains. Panoramic views over sea and mountain landscapes , surrounded by fynbos and wild birdlife , close to Capetown (55 km), airport, (40km) shopping amenities (7km) . Unwind after a busy day and relax at your private boma or around the pool.

Top Guest favourite
A serene outdoor area features a swimming pool surrounded by a stone patio. Comfortable seating and a dining table are visible on the shaded terrace, complemented by lush greenery and distant mountains. The building showcases a light-colored facade with large glass doors that enhance the connection with nature.
Home in Franschhoek
4.99 out of 5 average rating, 183 reviews

Mongoose Manor by Steadfast Collection

This is the most perfect ever listing. Privacy, location, quality. FULLY SOLAR POWERED. Completed by a top designer, breathtaking views of the mountains and wine valley, next to Le Lude champagne estate and restaurant, on an equestrian estate. And under 10 minutes walk to the centre of town, 5 minutes to Le Lude or Haute Cabriere estates, the monument, museum etc. There is even a friendly water mongoose named Tilly who will come to visit! NO CHILDREN of any age allowed, including infants.  

Top Guest favourite
The exterior of the cottage features a thatch roof and is surrounded by a lush garden filled with various plants. A pathway winds through the garden, leading to a cozy seating area with cushions. Sunlight brightens the scene, enhancing the tranquil setting.
Bungalow in McGregor
4.96 out of 5 average rating, 191 reviews

Wild Almond "THE COTTAGE"

Wild Almond Cottage is a delightful two-bedroom cottage comprising two bathrooms, a lounge, kitchen, lovely patio and a refreshing plunge pool, guests are welcome to cool off after their travels 5 min walk to restaurants and pubs. McGregor is a working farm village PLEASE NOTE.....The minimum cost per night is ZAR 1140 for 1 or 2 guests The minimum stay is 2 x nights Extra guests are ZAR570 per guest per night Children under the age of 12 years are charged at half price per child

Top Guest favourite
A tree stands prominently in the foreground, with the EcoTreehouse nestled among a vibrant garden of flowers. Morning light streams through, casting a warm glow on the cabin and surrounding landscape, enhancing the serene atmosphere of the natural setting.
Treehouse in Swellendam
4.98 out of 5 average rating, 284 reviews

EcoTreehouse luxury off-grid cabin

Tucked into the lush Hermitage Valley just outside Swellendam, the EcoTreehouse is a peaceful off-grid cabin designed for comfort, simplicity, and connection to nature. It’s perfect for couples, solo travellers, or small families wanting to unplug without compromising on comfort. Wake to mountain views, fall asleep to frog-song, and soak under the stars in your private wood-fired hot tub. Swim, stargaze, wander the trails, or meet the horses — this land invites you to slow down.

Guest favourite
The open-plan lounge and dining area features a central wooden table surrounded by classic chairs. A cozy seating arrangement with woven chairs sits beside a rustic broom. Light enters through windowpanes, illuminating the clay-tiled floor and highlighting the textural elements of the thatched-roof interior.
Cottage in Greyton
4.86 out of 5 average rating, 260 reviews

Potato Patch Self Catering Cottage

This versatile thatched roofed cottage is centrally located in a private setting offering contemporary country comfort with a dash of history. It is one of the two cottages located on the owners property with its own entrance and secluded garden. The cottage consists of 3 en suite bedrooms furnished with king sized beds. The rates are based on 2 people sharing a room. Using additional rooms comes with an additional charge. Pets are permitted on request at an additional charge.

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, 109 reviews

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.

Guest favourite
A grassy area is populated with trees and a variety of plants, showcasing a peaceful rural landscape. In the foreground, a dog is seen exploring, while a flock of sheep grazes peacefully in a fenced section. The backdrop features majestic mountains under a clear blue sky.
Home in Western Cape
4.88 out of 5 average rating, 293 reviews

Tranquil poolhouse in the Winelands

Relax, sip on local wines, and take in the spectacular mountain views from the poolside deck. Neighbor to award winning wine farms, situated in the pristine Banhoek Valley. 8 minutes drive to central Stellenbosch, 25 minutes to Franschhoek. Complimentary Tokara wine on arrival with cheese, local nuts and fruits. Basic breakfast supplies provided: coffee, milk, eggs, bread, yogurt, muesli, rusks, orange juice. Bathroom: Soap, shower gel, shampoo, body lotion provided.

Guest favourite
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
4.96 out of 5 average rating, 289 reviews

Vineyard House

30km outside Worcester (towards Villiersdorp) The perfect romantic getaway in beautiful and tranquil surroundings. Vineyard House is surrounded by a 360° view of vineyards and mountains. We offer a modern, private stay just outside Worcester, approximately 1½ hours drive from Cape Town. Vineyard House offer a 2 bedroom house (sleeps 4), a bathroom, fully furnished kitchen, livingroom with a fire place and a stoep looking onto the vineyards.

Guest favourite
The beautifully structured building features two attached suites with large windows and sliding doors. Each suite is highlighted by an outdoor balcony, providing views of the surrounding landscape. Steps lead to the entrance, complemented by natural stone walls and a terraced garden.
Loft in Franschhoek
4.91 out of 5 average rating, 266 reviews

La Roche Estate Pinot Noir Suite 1.

Nestled in the tranquil Robertsvlei valley in Franschhoek lies our luxury vineyard suites with picturesque views of La Roche Estate, Robertsvlei road. 5km away from the centre of Franschhoek and surrounded by many mountain biking/ hiking trails, as well as wine farms . Each suite has their own private wood fired hot tub, fireplace and a welcome basket with bubbly for you to enjoy in this tranquil setting.

Superhost
A modern architect-designed house features large glass doors and a sloped roof. Wooden decks extend into the surrounding greenery, providing a connection to the outdoors. Comfortable seating is visible, enhancing the spacious interior that invites natural light.
Cottage in Suurbraak
4.89 out of 5 average rating, 500 reviews

Wild, off-the-grid, style & comfort solar-powered.

When we first opened our spot we were truly over the hills and far away... now the village has grown around us a bit, but the place can still feel pretty secluded. The architect-designed house mixes inside/outside space with plenty of room for family.. Explore wetland, river and the Langeberg mountains. With plenty of comforts this spot is paradise for children, dogs and a retreat for adults.

Top Guest favourite
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.
Farm stay in Stellenbosch
4.97 out of 5 average rating, 431 reviews

Romantic cottage with a pool AND an open air tub!

RiverStone Cottage lies at the foot of the majestic Simonsberg mountain with panoramic views in all directions. Whether you are relaxing under vast oaks or at the plunge pool and watching the sunset turn the mountains pink or are an early bird and watching the sun rise behind cheeky, pointed Botmanskop, there are moments aplenty to ooh and aah at the majesty that surrounds this very special place.

Top Guest favourite
Home in Swellendam
4.91 out of 5 average rating, 461 reviews

Exclusive Poolside Cottage in Prime Location

The best location in town with complete privacy. Our charming cottage combines timeless character with modern comforts, featuring luxury bedding, a cozy fireplace, and backup power. Outside, enjoy a secluded garden oasis with a sparkling pool and spacious patio — perfect for couples seeking exclusivity or families wanting a private retreat just steps from cafés and shops.

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