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Holiday rentals with a pool in Cape Winelands District Municipality

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Top-rated rentals with a pool in Cape Winelands District Municipality

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

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Guest favourite
A stone cottage is set against a dramatic sky, surrounded by rugged rocks and a landscape of rolling hills. The outdoor patio is visible, providing a space for relaxation. Clouds drift lazily, creating a serene atmosphere in the secluded location.
Home in Cape Winelands District Municipality
4.98 out of 5 average rating, 98 reviews

Peace and Quiet Stone Cottages

Rust en Vrede means rest and peace in Afrikaans which describes the experience of staying in these these two stone cottages. They are 20m apart and are ONLY offered as a pair, and have exclusive use of a rock pool. Each cottage has two 3/4 beds, bathroom, kitchenette and patio. The pair of cottages accommodate a MAX of 4 people in TOTAL in a private setting, with expansive views. These new cottages are in the same format as the other four on the farm which have received hundreds of 5* reviews.

Top guest favourite
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.
Home in Franschhoek
4.92 out of 5 average rating, 156 reviews

Nooks Pied-a-Terre | Architecturally Stunning Home

Our stunning home is a 5 min walk into the village and its award winning restaurants, shops and galleries. Black Elephant, Chamonix, Dieu Donne winery's and the famous Winetram are just a short walk away. Nooks is sumptuous, private, cosy, relaxing, full of original art, high ceilings, log fires, beautiful generous spaces and mountain views. Nooks comes alive at night and is great for couples, solo adventurers, who want to be near the soul of this beautiful village. We take up to 4 adults max.

Top guest favourite
A stone cottage is nestled among diverse greenery, surrounded by rolling hills and mountainous terrain. The neutral-toned exterior complements the natural landscape, while a covered porch offers outdoor seating. Sunlight casts soft shadows, highlighting the peaceful and remote setting of this off-grid accommodation.
Cottage in between Barrydale and Ladismith
4.97 out of 5 average rating, 223 reviews

Cottage in private game reserve, Little Karoo

Off grid cottage set in the heart of the Little Karoo within the Touwsberg Nature and Game Reserve. The reserve is well known for it's biodiverse fauna and flora and stunning scenery. Located off Route 62, midway between Barrydale and Ladismith, accessible with an average car/sedan, that has at least 17cm off ground clearance. The Cottage is well equipped, with indoor fireplace, cosy and completely private - the perfect Winter stay. Note: cell/3G reception requires a 2 minute walk; no wifi.

Guest favourite
Large glass doors open to a serene view of a natural pond, framed by soft drapes. A cozy seating area is visible, with a plush sofa adorned with neutral cushions. Outside, a small bistro table and chairs are positioned on the lawn, enhancing the tranquil setting.
Farm stay in Worcester
4.98 out of 5 average rating, 146 reviews

Lily Pond

Lily Pond, is a luxurious guest house just an hour and a half from Cape Town. Lily Pond is set on a natural pond brimming with incredible bird life, creating a serene atmosphere unmatched anywhere else. With no other cottages in sight and located on a picturesque wine farm, it offers a rare blend of privacy and luxury. The indulgent outdoor bath overlooking the pond, combined with the beautiful walking trails, enhances the sense of peace and seclusion, making this retreat truly one of a kind.

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, 324 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.

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, 153 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.

Top guest favourite
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
4.97 out of 5 average rating, 228 reviews

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.

Top guest favourite
A view showcases an inviting indoor dining area with a wooden table and chairs, leading to a cozy living space with a sofa. The space is framed by elegantly arched glass doors, revealing a beautifully designed indoor-outdoor intersection. Decorative tile patterns are visible at the entrance.
Home in Western Cape
4.97 out of 5 average rating, 182 reviews

Dassieshoek - Or Skool

Situated in the mountains of Robertson, this double volume, beautifully restored Old School is a tranquil getaway for the whole family. There is a gorgeous eco pool and plenty of amenities for children. Located next to the Marloth Nature Reserve, the house is at the beginning of the Arangieskop Hiking Trail. Mountain biking, hiking, birding and river and dam access mean that there are plenty of outdoor activities for the whole family.

Guest favourite
Home in Wolseley
4.94 out of 5 average rating, 115 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.

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
4.98 out of 5 average rating, 500 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
An outdoor patio area features comfortable wooden lounge chairs under a shaded pergola. A small swimming pool is visible in the background, surrounded by lush greenery. Potted plants add natural beauty to the space, creating a serene atmosphere for relaxation.
Home in Swellendam
4.91 out of 5 average rating, 513 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.

Top guest favourite
Home in Franschhoek
4.96 out of 5 average rating, 159 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.

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