
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.

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.
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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.
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SUGARBIRD HOUSE EDENVELDT FARM
I have decided to rent out my personal farm house\ guest house to happy road trippers seeking solitude and a peaceful surrounding. The house is within a valley surrounded by 48 hectares of open land,beautiful mountain (cederberg) backdrops and a river with three natural swimming areas within walking distance of the guest house and the place include a 25m lap pool right in front of the veranda! Oh and plenty of clean breathable air :). There is one full sized bed so its best suited for couples.
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Walk to Wine Dining • Private Pool • Mountain View
VILLAGE CENTRAL | WALKABLE | MOUNTAIN VIEWS | SWIMMING POOL Experience the charm of Franschhoek, the Valley of Dreams, from a beautifully positioned home designed for comfort, style, & effortless village living. Located within easy walking distance of the renowned main street — home to award-winning restaurants, cafés, boutiques, galleries & celebrated wine estates. This elegant escape is set in a private gated complex offering the perfect balance of convenience & picturesque surroundings.
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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.
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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.
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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.
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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.
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Gorgeous Cottage in the ❤️ of Town
This beautiful, renovated heritage cottage sits on one of Franschhoek's most beautiful old lanes, in the heart of everything! Walk one street down to all the wonderful restaurants, wine bars and shops the village has to offer or stay in and cook, the kitchen is fully kitted for it. Sunny, slow, sun-warmed and absolutely lovely. A red door, a leafy courtyard, a plunge pool and a fireplace. It's the little escape you've been dreaming of.
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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.
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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.
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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.
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Popular amenities for Cape Winelands District Municipality rentals with a pool
House rentals with a pool

Nooks Pied-a-Terre | Architecturally Stunning Home
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Contemporary Barn style house
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Spacious Elandsrivier Farmhouse
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Akademie House - your home from home
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Bellevlei Estate | The Rock House
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Exclusive Poolside Cottage in Prime Location
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Magnificent views / luxurious setting- Sérendipité
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Rust du Stal
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Condo rentals with a pool

Shades of Africa - The Studio
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J Spot • Safe & Convenient • Backup Power
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Unique Stay at The Den Stellenbosch
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Villa Verde, farm stay with views for days.
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Avemore Vineyard View
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Serenity Haven - Two Bedroom
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Gemsbok House - Drie Kuilen Nature Reserve
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Thyme Out - Private Apartment
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Other holiday rentals with a pool

Obiekwa Country House
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Off Grid Getaway with Breathtaking Mountain Views
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Country House - Goedemoed Farm
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Potato Patch Self Catering Cottage
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Four Seasons, Franschhoek
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Jonker Suite I - Serene stay on Helshoogte Pass
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Luxury apartment Kandinsky with panoramic views
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SKILPAD FARM HOUSE EDENVELDT FARM CEDERBERG
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