Holiday rentals with a pool in Drakenstein

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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 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.
Guest house in Riebeek-Kasteel
4.85 out of 5 average rating, 158 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
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.

Guest favourite
Villa in Clifton
4.9 out of 5 average rating, 112 reviews

Private Villa & Heated Pool, 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.

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 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.

Guest favourite
A wooden cabin is nestled among lush greenery and tall trees, showcasing a welcoming exterior with a covered deck. Large windows reflect the surrounding natural landscape, with the sun casting a warm light on the structure. The adjacent mountains provide a scenic backdrop.
Home in Hout Bay
4.86 out of 5 average rating, 409 reviews

Blackwood Log Cabin

A tranquil and private mountain retreat where water, forest and mountains will re-awaken the soul. Set high on the mountain slopes of Constantia Nek, Blackwood Log Cabin has panoramic views across the lush valley to the mountains beyond. The 2 bedroomed house sleeps 4 with 2 bathrooms. Power outages are being experienced by SA - the oven/stove is gas, the hot water is gas, the internet is solar driven and we have 2 battery lights for guests use.

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
A tranquil outdoor space features a pool with clear water, surrounded by stone tiles. Two sun loungers are positioned near the edge, offering a view of the nearby mountain and bay. Natural light enhances the serene atmosphere, with greenery framing the area.
Villa in Simon's Town
4.84 out of 5 average rating, 209 reviews

180• Sea Views from a Hillside Villa, Solar Power

180 degree fantastic view of False bay Guests have access to all area's of the house If a guest needs any help or information I am there to assist The house is in a quiet, safe, and beautiful area surrounded by beaches. Penguin Beach is five minutes away, and the excellent Lighthouse restaurant in Simonstown is a must-do. Trendy Kalk Bay is a 10-minute drive, and has shops and restaurants. The train is a 10minute walk

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 Wellington
4.97 out of 5 average rating, 106 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
A spacious pool area features a tranquil swimming pool reflecting the surrounding trees. Sun loungers are arranged neatly beside the pool, with an umbrella providing shade. The interior of the cottage is visible through large glass doors, showcasing a modern living space with ample natural light.
Cottage in Koringberg
4.96 out of 5 average rating, 171 reviews

The Red House

The Red House is a charming, rustic cottage nestled in the heart of the small village of Koringberg. Surrounded by wheat farms, this retreat offers the best of countryside living - stargazing, farmland scenery, and the area’s largest swimming pool! Ideal for families or a small group of friends. Our house is not perfect, but we love it to bits, and we hope you'll enjoy it just as much as we do!

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, 501 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.

Popular amenities for Drakenstein rentals with a pool

When is the best time to visit Drakenstein?

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Avg. price£91£87£85£71£72£68£68£68£74£75£75£94
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Quick stats about holiday rentals with a pool in Drakenstein

  • Total holiday rentals

    Explore 790 holiday rentals in Drakenstein

  • Nightly prices starting at

    Drakenstein holiday rentals start at £7 per night before taxes and fees

  • Verified guest reviews

    Over 15,220 verified reviews to help you choose

  • Family-friendly holiday rentals

    350 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wifi availability

    760 of Drakenstein holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi 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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