
Holiday rentals with a pool in Drakenstein
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Drakenstein
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

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.

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.

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.

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.

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.

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.

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.

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

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.]

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!

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
House rentals with a pool

Villa Ondine: Cape Town Beach House

Pebble beach Manor

Bungalow 21 - Clifton 3rd by Steadfast Collection

Sunny 3 Bedroom House with Mountain Views

The heart of Franschhoek

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

Magnificent views / luxurious setting- Sérendipité

Mountain House
Apartment rentals with a pool

Stylish 1Bedroom - Large Balcony & Seaviews & pool

Unique Stay at The Den Stellenbosch
Terrace Suite - own pool, jacuzzi bath, fireplace

Perfect Views Of Table Mountain and Atlantic Ocean

Mountain View Penthouse | Secure 2BR, Views & Pool

Stunning Studio Close To Beach

Breathtaking city and harbour views

Luxury secure V&A Marina apartment; best location!
Home rentals with a private pool

Watch the Sunrise in a Home with a Mountain View

Villa Claybrook - Sun. Sea. Serenity.

Chic Penthouse with Private Pool & Breathtaking Views

Glen Beach Penthouse A on Glen Beach in Camps Bay

Constantia Klein 4 Bedroom Villa on the Vineyards
Contemporary Farmhouse with Garden and Pool

Table Mountain Home with Ocean View
Solar-Powered Mountain Retreat with Natural Pool
When is the best time to visit Drakenstein?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £91 | £87 | £85 | £71 | £72 | £68 | £68 | £68 | £74 | £75 | £75 | £94 |
| Avg. temp | 22°C | 22°C | 21°C | 18°C | 15°C | 13°C | 13°C | 13°C | 15°C | 17°C | 19°C | 21°C |
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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- Rentals with pools Cape Winelands District Municipality
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- Cbd
- Cape Town Stadium
- Fish Hoek Beach
- Bloubergstrand Beach
- V & A Waterfront
- GrandWest Casino and Entertainment World
- Muizenberg Beach
- Glencairn Beach
- Green Point Park
- Boulders Beach
- Long Beach
- Cape Town International Convention Centre
- Clifton 4th
- St James Beach
- Hout Bay Beach
- Stellenbosch University
- District Six Museum
- Babylonstoren
- Noordhoek Beach
- Tyger Waterfront Apartments Deck
- Jonkershoek Nature Reserve
- Big Bay Beach
- Cavalli Estate
- Newlands Forest
- Things to do Drakenstein
- Things to do Cape Winelands District Municipality
- Food and drink Cape Winelands District Municipality
- Things to do Western Cape
- Sports activities Western Cape
- Nature and outdoors Western Cape
- Food and drink Western Cape
- Sightseeing Western Cape
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