
Holiday rentals with a pool in Drakenstein
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Drakenstein

Total holiday rentals
Explore 760 holiday rentals in Drakenstein

Nightly prices starting at
Drakenstein holiday rentals start at $28 AUD per night before taxes and fees

Verified guest reviews
Over 15,340 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wi-Fi availability
740 of Drakenstein holiday rentals include Wi-Fi 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!
Top-rated rentals with a pool in Drakenstein
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Glen Beach Bungalow Main House
Soak up sea breezes and uninterrupted views on the expansive wooden pool deck attached to this immaculate modern beach house. Relax on the sun loungers to the sound of the waves. Indoors, stretch out in the open-plan living spaces of two lounge areas - open planned to the kitchen and dining room areas. The Main House level of the beach house is equipped with 4 bedrooms and 4 bathrooms. Three bedrooms are on the ocean level and the 4th master bedroom is downstairs. (The Upper Penthouse level is completely separate to the Main House Level) This Beach Villa - this property is situated directly on Glen Beach. (The small enclave nestled between Camps Bay and Clifton Beaches) Paradise at its best. The open plan kitchen, lounge and dining room open out onto a large decked pool area. Your beach gate leads right onto the beach. Uninterrupted sea views. Glen Beach is uniquely situated with only 15 beach homes. We are within walking distance to the local restaurant strip. The Main House section has 4 bedrooms and can sleep 8. Should your party be larger, the upper penthouse can be combined to allow for a maximum of 12 guests. The Main House is completely private, with it's own private pool. The upper penthouse has it's own pool and balconies. The Beach Gate is communal. Sean, Mary-Louise or another member of our family will be there to check you in and make sure that you are comfortable. We are contactable at all times, should there be any questions needing answers to. The home is situated in the famous international landmark that is Camps Bay. The locale’s crystal clear oceans and soft white beaches—which are within walking distance—draw tourists. Indulge at one of the acclaimed restaurants on the strip. If you want to relax and soak up the sun, walking within the Camps Bay area is easy. Should you wish to explore all Cape Towns other beautiful spots, we recommend to hire a car. This is also extremely easy and can be done at the airport, or once you are at the villa. Cape Town also has a reliable bus system call the Myciti bus. Wifi Bath towels Beach Towels Hairdryers - all included. Please note that a breakage deposit of R20 000.00 will need to be signed on arrival. Please make sure that you have a Master or Visa Credit Card available for this. No Debit Cards accepted. Please note that this villa is for Accommodation only and we do not allow Function Venues. Certain times of the year have a minimum stay attached - please inquire and we will be able to advise.
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Olifantskop Cottage - Cosy Farm Stay
Enjoy the best of the Cape Winelands in this cosy 2 bedroom (4 people) farm cottage. Situated between two big dams, the cottage offers beautiful views stretching as far as Table Mountain on a sunny day. We allow catch-and-release Bass fishing and you are welcome to take a stroll around the farm to see the cows and many calves that roams next to the dams. The farm is 75 km from Cape Town International Airport and 6 km outside Wellington - the closest town. We'd love to host you on our farm!
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Magnificent views / luxurious setting- Sérendipité
SOLAR Powered Enjoy breathtaking mountain views from one of the two balconies or curl up next to the indoor fireplace in this spacious open-plan apartment. French doors lead to both balconies that overlook the garden and olive orchard where you can enjoy a barbecue in your own private space. This tastefully furnished with stylish en-suite bathrooms is yours to make home away from home, whilst you enjoy the picturesque winelands and elegant restaurants. Seven minutes walk to the centre of town.
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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.
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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.
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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.
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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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Bellevlei Estate | The Rock House
Welcome to our spacious, independent and stylish 1-bedroom retreat, located on the Blauwklippen road just minutes from Stellenbosch. The Rock House is perfect for taking in the sights of the historical town of Stellenbosch, mountain biking trails or a quick round of golf. Although shops and restaurants are only a five-minute drive away, the area feels peaceful and secluded. Whether you're here for a weekend getaway or a longer stay, the Rock House has all that you need.
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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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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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De Villiers House
Modern, newly renovated and decorated house situated within walking distance to the main road. Great double volume living spaces, generous size pool and fantastic outside living space - perfect for a family holiday. All 3 rooms are ensuite with fresh crisp linen. The modern kitchen is well equipped, open plan and interactive. Great news is we have an inverter for lights and wifi to assist during load shedding.
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Popular amenities for Drakenstein rentals with a pool
House rentals with a pool

The heart of Franschhoek
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Sunny 3 Bedroom House with Mountain Views
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Doran Vineyards Manor House
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Blackwood Log Cabin
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Luxury 2 bed Villa & pool, Sandstone, Franschhoek
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Villa Isidora
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Newly renovated, dreamy 3 bedroom house with Solar
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Berghuis - Mountain Hideaway
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Condo rentals with a pool

Stylish Studio | Aircon, Jacuzzi & Walk to Beach
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Penthouse Bliss with Mountain Views@ The Docklands
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On the Rocks in Bantry Bay
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Penthouse w/ Infinity Pool / Bar / BBQ / Balcony
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Mountain View Penthouse | Secure 2BR, Views & Pool
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Parker’s Park Lagoon
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V&A Marina - Gulmarn 101 - With Power Backup
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Modern luxurious sea view apartment
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Home rentals with a private pool

Modern Contemporary Zen Tree House Sparkling Pool
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Villa Claybrook - Sun. Sea. Serenity.
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Chic Penthouse with Private Pool & Breathtaking Views
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Constantia Klein 4 Bedroom Villa on the Vineyards
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Contemporary Farmhouse with Garden and Pool
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Rooftop Pool | Views | 24h power
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Solar-Powered Mountain Retreat with Natural Pool
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Table Mountain Home with Ocean View
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When is the best time to visit Drakenstein?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $173 AUD | $166 AUD | $164 AUD | $158 AUD | $138 AUD | $138 AUD | $129 AUD | $131 AUD | $142 AUD | $144 AUD | $144 AUD | $179 AUD |
| 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 |
Destinations to explore
- Cape Town Holiday rentals
- Overstrand Local Municipality Holiday rentals
- Stellenbosch Holiday rentals
- Saldanha Bay Local Municipality Holiday rentals
- Greater Plettenberg Bay Holiday rentals
- Franschhoek Holiday rentals
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- Plettenberg Bay Holiday rentals
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- Rentals with a beach view Drakenstein
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- Family-friendly rentals Drakenstein
- Chalet rentals Drakenstein
- Farmstay rentals Drakenstein
- Rentals with pools Cape Winelands District Municipality
- Rentals with pools Western Cape
- Rentals with pools South Africa
- Fish Hoek Beach
- GrandWest Casino and Entertainment World
- Cape Town International Convention Centre
- Boulders Beach
- Green Point Park
- Bloubergstrand Beach
- Glencairn Beach
- Cape Town Stadium
- Cbd
- Stellenbosch University
- Muizenberg Beach
- Hout Bay Beach
- Clifton 4th
- Atlantic Seaboard Community
- St James Beach
- Canal Walk Shopping Centre
- Noordhoek Beach
- District Six Museum
- Jonkershoek Nature Reserve
- Glen Beach
- Cavalli Estate
- Long Beach
- Tyger Waterfront Apartments Deck
- 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
- Food and drink Western Cape
- Sightseeing Western Cape
- Sports activities Western Cape
- Art and culture Western Cape
- Tours Western Cape
- Nature and outdoors Western Cape
- Things to do South Africa
- Art and culture South Africa
- Sports activities South Africa
- Food and drink South Africa
- Sightseeing South Africa
- Nature and outdoors South Africa
- Tours South Africa







