
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.

Feed Your Soul at a Glamorous Villa Set in a Vineyard
Slide back a concertina wall of windows and invite the vineyards and sweeping mountain views inside. Gleaming marble floors lead from one expansive vista to the next. Feature fireplaces, crystal chandeliers, and epic ceilings add to the romance. You are welcome to enjoy a walk or cycle through our 25HA of planted vineyards The entire Villa is reserved for your exclusive use Send a text and we will be on standby for anything you may need Set on a small wine farm just outside Stellenbosch, at the foot of the Cape Fold mountain range, the home is in the heart of South Africa's famous wine country. Take a tasting tour or seek out some of the gastronomic hotspots nearby. It is recommended that you hire a vehicle to get around. However Uber is available in the area Our farm manager lives next door to the property and is available 24/7 should you require anything

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!

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.

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.

Aloe Suite surrounded by mountains
The Aloe Suite is nestled in the leafy neighbourhood of Courtrai in Southern Paarl. The double story space includes a kitchen, lounge and dining area on the lower level.Upstairs you’ll find a bedroom, en suite bathroom and a balcony overlooking the pool. Guests have a private entrance,patio and barbeque area and shared use of the pool . There is parking on the premises, TV (with netflix ) and Wi-Fi. Laundry can be arranged at a fee. Bed for a minor /child can be arranged on request too

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.

Vineyard Cottage at Bosman Wines
Secluded cottage surrounded by vineyards and mountains with romantic, farm-style décor, open-plan kitchen, vineyard-covered front and back porch overlooking the beautiful Wellington wine valley. Fresh white linen bedding, private bathroom and a room with a view of the vineyards and the nursery vines. Small splash pool (cold water) in the backyard, private garage for parking, wine cellar on the farm, we include a complimentary wine tasting. Home to world renowned mountain bike trails.

Heidi's Child, 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.

Primaview, Camps Bay, Cape Town
Primaview is situated in beautiful Camps Bay, Cape Town. Offering comfortable accommodation, alongside an inviting pool and surrounded by panoramic views of mountains and sea. Camps Bay is a scenic residential area, close to the city, as well as the famous Clifton Beaches. There are shops and popular restaurants along the Camps Bay Promenade. The Table Mountain Cable Way is a few minutes drive away. Access to nearby hiking trails are within a few minutes walk.

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.

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.]

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

Pebble beach Manor

X Lanzerac - Luxurious 4 bedroom house with solar

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

Berghuis - Mountain Hideaway

Tockie's: An idyllic & historic 2-bedroom cottage

Newly Renovated Family Home with Plunge Pool

Hilltop House

winelands living - house with sauna and pool
Apartment rentals with a pool

Camps Bay The View Villa Gdn apt & Pvt Pool
Terrace Suite - own pool, jacuzzi bath, fireplace

Mountain View Penthouse

Perfect Views Of Table Mountain and Atlantic Ocean

Modern Ocean View Retreat in Camps Bay

V&A Marina - Gulmarn 101 - With Power Backup

Parker’s Park Lagoon

Skyline Deluxe - 3002 - 16 On Bree
Home rentals with a private pool

Elegant guest wing with own private garden & pool.

Watch the Sunrise in a Home with a Mountain View

Modern Contemporary Zen Tree House Sparkling Pool

Glen Beach Penthouse A on Glen Beach in Camps Bay

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

Upper Constantia Guest House

Chic Boutique-Hotel Feel at a Seafront Pad, Clifton
When is the best time to visit Drakenstein?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £74 | £72 | £76 | £72 | £73 | £69 | £69 | £69 | £75 | £76 | £76 | £95 |
| 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 740 holiday rentals in Drakenstein

Nightly prices starting at
Drakenstein holiday rentals start at £8 per night before taxes and fees

Verified guest reviews
Over 14,000 verified reviews to help you choose

Family-friendly holiday rentals
340 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
700 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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- Bo-Kaap Museum
- Cbd
- Cape Town International Convention Centre
- Atlantic Seaboard Community
- Cape Town Stadium
- Fish Hoek Beach
- Bloubergstrand Beach
- V & A Waterfront
- Muizenberg Beach
- GrandWest Casino and Entertainment World
- Boulders Beach
- Long Beach
- Green Point Park
- Canal Walk Shopping Centre
- Clifton 4th
- St James Beach
- Hout Bay Beach
- Stellenbosch University
- Babylonstoren
- District Six Museum
- Tyger Waterfront Apartments Deck
- Jonkershoek Nature Reserve
- Noordhoek Beach
- Two Oceans Aquarium




