Holiday home rentals in Cape Winelands District Municipality

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Cape Winelands District Municipality

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top guest favourite
A tranquil seascape is captured during sunset, with vibrant orange and yellow hues reflecting on the water. Silhouetted figures stand on the shoreline, creating a serene ambiance as the sun sets behind distant mountains, providing a peaceful backdrop.
Holiday home in Cape Town
4.96 out of 5 average rating, 51 reviews

Prime One-Bed, Stroll to Eateries and Beach!

Elegant One-Bed in Exclusive Paardevlei, Somerset-West, Cape Town. Modern, north-facing apartment with mountain views, private balcony & 24/7 security, just minutes from Strand Beach. Enjoy a private furnished balcony, perfect for morning coffee or evening wine, directly accessible from the bedroom. Thoughtfully designed for both short getaways and extended stays (28+ days welcome), this apartment is an ideal retreat for couples, professionals, or anyone seeking refined coastal living.

Top guest favourite
Holiday home in Cape Town
4.93 out of 5 average rating, 68 reviews

The Glen Cottage

Come relax and explore the beautiful winelands from The Glen Cottage, tucked away in a secluded blue gum tree glen at the foot of the Helderberg with stunning views towards Gordons Bay. Enjoy the tranquility of The Glen Cottage with your own separate entrance, secure parking, private entertainment / barbecue patio and fully equipped cottage. PLEASE NOTE: The cottage is on one level, but an outdoor staircase with 14 steps will lead you from the parking area to the cottage (see photos).

Holiday home in Stellenbosch
4.58 out of 5 average rating, 36 reviews

Old School Apartment

Home away from home, the Old School can sleep the whole family (up to 8 people). It has 2 separate bedrooms with double beds, 2 single beds and a bunk bed for the kids. It has a large bathroom, with corner bath and large shower. A fully equipped kitchen. Braai facilities outside. Electric blankets on our beds. Old School also has a very large sun-room for the whole family to enjoy their morning breakfast or lunch. PETS ARE R100 EXTRA. The pool is available from 08h00 to 17h00.

Top guest favourite
Holiday home in Stellenbosch
4.92 out of 5 average rating, 251 reviews

Saffron Place, Stellenbosch

Saffron Place is a spacious 2 bedroom self-catering apartment with an open-plan living area leading to a large patio on the first floor. The family suite with main bedroom shares an open bathroom with a small single bedroom. The 3rd bedroom with double bed and en-suite bathroom is on the other side of the lounge. Location is close to Orthopedic Hospital, shopping centre and schools. Within walking distance to historic Stellenbosch town centre. Modern. Secure. Convenient.

Guest favourite
An outdoor deck area features a wooden dining table paired with matching chairs, inviting seating for relaxation. A bottle of wine and two glasses sit on the table, with an umbrella providing shade. The entrance to the unit is visible, showcasing large glass doors.
Holiday home in Cape Town
4.9 out of 5 average rating, 51 reviews

16 on Gruythof - 1 Bed unit - Helderberg

This is a beautiful spot to spend longer terms stays, although shorter stays are also welcome. The flat is fully equipped with 1 bedroom with a queen bed, 1 full bathroom and a full kitchen. We’ve recently put a big fridge in for those who enjoy having fresh foods on hand. The space also has a small lounge with TV and Netflix as well as a dining area in the kitchen. Outside guests can enjoy the deck for a drink or some sun. Safe parking inside the property.

Superhost
The image showcases a serene beach scene with gentle waves lapping at the shore. A sign identifies the property as Unit B at The Oyster Catcher. The garage's exterior, a cozy bedroom with neatly arranged linens, and a scenic view of the Lourens River with lush greenery are also depicted.
Holiday home in Cape Town
4.63 out of 5 average rating, 16 reviews

OysterCatcherSelfCatering Unit B by the beach

Take it easy at this delightful, unique, and tranquil getaway by the beach! Peaceful, well-equipped, self-catering individual unit with its garage, conveniently located across the road from the beautiful Strand coastline. With its prime location, Oyster Catcher Self-catering is the perfect base for guests that need to work online or longer stays. Explore Cape Town’s attractions or for guests that just want to relax and enjoy beach time!

Top guest favourite
A modern structure is observed amid lush orchard and mountain landscapes. The building, with a flat roof and solar paneling, is surrounded by greenery. A spacious outdoor area is visible, highlighting the natural beauty of the farm setting, with mountains in the distance.
Holiday home in Wolseley
5 out of 5 average rating, 26 reviews

Orchard View

Find yourself surrounded by panoramic orchard and mountain views. Orchard View is purpose built with a luxurious modern feel, featuring all mod cons every perfect getaway requires, nestled in the heart of Platvlei Fruit Farm, just outside of Wolseley, Western Cape. Orchard View offers an off the grid retreat for a few nights break or make it a longer stay getaway to experience farm life. .

Guest favourite
A modern cabin exterior features a spacious deck with several chairs arranged for outdoor seating. A panoramic view of the surrounding landscape and water is visible, with mountains in the distance. The interior space includes a large window where a person is seated, engaging with a device.
Holiday home in Montagu
4.92 out of 5 average rating, 73 reviews

HIDE | MONTAGU - Escape Into Nature

Reconnect with nature at this unforgettable escape. Big stacking doors open up towards the breathtaking views over the Montagu (CBR) Dam on the reserve, which shows off with its abundance of birdlife, most notably African Fish Eagles. It is a perfect luxurious and intimate escape from the busy city life for couples and small families.

Top guest favourite
A modern guesthouse is mirrored in the serene water of a pond, surrounded by green lawns and trees. The structure features a spacious terrace with outdoor seating, inviting relaxation and views of the clear blue sky and distant mountains.
Holiday home in Wolseley
4.98 out of 5 average rating, 152 reviews

Orchard Stay

We offer country living at its best. A self-catering guesthouse nestled between pear orchards, Orchard Stay offers you space and freedom inside and out. Comfort is a priority in this two bedroom farm house with both rooms having en-suite bathrooms and wow factor views of the orchards and Mostertshoek Mountain.

Guest favourite
Holiday home in Heidelberg
4.88 out of 5 average rating, 67 reviews

The Heidelberger Self-catering Guest Suite

The Self-catering apartment for your exclusive use consists of two rooms (4 x 3.5m each), an open plan lounge, dining area, fully-equipped kitchen (5 x 4m) and a bathroom (4 x 2m). The Couples Room contains a queen-size bed and the Family Room contains a double bed and a bunk bed. Sleeps 6 max.

Superhost
A cozy sleeping area is presented with a wooden bed adorned with a striped blanket and an array of decorative pillows. A quilt featuring colorful fan designs is mounted above the bed. Two bedside lamps provide soft illumination, enhancing the tranquil atmosphere.
Holiday home in Heidelberg
4.69 out of 5 average rating, 42 reviews

Stone Cottage - Two bedroom, kitchen and lounge

Stone Cottage offers a relaxing experience on a beautiful rural setting. Enjoy the fresh mountain air and vistas with breath taking views from the comfort of your cottage.

A serene landscape features a calm body of water surrounded by lush green foliage. Towering mountains in the background are capped with snow, contrasting with the greenery. Soft clouds drift across a blue sky, enhancing the tranquil setting.
Holiday home in Worcester

Breathtaking view in a jewel between the Mountains

Come and relax in this peaceful, tranquil environment and enjoy the best views nature and the beautiful valley has to offer.

Popular amenities for holiday home rentals in Cape Winelands District Municipality

Destinations to explore