Vacation home rentals in Cape Winelands District Municipality

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.

4.95 out of 5 average rating, 43 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.

Vacation home in Robertson

A modern house is depicted alongside a calm pond, reflecting its stylish structure. Large windows and a covered veranda are visible, surrounded by green grass and landscaping. The Langeberg Mountains form a scenic backdrop, enhancing the peaceful rural atmosphere.

4.95 out of 5 average rating, 59 reviews

Gecko Lodge Robertson

Gecko Lodge is a self-catering house with luxury finishes and quality appliances. It offers a lovely pool for those hot summer months. The house caters for up 8 guests (ideally 6 adults & 2 children). A battery backup system has been installed for your convenience, making your stay more comfortable. This Modern & Chick house is waiting to welcome you. Situated in the shadow of the Langeberg Mountains, near the Breede River and the quaint town of Robertson. Not far from Cape Town.

The open-plan living area features a comfortable gray sofa adorned with a decorative pillow. A round dining table with four chairs complements the kitchen, which includes modern appliances. A large landscape photograph hangs on the wall, and a softly lit fixture adds a gentle ambiance.

4.91 out of 5 average rating, 57 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).

Superhost

The exterior of the property features a charming facade with large windows and double doors framed by greenery. A paved pathway leads to the entrance, while outdoor seating is arranged on a neat lawn, enhancing the inviting atmosphere of the cottage.

Vacation home in Stellenbosch

4.61 out of 5 average rating, 33 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.

A queen bed is centered against a decorative floral headboard, adorned with two pillows and a soft throw. Bedside tables with lamps are placed on either side, and light gray curtains frame a window in the background.

Vacation home in Paarl

4.75 out of 5 average rating, 12 reviews

Ons Gim Huisie - Paarl

Enjoy a stylish experience at this central-located apartment. Right next to Paarl Gym with a gate leading onto the sports fields. Tastefully decorated with fine finishes. A super comfortable queen bed & big walk-in shower awaits you after a long day. The open plan living area with kitchen has everything you need to prepare meals or have a braai. There is an extra sofa bed for children, we can accommodate 2 adults and 1 child per booking. Safe parking available under the trees.

Vacation home in Stellenbosch

An open-plan kitchen and living area are visible, featuring a large island with a gas cooktop. Modern black dining chairs surround the island. Natural light floods the space through a large window, showcasing greenery outside. A comfortable seating area can be seen in the background.

4.91 out of 5 average rating, 222 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.

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.

4.9 out of 5 average rating, 49 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.

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.

4.85 out of 5 average rating, 13 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 to explore Cape Town’s attractions or to enjoy beach time! In addition, guests with electric vehicles can make use of our charging station during day time hours.

A cozy dining area features a wooden round table surrounded by four chairs. The space includes a comfortable seating arrangement with a floral-patterned cushion and a tall floor lamp. Natural light is filtered through large windows, creating a warm ambiance.

4.76 out of 5 average rating, 33 reviews

Lovely Kaapgracht, rental unit with free parking.

In the winelands close to the sea of Strand, 20 minutes from student city Stellenbosch, 35 minutes from the international airport Cape town and 45 minutes from Table Mountain . This Unit in a peaceful neighborhood with own entrance and free secured parking for you and last but not least morning sun welcomes you to enjoy a breakfast in yr own garden sitting area next to your room.

4.93 out of 5 average rating, 57 reviews

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.

Vacation home in Montagu

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.

Vacation home in Wolseley

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.

4.98 out of 5 average rating, 138 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.