Family-friendly holiday rentals in Observatory

Sunny Victorian cottage in hip neighbourhood

Charming Victorian cottage in the heart of Observatory, one of Cape Town's most characterful suburbs. This peaceful home features two private gardens, large living spaces with high ceilings, fireplaces, and a modern bathroom. A fully equipped kitchen and secure off-street parking add everyday ease. The City Centre is just 10 minutes away, while the walkable neighbourhood is full of independent cafés, restaurants, bars, and shops. A rare blend of period character, comfort, and a true local feel.

Indoor spaces · Kitchen · Walkability

Table Mountain Villa

Set on the slopes of Table Mountain bordering the national park, this spectacular property offers panoramic views of the mountain, forest and city. Guests have a private entrance to mountain trails. A short walk from Kirstenbosch Botanical Gardens. 5-10 min drive to Constantia Wine Estates; Newlands Cricket, Rugby Stadiums; 1 traffic light to the city centre ; 15-20 min to the city's iconic beaches. Comprehensive security; unlimited WIFI, basement parking. A perfect base to explore Cape Town.

Kitchen · Indoor spaces · Access

Cardew Cottage

Cardew Cottage in Little Mowbray is nestled in one of Cape Town's charming southern suburbs, cradled by views of the majestic Table Mountain range. Centrally located, our cottage is a haven for travelers eager to explore all that Cape Town has to offer. With the perfect blend of convenience and serenity, whether you're here for a brief escape or an extended stay, you can rest easy knowing your vehicle is secure in our off-street parking. Welcome to your home away from home in Cape Town.

Kitchen · Indoor spaces · Hospitality

Mowbray. Self-catering, tranquil garden cottage

Welcome to my home! Part of my house is a tranquil apartment, ideal for short and long stays. Perfect for a couple, friends, solo adventurer, business traveller. Comprises Living/Dining Room, Bedroom with full en-suite Bathroom, fully equipped kitchen, opening onto shaded private garden courtyard. Mowbray is very central; minutes away from all freeways; 10 minutes from Cape Town Airport and City Centre. 5 minutes walk to vibey shops, restaurants and bars. Central to several hospitals.

Family · Kitchen · Long stay

cozy garden cottage in Upper Woodstock with pool

We have added a small, cozy guest suite to our family home in upper Woodstock and welcome guests from all over the world. We, that is Kent and Susanne with our daughter Alba (10) and our lovely dog Vivienne Westwood (Vivi). Our approximately 25 square meter cottage is located in our beautiful shared garden with saltwater pool and has its own bathroom and kitchenette. Our guests appreciate the Upper Woodstock location and the garden while having us around for questions. Streetparking

Family · Kitchen · Heating

Charming studio space in leafy suburb

You’ll love the charming décor of this stylish and cosy guest suite which is load shedding free! Your own private space and free secure parking. A king size bed and a day bed converts to two single beds,making it family friendly. We are conveniently located fifteen minutes from the Airport, twenty minutes to most beaches as well as Cape Town city centre.University of Cape Town and Kirstenbosch Botanical Gardens are a ten minute journey. Newlands cricket is five minutes walk .

Indoor spaces · Family · Walkability

Cozy living in a boutique heritage Woodstock home

Modern living in this neat Pinterest style home in upper woodstock. The two cozy bedrooms are bright and have a queen and a double sized bed and workspace areas. The entire space has recently been renovated so expect a beautiful modern bathroom, kitchen and lounge. This entire space is perfect for those who like houses with lots of sunshine and and a ton of greenery. Ideal for a small family travelling or a group of friends looking for a nice, stylish space close to the city.

Kitchen · Family · Hospitality

Quirky Courtyard Studio with Deck

This well-equipped, cottage-style studio opens onto a sheltered courtyard and offers access to a rooftop deck — ideal for relaxing or working outdoors. Set in leafy Rosebank, known for its Victorian homes and views of Table Mountain, the studio is within walking distance of UCT and close to the city centre and attractions. Perfect for short or longer stays, with all essentials included and optional weekly cleaning and laundry services. Pets are welcome if well supervised.

Family · Indoor spaces · Decor

Mountain and Harbour Views - Grand Vue Cottage

The property is situated in Cape Town's Walmer Estate suburb, high up the mountain below Devil's Peak. The views from the property are spectacular, you can see Lion's Head, Signal Hill, Table bay and Cape Town harbour. The property has great decor and furniture for your comfort and it's ideal for families or groups who want to be near the city but also to escape it and relax. Solar panels and battery backup system is fitted to escape electricity outages.

Family · Indoor spaces · Long stay

Charming Rosebank Cottage

Sunny, characterful cottage in a quiet street, with a private leafy courtyard. Walking distance to shops, Rondebosch Common, and public transport. Easy access into the centre of town, as well as the southern and northern suburbs. 20 minute drive to Cape Town International Airport. Close to UCT, Hartleyvale Stadium, Bishops, Rustenberg Girls and Rondebosch Boys. The cats shown in some of the pictures are no longer in the house!

Indoor spaces · Family · Walkability

Spacious city loft with large terrace

PLEASE DO NOT USE INSTANT BOOK- Please send a message first to discuss details of your trip. The apartment is located in Upper Woodstock on the border with Salt River, within walking distance of the lively Roodebloem Road. Woodstock has become Cape Town's design hub and a vibrant and trendy neighbourhood with markets and designer boutiques. The loft has been completely renovated and consists of three levels.

Indoor spaces · Kitchen · Comfort

Paragon LUXE Modern Rooftop Pool

A contemporary, light and airy unit, with lots of natural light, a fully equipped kitchen, uncapped WiFi, and cable television (DSTV/ Smart TV). Stylishly furnished one bedroom, modern apartment. Centrally located, easy access to major transport routes, close to UCT and Groote Schuur Hospital. You have full use of the gym and swimming pool area for the duration of your stay.

Indoor spaces · Kitchen · TV