Holiday rentals in Simon's Town

The Lookout - dream, hide, explore!

Calling all explorers, dreamers and creatives! Come for a quick retreat or stay to write that book. The lookout was built by owner Rob himself over ten years. There is thought and love behind every little detail. The house isn't perfect, there is raw wood, some things aren't finished, the furniture is vintage and may appear worn but if you look past that, you will find that everything there has its own story and that this house is made for the big things: sunrises, ocean dreaming and full-moons

Misty Cliffs Work and Surf

Please inquire for available dates! Enjoy stunning sea views, peaceful nature and a refined yet homely interior. Watch glowing sunsets or whales and dolphins and the romantic mist over the cliffs with the sound of waves as your constant backdrop. Relax by the fireplace in the spacious double‑storey lounge, cook in the fully equipped open‑plan kitchen and work with fast fibre and a “ready‑to‑plug‑in” office setup. Please do read the info about steep stairs to the house + additional points below.

Glencairn Beach Bungalo

Reconnect with nature at this unforgettable escape. Surf and swim at this safe beach or snorkel in the African Kelp forest below the surface. Hike the iconic Elsie's Peak with its incredibly diverse flora and of course the stunning views of False Bay. In winter you can hear the Southern Right whales breathe on a still night or watch in awe as they breach playfully once the calving season is over. A stay at the Glencairn Beach Bungalo will revive your connection to the natural world. Soulfood.

Cape Point Mountain Getaway - Villa

A magnificent historical home surrounded by fynbos, overlooking False Bay with stunning sea views and an imposing mountain backdrop. The villa is located in a nature conservancy. It is completely off the grid: solar energy, water from a mountain stream. This place is for people who want beauty and tranquillity and a getaway experience in a 100% environmentally friendly place right on the urban edge - 8kms from Simonstown. Fully equipped open plan kitchen, exquisite bedrooms and awesome decks.

Apartment with panoramic ocean and mountain views

A minute walk from the beach, this space is ideal for you to recharge and reset. Grab a bit to eat in the picturesque fishing village of Kalk Bay before taking a sunset stroll along the catwalk. With no shortage of activities from a round of golf at the Clovelly Golf Course, spying on the penguins residing at Boulder’s Beach as they go about their business to catching a wave at Muizenberg surfer’s corner. You are perfectly located to take advantage of all the Southern Penisula has to offer.

Perfect holiday location with stunning sea views

Holiday home outside Simonstown on the Cape Peninsula, close to the "penguin beach". Sleeps four in two bedrooms. Open plan kitchen/lounge flows onto a large deck with expansive sea views. Two full bathrooms (main en-suite). Within easy reach of Cape Point Reserve, and the delightful shops & restaurants of Simonstown, Kalk Bay & Muizenberg. Walking distance to swimming spots. Tasteful decor with modern appliances, a smart Google TV and pure cotton linen on the beds. Minimum stay is two nights.

Plumbago Cottage

A beautiful , separate entrance flatlet with magnificent views of the ocean over False Bay. Spacious, light and stylish , with quirky touches to make you feel at home. Situated within walking distance of beautiful beaches .We are a 10 minute walk to the Boulders Beach penguin colony and 20 minutes walk from restaurants and historical sites in Simon's Town .The flatlet is attached to our home yet totally private with own entrance via a pathway flanked by plumbago and views of the mountain.

The Sky Cabin Misty Cliffs

Experience one of the most pristine stretches of the south peninsula coastline from our laidback house.

 

The upstairs offers spectacular ocean views with a big open plan bathroom. Downstairs is the perfect setting for dinners around the dining table leading onto the open plan kitchen. The downstairs double bedrooms share a bathroom and the front bedroom has beautiful sea views. While the downstairs deck is great for sundowners. Situated 45 minutes from Cape Town’s city centre.

Breathtaking Mountain & Ocean views in Simons Town

The Loft is situated in Simons Town on the Cape Peninsula, an area of incredible natural beauty & gateway to the Marine Big 5. This spacious loft apartment offers beautiful light accommodation with folding doors leading onto a large private balcony & spectacular views of False Bay. The loft includes an open plan bedroom area, sitting room, fitted kitchen & separate bathroom. Private entrance & parking & is only 5 minutes walk to Simons Town amenities, harbour & beaches close by.

Endless Views & Privacy

Our studio apartment opens up onto a 40sq meter balcony with a panoramic view of the Hout Bay Valley and the Helderberg mountains beyond. Large sliding doors disappear into the walls creating an unimpeded indoor/outdoor flow while the elevated position protects your privacy. The open plan bathroom faces onto an enclosed secret garden which includes a frame-less glass shower. The unit has a fully equipped kitchenette and is serviced daily except weekends and public holidays.

The Lookout at Froggy Farm

Just a few minutes walk from the beautiful False Bay beaches, The Lookout is a mezzanine level house with breathtaking views sitting in a quiet part of Simon's Town. Next to the iconic Froggy Farm, it is just the place for a relaxing stay away from the crowds. With a dedicated work area and 100mbps fibre, it is also perfect for escaping the city yet remaining connected for a peaceful remote working experience. Ideally suited for couples or families with children.

(1 ) Sun Sea Sleep - Simon's Town, Cape Town

ONLY TWO PEOPLE ALLOWED. Private self-catering apartment with one bedroom and on suite bathroom, open plan lounge, kitchen and dining area. Fridge/freezer, induction stove and microwave oven. Complementary shampoo, body lotion, coffee, tea sugar and biscuits. Own Patio. We are situated in picturesque Simon's town, home of the SA navy, 10 minutes drive from the famous Boulders beach, where the African Penguins swim among bathers in the sheltered beach.