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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

Chic Studio in Cairnside Simonstown with Sea Views

Modern, spacious, self catering apartment on mountain side overlooking False Bay, Glencairn beach and tidal pool. Facing East and enjoying spectacular sunrises over sea and mountain this two person apartment is situated near top rated restaurants, shopping malls, scenic drives and world renown tourists attractions within easy reach. Away from busy city life, this luxurious unit based in Cairnside, Simon's Town is close enough to enjoy peace and tranquility in a modern and secure environment.

180°SeaViews•Big Villa• Beaches•Penguins

Price include Airbnb 15.5% fee. Wake up to sweeping ocean views. Villa perched on hillside in Simon’s Town. Easy, well marked, walks to many penguin colonies, & secret wind free beaches. Chef’s kitchen fully equipped. A big balcony with big BBQ. Indoor built-in BBQ fireplace for heating areas/cooking. Gas heaters in all bedrooms. Back up Inverter & solar geyser if electricity disruption. Stable fiber& mesh system. Smart TV in bedrooms. High quality beds & linen Lots activities to suit all ages

Cape Point Mountain Getaway - Oceanside 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.

3 Bedroom Cottage in the heart of Simon’s Town

A beautiful cottage situated in the heart of historic Simon's Town. Perfect for exploring the Southern Peninsula. Watch the sunrise over False Bay from the balcony. A short walk down the historical Drostdy Steps to Jubilee Square, you will find great restaurants with idyllic views of the yacht basin. Stand-up paddle boarding, kayaking and ferries are available right there. The famous Boulders Beach with its colony of penguins is nearby, as are the beaches. Cape Point is a short drive away.

WhaleDance

Our home is on the Historical Mile with panoramic views, just one block up from the Main Road and near all the cafes and eateries Simon's Town offers. Boulders Beach and the famous penguins are an easy 20 minute walk away and Long Beach is 10 minutes away as is the railway station. This is a high quality accommodation, All three bedrooms are en-suite, with spacious and sound-proofed rooms. A well equipped kitchen with an outside deck with South African 'Braai', pool and seating area.

Modern home with breathtaking ocean views

Nestled in the exclusive area of Cairnside, this semi-detached house offers the perfect place to enjoy beautiful views of False Bay and is less than 5 mins from the local beach and tidal pool. One of our favourite past times is watching the water activities from the sheltered deck. Whale spotting, kite surfers jumping in the bay, sailing regattas and flocks of birds migrating along the coast. The sun rises across this side of the bay, if you're up early you'll be mesmerised by the view.

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.

Misty Cliffs Work and Surf

Please DM 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 a fully equipped open‑plan kitchen and work with fast fibre and a “ready‑to‑plug‑in” office. Please read the info about steep stairs to the house + additional points below.

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.

Seaview Cottage. Walk to Beach and Penguins

This 3 bedroomed, all ensuite, home is located a short 5 minute walk to Windmill Beach. Windmill Beach was recently voted by as one of the top 10 beaches in Cape Town. You can walk a short distance to see the penguins at Boulders Beach. This home is perfect for those who are looking for tranquility but still centrally located for exploring the South Peninsula. This home perfect for the Cape Town staycationers and loved by local and international travellers.