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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

"Beachfront Bliss: Ocean Views, Serene Getaway"

Welcome to our contemporary beachfront apartment with stunning ocean views. Enjoy a stylish self-catering space, tastefully furnished for your comfort. Step onto the wooden deck and access Glencairn Beach just 15 minutes away. Explore vibrant Kalk Bay for unique dining and shopping. Discover Simons Town's rich history with the Naval Museum and Arts and Crafts stores. Don't miss the famous penguins at Boulders Beach. Staying in then the nearby Harbour Bay Mall offers dine-in or take-away options.

180° Exclusive Coastal Splendor

Escape to Villa Sama Sama, your perfect getaway in the heart of Simon's Town. Nestled just a 10-minute walk from the iconic Boulder's Beach, home to the famous African penguins, our guest house offers a serene retreat where comfort meets coastal charm. Whether you're looking for a relaxing break by the sea, an adventure exploring the Cape Peninsula, or simply a cozy hideaway with breathtaking views, our villa is ready to welcome you. Come stay with us and experience the beauty of Simon’s Town!

At the Heart of The Bay

A second floor flat located centrally in a quiet cul de sac with stunning views over the bay. Mountains behind and sea below. it's own private access via internal stairs. Four minutes walk to shops and restaurants. Beautiful beaches and coves everywhere. Catch an old steam train around the Bay to Cape Town or drive through Cape Point Nature Reserve to the Cape of Good Hope. Parking immediately below the flat. Safe and secure with street camera surveillance and security guard patrols at night.

Luxury Ocean-front 1BR Apartment at Harbour Bay

Enjoy a stylish experience at this centrally-located apartment in Glencairn, Simons Town. Luxury level furniture and fittings throughout the apartment. The Apartment is in the secure Harbour Bay Apartments in Block B, and is a sought after corner unit facing the Ocean with magnificent views. Enjoy ocean views with quick & easy access to the beach. Wide variety of shops, restaurants & supermarkets available at the Shopping Mall at Harbour Bay Mall with easy access from your apartment.

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.

Chic Heritage Hideaway near the penguins

Welcome to The Dragonfly — a beautifully restored Victorian Heritage Cottage nestled in a quiet historic street in charming Seaforth/Simonstown, a five minute walk from the famous Boulders Beach penguins. This stylish, family-friendly and joyful two-bedroom home with private terrace blends timeless character with modern comfort. Designed by a Cape Town Interior Designer, The Dragonfly features curated brand new finishes, top-tier amenities, a private parking bay, and a secure alarm system.

Luxury Apartment with Unobstructed Sea Views

This is the perfect place to relax and rejuvenate. Our luxury apartment boasts unparalleled 180-degree views of False Bay, stretching from Kalk Bay Harbour to Simon’s Town. Experience daily sunrises that are nothing short of inspirational! Minutes away from the vibrant restaurants and atmosphere of Kalk Bay to the North, and the serene nature of Simon’s Town to the South, our location offers the best of both worlds. The CBD is just 35 km away and solar power ensures a seamless stay.

Mountain Hideout | Firepit | Inverter | "On" Sea

Stylish mountainside escape overlooking the sparkling waters of False Bay — where sunrises glow and firepit evenings linger. Whytes is a beautiful, multi-level retreat for families, couples, remote workers and small groups. With panoramic sea views, quiet rocky nooks, an inverter and private spaces across two levels, it offers calm, comfort and Cape Town magic. Walk to the beach. Watch whales. Have morning coffee in a peaceful mountain corner, and end your day with a sunset drink.

3 BR Simons Town. Panoramic views! With inverter.

Tranquility on Harbour Heights boasts panoramic views of the Simons Town Harbour and false bay. The townhouse is situated in a serene and tranquil complex and borders the Cape Point nature reserve at the rear. The 3 bedroom, 2.5 bathroom spacious townhouse with wind sheltered entertainers balcony is fully equipped for your holiday to remember. With 5 beaches, the boulders penguin colony, interesting museums and the historic village to explore there’s something for the whole family.

The Carved Rock-Entire studio

With it's contemporary design, rock-rustic features incorporated with stunning elevated views of the Fish Hoek area and modern amenities, the Carved rock provides a tranquil, earthy grounding sensation that brings about comfort and relaxation to all guests. Special thought had gone into the process of accommodating each guest for either business or leisure. This listing is located on a quiet secluded gravel road on a mountain and not ideal for those who demand fast conveniences.

Sea view home unit in self-contained house

Our Rock House is something special! It has been recently built from stone found on the property. Watch spectacular sunrises over False Bay and the beach and tidal pool are a short walk away. Lovely and cosy in winter as well, with a wood-burning stove. The Rockery apartment consists of an open plan living room and kitchen leading out onto a wooden deck and two en suite bedrooms. There is secure off-street parking for one car and a braai area with a view.