Vacation rentals with a patio 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

"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!

Sugar Suite Beachside Apartment

Welcome to the Sugar Suite, an exclusive eco-luxury retreat for discerning couples seeking serenity and romance. Perched above uncrowded beaches, this elegant studio apartment/flat features a King bed, a well equipped kitchenette, private oceanview deck, upscale finishes, and a soaking tub and shower—all with sweeping ocean views. A short walk to local cafes and restaurants. Prebook extras: In-room massage and/or custom-stocked fridge. A tranquil haven for an intimate, nature-inspired escape.

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 two-bedroom home with private terrace blends timeless character with modern comfort. The Dragonfly features curated brand new finishes, top-tier amenities and a private parking bay. Note: It is not suitable for any sort of entertainment but only a peaceful stay.

Kelp House. Amazing sea, breaker and boulder views

Looking over beautiful False Bay, peaceful Kelp House has direct views of breakers, boulders and kelp beds. Quiet neighborhood. Amazing sea-views from 2 bedrooms and a spacious open plan lounge, kitchen and dining area, with Hangklip visible across the Bay . Enjoy beautiful sunrises, sunsets and moon risings on big deck with outdoor dining area, firepit and barbecue. Only 5 minutes to walk down to the shoreline, 15 min walk to a swimming beach and 5 minute walk up the road to a mountain path.

Boulders Beach Lookout Apartment

Boulders Beach Lookout is a light and spacious penthouse apartment with a wrap-around deck, 2 bedrooms, 2 bathrooms, an equipped kitchen and a stylish, open-plan living space. You will feel on top of the world as you experience magnificent ocean views from every room (even the bathroom!) and a relaxed ambience. And we are only 3 minutes' walk down the hill to Boulders Beach with its nearby penguin colony. Although there is a holiday home below the apartment, your space is completely private.

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.

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.

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.

Dream View Studio

Dream View Studio is a dreamy 1 bedroom Misty Cliffs hideaway, located on a beautifully preserved mountainside, this studio apartment offers magical views of the Atlantic Ocean and the Baskloof Nature Reserve, perfect for those looking to relax in a private space surrounded by exquisite nature and enjoy the wide range of activities the area has to offer. A beautiful space for a sneaky weekend away or over night stays exploring the area.