Holiday rentals with a patio near Boulders Beach

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

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!

Spacious family home | 5-min stroll to the beach

Location: Simon's Town, 5 min to penguins, 15 min to Kalk Bay, walk to beach Ideal for: Families, couples, friends Features: - King-sized primary bedroom w/ en-suite bathroom - Twin room w/ en-suite bathroom - Guest bathroom w/ Victorian bath - large kitchen w/ washer/dryer & dishwasher - Open-plan dining/lounge area - Balcony w/ breathtaking False Bay view - restored Victorian fireplace in lounge - additional fireplace near bedrooms to heat them up too - SPOT MARINE LIFE from your balcony

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.

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.

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.

Pool*Braai* 2 minute drive to Boulders Beach

Just a quick 2-minute drive from Boulders Beach, this charming 2-bedroom, 2-bathroom semi-detached home awaits. With a plethora of activities to enjoy including a swimming pool, swings and braai area, there's something for everyone. Take in partial sea views and unwind with your loved ones in this serene haven. We invite you to come and experience relaxation at its finest. Limited to a maximum of 4 adults and 2 children. Please note there is no longer a jacuzzi!!!

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.

Charming seaside house near penguin reserve

Amberley house was built in the 1940’s it is comfortable, sunny and spacious with a beautiful sea view and only three minutes walk from waters edge beach and six minutes from boulders penguin colony. Beautiful snorkelling, diving, hiking ,sailing and cycling all right on your doorstep! A front garden for the morning sun and a back garden for afternoon shade make it easy to find a spot to relax.