Waterfront vacation 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

Bungalow with spectacular views.

This three bedroom bungalow is a hidden gem behind a fountain with a 180 degree sea view that has been refurbished completely and designed tastefully. Listen to the waves breaking on the rocks while soaking in the hot tub. The open plan living area flows effortlessly towards a covered deck area with spectacular views. Situated a short walk from the famous St James tidal pool with its brightly colored dressing cabins, and minutes from Muizenberg surfing beach. Barefoot luxury never got better!

"Seaside Serenity : Ocean Views, Relaxing Retreat"

Escape to our modern self-catering apartment with direct ocean views, a serene atmosphere, meticulous cleanliness, and ample natural light which create the perfect soothing retreat. Take a leisurely 15-minute stroll to unwind on Glencairn Beach or explore the eclectic charm of Kalk Bay with its bohemian vibes and abundant dining and shopping options. Immerse yourself in Simons Town's rich history at the Naval Museum and Arts and Crafts stores. Don't miss the adorable penguins at Boulders Beach.

Spectacular sea views in quaint Kalk Bay

The sea views from our airbnb suite (2 bedrooms and a lounge) are fabulous. Behind us is the mountain reserve and in front lies the wide expanse of False Bay. Down below on the rocks is a natural tidal pool, safe for swimming. We are close to Kalk Bay fishing harbour, the quaint Kalk Bay village, several other tidal pools (perfect for cold swimmers!) and Fishhoek & Muizenberg beaches. We have newly renovated and enlarged our Airbnb space which is now separate from our living space and private.

Sunset Apartment, Arum Place Kommetjie Beach House

Sunset Apartment is a stunning beach retreat in Kommetjie, nestled in a serene cul-de-sac. This beautifully furnished getaway offers everything you could desire—air-conditioning, a covered deck, and breathtaking ocean and mountain views. Just steps away from the beach, the soothing sound of crashing waves can be enjoyed from the balcony and bedrooms. It’s the perfect escape for couples seeking a romantic getaway, with a seamless power backup system ensuring comfort even during load shedding.

Kalk Bay Hamster House

A beautiful one-bedroom apartment in the picturesque town of Kalk Bay. An amazing space if you are on holiday or a business trip. Situated 25m from the main road and walking distance from many delicious restaurants. This apartment has its own fully functioning kitchen with everything you will need to cook up a storm or you could order food and sit by the fire for an evening in. It also has its own private courtyard with shutter doors that can be opened all the way to invite the outside in.

Magnificent Clifton Retreat with Unparalleled Ocean Views

A perfect haven for couples or individuals seeking a holiday that will be truly memorable. Ezulwini is set in central Clifton, an exclusive area 5 minutes from Town and the V&A Waterfront. The apartment offers unrivalled sea and beach views. The interior is flooded with natural light, beautifully curated in a rich beachside palette of sandy hues with a touch of something nautical. Safety wise, the apartment is a lock up and go and there is battery Back with solar to deal with load shedding.

Amazing home on the beach in Klein Slangkop

Modern wood and glass home with solar-heated pool on the beach in Klein Slangkop private security estate. Step from the front deck onto beautiful beach sand and direct access to some of the most pristine beaches in the Cape. Breathtaking views. Great surfing. Nature. Stunning sunsets. Situated on the west coast of the Peninsular 50 minutes to Cape Town City Center one way and 25 mins to Cape Point gate the other way. Noordhoek beach is to the right and Long Beach to the left of the house.

Cairnside Studio Apartment

This new studio apartment is situated in the quiet exclusive suburb of Cairnside Simon's Town and enjoys stunning views over False Bay. The apartment has a fully equipped kitchenette with a 2-plate stove with mini oven, along with a combination microwave and Nespresso coffee machine (pods included). Free WiFi (40mps) and 50'' TV with Netflix, Spotify and a sound system. The apartment is SOLAR POWERED so NO ELECTRICITY BLACKOUTS. Close to some excellent eateries, beaches and a tidal pool.

The Lobster Pot - Simons Town Holiday Cottage

The Lobster Pot is an old family cottage that has been the location of many a memorable holidays down at the sea, snorkeling in the marine reserve, paddling around the rocky islands and going for hikes up the mountain. The Lobster Pot is a cosy little wooden cottage that is perfect for summer and winter, boasting beautiful views of False Bay and surrounding Cape point vista. The Lobster Pot is 5 Km out of Simonstown, between Bolders beach,penguin colony, and Cape Point. Come make memories!

Private poolside luxury studio with sea view

Wake up in Blue Skies Studio and look across your private swimming pool to see the sun rise over the ocean. This 72 square meter studio with its outdoor lifestyle has private access, parking on the property and excellent security. It is in the mountains, sheltered from the wind and walking distance from Boulders Beach and the penguins. There's lots to do, but you may not want to leave. It is a perfect haven for a short escape, longer-term retreat or the ideal “Work-from-Home” location.

Sea view home unit in self-contained house

Our Rockery 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.