Vacation rentals with a patio in Simon's Town

Apartment in Glencairn

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

Jul 29 – Aug 5

Home in Simons Town

Paradise Views: Family Fun w/ views in Simons Town

Your family's gateway to the South Peninsula's wonders, awaits! Ideal for families, couples & friends, this home boasts a king-sized primary bedroom & additional twin room: both rooms offering en-suite bathrooms with showers, & a guest bathroom with Victorian bath. The modern kitchen, with washer/dryer & dishwasher, flows into an open-plan dining/lounge area, perfect for special gatherings. The true highlight is the balcony, furnished for alfresco dining, offering breathtaking False Bay vistas.

Jul 10 – 17

Guest suite in Cape Town

Your best dose of Vitamin-Sea!

Tucked away on the mountainside and overlooking the sea, this secret hideaway oozes the kind of relaxed & lazy holiday feeling that makes you want to put your feet up and stay forever. Nestled between the trees and with the sounds of waves crashing below, the comfy & cozy space is surrounded by sun, sea, sky, birds and such tangible tranquility that it will leave your Soul realising just how desperately it needed to breathe. This is an escape that is entirely unique and impossible to forget.

Apr 27 – May 4

Condo in Simons Town

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.

Cottage in Glencairn

Self-contained stone house overlooking the sea

Our Rock House is something special! It has been recently built from stone found on the property. Watch spectacular sunrises over the Hottentot’s Holland Mountains and False Bay. The beach and tidal pool are a short walk away. The home 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 two cars and a braai area with a view. Have a sneak peak at the view from the upper Deck - listing in October!

Jun 14 – 21

Apartment in Simons Town

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.

Jun 4 – 11

Home in Simons Town

Seaside Oasis - no power interruptions

Welcome to my charming seaside retreat! Nestled in a tranquil neighborhood, my home offers the perfect blend of modern elegance & soulful comfort. Perched on the edge of a hill, my home boasts stunning panoramic views that will take your breath away. Whether you’re sipping your morning coffee or enjoying a glass of wine at sunset, the vista is simply mesmerizing. The space is flooded with natural light with modern fittings & tasteful decor to create an inviting atmosphere. Book now!

May 13 – 20

Townhouse in Simons Town

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.

Aug 9 – 16

Home in Simons Town

Stunning Simons Town Ocean View Cottage w Inverter

Enjoy beautiful Simons Town from our peaceful sea cottage with breathtaking ocean views of False Bay. Our cottage is the perfect tranquil getaway and comes well equipped with 3 bedrooms and 2 bathrooms. Take in the views from the deck or get out and explore one of South Africa’s most historic towns. If you’re working we’ve got you covered with a 100mb fibre line that’s setup with a range extender ensuring connectivity from the bedroom to the deck.

Mar 15 – 22