House holiday rentals in Simon's Town

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Top-rated house rentals in Simon's Town

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Guest favourite
An outdoor deck features a wooden dining table surrounded by six chairs, overlooking expansive sea views. The clear blue sky enhances the serene atmosphere, while the palm trees at the edge of the deck provide a touch of greenery.
Home in Simon's Town
4.89 out of 5 average rating, 163 reviews

Perfect holiday location with stunning sea views

Holiday home outside Simonstown on the Cape Peninsula, close to the "penguin beach". Sleeps four in two bedrooms. Open plan kitchen/lounge flows onto a large deck with expansive sea views. Two full bathrooms (main en-suite). Within easy reach of Cape Point Reserve, and the delightful shops & restaurants of Simonstown, Kalk Bay & Muizenberg. Walking distance to swimming spots. Tasteful decor with modern appliances, a smart Google TV and pure cotton linen on the beds. Minimum stay is two nights.

Guest favourite
Home in Fish Hoek
4.94 out of 5 average rating, 232 reviews

Dream Family Villa CapeTown-StunningSeaView

If you dream of an unforgettable FAMILY Stay in a fantastic villa in Western Cape, in a very quiet neighborhood: indulge yourself at SummerPlace, fully equipped w/ SOLAR PANELS/INVERTERS/BATTERIES. Our stunning contemporary home is backed by a super bright mountain w/ panoramic views of False Bay. Breath taking views of the ocean are in absolutely every window, in every bedroom, living room areas, kitchen... Enjoy both pool and beach (7min walk), take a deep breath: this beauty is all yours.

Top guest favourite
An outdoor deck features a dining table with intricate metalwork, surrounded by several chairs. Comfortable seating arrangements are positioned nearby, overlooking expansive sea views. The ocean sparkles in the sunlight, while a distant horizon is framed by rolling waves.
Home in Simon's Town
4.92 out of 5 average rating, 171 reviews

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.

Top guest favourite
A spacious outdoor deck features a wooden seating area with plush cushions, overlooking the ocean waves. A small round table holds potted plants, and the backdrop consists of rugged cliffs under a clear blue sky, creating a serene coastal environment.
Home in Misty Cliffs
4.99 out of 5 average rating, 167 reviews

Seaside Mountain Retreat in Misty Cliffs w/ Sauna

Seaside mountain retreat in exclusive Misty Cliffs nature reserve with endless views, pool and large fynbos garden with private path down to the beach. This architect designed wooden bungalow is perfect for exploring Cape Point and the Southern Peninsula or just switching off and relaxing in the verdant immersion of a conservation village. Featuring 2 large en-suite bedrooms as well as a cosy loft and additional bunkbeds for the kids. The house is just 45 minutes from Cape Town city centre.

Guest favourite
The exterior of a modern home features a pool surrounded by a wooden deck, with a view of the ocean in the background. Large windows reflect sunlight, and various potted plants add a touch of greenery. Clear skies and sailboats can be seen on the tranquil water.
Home in Simon's Town
4.92 out of 5 average rating, 119 reviews

WhaleDance

Our home is on the Historical Mile with panoramic views, just one block up from the Main Road and near all the cafes and eateries Simon's Town offers. Boulders Beach and the famous penguins are an easy 20 minute walk away and Long Beach is 10 minutes away as is the railway station. This is a high quality accommodation, All three bedrooms are en-suite, with spacious and sound-proofed rooms. A well equipped kitchen with an outside deck with South African 'Braai', pool and seating area.

Top guest favourite
A dining table with several chairs is positioned on a deck, overlooking a calm bay. In the distance, mountains are visible along the shoreline, while a singular ship floats on the water. The scene is bathed in soft light, suggesting dawn or dusk.
Home in Cape Town
4.95 out of 5 average rating, 195 reviews

Modern home with breathtaking ocean views

Nestled in the exclusive area of Cairnside, this semi-detached house offers the perfect place to enjoy beautiful views of False Bay and is less than 5 mins from the local beach and tidal pool. One of our favourite past times is watching the water activities from the sheltered deck. Whale spotting, kite surfers jumping in the bay, sailing regattas and flocks of birds migrating along the coast. The sun rises across this side of the bay, if you're up early you'll be mesmerised by the view.

Top guest favourite
Natural light floods a welcoming entrance, featuring a blend of stone and wooden accents. A large window reveals a framed sea view, with a cozy sitting area and dining space visible beyond. A mirror reflects the space, enhancing the open feeling.
Home in Kalk Bay
4.97 out of 5 average rating, 105 reviews

Beachball B&B

Beachball B&B is located in the heart of the old village of Kalkbay. Set on a cobbled road that ends in a short flight of stairs it is not a thoroughfare. It is within easy walking distance of the tidal pool, the park, numerous restaurants and coffee shops, and the mountain behind with walking trails. The house dates back to 1875 and the unit is an independent wing with its own street access. The station is also close at hand, and there are wonderful shops to explore along the main road.

Guest favourite
A spacious deck features a round dining table surrounded by four white chairs. Behind, large glass doors provide an unobstructed view of the ocean. The serene surroundings are enhanced by greenery and coastal scenery, with sunlight illuminating the area.
Home in Misty Cliffs
4.91 out of 5 average rating, 215 reviews

The Sky Cabin Misty Cliffs

Experience one of the most pristine stretches of the south peninsula coastline from our laidback house.

 

The upstairs offers spectacular ocean views with a big open plan bathroom. Downstairs is the perfect setting for dinners around the dining table leading onto the open plan kitchen. The downstairs double bedrooms share a bathroom and the front bedroom has beautiful sea views. While the downstairs deck is great for sundowners. Situated 45 minutes from Cape Town’s city centre.

Guest favourite
A coastal view is captured, showcasing a modern multi-level house nestled among green vegetation. The ocean stretches to the horizon, with rocky formations visible in the water. Mountains rise gently in the background, creating a picturesque natural setting.
Home in Simon's Town
4.94 out of 5 average rating, 134 reviews

Boulders Seaside Home by Steadfast Collection

Charming, homey and convenient, Coppers is just 100m to the entrance to Boulders Beach. With views from every bedroom – the sunrise is not to be missed, nor the night skies and moonlit water, – and 180-degree vistas from Simonstown, around False Bay to Hangklip, the southern ocean swells and fishing boats coming in from Cape Point, it’s the textbook definition of a coastal idyll. Top tip: walk across the golf course before the tourists arrive and swim at Windmill Beach.

Guest favourite
A welcoming living area features a soft-colored sofa and light chairs, arranged around a low table. Natural light filters through sheer curtains, highlighting a decorative painting on the wall. A vase of fresh flowers adds a touch of warmth, creating a comfortable space for relaxation.
Home in Simon's Town
4.83 out of 5 average rating, 173 reviews

Seaview Cottage. Walk to Beach and Penguins

This 3 bedroomed, all ensuite, home is located a short 5 minute walk to Windmill Beach. Windmill Beach was recently voted by as one of the top 10 beaches in Cape Town. You can walk a short distance to see the penguins at Boulders Beach. This home is perfect for those who are looking for tranquility but still centrally located for exploring the South Peninsula. This home perfect for the Cape Town staycationers and loved by local and international travellers.

Top guest favourite
The open-plan living area features a rustic wooden dining table surrounded by light grey chairs. A comfortable seating arrangement, accented by a blue couch, offers a view through large sliding doors that open onto a wooden deck overlooking the ocean.
Home in Cape Town
4.93 out of 5 average rating, 124 reviews

Stunning, sea-front sunrises, whales and dolphins.

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.

Superhost
An elevated view from the sun deck showcases sweeping ocean vistas, framed by gentle mountain contours. The wooden deck is complemented by greenery, enhancing the serene atmosphere. The clear sky allows for ample natural light, creating an inviting outdoor space for relaxation.
Home in Simon's Town
4.81 out of 5 average rating, 272 reviews

Beautiful home, fantastic sea views in Simonstown

Light and airy, spacious, Christian-owned home. Large and sheltered sun deck with sweeping views of the ocean and surrounding mountains. Walking distance to the village and a choice of beaches. If you are looking for a beautiful place to relax, refresh and renew, then this is the home for you! Regret no parties or excessive drinking. No smoking. Noize needs to be controlled as it is a neighbourhood with permanent residents.

Popular amenities for house rentals in Simon's Town

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Avg. price$227 SGD$208 SGD$195 SGD$159 SGD$157 SGD$139 SGD$147 SGD$152 SGD$155 SGD$170 SGD$169 SGD$246 SGD
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Quick stats about house rentals in Simon's Town

  • Total holiday rentals

    Explore 160 holiday rentals in Simon's Town

  • Nightly prices starting at

    Simon's Town holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    150 of Simon's Town holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Simon's Town rentals

  • 4.8 Average rating

    Simon's Town stays are highly rated by guests – averaging 4.8 out of 5!

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