Vacation rentals in Simon's Town

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Top-rated vacation rentals in Simon's Town

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Guest favorite

Guest suite in Hout Bay

4.99 out of 5 average rating, 287 reviews

BIRDSONG-Whirlpool+Outdoor Shower+Mountainview

A former art studio has been converted into a beautiful little home that is attached to main house with panoramic valley view from your bed and garden. Further up in the mountain of Kronenzicht in a quiet cul-de-saq you can unsettle while having a dip in your private and heated hot tub, relax under the rain shower with stunning views on the back of table mountain and little lionshead or start your sunset walk on the beautiful sand dunes next to our property, even all the way down to Sandy Bay.

Guest favorite

Rental unit in Glencairn

4.97 out of 5 average rating, 150 reviews

'Lewatle' - luxury apartment with sea views

Stunning, self-catering apartment, a 10-minute drive from the famous penguins at Boulders Beach in Simonstown. The apartment is on the second floor of a secure mixed-use complex. Supermarkets, restaurants, coffee shops, pharmacy, gym and beauty spa are an elevator-ride away. The modern layout is complemented by superb unobstructed views over False Bay; the beach is across the road. Ideally situated - 20 minutes from Cape Point and 1 hour from Cape Town CBD. Julian’s guidebook has more detail.

Guest favorite

Cottage in Simon's Town

4.87 out of 5 average rating, 183 reviews

Cape Point Mountain Getaway - Cottage

This is one of Cape Town's environmental and historic treasures. It is a candle-lit hideaway with stunning views of mountain and sea. The Cottage is completely off grid, with fresh water coming off the mountain and energy from the sun. The cottage is built from local materials - stone walls, reed ceilings, blue gum supports. There are glass doors and windows throughout the cottage. The cottage has a beautiful open-plan bedroom and bathroom. The bathroom includes a tub, a toilet and a basin.

Guest favorite

Home in Simons Town

4.89 out of 5 average rating, 121 reviews

A perfect holiday location with stunning sea views

Holiday house just 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. Within easy reach of Cape Point Reserve, and the delightful shops & restaurants of Simonstown, Kalk Bay & Muizenberg. Easy walking distance to swimming spots. Tasteful decor with modern appliances and pure cotton linen. Minimum stay is two nights, and seven nights between 15 December and 14 January.

Guest favorite

Home in Simons Town

4.91 out of 5 average rating, 101 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.

Guest favorite

Home in Scarborough

4.99 out of 5 average rating, 122 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 favorite

Cabin in Kommetjie

4.99 out of 5 average rating, 158 reviews

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.

Guest favorite

Bungalow in Cape Town

4.94 out of 5 average rating, 161 reviews

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!

Guest favorite

Home in Simons Town

4.92 out of 5 average rating, 106 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.

Guest favorite

Cottage in Simons Town

4.94 out of 5 average rating, 106 reviews

The Lookout at Froggy Farm

Just a few minutes walk from the beautiful False Bay beaches, The Lookout is a mezzanine level house with breathtaking views sitting in a quiet part of Simon's Town. Next to and with access to the iconic Froggy Farm, it is just the place for a relaxing stay away from the crowds. With a dedicated work area and 100mbps fibre, it is also perfect for escaping the city yet remaining connected for a peaceful remote working experience. Ideally suited for couples or families with children.

Guest favorite

Loft in Simons Town

4.85 out of 5 average rating, 264 reviews

Breathtaking Mountain & Ocean views in Simons Town

The Loft is situated in Simons Town on the Cape Peninsula, an area of incredible natural beauty & gateway to the Marine Big 5. This spacious loft apartment offers beautiful light accommodation with folding doors leading onto a large private balcony & spectacular views of False Bay. The loft includes an open plan bedroom area, sitting room, fitted kitchen & separate bathroom. Private entrance & parking & is only 5 minutes walk to Simons Town amenities, harbour & beaches close by.

Guest favorite

Rental unit in Simons Town

4.88 out of 5 average rating, 268 reviews

Swim (and walk) with the penguins

Walk to safe swimming beaches and to the penguins in 3 minutes, or wander into historic Simonstown village. Our guest suite is small (6m X 2m), but offers everything you need, plus a view of the sea: wi-fi, a comfortable double bed, the means to make breakfast, place to eat or check emails – and privacy from the main house. It has a separate entrance and a private bathroom. A small garden for your exclusive use offers a table, chairs and Weber.