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Holiday homes in Simon's Town and Chalets - Holiday Lettings - Holiday Rentals Simon's Town

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1,515 Holiday homes

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 4

1 Reviews

from £109 / night

£762 / week

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

1 Reviews

from £97 / night

£679 / week

Holiday studio with golf nearby in Simon's Town

Simon's Town studio

Studio • 1 bathroom • sleeps 3

3 Reviews

from £63 / night

£441 / week

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom • 2 bathrooms • sleeps 4

2 Reviews

from £98 / night

£682 / week

Boulders holiday home rental

Simon's Town house

3 bedrooms • 2 bathrooms • sleeps 6

“A view worth making the trip for!” Amazing place to stay in Simons Town, about 45 mins from central Cape Town and quick walk to the beach. The house has 3 large double bedrooms one ensuite... Grant , owner of the house looked after us very well and met our needs with the fact we has a one year old and couldn't have been more of a help to us all. The house is very well stocked and the bbq is great, the view is amazing , if you wake early you may even see the whales swimming by!.. Was a great place for exploring and would advise a car to do so, highlights include roben Island, table mountain, Aquila Safari , and Cape point which is only a 20 min drive - it is also a very short walk to boulders beach where you can see the gorg penguins - fantastic holiday and fantastic place to stay - highly recommend to anyone , thanks grant for the great hospiitality

16 Reviews

from £115 / night

£802 / week

Holiday villa rental

Simon's Town villa

4 bedrooms • 2 bathrooms • sleeps 7

“Brilliant house to relax in” We all enjoyed staying in this well furnished family home which is in a quiet area. The beach at Fish Hoek nearby was lovely and had fun body boarding. We enjoyed a family barbecue and used the plunge pool to cool off on the hottest days. Most of all loved the views from all the rooms at the front -miss having breakfast outside with such a view !

41 Reviews

from £98 / night

£682 / week

Simon's Town holiday apartment rental

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £62 / night

£377 / week

Holiday apartment in Simon's Town

Simon's Town apartment

2 bedrooms • 1 bathroom • sleeps 6

from £90 / night

£564 / week

Holiday apartment with swimming pool, golf nearby in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 3

from £86 / night

£602 / week

Simon's Town holiday villa rental

Simon's Town villa

2 bedrooms • 2 bathrooms • sleeps 5

from £102 / night

£712 / week

Holiday home rental

Simon's Town house

5 bedrooms • 4 bathrooms • sleeps 14

9 Reviews

from £424 / night

£2,965 / week

Holiday home in Simon's Town

Simon's Town house

3 bedrooms • 2 bathrooms • sleeps 6

from £102 / night

£690 / week

Simon's Town holiday cottage rental

Simon's Town cottage

3 bedrooms • 1 bathroom • sleeps 5

1 Reviews

from £207 / night

£1,140 / week

Simon's Town holiday home rental

Simon's Town house

4 bedrooms • 4 bathrooms • sleeps 9

3 Reviews

from £241 / night

£1,684 / week

Holiday home in Simon's Town

Simon's Town house

3 bedrooms • 2 bathrooms • sleeps 5

from £102 / night

£712 / week

Holiday studio rental

Simon's Town studio

Studio • 1 bathroom • sleeps 2

from £55 / night

£321 / week

Holiday apartment in Simon's Town

Simon's Town apartment

2 bedrooms • 1 bathroom • sleeps 3

from £52 / night

£361 / week

Holiday home in Simon's Town

Simon's Town house

2 bedrooms • 2 bathrooms • sleeps 5

from £102 / night

£712 / week

Holiday manor house with golf nearby in Simon's Town

Simon's Town manor house

6 bedrooms • 3 bathrooms • sleeps 10

8 Reviews

from £573 / night

£4,008 - £20,038 / week

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £113 / night

£791 / week

Holiday home with golf nearby in Simon's Town

Simon's Town house

5 bedrooms • 3 bathrooms • sleeps 8

from £206 / night

£1,437 / week

Holiday villa with swimming pool, golf nearby in Simon's Town

Simon's Town villa

3 bedrooms • 4 bathrooms • sleeps 11

1 Reviews

from £224 / night

£1,563 / week

Holiday home in Simon's Town

Simon's Town house

2 bedrooms • 2 bathrooms • sleeps 4

from £113 / night

£631 / week

Holiday studio with golf nearby in Simon's Town

Simon's Town studio

Studio • 1 bathroom • sleeps 2

from £75 / night

£521 / week

Holiday apartment in Simon's Town

Simon's Town apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £109 / night

£762 / week

Simon's Town holiday home rental

Simon's Town house

3 bedrooms • 2 bathrooms • sleeps 6

2 Reviews

from £99 / night

£834 - £1,326 / week

Holiday villa with swimming pool, golf nearby in Simon's Town

Simon's Town villa

2 bedrooms • 2 bathrooms • sleeps 6

from £161 / night

£1,123 / week

Holiday apartment with swimming pool in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

1 Reviews

from £168 / night

£1,173 / week

Simon's Town holiday apartment rental

Simon's Town apartment

3 bedrooms • 1 bathroom • sleeps 6

1 Reviews

from £98 / night

£573 / week

Holiday apartment rental

Simon's Town apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £54 / night

£369 - £951 / week

Simon's Town holiday home rental

Simon's Town house

3 bedrooms • 3 bathrooms • sleeps 6

from £287 / night

£2,004 / week

Simon's Town holiday home rental

Simon's Town house

4 bedrooms • 3 bathrooms • sleeps 8

5 Reviews

from £132 / night

£924 - £2,360 / week

Simon's Town holiday cottage rental

Simon's Town cottage

3 bedrooms • 2 bathrooms • sleeps 6

from £71 / night

£492 - £1,476 / week

Holiday apartment rental

Simon's Town apartment

2 bedrooms • 6 bathrooms • sleeps 5

from £95 / night

£565 / week

Holiday home in Simon's Town

Simon's Town house

3 bedrooms • 1 bathroom • sleeps 6

from £223 / night

£1,646 / week

Holiday penthouse in Simon's Town

Simon's Town penthouse

2 bedrooms • 3 bathrooms • sleeps 4

2 Reviews

from £189 / night

£1,318 / week

Holiday studio in Simon's Town

Simon's Town studio

Studio • 1 bathroom • sleeps 2

from £48 / night

£292 / week

Holiday apartment in Simon's Town

Simon's Town apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £99 / night

£689 / week

Simon's Town holiday apartment rental

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £52 / night

£363 / week

Villa rental in Simon's Town with shared pool

Simon's Town villa

2 bedrooms • 2 bathrooms • sleeps 6

from £103 / night

£719 / week

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Top Destination reviews

The Rectory
Historic Simon's town at its best!

Witness, our host, is an absolute legend. He was friendly and always happy to clean up after us. Beautiful family home. A bit pricy but all in all a great holiday. … see more
Camilla
Beautiful property

Four of us stayed at this property over New Year , as we were going to the Cricket at Newlands. It is located in Glencairn Heights , which is near a petrol station , Spa and Liquor store. There are also a couple of bars nearby , we spent New Year in the Stoep and Swing which is a really nice friendly relaxed bar that also has good food. Dixies is about a ten minute walk away, as is the train station. The trains were not running from Glencairn as maintenance on the track is happening currently. However there is a bus replacement service which takes you to Fish Hoek station where you can get the train. This was a nice way to get to Newlands. Glencairn is in a nice area being between Kalk Bay and Simons Town ( so near to the Penguins) . The views are lovely as well . As for 11 Camilla it is kept to such a high standard , the décor is tasteful and neat , and it was all kept very clean. The rooms are good sizes , and it was lovely to have the various outdoor spaces as the sun moved around. The kitchen is incredibly well stocked with all the equipment you will ever need. Wi-Fi is available , but you will need to buy the data , this is all clearly explained in the information pack , which has lots of helpful advice and notes. There are plenty of guides and leaflets for you to peruse as well. Pat the owner responses to any emails sent very quickly and is very helpful. All four of us loved our stay there and it really did become our home for the nine nights we stayed, and we were sad to leave.see more
The House
An Unforgettable Slice of Peace and Tranquility

We (my husband, 18 year old daughter and 15 year old son), booked La Maison for 6 nights in August 2016. The reaction from all of us as we entered the property was “WOW”! We had been travelling for 18 hours and were tired and jet lagged, but the sight of False Bay from the wonderful balcony instantly revived us all. Grant lives in an apartment downstairs and was wonderful – he was always available if we had a query, and is a thoroughly nice man. The house was very clean and well maintained. It had everything we needed for our stay including lovely blankets to wrap up in on the balcony in the evening! Although we were out and about every day seeing the sights – we were able to come home to the peace and tranquillity of La Maison in the evening and enjoy a glass of wine on the balcony overlooking the Bay. Therefore by the time we left to continue on our holiday we felt well rested, and were all sad to say goodbye. I wouldn’t hesitate to book La Maison again if we are ever fortunate enough to return to the Western Cape.see more

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