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

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1,609 Holiday homes

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom / 1 bathroom / sleeps 4

1

from £109 / night

£762 / week

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom / 1 bathroom / sleeps 2

1

from £97 / night

£679 / week

Holiday home in Simon's Town

Simon's Town house

4 bedrooms / 2 bathrooms / sleeps 8

5

from £207 / night

£1,443 / week

Holiday studio with golf nearby in Simon's Town

Simon's Town studio

Studio / 1 bathroom / sleeps 3

3

from £63 / night

£441 / week

Holiday home with swimming pool, golf nearby in Boulders

Simon's Town house

6 bedrooms / 6 bathrooms / sleeps 13

from £344 / night

£1,840 - £2,321 / week

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom / 2 bathrooms / sleeps 4

2

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

15

Responds fast! avg. 54 minutes

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

Responds fast! avg. 1 hour 59 minutes

from £115 / night

£567 - £1,386 / 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

Simon's Town holiday guest house rental

Simon's Town guest house

4 bedrooms / 3 bathrooms / sleeps 8

4

from £207 / night

£1,393 / 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 £103 / night

£719 / week

Holiday home in Simon's Town

Simon's Town house

3 bedrooms / 2 bathrooms / sleeps 6

from £150 / night

£1,050 / week

Holiday home rental

Simon's Town house

5 bedrooms / 4 bathrooms / sleeps 14

9

from £424 / night

£2,965 / week

Holiday home in Simon's Town

Simon's Town house

3 bedrooms / 2 bathrooms / sleeps 6

from £118 / night

£800 / week

Simon's Town holiday cottage rental

Simon's Town cottage

3 bedrooms / 1 bathroom / sleeps 5

1

from £207 / night

£1,140 / week

Simon's Town holiday home rental

Simon's Town house

4 bedrooms / 4 bathrooms / sleeps 9

3

from £241 / night

£1,684 / week

Holiday home in Simon's Town

Simon's Town house

3 bedrooms / 2 bathrooms / sleeps 5

from £103 / night

£719 / week

Holiday studio rental

Simon's Town studio

Studio / 1 bathroom / sleeps 2

from £55 / night

£321 / week

Simon's Town holiday apartment rental

Simon's Town apartment

1 bedroom / 1 bathroom / sleeps 2

2

from £46 / 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 £103 / night

£716 / week

Holiday manor house with golf nearby in Simon's Town

Simon's Town manor house

6 bedrooms / 3 bathrooms / sleeps 10

8

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

from £224 / night

£1,563 / week

Bungalow rental in Simon's Town

Simon's Town bungalow

3 bedrooms / 1 bathroom / sleeps 6

from £140 / night

£975 / week

Holiday home in Simon's Town

Simon's Town house

2 bedrooms / 2 bathrooms / sleeps 4

from £113 / night

£631 / week

Holiday apartment in Simon's Town

Simon's Town apartment

2 bedrooms / 1 bathroom / sleeps 4

3

from £58 / night

£401 / 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

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

from £168 / night

£1,173 / week

Simon's Town holiday apartment rental

Simon's Town apartment

3 bedrooms / 1 bathroom / sleeps 6

1

from £98 / night

£573 / week

Simon's Town holiday home rental

Simon's Town house

3 bedrooms / 3 bathrooms / sleeps 6

from £155 / night

£1,082 / week

Holiday guest house in Simon's Town

Simon's Town guest house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 39 minutes

from £95 / night

£659 / week

Simon's Town holiday home rental

Simon's Town house

4 bedrooms / 3 bathrooms / sleeps 8

5

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

Viewing 40 of 1,609
rentals in Simon's Town

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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
Rocklands House
Fantastic Location

The view was really amazing! Pool and outside area are fantastic and really cosy. All bedrooms are great and good comfort and bathroom for each room in upper level. You feel really safe in the area, especially with the íntegrated alarm system. It is also good to know that Lendro lives next door and is very helpful! However, you can see furniture dated from the 80's but it was very ok for us and we felt really comfortable, because we spent most time in the fantastic outside area and in the basement with the really cool billiard table and table tennis. There is also a Sauna, but we did not used during summer.... House is very close to Boulders Beach and the Penguins and restaurants. Travel to cape town 45 minutes.see more
Penguin Blue - Whale Self-Catering Apartment
peaceful,relaxing areacomfortable,clean and modern apartment in a relaxing and beautiful area

on the day of arrival,we were welcomed by Erica Roux , who is kind, friendly, very pleasant, and who also went the extra mile to ensure that our stay was pleasant.the apartment was well maintained and clean apartment with absolutely stunning modern decor, furniture and clean linen plus many other extras.(such as chocolates on the beds, and wine in the kitchen :) ).one doesnt normally get spoilt when staying in a self catering apartment. I loved the area where the apartment is situated because it was safe, clean ,peaceful and boasted a beautiful view of Simonstown which looked breathtaking at sunset as well as at sunrise. other areas such as muizenberg,fishhoek and Simonstown are situated very close to the apartment. I enjoyed going to nearby restaurants, Boulders Beach as well as to the naval base.Also had the best cocktail at Cape to Cuba which is not far from the apartment. Thank you for a pleasant,comfortable and relaxing stay :) Debbiesee 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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