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

Close

View larger map

Also consider

Africa Holidays
14223 properties
South Africa Holidays
4802 properties
Log Cabin Holidays
238 properties

Simon's Town

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,414 Holiday homes

(1) Excellent 

31

Holiday apartment in Simon's Town

Cape Town / Simon's Town

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0.5 km
  • Child friendly
  • Private garden

from £62 / night

£434 / week

Book View

from £62 / night

(8) Excellent 

24

Holiday home rental

Cape Town / Simon's Town

5 18 2 nights min

  • 5 bedrooms
  • sleeps 18
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

from £353 / night

£2,470 / week

Book View

from £353 / night

(1) Excellent 

14

Holiday apartment in Simon's Town

Cape Town / Simon's Town

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 2 km

from £81 / night

£566 / week

Book View

from £81 / night

(37) Excellent 

32

Holiday villa rental

Cape Town / Simon's Town

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
“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 !

from £75 / night

£525 - £1,045 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from £75 / night

(2) Excellent 

22

Holiday apartment rental

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 1 km
  • Child friendly

from £75 / night

£525 / week

Book View

from £75 / night

15

Holiday home rental

Cape Town / Simon's Town

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £60 / night

£420 / week

Book View

from £60 / night

20

Holiday apartment in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly

from £95 / night

£665 / week

Book View

from £95 / night

28

Holiday apartment in Simon's Town

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 0.5 km
  • Child friendly
  • Air conditioning

from £75 / night

£525 / week

Book View

from £75 / night

10

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

Cape Town / Simon's Town

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 500 km
  • Swimming pool

from £145 / night

£1,015 / week

Book View

from £145 / night

5

Apartment rental in Simon's Town

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly

from £50 / night

£300 / week

Book View

from £50 / night

5

Holiday apartment in Simon's Town

Cape Town / Simon's Town

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly

from £94 / night

£659 / week

Book View

from £94 / night

15

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

Cape Town / Simon's Town

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Nearest beach 0.5 km
  • Swimming pool
  • Child friendly

from £55 / night

£385 / week

Book View

from £55 / night

63

Holiday home in Simon's Town

Cape Town / Simon's Town

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min

from £230 / night

£1,610 / week

Book View

from £230 / night

20

Holiday home with golf nearby in Simon's Town

Simon's Town / Historic Mile

5 8 14 nights min

  • 5 bedrooms
  • sleeps 8
  • 14 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £179 / night

£1,250 / week

Book View

from £179 / night

(1) Excellent 

22

Holiday apartment in Simon's Town

Cape Town / Simon's Town

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0.5 km
  • Child friendly

from £65 / night

£455 / week

Book View

from £65 / night

(3) Very Good 

20

Holiday studio with golf nearby in Simon's Town

Simon's Town / Murdock Valley North

Studio 3 2 nights min

  • Studio
  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £55 / night

£385 / week

Book View

from £55 / night

(5) Excellent 

10

Holiday home in Simon's Town

Cape Town / Simon's Town

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 0.9 km
  • Swimming pool
  • Child friendly

from £180 / night

£1,260 / week

Book View

from £180 / night

13

Holiday home in Simon's Town

Cape Town / Simon's Town

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £93 / night

£624 - £667 / week

Book View

from £93 / night

16

Simon's Town holiday villa rental

Cape Town / Simon's Town

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £90 / night

£625 / week

Book View

from £90 / night

8

Holiday apartment in Simon's Town

Cape Town / Simon's Town

2 3 7 nights min

  • 2 bedrooms
  • sleeps 3
  • 7 nights min
  • Child friendly

from £45 / night

£315 / week

Book View

from £45 / night

17

Holiday home in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £131 / night

£917 / week

Book View

from £131 / night

14

Holiday studio rental

Cape Town / Simon's Town

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
  • Child friendly

from £44 / night

£280 / week

Book View

from £44 / night

(14) Excellent 

18

Boulders holiday home rental

Simon's Town / Boulders

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“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

from £160 / night

£1,120 / week

Book View

Responds fast!
avg. 3 hours 13 minutes

from £160 / night

23

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

Cape Town / Simon's Town

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Nearest beach 0.6 km
  • Swimming pool
  • Child friendly

from £125 / night

£875 / week

Book View

from £125 / night

(2) Very Good 

17

Simon's Town holiday apartment rental

Cape Town / Simon's Town

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Child friendly

from £40 / night

£280 / week

Book View

from £40 / night

14

Holiday studio with golf nearby in Simon's Town

Cape Town / Simon's Town

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £65 / night

£455 / week

Book View

from £65 / night

15

Holiday home with swimming pool, golf nearby in Boulders

Simon's Town / Boulders

6 13 2 nights min

  • 6 bedrooms
  • sleeps 13
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £300 / night

£1,607 - £2,027 / week

Book View

from £300 / night

19

Bungalow rental in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £116 / night

£813 / week

Book View

from £116 / night

15

Holiday home in Simon's Town

Simon's Town / Historic Mile

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £90 / night

£626 / week

Book View

from £90 / night

(1) Excellent 

18

Holiday villa rental

Cape Town / Simon's Town

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 0.5 km
  • Swimming pool
  • Child friendly

from £99 / night

£599 - £1,299 / week

Book View

from £99 / night

(3) Excellent 

40

Simon's Town holiday home rental

Cape Town / Simon's Town

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child friendly

from £210 / night

£1,470 / week

Book View

from £210 / night

26

Holiday penthouse in Simon's Town

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly

from £157 / night

£1,098 / week

Book View

from £157 / night

(1) Very Good 

89

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

Cape Town / Simon's Town

3 11 2 nights min

  • 3 bedrooms
  • sleeps 11
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £195 / night

£1,365 / week

Book View

from £195 / night

(1) Excellent 

7

Simon's Town holiday cottage rental

Cape Town / Simon's Town

3 5 2 nights min

  • 3 bedrooms
  • sleeps 5
  • 2 nights min
  • Child friendly

from £180 / night

£995 / week

Book View

from £180 / night

(8) Excellent 

10

Holiday manor house with golf nearby in Simon's Town

Cape Town / Simon's Town

6 10 7 nights min

  • 6 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Suitable for children age 5+

from £500 / night

£3,500 - £17,500 / week

Book View

from £500 / night

11

Holiday studio in Simon's Town

Cape Town / Simon's Town

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Ask owner if suitable for children

from £39 / night

£255 / week

Book View

from £39 / night

(3) Very Good 

18

Holiday apartment in Simon's Town

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

from £50 / night

£350 / week

Book View

from £50 / night

(4) Excellent 

16

Simon's Town holiday home accommodation

Cape Town / Simon's Town

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Private garden

from £180 / night

£1,260 / week

Book View

from £180 / night

8

Holiday home in Simon's Town

Cape Town / Simon's Town

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden

from £90 / night

£625 / week

Book View

from £90 / night

(10) Excellent 

24

Guest house rental in Simon's Town with golf nearby

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Brilliant house, gorgeous view, great location and very kid friendly” It's obvious that the owners, Gail and Rene, have put a lot of effort into making Felsensicht a comfortable holiday home. From a friendly greeting at the start by caretaker Jim to the well appointed and very modern furnishings, I think they've thought of just about everything. Gail was thoroughly friendly but professional throughout and I've come away very impressed! We stayed for a week in November with our 19 month old son and it was a delight. The patio is large and very safe for a toddler (we picked the house in part because the railing appeared secure enough for a little one - it was). The beach is 200 metres away and offered endless entertainment - and 1/4 mile further is a beach full of penguins! Only challenge would be for those aiming to walk everywhere - the shops are close but still require a very short (5 min) drive. Highly recommended in every way.

from £184 / night

£1,288 / week

Book View

Responds fast!
avg. 1 hour 14 minutes

from £184 / night

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
Felsensicht Holiday Home
The Perfect Place

Felsensicht Holiday Home is the perfect place to relax. It is decorated tastefully and equipped with everything you may need. The views are beautiful, the location is quiet. We will definitely come back as soon as possible!!! … 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