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

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Simon's Town

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1,400 Holiday homes

(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

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from £75 / 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 £89 / night

£599 - £640 / week

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from £89 / night

14

Cottage rental 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
  • Pet friendly

from £100 / night

£700 / week

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from £100 / 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 £78 / night

£543 / week

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from £78 / 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

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from £230 / 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 £71 / night

£495 - £1,045 / week

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Responds fast!
avg. 1 hour 32 minutes

from £71 / 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

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from £131 / 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

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from £180 / 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

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from £300 / 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

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Responds fast!
avg. 1 hour 38 minutes

from £60 / 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

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from £65 / 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

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from £55 / 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 £88 / night

£612 / week

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from £88 / 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 £88 / night

£612 / week

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from £88 / 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 £88 / night

£612 / week

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from £88 / night

(14) Excellent 

18

Boulders holiday home rental

Simon's Town / Boulders

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • 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

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Responds fast!
avg. 2 hours 59 minutes

from £160 / night

(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

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from £62 / 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

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from £55 / 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

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from £95 / 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 £175 / night

£1,224 / week

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from £175 / night

(4) Very Good 

23

Simon's Town holiday guest house rental

Cape Town / Simon's Town

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £166 / night

£1,114 / week

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Responds fast!
avg. 1 hour 3 minutes

from £166 / 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 £339 / night

£2,371 / week

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from £339 / 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

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from £145 / 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

(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

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from £210 / 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 £112 / night

£780 / week

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from £112 / 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

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from £180 / night

(1) Excellent 

14

Holiday home with golf nearby in Simon's Town

Simon's Town / Boulders

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

from £235 / night

£1,630 / week

Book View

from £235 / 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

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from £39 / night

(1) Average 

20

Simon's Town holiday home rental

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 £94 / night

£660 - £727 / week

Book View

from £94 / 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

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

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

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from £44 / 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 £151 / night

£1,054 / week

Book View

from £151 / 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

(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

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from £195 / 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

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from £500 / night

(4) Very Good 

18

Simon's Town holiday home rental

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £153 / night

£787 - £2,011 / week

Book View

from £153 / 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 £91 / night

£633 / week

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from £91 / 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