Holiday homes - Holiday rentals

Close

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

35 Holiday homes

Filters applied: Private garden

(7) Excellent 

21

Holiday home accommodation

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Where the mountains and heavens meet with the Penguins, Whales and Dolphins” This beautiful home (with pool, outdoor deck and magical views of Boulders Beach ) was the perfect location for a sun filled holiday swimming with the penguins and watching t
…see more

from £79 / night

£508 - £836 / week

Book View

from £79 / 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 £85 / night

£594 / week

Book View

Responds fast!
avg. 3 hours 30 minutes

from £85 / night

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 £91 / night

£571 - £676 / week

Book View

from £91 / 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+
“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

from £500 / night

£3500 - £17500 / week

Book View

from £500 / 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 £85 / night

£594 / week

Book View

Responds fast!
avg. 3 hours 30 minutes

from £85 / night

(1) Excellent 

32

Holiday apartment in Simon's Town

Cape Town / Simon's Town

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask owner if suitable for children
  • Private garden

from £65 / night

£455 / week

Book View

from £65 / night

20

Holiday home with golf nearby in Simon's Town

Simon's Town / Historic Mile

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

Pricing unknown

Book View

Pricing unknown

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 £230 / night

£1607 / week

Book View

from £230 / night

10

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

Cape Town / Simon's Town

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 500 km
  • Swimming pool

from £200 / night

£1500 / week

Book View

from £200 / night

(4) Very Good 

18

Simon's Town holiday home rental

Cape Town / Simon's Town

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £103 / night

£721 - £2034 / week

Book View

from £103 / 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
“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 a
…see more

from £172 / night

£1157 / week

Book View

from £172 / night

(4) Excellent 

16

Simon's Town holiday home accommodation

Cape Town / Simon's Town

5 10 2 nights min

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

from £190 / night

£1330 / week

Book View

from £190 / night

(3) Very Good 

22

Holiday cottage in Simon's Town

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £140 / night

£700 - £1875 / week

Book View

Responds fast!
avg. 3 hours 20 minutes

from £140 / night

(2) Excellent 

9

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

£1260 / week

Book View

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

£1630 / week

Book View

from £235 / night

17

Holiday apartment with shared pool in Simon's Town

Cape Town / Simon's Town

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Private garden

from £42 / night

£294 / week

Book View

from £42 / night

(2) Average 

17

Villa letting in Simon's Town

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £250 / night

£1750 - £3500 / week

Enquire View

from £250 / night

13

Holiday home in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £75 / night

£469 / week

Book View

from £75 / night

18

Holiday villa rental

Cape Town / Simon's Town

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £117 / night

£743 - £1594 / week

Book View

from £117 / night

23

Holiday villa with swimming pool in Simon's Town

Cape Town / Simon's Town

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £155 / night

£1085 / week

Book View

from £155 / night

13

Cape Town / Simon's Town

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0.5 km
  • Child friendly
  • Pet friendly

from £79 / night

£508 - £625 / week

Book View

from £79 / night

(9) Very Good 

25

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Swimming pool

from £136 / night

£950 / week

Book View

from £136 / night

31

Cape Town / Simon's Town

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £72 / night

£504 / week

Book View

Responds fast!
avg. 3 hours 53 minutes

from £72 / night

(1) Very Good 

12

Cape Town / Simon's Town

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Private garden

from £283 / night

£1975 / week

Book View

from £283 / night

(2) Very Good 

12

Cape Town / Simon's Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £63 / night

£438 / week

Book View

from £63 / night

(1) Average 

8

Cape Town / Simon's Town

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 2 km
  • Child friendly
  • Private garden

from £51 / night

£280 - £404 / week

Book View

from £51 / night

29

Cape Town / Simon's Town

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Private garden

from £313 / night

£2188 / week

Book View

from £313 / night

(1) Excellent 

14

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.68 km
  • Child friendly

from £100 / night

£700 / week

Book View

from £100 / night

16

Cape Town / Simon's Town

4 9 5 nights min

  • 4 bedrooms
  • Sleeps 9
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £938 / night

£6563 / week

Book View

Responds fast!
avg. 3 hours 1 minutes

from £938 / night

(10) Very Good 

16

Cape Town / Simon's Town

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £157 / night

£938 / week

Book View

from £157 / night

(2) Excellent 

19

Cape Town / Simon's Town

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 0.05 km
  • Child friendly
  • Car not necessary

from £47 / night

£313 - £508 / week

Book View

from £47 / night

17

Cape Town / Simon's Town

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden

from £47 / night

£329 / week

Book View

from £47 / night

13

Cape Town / Simon's Town

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Private garden

from £204 / night

£1422 / week

Book View

from £204 / night

18

Cape Town / Simon's Town

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.25 km
  • Swimming pool
  • Child friendly

from £157 / night

£977 / week

Book View

from £157 / night

(1) Excellent 

12

Cape Town / Simon's Town

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £172 / night

£1204 / week

Book View

from £172 / night

1