Holiday homes - Holiday rentals

Close

View larger map

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

7 Holiday homes

Filters applied: Pets allowed (7)

Don't let other travellers get your favourite Simon's Town holiday home. You're so close to securing your perfect getaway. Book today.

(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

£512 - £843 / week

Book View

from £79 / night

15

Holiday home with swimming pool, golf nearby in Boulders

Simon's Town / Boulders

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
A seaside paradise above Boulders Beach.Fisherman's Cove is a wonderful place for two families on holiday or larger groups of friends.  …see more

from £230 / night

£1607 / week

Book View

from £230 / night

(2) Excellent 

20

Holiday villa with golf nearby in Simon's Town

Simon's Town / Boulders

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Let us help you plan the perfect visit to Cape Town. We can fill the fridge, chill the best Cape wine for you and organize a babysitter! If you'd like a personal driver, we can arrange that too. Need a daily itinerary? We'll introduce you to the very best of t  …see more

from £276 / night

£3308 / week

Book View

from £276 / night

17

Holiday penthouse in Boulders

Simon's Town / Boulders

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Ask about pets
The Flying Penguin is a haven, offering complete relaxation close to nature yet within easy reach of the city. Featuring a family-sized penthouse as well as two cozy suites for two, this farmhouse-styled holiday accommodation is situated in Simon's Town.It is a pea  …see more

from £64 / night

£435 / week

Book View

from £64 / 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
Beautiful Victorian family home overlooking world famous Boulders Beach. A true seaside paradise that leaves you feeling like you have stepped into a true gem .... watch the whales while sipping your morning coffee - you simply could not be closer to the ocean  …see more

from £235 / night

£1630 / week

Book View

from £235 / night

(6) Very Good 

10

Cape Town / Simon's Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from £65 / night

£452 - £497 / week

Book View

from £65 / 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

 …see more

from £158 / night

£945 / week

Book View

from £158 / night

Top Destination reviews

La Maison
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 sig … see more