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28 Holiday homes

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Travellers going to Simon's Town are booking December dates now. Secure your holiday home today and have the perfect trip.

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
The home it's near the beach Boulders and nice small beaches for swimm.  …see more

from £128 / night

£712 - £890 / week

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from £128 / 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

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from £230 / night

(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 £80 / night

£516 - £850 / week

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from £80 / night

(12) Excellent 

18

Boulders holiday home rental

Simon's Town / Boulders

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Slice of Heaven” We could not have been happier with this rental experience! The ocean views are spectacular and furnishings are plush. The open floor plan spilling onto the patio gives you a feeling of private luxury. A short drive gets you to quain  …see more

from £160 / night

£1120 / week

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from £160 / 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 £278 / night

£3334 / week

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from £278 / 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
Family home with unsurpassed view of sea and Simons Town and the harbour. This ideally located and recently renovated house has an ultra modern and fully equipped kitchen and laundry. It is in a quiet cul de sac, yet close to Cape Town and many other atractionsGarden wi  …see more

from £170 / night

£763 - £2500 / week

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from £170 / 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
2 bedroom, studio, 2 bathroom, living room, dining room, deck, garden with a fantastic view on the False Bay, garden on the back with view on the montain, laundry, garage.  …see more

from £102 / night

£594 / week

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from £102 / 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
Spacious, character full, holiday vacation rental, long stay, second home  …see more

from £124 / night

£865 / week

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from £124 / 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

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from £64 / night

(3) 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 £175 / night

£1175 / week

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from £175 / night

(2) Very Good 

23

Simon's Town holiday guest house rental

Simon's Town / Boulders

7 14 3 nights min

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
You are invited to enjoy the peaceful atmosphere of Boulders Beach House with uninterrupted False Bay views. Watch the whales and dolphins from your patio, stroll on the sandy beach and immerse yourself in the tranquility of the warm ocean.  …see more

from £120 / night

£834 / week

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from £120 / 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
The views are marvellous and the furnishing in a style reminiscent of Asia. Our nearest beach is a 5 minute walk away and the shops and eateries plus Simonstown' s Historic Mile are a mere 15 minute walk away You can relax and watch the whales from our balcony in seas  …see more

from £40 / night

£260 - £300 / week

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from £40 / night

(10) Excellent 

24

Guest house rental in Simon's Town with golf nearby

Cape Town / Simon's Town

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“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

from £146 / night

£1022 / week

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from £146 / night

7

Villa rental in Simon's Town with golf nearby

Simon's Town / Historic Mile

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Private garden
Wonderful views over False Bay, everyday an different view.Large terrace, privacyAll necessary equipmentDSTVGolf nearbySwimming nearbyVery good restaurants in the neighbourhood  …see more

from £146 / night

£1017 / week

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from £146 / 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

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from £235 / night

(4) Excellent 

21

Cape Town / Simon's Town

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly

 …see more

from £136 / night

£1381 / week

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from £136 / night

17

Villa letting in Simon's Town

Cape Town / Simon's Town

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
The house is on two levels, with open-plan kitchen, 2 lounges dining table, guest toilet, fire place and an en-suite bedroom. All areas have incredible mountain and sea views and access via sliding doors to the deck. Three bedrooms downstairs leading to the pool.Spark  …see more

from £250 / night

£1750 / week

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from £250 / night

(7) 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

 …see more

from £128 / night

£1068 - £1365 / week

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from £128 / night

18

Cape Town / Simon's Town

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask owner if suitable for children

 …see more

from £53 / night

£367 - £739 / week

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from £53 / 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

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from £500 / night

15

Home letting in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
Breathe in the scent of the ocean and luxuriate in ultimate privacy. South Winds is a first-class, wooden bungalow perched on the rocks of Castle Rock Marine Reserve on the Cape Peninsula. After a day’s diving, whale-spotting, swimming or boating, relax on the wooden  …see more

from £112 / night

£778 / week

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from £112 / night

32

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly

 …see more

from £401 / night

£2806 / week

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from £401 / night

14

Cape Town / Simon's Town

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.68 km
  • Child friendly

 …see more

from £100 / night

£700 / week

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from £100 / 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 £159 / night

£953 / week

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from £159 / night

(1) Very Good 

44

Cape Town / Simon's Town

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Child friendly

 …see more

from £107 / night

£1102 / week

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from £107 / night

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

 …see more

from £175 / night

£1223 / week

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from £175 / night

16

Cape Town / Simon's Town

4 9 2 nights min

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

 …see more

from £1020 / night

£7139 / week

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from £1020 / night

15

Cape Town / Simon's Town

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Ask owner if suitable for children

 …see more

from £64 / night

£420 / week

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from £64 / 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

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