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25 Holiday homes

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

(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 £82 / night

£529 - £870 / week

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from £82 / 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.<br />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

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

Pricing unknown

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Pricing unknown

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.<br />  …see more

from £64 / night

£435 / week

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from £64 / night

(1) Very Good 

26

Simon's Town holiday home rental

Cape Town / Simon's Town

5 14 1 night min

  • 5 bedrooms
  • Sleeps 14
  • 1 night min
  • Child friendly
A perfect place for a large group who enjoys the easy life. The main house holds three bedrooms (two with stunning sea views over False bay + one with garden views). The lounge area, which is reached from the entrance is large and have a great 160 degrees sea views. The  …see more

from £130 / night

£647 / week

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from £130 / 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
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 atractions<br /&  …see more

from £173 / night

£733 - £2069 / week

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from £173 / night

17

Holiday home in Simon's Town

Cape Town / Simon's Town

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
A gorgeous maisonette that is on the iconic Kleintuin Road that connects Seaforth Beach to Boulders overlooking the Cape’s best kept secret beach – Water’s Edge Beach. Watch the penguins from the comfort of your holiday home. 3 Bedrooms upstairs &  …see more

from £131 / night

£917 / week

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from £131 / 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
The home it's near the beach Boulders and nice small beaches for swimm.  …see more

from £87 / night

£725 - £906 / week

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from £87 / night

(2) Excellent 

20

Holiday villa with golf nearby in Simon's Town

Simon's Town / Boulders

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • 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 £285 / night

£1992 / week

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from £285 / night

15

Home letting 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 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 woo  …see more

from £114 / night

£797 / week

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from £114 / 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
Overlooking Simon’s Town and False Bay, Penguin Blue offers two spacious, comfortable self-catering apartments. The apartments are situated on the hillside of Glen Marine between sea and mountain, making Penguin Blue an excellent holiday destination. Dolphin Apa  …see more

from £40 / night

£280 / week

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from £40 / 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

(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
“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 p  …see more

from £50 / night

£350 / week

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from £50 / 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.<b  …see more

from £250 / night

£1750 / week

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from £250 / 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 £104 / night

£604 / week

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from £104 / night

9

Apartment rental in Simon's Town

Cape Town / Simon's Town

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
A nice little apartment located in safe a friendly neighbourhood. 5 minutes walks to beach and restaurants. Perfect for a couple or small family looking for a comfortable vacation. Seperate entrance, but a part of a larger house. Great pool right by the doorstop. Cars c  …see more

from £44 / night

£216 / week

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from £44 / 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 £179 / night

£1204 / week

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from £179 / night

(1) Excellent 

8

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
Backing onto the mountain above Simonstown, The View boasts a stunning panorama of False Bay from two bedrooms as well as the dining room and lounges. The open plan living area opens out onto a patio which is the ideal spot to soak up the sun and the view of the sea.  …see more

from £180 / night

£1260 / week

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from £180 / 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
Spectacular sea views, self catering home with five bedrooms and bathrooms.  …see more

from £190 / night

£1330 / week

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from £190 / night

20

Holiday apartment rental

Cape Town / Simon's Town

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
Situated directly above the historical town of SImon's Town. Albatross House offers comfortable accommodation and spectacular and uninterrupted views of false bay and the mountains beyond.  …see more

from £82 / night

£488 / week

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from £82 / night

(3) Excellent 

13

Cape Town / Simon's Town

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £44 / night

£285 / week

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from £44 / night

8

Cape Town / Simon's Town

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly

 …see more

from £49 / night

£269 - £843 / week

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from £49 / 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 £163 / night

£976 / week

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from £163 / 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 £109 / night

£1121 / week

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from £109 / 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

 …see more

from £179 / night

£1253 / week

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from £179 / night