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Simon's Town

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55 Holiday homes

Filters applied: Parking (55)

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

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

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 £88 / night

£737 - £922 / week

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from £88 / 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 £84 / night

£542 - £892 / week

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from £84 / 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 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
•Well Equipped Kitchenette with Granite Worktop, 2 plate stove, Microwave, Toaster, Kettle and Coffee Machine •Extra Large Double Room with Queen Bed, Single Bed and Built In Wardrobes, Dressing Table and Stool •Living room with Leather Couches and Flat S  …see more

from £42 / night

£294 / week

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from £42 / night

(3) Very Good 

25

Holiday cottage in Simon's Town

Cape Town / Simon's Town

4 6 4 nights min

  • 4 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Flexible beds, as two of the bedrooms can be made up as either twin beds or super king size doubles  …see more

from £140 / night

£700 - £1100 / week

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from £140 / night

(3) Very Good 

20

Holiday studio with golf nearby in Simon's Town

Simon's Town / Murdock Valley North

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Studio 4 - Luxury Studio with Balcony and Spectacular Sea View·This studio is very spacious and has the best sea view of all of the studios·Studio has just been fully renovated, so new bathroom with Shower, and new kitchenette with granite work  …see more

from £49 / night

£350 / week

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from £49 / night

(13) 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

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
At Seascapes offers a secure and peaceful seaside location close to historic Simonstown on the False Bay coast. The house is well appointed, well equipped and offers spectacular views over False Bay. A five minute walk will take you to fishermans beach (featured on Get  …see more

from £150 / night

£1050 / week

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from £150 / night

(3) Excellent 

14

Simon's Town holiday cottage rental

Simon's Town / Boulders

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Whale watching from your private deck (in season). Boulders Beach less than 5 minutes by car / 15 minute walk. Penguin viewing at Boulders Beach.Historic Simon's Town.Close to Cape Point.Private heated splash-pool.Private garden with an array of bird-life.<br /&  …see more

from £60 / night

£400 / week

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from £60 / 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 £117 / night

£817 / week

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from £117 / night

(2) Excellent 

40

Simon's Town holiday home rental

Cape Town / Simon's Town

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Child friendly
This is a large house that was converted into 4 self contained Studios that allows for big groups to stay whilst having their self contained unit within the building with private access, rooms, kitchenette's, bathroom with shower, Lounge area and or seating are wit  …see more

from £230 / night

£1610 / week

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from £230 / 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 £176 / night

£746 - £2106 / week

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from £176 / 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

(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

(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 £292 / night

£2042 / week

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from £292 / 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

(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
This top floor apartment boosts with amazing views of the ocean - 180 degree views of the sea from your living room really makes this apartment. The apartment has been furnished to a cottage style with white wooden floors, kitchenette with granite worktops, flat screen  …see more

from £65 / night

£455 / week

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from £65 / 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 £125 / night

£875 / week

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from £125 / 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
  • Ask owner if suitable for children
Studio 2 with Partial Sea View and Private Patio with BBQ - Sleeps 2 ·Our smallest studio has a queen bed, with lounge chairs and flat screen TV ·Studio has just been fully renovated, so new bathroom with Shower, and new kitchenette with granite worktops &  …see more

from £39 / night

£255 / week

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from £39 / 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

(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

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
New listing: Unlimited, uninterrupted sea-views from this large, modern, open plan apartment (top floor of a double story home with own entrance). Full kitchen, separate bathroom (shower only). Just a few minutes walk from beautiful beaches and on the edge of the Cape P  …see more

from £50 / night

£350 / week

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from £50 / night

14

Holiday studio rental

Cape Town / Simon's Town

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Child friendly
Studio 3 with Balcony and Sea View - Sleep 2 ·This studio is a nice and spacious with a good sea view ·Has queen bed with sofa and chairs to watch TV, and dining table ·Flat screen TV with selected DSTV channels (Hotel Package) ·The establish  …see more

from £40 / night

£280 / week

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from £40 / 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 £184 / night

£1234 / week

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from £184 / night

22

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
This is a Superior One Bedroom Beach Apartment, largest of the 3 self contained apartments with a 180 degree Sea View within a Villa. A lot of detail on modern yet luxury furniture, built in bay window in order to read a book whilst watching the sea, and areas for comfo  …see more

from £65 / night

£455 / week

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from £65 / 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

8

Holiday apartment in Simon's Town

Cape Town / Simon's Town

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Child friendly
This is a very simple self-catering home - wooden floors ... set against mountain - spectacular views. from every window... Mountain behind and entire view of False Bay at your feet. Access to spectacular beaches.... Surrounded by nature.... An ideal retreat for nature  …see more

from £45 / night

£315 / week

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from £45 / 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 

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

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
Harbour Lights is nestled between mountain and sea and offers you affordable, comfortable, relaxed spacious self-catering accommodation with superb patio and wooden deck for relaxing and outdoor entertainment, braais etc. It has endless panoramic views of the whole of t  …see more

from £97 / night

£609 - £721 / week

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from £97 / 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

£492 / week

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from £82 / 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

 …see more

from £59 / night

£409 / week

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from £59 / night

17

Cape Town / Simon's Town

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children

 …see more

from £34 / night

£236 - £528 / week

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from £34 / night

10

Cape Town / Simon's Town

2 4 7 nights min

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

 …see more

from £80 / night

£555 / week

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from £80 / night

(2) 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

£290 / week

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from £44 / night

17

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool

 …see more

from £133 / night

£930 - £1900 / week

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from £133 / night

26

Cape Town / Simon's Town

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from £123 / night

£858 - £1290 / week

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from £123 / 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 £132 / night

£922 / week

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from £132 / night

13

Cape Town / Simon's Town

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.5 km
  • Child friendly
  • Pet friendly

 …see more

from £84 / night

£534 / week

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from £84 / night