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17 Holiday homes

Filters applied: Cycling holidays (17)

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

(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

(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 £169 / night

£757 - £2479 / week

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from £169 / 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

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from £276 / 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 worktops·Lo  …see more

from £49 / night

£350 / week

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from £49 / 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

10

Holiday apartment in Simon's Town

Cape Town / Simon's Town

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
rk Rock – Unit 2 - Downstairs unit. A beautiful self-catering three bedroom unit which is part of the Villa, the bottom unit. Situated in the coastal suburb of Simons Town, it offers lovely sea views and is within easy walking distance to secluded beaches and the harb  …see more

from £106 / night

£742 / week

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from £106 / night

25

Simon's Town holiday villa rental

Cape Town / Simon's Town

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
Ark Rock Villa – Simon’s Town A beautiful self-catering six bedroom villa situated in the coastal suburb of Simons Town. It offers lovely sea views and is within easy walking distance to secluded beaches and the harbour. The top level has three bedrooms, 1 en-suit  …see more

from £214 / night

£1495 / week

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from £214 / 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

(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 £174 / night

£1166 / week

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from £174 / 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.Spark  …see more

from £250 / night

£1750 / week

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from £250 / 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 £111 / night

£772 / week

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from £111 / night

13

Holiday apartment in Simon's Town

Cape Town / Simon's Town

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
Ark Rock – Unit 1 -Upstairs Unit A beautiful self-catering three bedroom unit which is part of the Villa, the top unit. Situated in the coastal suburb of Simons Town. It offers lovely sea views and is within easy walking distance to secluded beaches and the harbour.  …see more

from £106 / night

£742 / week

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from £106 / 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 £79 / night

£473 / week

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from £79 / 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

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from £158 / 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

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 £174 / night

£1213 / week

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from £174 / 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