Watersports holiday villas and apartments Simon's Town | Holiday Lettings

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28 Holiday homes

Filters applied: Water sports (28)

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

15

Fisherman's Cove on Boulders Beach - Boulders house sleeps 13

Simon's Town / Boulders

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
At Fisherman's Cove, you'll be staying in one of the houses for which the now famous Boulder's Beach at Simons Town was once a private paradise. Incredible views from your bed and breakfast table. Watch the penguins jumping off the rocks in serried ranks  …see more

from £230 / night

£1607 / week

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from £230 / night

(7) Excellent 

21

Cape Town: Boulders Skye - Simon's Town house sleeps 8

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
Large family home with glorious sea and mountain views, a pool, and just a two minute walk from one of Cape Town's most famous beach, Boulders, known for its penguin colony. It is across the road from the Simonstown golf-course, and just 2kms from the quaint and a  …see more

from £77 / night

£500 - £824 / week

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from £77 / night

15

Marine View Villa - Historic Mile house sleeps 5

Simon's Town / Historic Mile

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Beautiful villa, recently renovated, with great views of the marina of Simon's Town with 2 bedrooms, 2 bathrooms, large kitchen, large living room, study room with sofa bed and satellite TV, garden with sea view and outdoor area with mountain view, laundry and gara  …see more

from £130 / night

£725 - £906 / week

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from £130 / night

(3) Excellent 

14

Whale Rock Cottage - Murdoch Valley Simon's Town - Boulders cottage sleeps 2

Simon's Town / Boulders

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Whale Rock Cottage (self-catering) lies behind the famous A-Frame dive-site, with 180 degree views stretching from Millers Point back into False Bay. Enjoy the view of yachts, Naval vessels, dolphins, whales and seals in the bay. Experience the historic village of Simon  …see more

from £60 / night

£400 / week

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from £60 / night

25

Ark Rock Villa - Simon's Town villa sleeps 12

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 £219 / night

£1533 / week

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from £219 / night

10

At Seascapes - Simon's Town house sleeps 6

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) Very Good 

20

Simon's Town Luxury Studio with 180degree Sea View - Murdock Valley North studio sleeps 3

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·Lounge area with c  …see more

from £42 / night

£350 / week

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from £42 / night

(4) Very Good 

18

Neptune Home - Simon's Town house sleeps 8

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
Neptune Home is the perfect location for people who want to explore Caetown and surroundings during their holiday.It is the idea place for a family, a couple or small group of friends who enjoy relaxing in a quiet, secluded hide away while enjoying unsurpassed views ove  …see more

from £130 / night

£690 - £2544 / week

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from £130 / night

(3) Very Good 

24

Dolphin Cottage, Simonstown - Simon's Town cottage sleeps 6

Cape Town / Simon's Town

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Dolphin Cottage is superbly located on the mountain but within easy walking distance of the local town with a choice of restaurants, cafes, shops, chemist and amenities. Dolphin Cottage has amazing views over False Bay from every room (each with its own balcony). You c  …see more

from £140 / night

£925 - £1325 / week

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from £140 / night

17

The Flying Penguin - Penthouse Suite - Boulders penthouse sleeps 4

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 pe  …see more

from £64 / night

£435 / week

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from £64 / night

10

Ark Rock Unit 2 - Simon's Town apartment sleeps 6

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 £109 / night

£761 / week

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from £109 / night

(2) Very Good 

23

Boulders Beach House - Boulders guest house sleeps 14

Simon's Town / Boulders

7 14 3 nights min

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
NEARBY FACILITIES AND ATTRACTIONS:-We are ideally situated to explore the delights of the Western Cape from Cape Point 15minutes away to the Wine lands 45min The Jewel of the False Bay Coastline is a sought after holiday destination for both local and overseas visitors  …see more

from £116 / night

£808 / week

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from £116 / night

17

Break-Away - Simon's Town villa sleeps 8

Cape Town / Simon's Town

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Situated on the rocks in the Castle Rock Marine reserve, you will find this spectacular accommodation for the discerning traveler. The views across False Bay are breathtaking. A modern 300sqm open plan Cape Cod styled Beach House. The central theme has been to bring th  …see more

from £250 / night

£1750 / week

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from £250 / night

(3) Very Good 

18

Penguin Blue - Whale Self-Catering Apartment - Simon's Town apartment sleeps 4

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
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 Apartme  …see more

from £50 / night

£350 / week

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from £50 / night

(3) Very Good 

23

Rocklands House - Simon's Town guest house sleeps 8

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
ROCKLANDS HOUSE, BEACH –FRONT HOLIDAY HOME Murdoch Valley Simon's Town. The perfect weekend getaway or holiday retreat to de-stress and unwind. So tranquil, it feels like you are sailing on your own Ocean Liner!Comfortably furnished, double-storey holiday home ov  …see more

from £170 / night

£1139 / week

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from £170 / night

(2) Very Good 

17

Penguin Blue - Dolphin Self-Catering Apartment - Simon's Town apartment sleeps 2

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 Apartme  …see more

from £40 / night

£280 / week

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from £40 / 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 £64 / night

£442 - £485 / week

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from £64 / 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 £117 / night

£1087 - £1569 / week

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from £117 / night

7

Oceanresidence - Historic Mile villa sleeps 8

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
Big family home situated in quiet, up market residential area. Stunning sea views and lovely sunny deck. Close to a swimming beach and Boulders Beach with the well known penguin colony. About 12km from the entrance to the Cape Point Nature Reserve and 45 min drive from  …see more

from £148 / night

£1035 / week

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from £148 / night

8

Cape Town / Simon's Town

1 5 1 night min

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

 …see more

from £47 / night

£254 - £797 / week

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from £47 / night

(4) Excellent 

16

Cambria - Simon's Town house sleeps 10

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
A beautiful fully self-catering holiday house with stunning views of the most beautiful environment, the Cape Peninsula, False Bay. Situated in Simon's Town, 45 - 60 minutes from the city of Cape Town, the Victoria & Albert Waterfront and Cape Town Internationa  …see more

from £190 / night

£1330 / week

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from £190 / night

13

Ark Rock Unit 1 - Simon's Town apartment sleeps 6

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 £109 / night

£761 / week

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from £109 / night

20

Albatross Guest House - Simon's Town apartment sleeps 5

Cape Town / Simon's Town

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
Boasting magnificent views of historical Simon's Town, False Bay and the mountains beyond, Albatross Guest House overlooks the naval harbour and False Bay Yacht club. Our two bedroom self vcatering apartment is perfect for families or couples who are travveling tog  …see more

from £77 / night

£462 / week

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from £77 / night

(2) Very Good 

11

Cape Town / Simon's Town

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 2 km
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £32 / night

£210 / week

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from £32 / 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 £170 / night

£1185 / week

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from £170 / night

(5) 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 £154 / night

£924 / week

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from £154 / 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

6

Cape Town / Simon's Town

1 2 1 night min

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

 …see more

from £32 / night

£224 / week

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from £32 / 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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