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

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24 Holiday homes

Filters applied: Water sports (24)

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

(2) Very Good 

1 / 17

Penguin Blue - Dolphin Self-Catering Apartment

Cape Town / Simon's Town

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: 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

(3) Excellent 

1 / 14

Whale Rock Cottage - Murdoch Valley Simon's Town

Simon's Town / Boulders

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: 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

1 / 17

Break-Away - Simon's Town villa sleeps 8

Cape Town / Simon's Town

4 8 5 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min stay
Key info: 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

1 / 15

Marine View Villa - Historic Mile house sleeps 5

Simon's Town / Historic Mile

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car essential;
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 £70 / night

£731 - £914 / week

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from £70 / night

(3) Very Good 

1 / 18

Penguin Blue - Whale Self-Catering Apartment

Cape Town / Simon's Town

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: 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

1 / 7

Oceanresidence - Historic Mile villa sleeps 8

Simon's Town / Historic Mile

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Suitable for children age 5+; No pets allowed;
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 £150 / night

£1044 / week

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from £150 / night

1 / 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
Key info: Beach / lakeside relaxation; Not suitable for children; 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

(3) Very Good 

1 / 24

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

Cape Town / Simon's Town

3 6 4 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car advised;
Dolphin Cottage is a spacious and comfortable beach house with stunning views overlooking the sea. Every room has a sea view and a balcony. Simons Town is a 5/10 minute walk away, and it makes a perfect location for a holiday.Gated driveway and entrance, secure parki  …see more

from £90 / night

£595 - £1325 / week

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from £90 / night

(4) Very Good 

1 / 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
Key info: 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 £131 / night

£696 - £2566 / week

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from £131 / night

1 / 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
Key info: 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

(7) Excellent 

1 / 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
Key info: 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

£497 - £1451 / week

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from £77 / night

(3) Very Good 

1 / 20

Simon's Town Luxury Studio with 180degree Sea View

Simon's Town / Murdock Valley North

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
Key info: 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

1 / 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
Key info: 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

(2) Very Good 

1 / 23

Boulders Beach House - Boulders guest house sleeps 14

Simon's Town / Boulders

7 14 3 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min stay
Key info: 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 £115 / night

£802 / week

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from £115 / night

(3) Very Good 

1 / 23

Rocklands House - Simon's Town guest house sleeps 8

Cape Town / Simon's Town

4 8 2 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: 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 £168 / night

£1130 / week

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from £168 / night

(4) Excellent 

1 / 16

Cambria - Simon's Town house sleeps 10

Cape Town / Simon's Town

5 10 2 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Suitable for children age 5+; Car advised;
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 £150 / night

£1050 / week

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from £150 / night

1 / 20

Albatross Guest House - Simon's Town apartment sleeps 5

Cape Town / Simon's Town

2 5 1 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Beach / lakeside relaxation; Child friendly ; No pets allowed;
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

£459 / week

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from £77 / night

1 / 6

Cape Town / Simon's Town

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Ask owner if suitable for children;
 …see more

from £32 / night

£210 / week

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from £32 / night

1 / 8

Cape Town / Simon's Town

1 5 1 night min stay

  • 1 bedroom
  • Sleeps 5
  • 1 night min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £46 / night

£252 - £791 / week

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from £46 / night

1 / 15

Cape Town / Simon's Town

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: 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

(2) Very Good 

1 / 11

Cape Town / Simon's Town

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 2 km; Ask owner if suitable for children; Ask about pets;
 …see more

from £32 / night

£210 - £215 / week

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from £32 / night

(7) Very Good 

1 / 25

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.4 km; Swimming pool;
 …see more

from £118 / night

£1096 - £1583 / week

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from £118 / night

(5) Very Good 

1 / 16

Cape Town / Simon's Town

4 8 2 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
 …see more

from £153 / night

£917 / week

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from £153 / night

(6) Very Good 

1 / 10

Cape Town / Simon's Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; Car advised;
 …see more

from £63 / night

£439 - £481 / week

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from £63 / night

Top Destination reviews

La Maison
Amazing views

Good location, large balcony with spectacular views of sunrise over False Bay, built in gas braai, spacious house for 4-6 people (3 bedrooms), well maintained, no problems. … see more

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