50 Best Vacation Rentals in Simon's Town - Holiday Lettings - Cabins

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78 Vacation rentals

15

Vacation home with swimming pool, golf nearby in Boulders

Simon's Town / Boulders

6 13 2 nights min

  • 6 bedrooms
  • Sleeps 13
  • 2 nights min
  • 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 as they set out …see more

from $293 / night

$2041 / week

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from $293 / night

20

Vacation home with golf nearby in Simon's Town

Simon's Town / Historic Mile

5 8 14 nights min

  • 5 bedrooms
  • Sleeps 8
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Spacious, double storey holiday home in historical Simon's Town (40 minutes from Cape Town). 180 degree views of the sea. 300 metres from the famous Boulder's beach. The house is equipped with everything you will need (including all appliances, boardgames, etc.). Quirky …see more

from $223 / night

$1560 / week

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from $223 / night

17

Vacation home in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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 – the Master bedroo …see more

from $167 / night

$1165 / week

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from $167 / night

(8) Excellent 

10

Vacation 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 mi
  • Suitable for children age 5+
The Rectory is an historic arts and crafts house designed by Sir Herbert Baker (who designed parts of Oxford University, and New Delhi with Lutyens). The house is large, cool and minimalist, with wooden floors and shutters on the windows. It is designed in a way that …see more

from $635 / night

$4445 - $22226 / week

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from $635 / night

8

Vacation home in Simon's Town

Cape Town / Simon's Town

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden
We have a fantastic sea view, we can walk to the beach, we need 5 minutes car at boulders beach (famous penguins beach) and 30 minutes from Cape Town. From the house you can watch the whales and we are nearby to Longbeach and Chapmans Peak. The house it's very conforta …see more

from $113 / night

$786 / week

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Responds fast!
avg. 3 hours 32 minutes

from $113 / night

(1) Good 

20

Simon's Town Vacation 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 $116 / night

$730 - $865 / week

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from $116 / night

(14) Excellent 

18

Boulders Vacation 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 mi
  • Child friendly
This beautifully furnished home is situated in Froggy Pond, a suburb of Simon's Town, just past Boulders beach which is world famous for its penguins. It offers spectacularly breathtaking unobstructed sea views across False bay from every room in the house. 2 mins walk …see more

from $205 / night

$1434 / week

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Responds fast!
avg. 2 hours 5 minutes

from $205 / night

10

Vacation 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 mi
  • 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 $256 / night

$1920 / week

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from $256 / night

(1) Excellent 

32

Vacation apartment in Simon's Town

Cape Town / Simon's Town

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 mi
  • Ask about 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 $81 / night

$565 / week

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from $81 / night

(4) Very Good 

18

Simon's Town Vacation 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 mi
  • 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 …see more

from $137 / night

$955 - $2695 / week

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from $137 / night

15

Vacation 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
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 garage, a …see more

from $113 / night

$786 / week

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Responds fast!
avg. 3 hours 32 minutes

from $113 / night

(1) Excellent 

7

Simon's Town Vacation cottage rental

Cape Town / Simon's Town

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
An original, recently renovated fisherman's cottage, offering spacious living with spectacular views of False Bay. Only 2 minutes from the beach and an excellent swimming and diving spot. Set in a Nature and Marine Reserve far from the madding crowd Thalassa cottage is …see more

from $231 / night

$1274 / week

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from $231 / night

(2) Excellent 

40

Simon's Town Vacation home rental

Cape Town / Simon's Town

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • 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 with fla …see more

from $218 / night

$1524 / week

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from $218 / night

(3) Very Good 

20

Vacation 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 mi
  • 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 ·Loung …see more

from $63 / night

$436 / week

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from $63 / night

(4) Excellent 

24

Vacation home rental

Cape Town / Simon's Town

5 18 2 nights min

  • 5 bedrooms
  • Sleeps 18
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Close to the southernmost tip of Africa, in the Cape Town Village of Simon's Town is where you will find Thalassa, a 5 bedroom, 4 bathroom Seaforth Holiday Villa. This magical family home overlooks Seaforth Beach, is a two minute walk to the more secluded Water's Edge B …see more

from $451 / night

$3151 / week

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from $451 / night

(4) Very Good 

23

Simon's Town Vacation 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 mi
  • 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 ho …see more

from $220 / night

$1481 / week

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from $220 / night

17

Vacation penthouse in Boulders

Simon's Town / Boulders

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • 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 peacefu …see more

from $82 / night

$553 / week

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Responds fast!
avg. 2 hours 7 minutes

from $82 / night

(1) Very Good 

26

Simon's Town Vacation 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 $169 / night

$843 / week

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from $169 / night

5

Apartment rental in Simon's Town

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
The views are marvellous and the furnishing in a style reminiscent of Asia. Our nearest beach is a 5 minute walk away and the shops and eateries plus Simonstown' s Historic Mile are a mere 15 minute walk away You can relax and watch the whales from our balcony in seas …see more

from $52 / night

$333 - $384 / week

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from $52 / night

(2) Very Good 

17

Simon's Town Vacation 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 mi
  • 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 Apartment …see more

from $52 / night

$359 / week

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from $52 / night

(2) Very Good 

23

Simon's Town Vacation 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
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 o …see more

from $150 / night

$1050 / week

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Responds fast!
avg. 3 hours 27 minutes

from $150 / night

15

Home rental 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 mi
  • 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 de …see more

from $140 / night

$980 / week

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Responds fast!
avg. 31 minutes

from $140 / night

(3) Very Good 

22

Vacation cottage in Simon's Town

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Dolphin Cottage is a four bedroom property. It 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 (ea …see more

from $178 / night

$889 - $2382 / week

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from $178 / night

(2) Good 

17

Villa rental in Simon's Town

Cape Town / Simon's Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $320 / night

$2240 - $4480 / week

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from $320 / 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 mi
  • Child friendly
Felsensicht Holiday Home is superbly situated near Boulders Beach, Simon's Town & is ideal for families. It is a large, attractive & wonderfully comfortable home with a 180° view of False Bay from Muizenberg in the north to Cape Point in the south. It is beautifully fur …see more

from $187 / night

$1309 / week

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from $187 / night

89

Vacation villa with golf nearby in Simon's Town

Cape Town / Simon's Town

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
This beautiful Beach Villa has recently opened and so far we are extremely lucky with fantastic reviews. The villa is split into 3 apartments which allows you to close interlocking doors if you need privacy, or open up the doors in order for a large group to entertain. …see more

from $254 / night

$1775 / week

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from $254 / night

26

Vacation penthouse in Simon's Town

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
Situated within 850 m of a swimming beach, Seabreeze Luxury Two Bedroom Self Catering Penthouse is located on the outskirts of Simon’s Town. Overlooking False Bay, this property is 1.5 km from Boulders Beach and the renown African Penguin Colony. Seabreeze features a f …see more

from $200 / night

$1400 / week

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from $200 / night

(2) Excellent 

9

Vacation 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 mi
  • 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 $229 / night

$1601 / week

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from $229 / night

11

Vacation studio in Simon's Town

Cape Town / Simon's Town

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Ask about children
Studio 2 with Partial Sea View and Private Patio with BBQ - Sleeps 2 ·Our 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 ·Flat screen TV with sel …see more

from $50 / night

$327 / week

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from $50 / night

8

Vacation 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 $58 / night

$404 / week

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from $58 / night

14

Vacation studio with golf nearby in Simon's Town

Cape Town / Simon's Town

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Roman Rock Accommodation Studio 1 with outside Wooden Deck and Beautiful 180 Degree Sea View - ·This studio Sleeps 2 ·This studio has a large queen bed and a desk where you can sit and work/study ·Inside you have a Lounge area with chairs and a coffee table, as well as …see more

from $61 / night

$427 / week

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from $61 / night

(1) Excellent 

14

Vacation 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
Dunearn is a beautiful family home with tall ceilings, open fires, antique furniture and a long balcony/terrace that allows sea and mountain views from every part of the house. Lovingly cared for over the last century by several generations of the same family, the brass …see more

from $301 / night

$2087 / week

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from $301 / night

13

Vacation home in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Wake up and fall asleep to the sound of the ocean. Watch the whales in season from your lounge breaching and frolicking with their young! Gaze at the stunning, uninterrupted sea views and savor the ever changing sunrises and romantic sunsets on cool evenings while enjoy …see more

from $95 / night

$600 / week

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from $95 / night

(4) Excellent 

16

Simon's Town Vacation home accommodation

Cape Town / Simon's Town

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 International airport …see more

from $205 / night

$1434 / week

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from $205 / night

(3) Very Good 

18

Vacation 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 mi
  • 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 Apartment …see more

from $64 / night

$448 / week

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from $64 / night

63

Vacation home in Simon's Town

Cape Town / Simon's Town

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
On the iconic Klein Tuin Road watch the penguins come marching past the gate. This beautiful home has recently been built and boasts beautiful marble throughout the house. Wonderful views and windows throughout make this a home that is bathed in sunlight. This home i …see more

from $295 / night

$2061 / week

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from $295 / night

20

Simon's Town Vacation apartment rental

Cape Town / Simon's Town

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 1 mi
Simonsberg is a self catering apartment located in Simon's Town, a historic town situated along the False Bay coast of Cape Town, in the Western Cape. This top floor apartment (three flights of stairs), boasts breathtaking uninterrupted sea and mountain views. This cos …see more

from $55 / night

$385 / week

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from $55 / night

22

Vacation apartment in Simon's Town

Cape Town / Simon's Town

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 mi
  • Ask about 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 $84 / night

$583 / week

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from $84 / night

25

Simon's Town Vacation villa rental

Cape Town / Simon's Town

6 12 2 nights min

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
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-suite ba …see more

from $262 / night

$1832 / week

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from $262 / night

14

Vacation 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 establishment is a WiFi zone, so you …see more

from $52 / night

$359 / week

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from $52 / night

1