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

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87 Vacation rentals

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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 gara  …see more

from $161 / night

$897 - $1122 / week

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from $161 / night

(12) 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 $202 / night

$1412 / week

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from $202 / night

(7) Excellent 

21

Vacation 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 mi
  • 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 $101 / night

$656 - $1079 / week

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from $101 / 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 $189 / night

$1323 / week

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from $189 / night

40

Simon's Town Vacation 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 with fla  …see more

from $290 / night

$2029 / week

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from $290 / night

(3) Excellent 

14

Simon's Town Vacation 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 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 $76 / night

$504 / week

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from $76 / night

(4) Very Good 

18

Simon's Town Vacation 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 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 $216 / night

$970 - $3177 / week

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from $216 / night

(1) Excellent 

7

Simon's Town Vacation cottage rental

Cape Town / Simon's Town

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • 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 $177 / night

$1197 / week

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from $177 / night

15

Vacation 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
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 $290 / night

$2025 / week

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from $290 / night

(2) Excellent 

10

Vacation apartment rental

Simon's Town / Murdock Valley North

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This light, airy self-catering apartment in close to the beach and offers breathtaking 180 degree views of False Bay.It accommodates 4. The bedroom sleeps 2, with the choice of kingsize or twin beds. The spacious living area has a sofa bed with pull out which  …see more

from $84 / night

$583 / week

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from $84 / 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·Lo  …see more

from $62 / night

$441 / week

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from $62 / night

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 $162 / night

$808 / week

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from $162 / night

(2) Excellent 

20

Vacation 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
This charming clapperboard house perched on a gentle slope overlooking Boulders Beach is the stuff of holiday dreams. With a mountain behind and all about the sea, it is the perfect place in which to restore, rejuvenate and renew. Sensitively configured for both private  …see more

from $353 / night

$4234 / week

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from $353 / night

20

Vacation 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, 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  …see more

from $157 / night

$1099 / week

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from $157 / 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
  • 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 $82 / night

$574 / week

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from $82 / night

25

Simon's Town Vacation 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 $274 / night

$1915 / week

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from $274 / night

(3) 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-st  …see more

from $222 / night

$1492 / week

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from $222 / night

17

Vacation 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 pe  …see more

from $81 / night

$549 / week

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from $81 / night

10

Vacation 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 $136 / night

$950 / week

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from $136 / night

16

Simon's Town Vacation villa rental

Cape Town / Simon's Town

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
2 bedroom, studio, 2 bathroom, living room, dining room, deck, garden with a fantastic view on the False Bay, garden on the back with view on the montain, laundry, garage.  …see more

from $130 / night

$754 / week

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from $130 / night

17

Vacation 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 about 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 Screen TV  …see more

from $53 / night

$371 / week

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from $53 / 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 $152 / night

$1059 / week

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from $152 / 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  …see more

from $51 / night

$353 / week

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from $51 / night

5

Vacation 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 $61 / night

$424 / week

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from $61 / 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 b  …see more

from $184 / night

$1288 / week

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from $184 / 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 $51 / night

$328 - $378 / week

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from $51 / night

(1) Excellent 

8

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 $227 / night

$1588 / week

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from $227 / night

11

Vacation 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 about 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 ·Flat screen  …see more

from $50 / night

$322 / week

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from $50 / 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
  • 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 $82 / night

$574 / week

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from $82 / 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 $271 / night

$1764 - $2451 / week

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from $271 / night

9

Apartment rental in Simon's Town

Cape Town / Simon's Town

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
A nice little apartment located in safe a friendly neighbourhood. 5 minutes walks to beach and restaurants. Perfect for a couple or small family looking for a comfortable vacation. Seperate entrance, but a part of a larger house. Great pool right by the doorstop. Cars c  …see more

from $54 / night

$270 / week

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from $54 / night

14

Vacation studio with golf nearby in Simon's Town

Cape Town / Simon's Town

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • 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  …see more

from $81 / night

$565 / week

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from $81 / night

10

Cape Town / Simon's Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

 …see more

from $96 / night

$671 / week

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from $96 / night

7

Villa rental in Simon's Town with golf nearby

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 $185 / night

$1293 / week

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from $185 / 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 Apartme  …see more

from $51 / night

$353 / week

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from $51 / 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 mi
  • Swimming pool

 …see more

from $162 / night

$1357 - $1734 / week

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from $162 / night

27

Cape Town / Simon's Town

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

 …see more

from $192 / night

$1341 / week

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from $192 / 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 $297 / night

$2054 / week

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from $297 / 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 $57 / night

$397 / week

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from $57 / 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 Apartme  …see more

from $63 / night

$441 / week

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from $63 / night

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