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Holiday homes in Simon's Town and Chalets - Holiday Lettings - Holiday Rentals Simon's Town

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1,286 Holiday homes

Holiday cottage in Simon's Town

Simon's Town cottage

1 bedroom • 1 bathroom • sleeps 3

from £58 / night

£315 / week

1 / 8

Simon's Town holiday home rental

Simon's Town house

3 bedrooms • 3 bathrooms • sleeps 6

from £332 / night

£2,325 / week

1 / 17

Villa rental in Simon's Town with shared pool

Simon's Town villa

2 bedrooms • 2 bathrooms • sleeps 6

from £96 / night

£668 / week

1 / 20

Holiday villa with shared pool in Simon's Town

Simon's Town villa

6 bedrooms • 4 bathrooms • sleeps 12

from £344 / night

£2,233 - £2,714 / week

1 / 24

Holiday apartment in Simon's Town

Simon's Town apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £109 / night

£762 / week

1 / 20

Holiday apartment in Simon's Town

Simon's Town apartment

2 bedrooms • 1 bathroom • sleeps 6

from £80 / night

£505 / week

1 / 10

Holiday studio in Simon's Town

Simon's Town studio

Studio • 1 bathroom • sleeps 2

from £55 / night

£353 / week

1 / 42

Holiday studio in Simon's Town

Simon's Town studio

Studio • 1 bathroom • sleeps 2

from £55 / night

£353 / week

1 / 19

Simon's Town holiday apartment rental

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £55 / night

£337 / week

1 / 6

Holiday home in Simon's Town

Simon's Town house

3 bedrooms • 1 bathroom • sleeps 6

from £227 / night

£1,681 / week

1 / 7

Holiday villa in Simon's Town

Simon's Town villa

3 bedrooms • 2 bathrooms • sleeps 6

from £181 / night

£1,265 / week

1 / 21

Holiday apartment rental

Simon's Town apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £92 / night

£642 / week

1 / 21

Holiday cottage in Simon's Town

Simon's Town cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £70 / night

£489 / week

1 / 17

Holiday apartment in Simon's Town

Simon's Town apartment

2 bedrooms • 1 bathroom • sleeps 3

from £52 / night

£361 / week

1 / 8

Simon's Town holiday apartment rental

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £72 / night

£501 / week

1 / 27

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £101 / night

£706 / week

1 / 5

Simon's Town holiday cottage rental

Simon's Town cottage

3 bedrooms • 2 bathrooms • sleeps 6

from £63 / night

£442 - £1,324 / week

1 / 14

Simon's Town holiday home rental

Simon's Town house

4 bedrooms • 3 bathrooms • sleeps 8

from £123 / night

£858 - £2,193 / week

1 / 18

Holiday cottage in Simon's Town

Simon's Town cottage

2 bedrooms • 2 bathrooms • sleeps 5

from £57 / night

£355 - £584 / week

1 / 18

Holiday apartment rental

Simon's Town apartment

2 bedrooms • 6 bathrooms • sleeps 5

from £84 / night

£505 / week

1 / 20

Holiday home with swimming pool in Simon's Town

Simon's Town house

4 bedrooms • 4 bathrooms • sleeps 8

Pricing unknown

1 / 18

Holiday home in Simon's Town

Simon's Town house

2 bedrooms • 2 bathrooms • sleeps 5

from £172 / night

£1,201 / week

1 / 15

Simon's Town holiday apartment rental

Simon's Town apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £68 / night

£471 / week

1 / 21

Holiday home in Simon's Town

Simon's Town house

3 bedrooms • 2 bathrooms • sleeps 5

from £172 / night

£1,201 / week

1 / 8

Holiday b&b in Simon's Town

Simon's Town b&b

1 bedroom • 6 bathrooms • sleeps 2

from £106 / night

£743 / week

1 / 5

Simon's Town holiday apartment rental

Simon's Town apartment

3 bedrooms • 1 bathroom • sleeps 6

from £98 / night

£573 / week

1 / 53

Holiday apartment with shared pool in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £55 / night

£383 / week

1 / 10

Holiday home in Simon's Town

Simon's Town house

2 bedrooms • 2 bathrooms • sleeps 4

from £101 / night

£564 / week

1 / 12

Simon's Town holiday cottage rental

Simon's Town cottage

3 bedrooms • 1 bathroom • sleeps 5

from £207 / night

£1,140 / week

1 / 7

Holiday apartment with shared pool in Simon's Town

Simon's Town apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £105 / night

£736 / week

1 / 12

Simon's Town holiday apartment rental

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £47 / night

£324 / week

1 / 20

Simon's Town holiday home rental

Simon's Town house

3 bedrooms • 3 bathrooms • sleeps 6

Pricing unknown

1 / 26

Holiday apartment in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £87 / night

£606 / week

1 / 14

Simon's Town holiday villa rental

Simon's Town villa

2 bedrooms • 2 bathrooms • sleeps 5

from £172 / night

£1,201 / week

1 / 16

Holiday penthouse in Simon's Town

Simon's Town penthouse

2 bedrooms • 3 bathrooms • sleeps 4

from £169 / night

£1,177 / week

1 / 26

Holiday villa rental

Simon's Town villa

4 bedrooms • 2 bathrooms • sleeps 7

“Brilliant house to relax in” We all enjoyed staying in this well furnished family home which is in a quiet area. The beach at Fish Hoek nearby was lovely and had fun body boarding. We enjoyed a family barbecue and used the plunge pool to cool off on the hottest days. Most of all loved the views from all the rooms at the front -miss having breakfast outside with such a view !

from £103 / night

£567 - £1,403 / week

1 / 25

Simon's Town holiday home rental

Simon's Town house

4 bedrooms • 3 bathrooms • sleeps 10

from £295 / night

£2,060 / week

1 / 78

Holiday apartment in Simon's Town

Simon's Town apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £89 / night

£618 / week

1 / 19

Holiday apartment with swimming pool in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £150 / night

£1,048 / week

1 / 21

Holiday apartment with golf nearby in Simon's Town

Simon's Town apartment

1 bedroom • 1 bathroom • sleeps 2

from £34 / night

£219 / week

1 / 13

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Top Destination reviews

The Rectory
Historic Simon's town at its best!

Witness, our host, is an absolute legend. He was friendly and always happy to clean up after us. Beautiful family home. A bit pricy but all in all a great holiday. … see more
Camilla
Beautiful property

Four of us stayed at this property over New Year , as we were going to the Cricket at Newlands. It is located in Glencairn Heights , which is near a petrol station , Spa and Liquor store. There are also a couple of bars nearby , we spent New Year in the Stoep and Swing which is a really nice friendly relaxed bar that also has good food. Dixies is about a ten minute walk away, as is the train station. The trains were not running from Glencairn as maintenance on the track is happening currently. However there is a bus replacement service which takes you to Fish Hoek station where you can get the train. This was a nice way to get to Newlands. Glencairn is in a nice area being between Kalk Bay and Simons Town ( so near to the Penguins) . The views are lovely as well . As for 11 Camilla it is kept to such a high standard , the décor is tasteful and neat , and it was all kept very clean. The rooms are good sizes , and it was lovely to have the various outdoor spaces as the sun moved around. The kitchen is incredibly well stocked with all the equipment you will ever need. Wi-Fi is available , but you will need to buy the data , this is all clearly explained in the information pack , which has lots of helpful advice and notes. There are plenty of guides and leaflets for you to peruse as well. Pat the owner responses to any emails sent very quickly and is very helpful. All four of us loved our stay there and it really did become our home for the nine nights we stayed, and we were sad to leave.see more

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