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

Close

Simon's Town

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,402 Vacation rentals

13

Vacation home 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
  • 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 $118 / night

$795 - $850 / week

Book View

from $118 / night

14

Cottage rental in Simon's Town

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Pet friendly
This beautiful cottage was recently refurbished very tastefully and gives wonderful sea views. The cottage is ideal for 2-4 people and has a lovely outside deck area. It boosts 2 bedrooms and 2 bathrooms, both bathrooms very large, with large showers and a bath. The …see more

from $133 / night

$928 / week

Book View

from $133 / night

(2) Excellent 

22

Vacation apartment rental

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
This apartment is newly built, very modern, very light and spacious, with lots of windows with the sea view around you. It has a very large open plan kitchen and entertainment area, with a seperate full lounge with flat screen TV and Satelite TV (Sports and Movies). A …see more

from $100 / night

$696 / week

Book View

from $100 / night

(1) Excellent 

14

Vacation apartment in Simon's Town

Cape Town / Simon's Town

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
La Pergola is located high on the mountainside above Simon's Town with breathtaking views over False Bay, surrounding mountains and the historic naval harbour. It is an ideal romantic getaway or base to explore the town. A 10 minute walk will take you to the town wit …see more

from $103 / night

$721 / week

Book View

from $103 / night

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 $398 / night

$2,130 - $2,687 / week

Book View

from $398 / night

(3) 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 $279 / night

$1,949 / week

Book View

from $279 / night

(8) 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 $450 / night

$3,150 / week

Book View

from $450 / 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 $174 / night

$1,216 / week

Book View

from $174 / 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
  • Private garden
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 $117 / night

$813 / week

Book View

from $117 / night

(1) Excellent 

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
  • Child friendly
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 $87 / night

$603 / week

Book View

from $87 / 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 $116 / night

$813 / week

Book View

from $116 / night

(37) Excellent 

32

Vacation villa rental

Cape Town / Simon's Town

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Camilla is a recently restored four bedroom individually designed villa with plunge pool, which is situated in a safe residential area within walking distance of the beach and local shops. The through lounge diner is comfortably furnished and leads to the well equippe …see more

from $94 / night

$656 - $1,385 / week

Book View

Responds fast!
avg. 1 hour 32 minutes

from $94 / night

(1) Excellent 

31

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
  • Child friendly
  • 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 $83 / night

$576 / week

Book View

from $83 / night

10

Vacation home with swimming pool, golf nearby in Simon's Town

Cape Town / Simon's Town

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 $193 / night

$1,346 / week

Book View

from $193 / night

(14) Excellent 

18

Boulders Vacation home rental

Simon's Town / Boulders

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • 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 $213 / night

$1,488 / week

Book View

Responds fast!
avg. 2 hours 59 minutes

from $213 / night

19

Bungalow rental in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Lobster Pot is an old family cottage that has been the location of many a memorable holidays down at the sea, snorkeling in the marine reserve, paddling around the rocky islands and going for hikes up the mountain. The Lobster Pot is a cosy little wooden cottage tha …see more

from $148 / night

$1,036 / week

Book View

from $148 / 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 $305 / night

$2,134 / week

Book View

from $305 / 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 $203 / night

$1,045 - $2,669 / week

Book View

from $203 / 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 $125 / night

$876 - $965 / week

Book View

from $125 / 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 $232 / night

$1,625 / week

Book View

from $232 / 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 $239 / night

$1,319 / week

Book View

from $239 / night

(5) Excellent 

10

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 $240 / night

$1,674 / week

Book View

from $240 / night

15

Vacation home rental

Cape Town / Simon's Town

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
A spectacular entire villa with sea views, a quiet oasis on the hillside of Glencairn overlooking interesting historic buildings of Simonstown. The house can accommodate up to six guests and is made up of three bedrooms, two bathrooms and two living areas. There are s …see more

from $80 / night

$557 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from $80 / night

(3) Very Good 

20

Vacation studio with golf nearby in Simon's Town

Simon's Town / Murdock Valley North

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • 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 $73 / night

$511 / week

Book View

from $73 / 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 $312 / night

$2,161 / week

Book View

from $312 / night

15

Vacation apartment with swimming pool, golf nearby in Simon's Town

Cape Town / Simon's Town

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
•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 with S …see more

from $73 / night

$511 / week

Book View

from $73 / 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 $67 / night

$398 / week

Book View

from $67 / night

(10) Excellent 

24

Guest house rental in Simon's Town with golf nearby

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 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 $244 / night

$1,707 / week

Book View

Responds fast!
avg. 1 hour 14 minutes

from $244 / 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 $663 / night

$4,639 - $23,193 / week

Book View

from $663 / night

20

Vacation apartment in Simon's Town

Cape Town / Simon's Town

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
Casabella is perfectly situated in the heart of the historic town of Simons Town on the Cape Peninsula. It has beautiful views over False Bay and is situated directly overlooking the Naval Base. The 3 bedroomed apartment is fully equipped with all the necessities to en …see more

from $126 / night

$882 / week

Book View

from $126 / 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

$1,480 / week

Book View

Responds fast!
avg. 1 hour 3 minutes

from $220 / 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 $116 / night

$813 / week

Book View

from $116 / night

(4) Excellent 

16

Simon's Town Vacation home accommodation

Cape Town / Simon's Town

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 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 International airport …see more

from $239 / night

$1,670 / week

Book View

from $239 / 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
  • 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 $52 / night

$338 / week

Book View

from $52 / 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 $120 / night

$840 / week

Book View

from $120 / 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 $60 / night

$419 / week

Book View

from $60 / 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
  • 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 $87 / night

$603 / week

Book View

from $87 / 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 $59 / night

$371 / week

Book View

from $59 / night

28

Vacation apartment in Simon's Town

Cape Town / Simon's Town

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning
This is a cottage feel apartment, with beautiful sea views over false bay with the Hottentots Hollands mountains on the opposite of the sea. The apartment is very spacious and has 2 bedrooms and bathrooms for a family or for 2 couples and or singles. Come and enjoy a …see more

from $100 / night

$696 / week

Book View

from $100 / 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 $53 / night

$371 / week

Book View

from $53 / night