50 Best Vacation Rentals in Overberg District - Holiday Lettings - Cabins

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Overstrand
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Napier
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Cape Agulhas
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Betty's Bay
11 properties
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6 properties

Overberg District

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262 Vacation rentals

11

Vacation guest house in Hermanus

Overstrand / Hermanus

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
The Vishuis is a stylish guesthouse situated in the heart of the old village in Hermanus. It is a newly renovated and modernized heritage fisherman's cottage. It has all the mod cons for guests to luxuriate, but has the whimsy of yesteryear. It is is conveniently situ …see more

from $80 / night

$560 / week

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Responds fast!
avg. 1 hour 43 minutes

from $80 / night

(1) Excellent 

28

Vacation home with swimming pool in Kleinmond

Overstrand / Kleinmond

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
Come and enjoy life in the slow lane - just 83 kilometres from Cape Town on very good tarred roads. Situated on an internationally acclaimed golf estate, close to the world renowned whale watching resort of Hermanus and Kleinmond, casual luxury on every level awaits y …see more

from $250 / night

$1,350 - $2,200 / week

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avg. 3 hours 45 minutes

from $250 / night

(3) Very Good 

25

Vacation home with shared pool in Hermanus

Overstrand / Hermanus

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Hermanus is the world’s foremost land based whale watching destination and it is here where you will find our beach house. A stylish decorated beach house situated on a private beach in Hermanus with magnificent sea views opening out to a kitchen/lounge/dining. 3 bedro …see more

from $139 / night

$973 / week

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from $139 / night

(2) Very Good 

14

Gansbaai Vacation home rental

Overstrand / Gansbaai

4 6 2 nights min

  • 4 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Built on a special location. An Architectural designed double storey house. A 160 degrees sea-view. Ground Floor: Lounge and dining room with an open-plan kitchen Bedroom and full bathroom A Spacious room with an BBQ Top Floor: Two bedroo …see more

from $226 / night

$875 / week

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Responds fast!
avg. 2 hours 17 minutes

from $226 / night

(2) Very Good 

12

Betty's Bay Vacation apartment rental

Overberg District / Betty's Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
This is a lovely downstairs apartment which is within a 100 meter walk to beautiful Silversands beach, it sleeps 4 adults comfortably but we also have blow up mattresses if needed for children. If you love long walks along the beach, playing in the surf, braai's (barbe …see more

from $70 / night

$420 / week

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Responds fast!
avg. 3 hours 12 minutes

from $70 / night

16

Vacation home in Kleinmond

Overstrand / Kleinmond

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
Situated on the picturesque Cape Whale Coast Route, in the village of Kleinmond, which is just an hours drive from Cape Town, Picollo Bocca Villa offers spacious accommodation with that “home away from home” feeling. At 700m walking distance from the Palmiet Beach, this …see more

from $156 / night

$1,086 / week

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from $156 / night

(5) Excellent 

15

Vacation cottage in Hermanus

Overstrand / Hermanus

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 0.3 mi
  • Child friendly
  • Pet friendly
Snails' End Cottage is an owner run establishment, close to the sea and many walking areas. It is situated on a quiet street and is a five minute drive from the centre of town. Close proximity to restaurants, three golf courses, shark cage diving and whale sighting bo …see more

from $57 / night

$353 / week

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Responds fast!
avg. 3 hours 16 minutes

from $57 / night

11

Vacation cottage rental

Hermanus / Stanford Village

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Loving restored labourers' cottage with a thatch roof in core architectural conservation area. Fireplace (Queen Anne) Large covered patio with braai (barbecue) facilities: ideal for outdoor entertaining and summer meals. Enclosed garden with many nooks and crannies Se …see more

from $69 / night

$437 / week

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from $69 / night

23

Apartment rental in Hermanus with shared pool

Overstrand / Hermanus

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
Situated in Hermanus on the southern coast of South Africa, bordered by the Atlantic and Indian oceans on one side and by the Kleinrivier mountains on the other. Hermanus is considered one of the best land based whale watching destinations in the world. This apartment …see more

from $99 / night

$693 / week

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from $99 / night

(17) Excellent 

Certificate of Excellence

27

Hermanus Vacation apartment rental

Overstrand / Hermanus

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Quiet and sought-after apartment complex located directly on the sea front Breathtaking sea-front lounge area with unparalleled 180' vista across Walker Bay allowing arm-chair whale watching from the windows 3rd (top) floor situation adjacent to lifts/stairwell Sea-faci …see more

Certificate of Excellence

from $140 / night

$978 - $2,063 / week

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Responds fast!
avg. 3 hours 33 minutes

from $140 / night

(2) Excellent 

82

Vacation home rental

Overberg District / Betty's Bay

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Nestled among hectares of pristine fynbos on the slopes of the mountain, the our house offers sea views from literally every room. Vaya con Dios is a modern 4-bedroom house that overlooks Jock's Bay and borders the hundred thousand hectare UNESCO-designated Kogelberg …see more

from $165 / night

$1,095 - $1,365 / week

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from $165 / night

9

Vacation home in Pringle Bay

Overstrand / Pringle Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Named after a lighthouse overlooking Vineyard Sound in Cape Cod Massachusetts Nobska House is located in the heart of beautiful Pringle Bay. It's open plan living area with French windows opening onto a courtyard surrounded by local fynbos is perfect for "al fresco" din …see more

from $170 / night

$1,190 / week

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from $170 / night

(6) Excellent 

12

Cottage rental in Greyton with swimming pool

Overberg District / Greyton

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Greyton Small House, Greyton, South Africa If you are looking for a true Greyton cottage, with a wonderful garden and sparkling big pool, but also for a well equipped kitchen, an eclectic style in the house, a home away from home feeling - you are welcome to the Greyton …see more

from $175 / night

$861 - $1,242 / week

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Responds fast!
avg. 52 minutes

from $175 / night

(3) Very Good 

17

Vacation apartment with shared pool in Hermanus

Overstrand / Hermanus

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The apartment is on the ground floor with an entertaining garden and sea views. From the apartment take your sundowner in hand and walk down the boardwalk to the beach and enjoy spectacular sunset and ocean views and watch the whales frolic in season (June to October a …see more

from $100 / night

$700 / week

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from $100 / night

11

Guest house rental in Hermanus with shared pool

Overstrand / Hermanus

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
The Vishuis is a stylish guesthouse situated in the heart of the old village in Hermanus. It is a newly renovated and modernized heritage fisherman's cottage. It has all the mod cons for guests to luxuriate, but has the whimsy of yesteryear. It is is conveniently situ …see more

from $80 / night

$560 / week

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Responds fast!
avg. 1 hour 43 minutes

from $80 / night

(4) Good 

14

Vacation apartment with shared pool in Hermanus

Overstrand / Hermanus

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Exceptionally positioned these luxury serviced apartments offer guests breathtaking ocean views and the perfect location from which to explore the eclectic town of Hermanus. Modern, luxurious and superbly appointed these sea-facing apartments are fully equipped and feat …see more

from $187 / night

$1,305 - $1,561 / week

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from $187 / night

18

Vacation apartment rental

Overstrand / Hermanus

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
Fully equipped, clean and neat Penthouse unit (Top floor) at Hermanus Beach Club. Absolutely stunning 360 degree view of sea and mountains.Hermanus Beach Club which is only 1 hours drive from Cape Town. It is a 24 hour security complex with loads of entertainment for bo …see more

from $90 / night

$580 / week

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from $90 / night

(31) Excellent 

31

Vacation villa rental

Overstrand / Gansbaai

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Perched on the ocean's edge, Whale Huys has beautiful unobstructed sea views from all living areas, dining areas and bedrooms. Fall asleep and wake to the sound of the waves gently lapping at the rocks below. Each of the four bedroom opens onto its own sea front balcony …see more

from $298 / night

$1,673 - $3,469 / week

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from $298 / night

(1) Very Good 

15

Villa rental in Botrivier with swimming pool

Overberg District / Botrivier

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Beautifully located at the secure Benguela Cove Wine Estate, with absolute stunning views over the lagoon, sea and the overberg maintains. Has 3,5 bedroom, 3 bathrooms, 2 kitchens, dining room, lounge, fireplace, TV, air-conditioning, a 15 meter infinity pool. In short …see more

from $357 / night

$2,496 / week

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from $357 / night

(11) Excellent 

18

Vacation chalet in Hermanus

Hermanus / Stanford Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
The spacious chalet-style cottage has 3 bedrooms: a double en-suite and two twins with a shared bathroom containing bath and shower. All towels and bedding are provided. The main living area is open plan with plenty of room so that you are not getting under each other’s …see more

from $112 / night

$707 - $1,470 / week

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from $112 / night

7

Vacation apartment in Hermanus

Overstrand / Hermanus

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
Exceptionally positioned these luxury serviced apartments offer guests breathtaking ocean views and the perfect location from which to explore the eclectic town of Hermanus. Modern, luxurious and superbly appointed these sea-facing apartments are fully equipped and feat …see more

from $187 / night

$1,305 - $1,433 / week

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from $187 / night

27

Vacation apartment in Struisbaai

Cape Agulhas / Struisbaai

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Ask about children
SEAGULLS NEST GROUND FLOOR APARTMENT: The ground floor apartment of the double storey house in Main Road: • 2 Bedrooms (One bedroom with a double bed, and one bedroom with 2 single beds and 2 daybeds in the lounge for children) • Kitchen • Lounge • Shower with toilet • …see more

from $62 / night

$434 / week

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from $62 / night

(6) Very Good 

17

Villa accommodation in Hermanus with swimming pool

Overstrand / Hermanus

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Spectacular historic beach villa, recently refurbished and outdoor pool, Jacuzzi and barbecue area added. La Gratitude has the best location in Hermanus, being the closest house to Grotto beach in Voelklip. Yet the house enjoys splendid seclusion, being built on 3000 sq …see more

from $529 / night

$3,995 / week

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from $529 / night

(3) Excellent 

51

Vacation apartment with shared pool in Hermanus

Overstrand / Hermanus

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Hermanus Beach Club No 165 offers luxurious self-catering accommodation in a security estate in Hermanus. This lovely holiday flat has stunning white waves over a rocky beach sea views, located within a holiday resort, convenient to local restaurants, pubs, boutique sho …see more

from $69 / night

$483 / week

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Responds fast!
avg. 2 hours 20 minutes

from $69 / night

(8) Excellent 

48

Vacation home with swimming pool in Witsand

Overberg District / Witsand

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This Luxury designer Beach Villa is situated in the safe seaside village of Witsand - THE GATEWAY TO THE GARDEN ROUTE - and caters to the discerning guest looking for up-market beach front self catering accommodation. The home is tastefully and luxuriously decorated i …see more

from $285 / night

$1,995 / week

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from $285 / night

(12) Excellent 

12

Vacation b&b with shared pool in Agulhas

Cape Agulhas / Agulhas

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Introduction: Our lovely apartment is located on the ocean front within walking distance of the lighthouse and Southern Tip icon. There is also a safe parking space available right outside the door. You will love it because of the location and the light colourful ambian …see more

from $91 / night

$637 / week

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Responds fast!
avg. 2 hours 15 minutes

from $91 / night

12

Apartment rental in Gansbaai

Overstrand / Gansbaai

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
Proche De La Mer offers couples or small groups a tranquil getaway in the seaside village of De Kelders. It is a great choice for guests visiting this scenic part of the Western Cape. The apartment has a comfortable downstairs living area with a sleeper couch fo …see more

from $90 / night

$630 / week

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from $90 / night

(5) Very Good 

41

Tented camp rental in Swellendam with shared pool

Overberg District / Swellendam

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
AfriCamps at Kam’Bati is situated on an Overberg farm about 20km west of Swellendam. AfriCamps Forest at Kam’Bati River Resort is a nature lovers’ paradise and the perfect getaway for the adventurous family. There are canoeing, mountain biking and fishing facilities and …see more

from $68 / night

$476 / week

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from $68 / night

(1) Excellent 

20

Gansbaai Vacation home rental

Overstrand / Gansbaai

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Boasting views of the Atlantic Ocean, Birkenhead 19 is a holiday home situated in De Kelders. The 4-bedroom house is located 30 km from Hermanus and 2 km from Gansbaai. This 2-storey home features an open-plan lounge, dining room, kitchen and main en-suite bedroom on th …see more

from $233 / night

$1,629 / week

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Responds fast!
avg. 2 hours 44 minutes

from $233 / night

(3) Excellent 

17

Vacation villa in Witsand

Overberg District / Witsand

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Truly exceptional accommodation, beautifully furnished, safe inside a gated community with its own harbor and private mooring. For the fishing enthusiast that wants to spoil his or her family on the pristine Breeda River. Only a stones throw away from the river and two …see more

from $270 / night

$1,890 / week

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Responds fast!
avg. 18 minutes

from $270 / night

25

Vacation apartment in Struisbaai

Cape Agulhas / Struisbaai

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Ask about children
The SEAGULLS NEST double storey house in Main Road Struisbaai is centrally situated. It is only a two minute walk away from the main beach and close to the harbour in Struisbaai. The top floor, ground floor apartments and flat of Seagulls Nest are rented out separatel …see more

from $77 / night

$539 / week

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from $77 / night

(1) Excellent 

22

Vacation bungalow rental

Hermanus / Sandbaai

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
The Chalet/bungalow is situated an hours drive from Cape town airport just outside of Hermanus in a nature reserve on the whale coast. Between Kleinmond and Hermanus The chalet is west facing so sunsets and spectacular beach end mountain views over the lagoon are …see more

from $163 / night

$1,093 / week

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from $163 / night

26

Home rental in Greyton with swimming pool

Overberg District / Greyton

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This historic, beautifully furnished and spacious self-catering house is situated 200m from the centre of Greyton, with its excellent restaurants, cafes and bars. It has 3 en-suite bedrooms and the fourth bedroom has a separate shower room. The house comprises of a spa …see more

from $250 / night

$1,747 / week

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from $250 / night

(1) Excellent 

7

Vacation cottage in Hermanus

Hermanus / Stanford Village

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 16 mi
  • Child friendly
  • Pet friendly
This is a lovely romantic getaway set in a tranquil garden in a lovely village called Stanford, approximately 150 km from Cape Town. It is the ideal place from which to explore the southern-most tip of Africa (which is NOT in Cape Town!) and enjoy South Africa's unique …see more

from $63 / night

$406 / week

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from $63 / night

14

Hermanus Vacation home rental

Overstrand / Hermanus

3 6 21 nights min

  • 3 bedrooms
  • Sleeps 6
  • 21 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Situated within a modern security estate on an internationally acclaimed golf course, in the whale watching village of Hermanus, just 90 kilometres from Cape Town, a luxury designer home. Walking distance from Cliff Paths and Fernkloof hiking trails. This property, off …see more

from $529 / night

$3,702 / week

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from $529 / night

(14) Excellent 

29

Vacation villa with golf nearby in Gansbaai

Overstrand / Gansbaai

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Villa the Cherry is a 5-star ocean front retreat, located on the cliff, next to perfect white beaches. Quiet, safe, private and peaceful, where whales frolic and give birth to their baby's. All rooms have sea view, all rooms have underfloor heating, all bedrooms have th …see more

from $280 / night

$1,955 - $4,288 / week

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from $280 / night

21

Sandbaai Vacation apartment rental

Hermanus / Sandbaai

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Child friendly
Sandbaai Solace is a peaceful self-catering apartment less than 3 blocks from the ocean in a quiet area beside Hermanus. It is the perfect location for experiencing the Overberg region, whether you are watching whales, shark diving, tasting wines, touring art galleries, …see more

from $55 / night

$385 / week

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from $55 / night

15

Vacation apartment with shared pool in Swellendam

Overberg District / Swellendam

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 64 mi
  • Swimming pool
  • Child friendly
The Melkhuisie is situated very close to the milking parlour, the small calves and the chicken pen! This was the old milking parlour converted into a house, the reason why it is called the Melkhuisie. Be aware you will hear farm animals already early morning. The house …see more

from $57 / night

$393 / week

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from $57 / night

7

Vacation apartment rental

Overstrand / Hermanus

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Pet friendly
Gannet is a one-bedroomed chalet adjacent to Seagull in the grounds of Kure Kure Accommodation. Kure Kure offers self-catering accommodation in Sandbaai, Hermanus. Hermanus and the surrounding area of the Overberg have much to offer visitors. The combination of the se …see more

from $49 / night

$343 / week

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Responds fast!
avg. 3 hours 9 minutes

from $49 / night

(1) Excellent 

27

Home rental in Franskraal

Overstrand / Franskraal

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
Heaven-On-Sea is a luxuriously appointed 8 sleeper spacious, self-catering beach front home, situated between Gansbaai and Pearly Beach in the beautiful coastal village of Franskraal. Just 2 hours from Cape Town and a stones throw from the sea you can enjoy uninterrupt …see more

from $240 / night

$1,680 / week

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from $240 / night