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

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Overstrand
193 properties
Swellendam
28 properties
Napier
19 properties
Cape Agulhas
12 properties
Betty's Bay
10 properties
Greyton
7 properties

Overberg District

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287 Vacation rentals

(10) Excellent 

30

Vacation cottage in Hermanus

Overstrand / Hermanus

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 6 mi
  • Child friendly
  • Private garden
Near the whale-watching coast of Hermanus, in the beautiful Hemel-en-Aarde Valley, you'll come across Earth Cottage. It's the ideal self-catering Hermanus breakaway. The cottage is tucked away on a smallholding in the valley, and yet it's only 6 km from the beach. It …see more

from $69 / night

$481 / week

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from $69 / night

(3) 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 $73 / night

$462 / week

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Responds fast!
avg. 2 hours 57 minutes

from $73 / night

13

Vacation home rental

Overstrand / Kleinmond

4 6 1 night min

  • 4 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
Next to the glorious rugged coastline of the Koggelberg Mountains discover a charming guest house, tastefully designed, which will relax your soul. After exploring nearby villages, towns, wine farms and watching whales at play, return to enjoy the elegant guest house r …see more

from $60 / night

$420 / week

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from $60 / night

18

Home rental in L'Agulhas

Cape Agulhas / L'Agulhas

2 9 2 nights min

  • 2 bedrooms
  • Sleeps 9
  • 2 nights min
  • Nearest beach 15 mi
  • Child friendly
  • Pet friendly
Die Maase Agulhas is situated in the very quiet part of Agulhas. Here you will be able to relax and sit back and listen to the ocean crashing below the mountain. This special place is a bird and wild animal lover must. There are two rooms namely Atlantic that sleeps 2 a …see more

from $120 / night

$840 / week

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avg. 9 minutes

from $120 / night

(10) Excellent 

76

Vacation home with swimming pool in Witsand

Overberg District / Witsand

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $320 / night

$2,240 / week

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avg. 3 hours 33 minutes

from $320 / 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

$700 / week

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from $99 / night

(1) Excellent 

7

Vacation apartment in Hermanus

Overstrand / Hermanus

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 $233 / night

$1,627 - $3,022 / week

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from $233 / night

(2) Very Good 

8

Vacation home in Pearly Beach

Overstrand / Pearly Beach

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Pearly gates is a cosy house situated in the Pearly beach resort, in Pearly beach. The house offers self-catering accommodation for families of four. The house is only 100 meters from the beach, and 20 kilometres from Gansbaai. This free-standing house has two bedroom …see more

from $75 / night

$525 / week

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from $75 / night

(4) Excellent 

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

54

Napier Vacation apartment rental

Overberg District / Napier

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 35 mi
  • Swimming pool
  • Ask about children
A loft shared space overlooking a garden.Double bed and three single beds. Includes kitchenette,bathroom and dining table. Access to garden and barbeque space.Horses and walks in a wine and food lover's paradise. Ideal detour from the Cape Garden route.Lovely deck and p …see more

from $82 / night

$394 / week

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Responds fast!
avg. 3 hours 28 minutes

from $82 / 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

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 $53 / night

$365 / week

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from $53 / night

(1) Excellent 

12

Cottage rental in Hermanus

Overstrand / Hermanus

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Ask about children
  • Ask about pets
  • Private garden
The separate secluded garden cottage sleeps up to 2 adult guests and 2 children under 10 years of age and has its own private entrance. It is strictly not suitable for more than 2 adults. The kitchenette is fully equipped for self-catering and the unit features Plasma T …see more

from $56 / night

$392 - $554 / week

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from $56 / 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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Responds fast!
avg. 3 hours 46 minutes

from $55 / night

(4) Very Good 

19

Hermanus Vacation home rental

Overstrand / Hermanus

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Nearest beach 4 mi
  • Child friendly
  • Ask about pets
The main house and separate flat will cater for your every need while relaxing in one of the prettiest tourist attractions in South Africa. The main house sleeps 10 people and the separate flat sleeps 4 people. The plot is fully walled with strong gates and an activated …see more

from $270 / night

$1,893 - $3,109 / week

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from $270 / night

33

Vacation home in Bredasdorp

Overberg District / Bredasdorp

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Ask about pets
  • Private garden
Home Pages Bloekomhuisie is a newly renovated historic cottage situated in a tree lined street in the century old town of Bredasdorp in the Western Cape and is situated conveniently between Arniston and Struisbaai. Offering simple but stylish self-catering with comfor …see more

from $76 / night

$532 / week

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from $76 / 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 $218 / night

$1,525 / week

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Responds fast!
avg. 2 hours 27 minutes

from $218 / night

(2) Very Good 

9

Home rental in Kleinmond

Overstrand / Kleinmond

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
La Mer is a Seafront Beach house sleeping 4: 1 room with a double bed and 1 room with 2 twin single beds. Bathroom is shared Fully equipped kitchen with dishwasher, gas stove, fridge etc. The house also has a fireplace and 3 braai areas of which one is covered. Stunning …see more

from $139 / night

$974 / week

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from $139 / night

15

Home rental in Betty's Bay

Overberg District / Betty's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
The house was built in 2015 as a private holiday home, is single and has a spacious garden. It also has two parking lots. Our Non smoking house is family friendly, accessible and can accommodate its equipment up to six guests. Bedrooms Three bedrooms, a living room with …see more

from $157 / night

$1,095 - $1,339 / week

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from $157 / night

11

Vacation private room rental

Overstrand / Hermanus

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Welcome to Seaside Guest Room Hermanus. Come and relax with authentic South African hospitality. We are situated a stone throw from the best whale watching in the world, shark cage diving, cycling and much much more. Get a relaxed and sound night sleep and wake up with …see more

from $65 / night

$455 / week

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Responds fast!
avg. 2 hours 23 minutes

from $65 / night

(5) 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

(3) Very Good 

16

Vacation bungalow with swimming pool, golf nearby in Hermanus

Overstrand / Hermanus

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Near sea, mountains and a 27 holes golf course, our beautiful bungalow with enclosed garden with swimming pool on 800 m2 plot. The bungalow has: fully equipped kitchen with oven, microwave, dishwasher, fridge with freezer, washing machine, tumble dryer, etc. < …see more

from $139 / night

$869 / week

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Responds fast!
avg. 3 hours 15 minutes

from $139 / 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 $331 / night

$2,318 / week

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from $331 / night

(4) 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 19 minutes

from $69 / night

17

Swellendam Vacation chalet rental

Overberg District / Swellendam

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 64 mi
  • Swimming pool
  • Child friendly
The Chalet has a thatched roof, and overlooks the green valley facing the Langeberg Mountains. This unit has two bedrooms that are equipped with either two single beds or a double bed, with a loft bedroom area. The open-planned kitchen is well equipped, and contains a f …see more

from $72 / night

$503 / week

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from $72 / 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 $64 / night

$406 / week

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from $64 / night

15

Vacation apartment in Gansbaai

Overstrand / Gansbaai

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Sunset View at Whale Cove is a seafront apartment that is located in De Kelders, Gansbaai. It is a comfortable self-catering apartment with spectacular sunsets and views across the bay to Hermanus. The apartment comprises 3 bedrooms and 2 bathrooms. The main bedroom h …see more

from $120 / night

$835 / week

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from $120 / 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 $152 / night

$1,023 / week

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from $152 / 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. 19 minutes

from $270 / night

(3) Excellent 

30

Bungalow rental in Onrus

Hermanus / Onrus

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
C’est Ça Cottage (“That’s it” in French) is newly completed and stylishly appointed with an open plan modern design comprising 32m². The cottage appeals to leisure or business guests who want comfort, privacy and full self-catering facilities in close proximity to Herm …see more

from $74 / night

$518 / week

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from $74 / night

(1) Excellent 

6

Vacation apartment in Hermanus

Overstrand / Hermanus

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Private garden
The Big Blue Boutique is a home away from home, the ideal getaway from the hustle and bustle of city life. Conveniently located a 5min drive from town centre and a 5 minute walk from the New Harbour where you will find several restaurants and an array of activities avai …see more

from $60 / night

$420 / week

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Responds fast!
avg. 1 hour 25 minutes

from $60 / night

(4) Excellent 

29

Vacation private room in Kleinmond

Overstrand / Kleinmond

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Car not necessary
Newly renovated 3-bedroom surf-style beach house available with mountain views a stone's throw from the beach. Two lounges, indoor BBQ area, outdoor patio and breakfast nook, outdoor braai, cottage-style kitchen with all amenities and appliances & a full organic vegetab …see more

from $100 / night

$700 / week

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from $100 / 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 $53 / night

$330 / week

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Responds fast!
avg. 3 hours 16 minutes

from $53 / night

(11) Excellent 

18

Vacation chalet in Stanford

Overstrand / Stanford

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Private garden
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 $106 / night

$667 - $1,386 / week

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Responds fast!
avg. 2 hours 47 minutes

from $106 / night

14

Vacation home in Sandbaai

Hermanus / Sandbaai

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 0.3 mi
  • Child friendly
  • Private garden
Description Will sleep six people (3 doubles) Rooms: • 2 bedrooms (1 en suite with bath/shower) • Toilet/shower • Equipped kitchen (with large fridge, electric stove/oven) • Dining room (with seating for six) • Living room (with double sleeper couch) • Braai room (with …see more

from $113 / night

$786 / week

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from $113 / night

31

Vacation apartment in Struisbaai

Cape Agulhas / Struisbaai

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights 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 $91 / night

$637 - $952 / week

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from $91 / night

11

Vacation home in Stanford

Overstrand / Stanford

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 10 mi
  • Child friendly
  • Private garden
The Buzz is a charming, self-catering home located in the historic village of Stanford. The property is ideally situated 20 to 30 minutes from central Hermanus, and popular whale watching spots. This fully furnished house consists of 3 bedrooms and 3 bathrooms. The ma …see more

from $200 / night

$1,200 - $1,800 / week

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from $200 / night

(32) 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 $279 / night

$1,565 - $3,245 / week

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from $279 / night

(2) Very Good 

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 $58 / night

$377 / week

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from $58 / night

(14) Very Good 

16

Vacation cottage in Hermanus

Hermanus / Sandbaai

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Situated in the Western Cape, South Africa, Vanhaven offers budget self catering holiday apartments in Sandbaai, Hermanus.Nestling between mountains and the cool Atlantic Ocean, Hermanus is famed for its mild climate, champagne air and famous vineyards. The annual Herm …see more

from $53 / night

$370 / week

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from $53 / night