50 Best Vacation Rentals in Overstrand - Holiday Lettings - Cabins

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230 Vacation rentals

(2) Excellent 

7

Rooiels Vacation home rental

Overstrand / Rooiels

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
Luxury beach accomodation in a tranquil setting. Exceptional views of the ocean and surrounding mountains. Experience nature and Cape fynbos vegetation on your doorstep and within an hour from Cape Town International Airport. Central location to explore the famous Cap …see more

from $229 / night

$1,600 / week

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from $229 / night

23

Vacation home in Sandbaai

Hermanus / Sandbaai

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 3 mi
  • Child friendly
  • Pet friendly
This lovely Family home boasts NO modern finishes. Neat, clean & well maintained. Fantastic getaway for a family with babies or kids. Offering everything from an optional bedside cot to a family sized jumping castle, play equipment, toys and more. Sunny North facing pat …see more

from $145 / night

$1,012 / week

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from $145 / 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 $79 / night

$553 / week

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Responds fast!
avg. 2 hours 10 minutes

from $79 / 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 $275 / night

$1,924 / week

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from $275 / night

8

Vacation home with shared pool in Stanford

Overstrand / Stanford

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
An elegant old lady on a big corner plot overlooking the Klein River in Stanford. The house is cool and airy with high ceilings. There is a great entertaining kitchen/dinning room leading onto a patio with barbecue and large swimming pool. A sun-downer side verandah ove …see more

from $310 / night

$2,168 / week

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from $310 / night

(2) Good 

12

Vacation apartment rental

Overstrand / Hermanus

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 7 mi
Welcome to Rock Inn, a self-catering apartment with a separate entrance. Each room has a double bed and there is secured parking behind a remote gate. The kitchen contains a bar fridge and 2 hot plates along with all essentials. No oven. Only a 7+- minute walk from the …see more

from $35 / night

$241 - $461 / week

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Responds fast!
avg. 48 minutes

from $35 / night

(11) Excellent 

30

Vacation cottage in Hermanus

Overstrand / Hermanus

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • 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 $60 / night

$417 / week

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from $60 / night

27

Vacation guest house with shared pool in Hermanus

Overstrand / Hermanus

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
The luxury Fisherman's cottage suite includes: queen sized bed with pure cotton bedding; modern en suite bathroom with hand loomed cotton towels and heated towel rail; guest toiletries; 2 flat screen TVs with DSTV; MORSO fireplace, with wood; fan; wall heater; h …see more

from $252 / night

$1,764 / week

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avg. 41 minutes

from $252 / night

(7) Excellent 

37

Hermanus Vacation guest house rental

Overstrand / Hermanus

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Private garden
The Vishuis is a newly renovated guesthouse. It is situated in the heart of the charming seaside village of Hermanus. Guests are within strolling distance of restaurants, coffee shops, bars, boutiques, art galleries and all the supermarkets. The famous Cliff Path (wher …see more

from $390 / night

$2,726 / week

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Responds fast!
avg. 41 minutes

from $390 / night

10

Hermanus Vacation home accommodation

Overstrand / Hermanus

4 11 1 night min

  • 4 bedrooms
  • sleeps 11
  • 1 night min
  • Nearest beach 0.2 mi
  • Child friendly
  • Pet friendly
Norfolkden Beachhouse is a family home in the heart of the Cape Whalecoast, Hermanus. Only 200m from the beach, it is the ideal place to take the family on holiday. With real old-world charm, we would like to welcome all travellers into our family beachhouse. The proper …see more

from $149 / night

$802 - $1,031 / week

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avg. 3 hours 53 minutes

from $149 / night

(21) Excellent 

44

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

from $147 / night

$1,025 - $2,163 / week

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avg. 1 hour 52 minutes

from $147 / night

(2) Very Good 

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 $63 / night

$441 / week

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from $63 / night

(2) Very Good 

20

Vacation cottage in Sandbaai

Hermanus / Sandbaai

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Sandbaai Cottages consists of 2 charming self-catering houses. The 2 units are separately fenced-in with a wall between the two units. A gate between the two makes it possible for 2 groups to use both units, have privacy, but can socialise together without leaving the s …see more

from $115 / night

$802 / week

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avg. 2 hours 31 minutes

from $115 / night

(8) Very Good 

18

Apartment rental in Hermanus

Overstrand / Hermanus

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child friendly
Luxury 2 bedroom / 2 bathroom Apartment 1 Queen bed with En Suite 2 Single or can be converted to Queen Secure Parking DSTV / Satellite 5 minutes away from town centre Mountain Views Fully Equipt Private large Balcony with BBQ facilities< …see more

from $119 / night

$828 / week

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avg. 30 minutes

from $119 / 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 $163 / night

$1,136 / week

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from $163 / night

(7) 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 $160 / night

$1,114 / week

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from $160 / night

(17) Excellent 

27

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 $293 / night

$2,050 - $4,496 / week

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from $293 / 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 $339 / night

$2,291 - $3,644 / week

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from $339 / night

11

Guest house rental in Hermanus with shared pool

Overstrand / Hermanus

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • 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 $126 / night

$882 / week

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avg. 41 minutes

from $126 / 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 $114 / night

$802 / week

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from $114 / night

7

Vacation home in Pearly Beach

Overstrand / Pearly Beach

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Pearly Sands is a lovely free standing holiday house situated in the Pearly Beach Resort, in Pearly beach. The house offers self-catering accommodation for families of four. The house is only 130 meters from the beach, and 20 kilometres from Gansbaai. This free-standin …see more

from $1,695 / night

$11,863 / week

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from $1,695 / night

(2) Excellent 

8

Sandbaai Vacation apartment rental

Hermanus / Sandbaai

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
10th on Laubie A self upper floor apartment situated in the beautiful seaside village of Sandbaai, nestled betwee the mountains and the Atlantic Ocean. The apartment offers its guests self-catering accomodation with magnificent mountain views(sleep 4 persons max). It is …see more

from $130 / night

$906 / week

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from $130 / 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 $69 / night

$481 / week

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Responds fast!
avg. 58 minutes

from $69 / night

(10) Very Good 

16

Vacation home in Hermanus

Hermanus / Onrus River

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Geheim is a spacious 3 bedroom home situated in Onrus, Western Cape, South Africa. With its double volume bedrooms it offers the very best in luxury and comfort. The famous Onrus beach is only a 3 minute walk away. This home has breathtaking views of the ocean and mo …see more

from $220 / night

$1,327 / week

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avg. 2 hours 19 minutes

from $220 / night

(4) Excellent 

29

Vacation private room in Kleinmond

Overstrand / Kleinmond

3 9 1 night min

  • 3 bedrooms
  • sleeps 9
  • 1 night min
  • 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 $115 / night

$802 / week

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from $115 / 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 $69 / night

$481 / week

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from $69 / night

(12) Excellent 

24

Hermanus Vacation home rental

Hermanus / Sandbaai

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Private garden
Seagull House Hermanus is a self catering holiday house situated in Sandbaai, Hermanus, featuring two individually decorated bedrooms with en-suite bathrooms.There is a fully equipped open plan kitchen, dining area and a lounge. The lounge comes equipped with DSTV, a DV …see more

from $111 / night

$774 / week

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from $111 / night

(3) Very Good 

14

Vacation cottage in Hermanus

Overstrand / Hermanus

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 5 mi
  • Child friendly
  • Car not necessary
This upmarket self-catering cottage is located only a few blocks away from several excellent restaurants, shops and the cliff path of Hermanus. Stylishly appointed, the cottage has a contemporary feel with its double volume, open-rafter living space, and tasteful decor. …see more

from $103 / night

$699 - $1,025 / week

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from $103 / night

(1) Excellent 

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 $261 / night

$1,824 - $2,612 / week

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from $261 / night

24

Vacation home in Hermanus

Overstrand / Hermanus

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Sandbaai Cottages consists of 2 charming self-catering houses. The 2 units are separately fenced-in with a wall between the two units. A gate between the two makes it possible for 2 groups to use both units, have privacy, but can socialise together without leaving the s …see more

from $115 / night

$687 - $1,088 / week

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avg. 2 hours 31 minutes

from $115 / 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 $126 / night

$789 - $1,667 / week

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Responds fast!
avg. 2 hours 20 minutes

from $126 / night

(8) Excellent 

11

Apartment rental in Hermanus with shared pool, golf nearby

Overstrand / Hermanus

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Le Paradis Penthouse is a luxury, self-catering apartment for the discerning guest. All the living areas offer spectacular ocean views of Walker Bay. It is perfectly situated in the heart of Hermanus, and within easy walking distance to shops and restaurants. The pentho …see more

from $516 / night

$3,613 / week

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Responds fast!
avg. 3 hours 43 minutes

from $516 / night

(1) Good 

32

Vacation home accommodation

Hermanus / Stanford Village

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fairhill is a private, self catering farmhouse situated on a nature reserve of 200 hectares of beautiful fynbos and has superb sea and mountain views. The property borders the Cape nature reserve and the 17km long Walker Bay private beach. The house is fully furnished a …see more

from $348 / night

$2,434 / week

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from $348 / 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 $170 / night

$1,143 / week

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from $170 / night

(2) Excellent 

65

Hermanus Vacation farmhouse rental

Overstrand / Hermanus

4 8 120 nights min

  • 4 bedrooms
  • sleeps 8
  • 120 nights min
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool
Contemporary homestead located at the luxury Benguela Cove Wine Estate on the outskirts of Hermanus, minimum 6 months rental, only an hour away from Cape Town International airport with breath-taking views over the lagoon,sea and the overberg mountains. This exquisite l …see more

from $443 / night

$2,949 / week

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from $443 / night

24

Home rental in Hermanus

Overstrand / Hermanus

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child friendly
Our holiday home is ideal for families/ couples wanting to get away and be close to the beaches in Hermanus. There is no need to get into a car as there are restaurants and cafe's within walking distance as well as a convenience store that offers home cooked meals. The …see more

from $292 / night

$2,044 - $2,477 / week

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from $292 / 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 $115 / night

$802 / week

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from $115 / night

34

Hermanus Vacation apartment rental

Overstrand / Hermanus

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
Hermanus Beachclub Penthouse #213 Everyone dreams of a holiday where you can lie in bed, listen to the waves, smell the sea breeze and look at the sunset over the ocean. At Nothing But View, this is exactly what you get. This penthouse flat is a 3-bedroom, two-bathroo …see more

from $103 / night

$722 / week

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from $103 / night

15

Pringle Bay Vacation villa rental

Overstrand / Pringle Bay

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Maritime on Moonlight Bay is an incredibly beautiful estate, with jaw-dropping views. Covered in flowering fynbos,the property stretches from the famous Hangklip Mountain to the Atlantic Ocean below. The 454-metre Hangklip Mountain, at times covered in a tablecloth of …see more

from $738 / night

$5,161 / week

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from $738 / night

(4) Excellent 

19

Vacation bungalow in Baardskeerdersbos

Overstrand / Baardskeerdersbos

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
The rondawel is on a pristine fynbos farm just outside of the small town of Baardskeerdersbos. Situated on a lily pond it has stunning views out across the valley ,birder's will love the endemics as well as a long specie list and there are wonderful hikes to a kloof wi …see more

from $69 / night

$481 / week

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from $69 / night

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