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

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331 Vacation rentals

(10) Excellent 

76

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 $367 / night

$2,565 / week

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from $367 / night

(1) Excellent 

32

Vacation home with shared pool in Swellendam

Overberg District / Swellendam

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Uitkyk Farmhouse is 26km from the town of Swellendam and Kam’Bati River Resort. The house is situated on a private Overberg Farm. Free access to the Kam'Bati River Resort during your stay. 4 Bedroom Self Catering house with 2 bathrooms. We rent out the house as one uni …see more

from $165 / night

$1,155 / week

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from $165 / night

(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

$1,598 / 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

$1,011 / 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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avg. 2 hours 10 minutes

from $79 / night

(7) 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 $183 / night

$914 - $1,839 / week

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avg. 36 minutes

from $183 / night

(1) Excellent 

36

Napier Vacation apartment rental

Overberg District / Napier

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Suitable for children age 5+
  • Ask about pets
The Napier Country Cottage is a downstairs apartment sleeping 5 and part of the larger Napier Country House. We offer great country living to destress you and come down to earth again. About 2 hours away from Cape Town along the coast lies the small village of Napier a …see more

from $111 / night

$542 / week

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from $111 / 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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Responds fast!
avg. 2 hours 31 minutes

from $115 / 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 $146 / night

$1,020 - $2,153 / week

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avg. 1 hour 52 minutes

from $146 / 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 $162 / night

$1,134 / week

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from $162 / 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

$2,165 / week

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from $310 / 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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avg. 41 minutes

from $390 / 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

(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

(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

(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

(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

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

(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 $295 / night

$2,063 - $4,526 / week

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from $295 / 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

(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 $118 / night

$825 / week

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Responds fast!
avg. 30 minutes

from $118 / night

15

Vacation home in Napier

Overberg District / Napier

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Ask about children
Close to the foot of Soetmuisberg lies deSkaap, Sandfontein. Embedded within a picturesque landscape of rolling farmlands characterizing the Overberg. A soothing soundtrack of freely roaming sheep and active bird life compliments the breathtaking views and memorable sun …see more

from $53 / night

$366 / week

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from $53 / 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

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 $105 / night

$730 - $1,090 / week

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from $105 / 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 birding lovers’ paradise and the perfect getaway for the adventurous family. There are canoeing, mountain biking and fishing facilities an …see more

from $92 / night

$640 / week

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from $92 / 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

(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

26

Home rental in Struisbaai

Cape Agulhas / Struisbaai

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
The beach front house in Beach Road Struisbaai: Close to Cape Agulhas the Southernmost Tip of Africa A Short walk away from the harbour and the main beach in Struisbaai. • 4 Bedrooms (One bedroom with a double bed, two bedrooms with 2 single/three quarter beds, and a …see more

from $105 / night

$730 - $1,163 / week

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from $105 / 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 $259 / night

$1,814 - $2,597 / week

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from $259 / 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 $195 / night

$1,363 / week

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from $195 / 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

(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

$1,326 / week

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Responds fast!
avg. 2 hours 23 minutes

from $220 / 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 $373 / night

$2,611 / week

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from $373 / 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

(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

9

Vacation guest house in Caledon

Overberg District / Caledon

2 3 1 night min

  • 2 bedrooms
  • sleeps 3
  • 1 night min
  • Nearest beach 41 mi
  • Air conditioning
  • Private garden
ZOOOP located in a quiet area, offers 2 units with comfortable accommodation, Each unit has its own entrance and parking area. There are lovely fire places to keep one warm on cold winter nights, free WiFi and DSTV. Private garden with BBQ facilities. Enjoy a meal f …see more

from $72 / night

$503 / week

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from $72 / night

16

Vacation home rental

Overberg District / Napier

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Ask about children
Close to the foot of Soetmuisberg lies deSkaap, Sandfontein. Embedded within a picturesque landscape of rolling farmlands characterizing the Overberg. A soothing soundtrack of freely roaming sheep and active bird life compliments the breathtaking views and memorable s …see more

from $53 / night

$366 / week

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from $53 / night

(5) Excellent 

12

Vacation lodge in Greyton

Overberg District / Greyton

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Pet friendly
Wake up to the sound of birds, sip your morning coffee in the shaded garden, and greet the curious donkeys (and curiously quirky villagers) on your leisurely stroll into town. Discover waterfalls, morning markets, secret nooks, local crafts and overgrown crannies. Need …see more

from $80 / night

$590 / week

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from $80 / 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 $366 / night

$2,298 - $3,656 / week

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from $366 / night

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