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

Close

View larger map

Also consider

Vacation rentals Hermanus
89 properties
Cape Agulhas
18 properties
Napier
13 properties
Betty's Bay
12 properties
Gansbaai
10 properties
Self catering Pringle Bay
9 properties
Estates Kleinmond
7 properties
Greyton
6 properties
Swellendam
5 properties

Overberg District

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

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

186 Vacation rentals

Travelers going to Overberg District are booking June dates now. Secure your vacation rental today and have the perfect trip.

(8) Very Good 

18

Apartment rental in Hermanus

Overberg District / 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 $99 / night

$689 / week

Book View

from $99 / night

(1) Very Good 

15

Villa rental in Bot River with swimming pool

Overberg District / Bot River

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 $459 / night

$3209 / week

Book View

from $459 / night

13

Vacation home rental

Overberg District / Hermanus

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Ask about pets
Modern cottage walking distance from Langbaai beach in Voelklip, Hermanus. Fully equipped modern kitchen including oven and glass hob, dishwashing and waching machines. Main bedroom with en-suite shower and toilet. Another full bathroom. Very close to walking paths and  …see more

from $106 / night

$742 / week

Book View

from $106 / night

17

Vacation apartment rental

Overberg District / 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 $86 / night

$596 / week

Book View

from $86 / night

(2) Excellent 

17

Vacation apartment with shared pool in Hermanus

Overberg District / 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 $101 / night

$701 / week

Book View

from $101 / night

12

Vacation home in Hermanus

Overberg District / Hermanus

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 3 mi
  • Child friendly
Birdsong lies nestled in a grove of Milkwood trees, overlooking the Vermont Saltpan, which is a bird sanctuary. This four bedroomed, three bathroomed house is fully equipped for eight people. It is an ideal location for nature lovers wanting to relax away from the bust  …see more

from $111 / night

$785 - $1206 / week

Book View

from $111 / night

(9) Excellent 

27

Hermanus Vacation apartment rental

Overberg District / 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  …see more

from $122 / night

$853 - $1800 / week

Book View

from $122 / night

(1) Very Good 

14

Gansbaai Vacation home rental

Overberg District / Gansbaai

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 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 kitchenBedroom and full bathroomA Spacious room with an BBQTop Floor: Two bedroo  …see more

from $111 / night

$689 / week

Book View

from $111 / night

11

Vacation home in Hermanus

Overberg District / Hermanus

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
Carole’s Cottage is a welcoming well appointed, self-catering cottage, in a secure private estate in Sandbaai, a suburb just 3km from the centre of Hermanus. You will have everything you need for a fabulous long holiday or just brief weekday breaks or weekends  …see more

from $71 / night

$491 / week

Book View

from $71 / night

(3) Excellent 

32

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
Luxury designer Beach Villa situated in Witsand - THE GATEWAY TO THE GARDEN ROUTE - located on the beach with direct beach access. The home has 5 double bedrooms of which 3 are en-suite and 2 bedrooms share a full bathroom. There is an additional guest WC. The villa  …see more

from $280 / night

$1960 / week

Book View

from $280 / 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 $134 / night

$696 - $1081 / week

Book View

from $134 / night

7

Vacation apartment in Hermanus

Overberg District / 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 $163 / night

$1138 - $1250 / week

Book View

from $163 / night

21

Vacation apartment in Hermanus

Overberg District / Hermanus

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
Modern and spacious 4 bedroom apartment with pool. Nursery lane is a secure and well appointed complex situated on the site of the old Onrus nursery Features & Amenities Private Pool Open plan kitchen, lounge and dining Out door beautiful braai and pool area Cover  …see more

from $126 / night

$882 / week

Book View

from $126 / night

(1) Excellent 

16

Vacation home with swimming pool in Kleinmond

Overberg District / Kleinmond

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Situated on a internationally acclaimed gated golf estate, close to the world renowned whale watching resort of Hermanus in South Africa's beautiful Cape, just 90 kilometres from Cape Town is Bella Bella, a luxury designer residence. This property, situated right o  …see more

from $380 / night

$2500 / week

Book View

from $380 / night

47

Pringle Bay Vacation home rental

Overberg District / Pringle Bay

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Private garden
Pringle Beach House is more than your average holiday home. It's beautifully furnished and just so comfortable - many personal touches add to the feeling of being in a home from home. The kitchen is incredibly well equipped, with absolutely everything you could pos  …see more

from $185 / night

$1845 / week

Book View

from $185 / night

(2) Excellent 

25

Vacation home with shared pool in Hermanus

Overberg District / 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  …see more

from $139 / night

$973 / week

Book View

from $139 / night

6

Vacation apartment rental

Overberg District / Hermanus

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
Welcome to Rock Inn. A self-catering unit with a separate entrance. It features two bedrooms with double beds in each along with secure parking. It is only a five minute walk from the city centre, shopping mall, numerous restaurants, and cliff path. Other listings are a  …see more

from $59 / night

$413 / week

Book View

from $59 / night

(9) Excellent 

18

Vacation home in Hermanus

Hermanus / Onrus River

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $136 / night

$861 - $1107 / week

Book View

from $136 / night

24

Vacation home in Hermanus

Hermanus / Voelklip

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+
  • Private garden
Newly renovated light and bright holiday home. Situated in the first enclave of Voelklip. Bedroom - Master King size bed, lounging room, full en suite bathroom, private balcony. Bedroom 2 Queen bed, separate bathroom with shower. Bedroom 3 Twin beds, shared full en su  …see more

from $180 / night

$1260 / week

Book View

from $180 / night

(3) Excellent 

8

Vacation apartment rental

Hermanus / Sandbaai

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Private garden
Seagull Apartment Hermanus is a self catering Holiday Apartment situated in Sandbaai, Hermanus. There one Double Bedroom and a fully equipped open plan kitchen and lounge. The lounge comes equipped with DSTV, a DVD player and free Wi-Fi. Guests can relax on the  …see more

from $74 / night

$517 - $732 / week

Book View

from $74 / night

22

Overberg District / Betty's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden

 …see more

from $89 / night

$621 - $1236 / week

Book View

from $89 / night

(27) Excellent 

20

Home rental in Hermanus with swimming pool

Overberg District / Hermanus

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
This magnificent seafront home is in a spotless condition, offering guests amazing sea views and unique luxuries, not usually associated with a self-catering facility. No wonder it was nominated as a finalist in the National Top Destinations Awards (2015). The open-pl  …see more

from $136 / night

$948 / week

Book View

from $136 / night

(6) Very Good 

17

Villa accommodation in Hermanus with swimming pool

Overberg District / 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 $480 / night

$3485 / week

Book View

from $480 / night

(11) Excellent 

24

Hermanus Vacation home rental

Hermanus / Sandbaai

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $99 / night

$689 - $948 / week

Book View

from $99 / night

(1) Excellent 

33

Vacation cottage with golf nearby in Hermanus

Overberg District / Hermanus

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 6 mi
  • Ask about children
  • Private garden
Welcome to Die Blou Deur, a quaint 1940’s well-loved Cape townhouse and heritage site, well-preserved and refurbished with a warm, romantic but rejuvenated atmosphere. Experience a holiday beyond the entrapment of machine, no traffic problems and no parking head  …see more

from $196 / night

$1365 / week

Book View

from $196 / night

10

Vacation cottage in Hermanus

Overberg District / Hermanus

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Ask about children
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 $101 / night

$701 / week

Book View

from $101 / night

22

Vacation home in Hermanus

Overberg District / Hermanus

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
Situated in walking distance of Langbaai beach and the best eating spots Voelklip has to offer. Comfortable, well equipped home. Features & Amenities Open plan kitchen, lounge and dining 3 out door dinning/seating areas Outdoor entertaining braai area DSTV Radio,  …see more

from $183 / night

$1281 / week

Book View

from $183 / night

(2) Excellent 

15

Vacation cottage in Hermanus

Overberg District / 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 sighti  …see more

from $50 / night

$308 / week

Book View

from $50 / night

(2) 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

$1890 / week

Book View

from $270 / night

(3) Very Good 

18

Vacation home in Hermanus

Overberg District / Hermanus

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Private garden
Open plan home in Voelklip, Hermanus, with stunning views of the mountain and the ocean, large grass area outside for braais, pool table, braai inside, sleeps 8 guests . Walking distance to the beaches, and very close to the mountain trails. Great spaces for kids. Larg  …see more

from $86 / night

$290 / week

Book View

from $86 / night

(2) Excellent 

65

Hermanus Vacation farmhouse rental

Overberg District / Hermanus

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 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, only an hour away from Cape Town International airport with breath-taking views over the lagoon,sea and the overberg mountains. This exquisite luxury newly completed hom  …see more

from $492 / night

$3075 - $3198 / week

Book View

from $492 / night

(3) Good 

23

Struisbaai Vacation home rental

Cape Agulhas / Struisbaai

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
You can't get any closer to the picturesque harbour in this idyllic little town. This ground floor unit is opposite the harbour and one of the two swimming beaches. Within walking distance of the supermarket, restaurants, bottle store and shops. The pier where Parr  …see more

from $140 / night

$981 / week

Book View

from $140 / night

(1) 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 (  …see more

from $62 / night

$369 / week

Book View

from $62 / 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 cranni  …see more

from $59 / night

$375 / week

Book View

from $59 / night

(1)  

10

Swellendam Vacation home rental

Overberg District / Swellendam

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
The Country cottage offers you a private self catering country stay, with all the winter luxuries that makes you fall in love with winter. Our beds are fitted with Egyptian cotton and luxury quilts.There is plenty of firewood and this quaint cottage warms up in no time  …see more

from $96 / night

$666 / week

Book View

from $96 / night

32

Struisbaai Vacation apartment rental

Cape Agulhas / Struisbaai

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Ask about children
SEAGULLS NEST FLAT: The flat adjacent to the double storey house in Main Road: • Two Bedrooms (One bedroom with a double bed, and one bedroom with two single beds) • Kitchenette and lounge  …see more

from $50 / night

$351 - $449 / week

Book View

from $50 / night

22

Home rental in Struisbaai

Cape Agulhas / Struisbaai

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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,  …see more

from $64 / night

$442 - $736 / week

Book View

from $64 / night

15

Pringle Bay Vacation villa rental

Overberg District / Pringle Bay

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • 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 $308 / night

$2153 - $4305 / week

Book View

from $308 / night

(1)  

6

Vacation apartment in Hermanus

Overberg District / Hermanus

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Private garden
A beautifully furnished apartment in the Hemel &Aarde valley, on the wine route, near the beaches close to town. A small town that nestles between the sea and mountains. Everything is near to cycle routes, restaurants, shops, walking trails, golf courses, and near s  …see more

from $50 / night

$350 / week

Book View

from $50 / night

(1) Good 

33

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 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 and serviced with 5 large en-suit bedroo  …see more

from $362 / night

$3040 / week

Book View

from $362 / night