South Shore Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for South Shore holiday rentals

Ocean-View Studio, Steps to Beaches, in Sunny Poipu

Ocean-View Studio, Steps to Beaches, in Sunny Poipu
Poipu
9.8 out of 10, Exceptional, (222 reviews)
"Place was quiet, clean and just right for our needs."
United States
Bryan D.
The price is NZ$762
includes taxes & fees
27 Feb - 28 Feb
Ocean-View Studio, Steps to Beaches, in Sunny Poipu

Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6

Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
Poipu
10.0 out of 10, Exceptional, (68 reviews)
"We loved having the option of preparing meals in such a well equipped kitchen. The grills are very close too!We were close to the pool as well, which we really enjoyed on the days we weren’t exploring the island!"
United States
julie w.
The price is NZ$1,268
includes taxes & fees
10 Mar - 11 Mar
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6

Rare Find w/ 2 AC! Newly renovated condo #128, ground flr, 3-4 min walk to beach

Rare Find w/ 2 AC! Newly renovated condo #128, ground flr, 3-4 min walk to beach
Poipu
10.0 out of 10, Exceptional, (145 reviews)
"Loved the condo and property! Easy access to several beaches by walking or short drive. We loved our stay here and will return"
United States
Tricia P.
The price is NZ$1,122
includes taxes & fees
6 Mar - 7 Mar
Rare Find w/ 2 AC! Newly renovated condo #128, ground flr, 3-4 min walk to beach

Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8

Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8
Poipu
9.6 out of 10, Exceptional, (83 reviews)
"Great location, easy check in, clean condo!"
United States
Komaki U.
The price is NZ$1,597
includes taxes & fees
1 Mar - 2 Mar
Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8

Poipu Vibes in Modern Comfort! AC- Washer Dryer in unit partial OV- Rare find

Poipu Vibes in Modern Comfort! AC- Washer Dryer in unit partial OV- Rare find
Poipu
9.8 out of 10, Exceptional, (82 reviews)
"Having AC and laundry was great. Short walk down to beach front and dinning options"
United States
Gareth H.
Poipu Vibes in Modern Comfort! AC- Washer Dryer in unit partial OV- Rare find

Quiet Kiahuna plantation #88 , New Remodel with AC

Quiet Kiahuna plantation #88 , New Remodel with AC
Poipu
10.0 out of 10, Exceptional, (31 reviews)
"Ivan was an excellent host, the property clean and beautiful. The hotel-style check-in was a fancy bonus!"
United States
Felix R.
The price is NZ$1,393
includes taxes & fees
13 Mar - 14 Mar
Quiet Kiahuna plantation #88 , New Remodel with AC

Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!

Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!
Poipu
9.0 out of 10, Wonderful, (99 reviews)
"The place is very nice, clean, well furnished, and in a great location. So convenient to Poipu Beach and the Koloa restaurants and shops."
United States
Buck B.
The price is NZ$822
includes taxes & fees
7 Mar - 8 Mar
Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!

Luxury Upgraded Condo #98, AC, Poipu Beach, Partial Ocean View

Luxury Upgraded Condo #98, AC, Poipu Beach, Partial Ocean View
Poipu
9.8 out of 10, Exceptional, (67 reviews)
"Great property, in a great location, at a great price. "
United States
Michael G.
Luxury Upgraded Condo #98, AC, Poipu Beach, Partial Ocean View

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned
Poipu
9.6 out of 10, Exceptional, (169 reviews)
"Great location and stay."
United States
Juan
The price is NZ$645
includes taxes & fees
24 Feb - 25 Feb
Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!

Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!
Poipu
10.0 out of 10, Exceptional, (125 reviews)
"Beautiful condo and wonderful location we had an amazing visit. "
United States
Denise B.
The price is NZ$1,219
includes taxes & fees
25 Feb - 26 Feb
Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!

Ocean View & AC! 3 Min Walk To Poipu Beach!

Ocean View & AC! 3 Min Walk To Poipu Beach!
Poipu
10.0 out of 10, Exceptional, (109 reviews)
"Excellent location for our Kauai vacation. Robert was very accommodating. Patio area has ocean view. "
United States
Ramon
Ocean View & AC! 3 Min Walk To Poipu Beach!

Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!

Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!
Poipu
9.8 out of 10, Exceptional, (192 reviews)
"Host was very accommodating and wonderful setting. Beautiful and relaxing. "
United States
Lora F.
The price is NZ$1,131
includes taxes & fees
17 Mar - 18 Mar
Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!

No stairs, Central AC, Steps to the pool, Jacuzzi, Gym, 2 car parking

No stairs, Central AC, Steps to the pool, Jacuzzi, Gym, 2 car parking
Poipu
10.0 out of 10, Exceptional, (90 reviews)
"Loved everything about our stay. The unit was spacious, comfy, great kitchen, lived the back patio and the well stocked garage full of beach equipment. Would definitely stay here again and would highly recommend this property and owners to other travelers. The location was perfectly between Poipu Beach and Old Koloa Town and the sound center nearby had great shops and eateries. "
United States
David p.
No stairs, Central AC, Steps to the pool, Jacuzzi, Gym, 2 car parking

Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6

Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
Poipu
9.6 out of 10, Exceptional, (80 reviews)
"Easy check in and check out. Great location, clean"
United States
PATRICK W.
The price is NZ$1,324
includes taxes & fees
2 Mar - 3 Mar
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.4 out of 10, Exceptional, (66 reviews)
"The property was excellent and the owner is a really helpful person."
United States
Svitlana
The price is NZ$744
includes taxes & fees
1 Mar - 2 Mar
An Affordable Alternative to Expensive Accommodations in Poipu

A/C • Pool/Spa • W/D • Walk to Poipu Beach 413, Spectacular Garden Oasis w/ W/D and AC, Pool

A/C • Pool/Spa • W/D • Walk to Poipu Beach 413, Spectacular Garden Oasis w/ W/D and AC, Pool
Poipu
9.8 out of 10, Exceptional, (147 reviews)
"Everything was accessible…clean and cheerful…we enjoyed our stay and definitely would return…"
United States
Judith S.
The price is NZ$1,606
includes taxes & fees
14 Mar - 15 Mar
A/C • Pool/Spa • W/D • Walk to Poipu Beach 413, Spectacular Garden Oasis w/ W/D and AC, Pool

Coco Cottage at Poipu Beach - 2BR/2BA, Luxury Home

Coco Cottage at Poipu Beach - 2BR/2BA, Luxury Home
Poipu
10.0 out of 10, Exceptional, (253 reviews)
"Amazing house in a great location with all the amenities. "
United States
Jason M.
The price is NZ$1,744
includes taxes & fees
14 Mar - 15 Mar
Coco Cottage at Poipu Beach - 2BR/2BA, Luxury Home

Air conditioned, Resort Location. Short Walks To Beaches & Restaurants

Air conditioned, Resort Location. Short Walks To Beaches & Restaurants
Poipu
9.4 out of 10, Exceptional, (140 reviews)
"Nice place for our 5 day stay. Perfect size "
United States
Rachel C.
The price is NZ$640
includes taxes & fees
21 Feb - 22 Feb
Air conditioned, Resort Location. Short Walks To Beaches & Restaurants

Pili Mai Family Condo 12D, Central AC, 3 Bedroom 3 Bath, Lanai Dining for 8

Pili Mai Family Condo 12D, Central AC, 3 Bedroom 3 Bath, Lanai Dining for 8
Poipu
9.6 out of 10, Exceptional, (110 reviews)
"The house was super comfortable and had everything we needed! Lots of space for my kids to run around. Great location, easy to get to everything in Poipu. I also really appreciated that the garage had beach stuff (umbrellas, boogie boards, chairs, etc.) and snorkeling equipment! "
United States
Grace V.
The price is NZ$1,396
includes taxes & fees
26 Feb - 27 Feb
Pili Mai Family Condo 12D, Central AC, 3 Bedroom 3 Bath, Lanai Dining for 8

Pili Mai Family Condo 10B, 4 Bedrooms, 3.5 bath, AC Lanai Dining w/ Sunsets!

Pili Mai Family Condo 10B, 4 Bedrooms, 3.5 bath, AC Lanai Dining w/ Sunsets!
Poipu
9.8 out of 10, Exceptional, (117 reviews)
"We had 5 adults and two boys and the boys were thrilled to have their own bed in the upstairs room with twin beds. Their parents were in the other upstairs room and it worked great for their family. We had plenty of room downstairs for our morning and evening family activities. The house had everything we needed. "
United States
Christopher M.
The price is NZ$1,666
includes taxes & fees
28 Feb - 1 Mar
Pili Mai Family Condo 10B, 4 Bedrooms, 3.5 bath, AC Lanai Dining w/ Sunsets!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top South Shore Hotel Reviews

Find out more about South Shore

Everything you need to know about South Shore holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Shore holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Shore holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Shore holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Shore. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Shore holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Shore holiday rentals we have selected for you start as low as NZ$589 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Shore rentals

At Expedia, we put the best South Shore holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top South Shore rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Shore holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Shore. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.