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

KP228 Garden View | Beach•Pool•Turtle•AC

KP228 Garden View | Beach•Pool•Turtle•AC
Poipu
9.6 out of 10, Exceptional, (12 reviews)
"KP228 was exactly as pictured in the photos, and also had a closetful of useful beach items for the guest to use (beach chairs, umbrellas, snorkel gear, etc.). Bed was very comfortable, and the A/C kept us cool throughout the house!"
United States
Kevin F.
The price is AU$938
includes taxes & fees
16 May - 17 May
KP228 Garden View | Beach•Pool•Turtle•AC

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.4 out of 10, Exceptional, (74 reviews)
"Location was perfect for 10 minute walk to convention at Grand Hyatt and beach. Never made it to the pool, not sure where it’s at. 2 minute drive to poipu beach where 20 large turtles were resting and beautiful sunset. The use of chairs, umbrella, ice chest and snorkeling gear was very convenient. "
United States
Charles
The price is AU$695
includes taxes & fees
18 May - 19 May
An Affordable Alternative to Expensive Accommodations in Poipu

Quiet Kiahuna plantation #88 , New Remodel with AC

Quiet Kiahuna plantation #88 , New Remodel with AC
Poipu
10.0 out of 10, Exceptional, (33 reviews)
"The openness of the unit and the patio were great. The bed was super comfortable and the maid service was very good. The support staff were helpful and kind. "
Canada
Lori T.
The price is AU$989
includes taxes & fees
3 May - 4 May
Quiet Kiahuna plantation #88 , New Remodel with AC

Pili Mai Family Condo 13F, Spacious 1st Floor Lanai,

Pili Mai Family Condo 13F, Spacious 1st Floor Lanai,
Poipu
9.8 out of 10, Exceptional, (63 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We absolutely loved staying here! It was clean, in a great location, and had a lot of space. We would absolutely stay here again."
United States
Jill C.
The price is AU$965
includes taxes & fees
9 May - 10 May
Pili Mai Family Condo 13F, Spacious 1st Floor Lanai,

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, (234 reviews)
"We loved our stay and would look to stay here again in the future. It was very relaxing and close to everything we wanted to do "
United States
Lori
The price is AU$684
includes taxes & fees
22 May - 23 May
Ocean-View Studio, Steps to Beaches, in Sunny Poipu

Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301

Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301
Poipu
10.0 out of 10, Exceptional, (13 reviews)
"Fantastic time!"
United States
Chris C.
The price is AU$1,075
includes taxes & fees
29 May - 30 May
Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301

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, (109 reviews)
"Loved the space and where it was located. Only thing that could be improved would be the communication of instructions and rules of the place."
United States
Ryan
The price is AU$516
includes taxes & fees
7 May - 8 May
Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas
4.0 star property
Poipu
9.2 out of 10, Wonderful, (774 reviews)
"Great Stay! Friendly staff, very clean……"
United States
Alonzo
The price is AU$605
includes taxes & fees
2 June - 3 June
Sheraton Kauai Resort Villas

NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation

NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation
Poipu
9.2 out of 10, Wonderful, (16 reviews)
"Convenient location near the beaches, very responsive owner, comfortable space. Would stay here again."
United States
Anush
The price is AU$1,139
includes taxes & fees
22 May - 23 May
NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation

Oceanview Penthouse Condo Just 50 Yards From the Beach! A/C, Pool, Hot Tub, Gym

Oceanview Penthouse Condo Just 50 Yards From the Beach! A/C, Pool, Hot Tub, Gym
Poipu
9.6 out of 10, Exceptional, (30 reviews)
"The property is beautiful and convenient to the beach"
United States
Rhonda
The price is AU$1,001
includes taxes & fees
28 May - 29 May
Oceanview Penthouse Condo Just 50 Yards From the Beach! A/C, Pool, Hot Tub, Gym

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, (73 reviews)
"Great place for families!"
United States
William N.
The price is AU$935
includes taxes & fees
25 May - 26 May
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6

Cozy 1-bedroom condo in beautiful Koloa with washer/dryer, AC fiber internet

Cozy 1-bedroom condo in beautiful Koloa with washer/dryer, AC fiber internet
Poipu
10.0 out of 10, Exceptional, (10 reviews)
"The home was perfect for our family of 4 to stay. Short 5 minute walk to the beach, quiet, conveniently located to restaurants and activities. The room was clean, ac was great! Kitchen was stocked well and it was nice to have a washer and dryer in the unit. The lawn area was great for the kids to play !"
United States
Krystal R.
The price is AU$1,190
includes taxes & fees
9 May - 10 May
Cozy 1-bedroom condo in beautiful Koloa with washer/dryer, AC fiber internet

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (65 reviews)
"I will definitely book here again! The place was perfect for my 19 year old daughter and I. It was clean, quiet and safe. Everyone was very friendly, and Cameron went above and beyond to answer any questions or provide assistance. Our new favorite place 😊"
United States
Jenifer
The price is AU$643
includes taxes & fees
13 May - 14 May
An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (109 reviews)
"Very nice hosts and a great place to stay "
United States
John H.
The price is AU$660
includes taxes & fees
13 May - 14 May
An Affordable Alternative to Expensive Accommodations in Poipu

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned
Poipu
9.6 out of 10, Exceptional, (173 reviews)
"Great location and stay."
United States
Juan
The price is AU$553
includes taxes & fees
6 May - 7 May
Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
Poipu
10.0 out of 10, Exceptional, (23 reviews)
"The house was beautiful, the location was great! And getting to go to the athletic club was such a wonderful bonus. Would absolutely stay here again!!!"
United States
Camille H.
The price is AU$951
includes taxes & fees
8 May - 9 May
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

Kiahuna Paradise condo with A/C

Kiahuna Paradise condo with A/C
Poipu
9.8 out of 10, Exceptional, (8 reviews)
"Top notch, vacation rental."
United States
Bill G.
The price is AU$1,104
includes taxes & fees
15 May - 16 May
Kiahuna Paradise condo with A/C

Oceanfront/Ground Floor, Sleeps 4, A/C!!, Steps to the ocean. LOCATION!!!!

Oceanfront/Ground Floor, Sleeps 4, A/C!!, Steps to the ocean. LOCATION!!!!
Poipu
9.8 out of 10, Exceptional, (76 reviews)
"The perfect place to stay for great food and stunning sunsets "
United States
matthew m.
The price is AU$924
includes taxes & fees
5 May - 6 May
Oceanfront/Ground Floor, Sleeps 4, A/C!!, Steps to the ocean. LOCATION!!!!

KP313 -Top FL | Partial Ocean •Pool•Gym•AC

KP313 -Top FL | Partial Ocean •Pool•Gym•AC
Poipu
10.0 out of 10, Exceptional, (48 reviews)
"This was a very nice last minute stay. We enjoyed 2 nights at this property and it was perfect. Everything we needed for our stay and the host was very helpful! Thank you"
United States
Kara
The price is AU$967
includes taxes & fees
17 May - 18 May
KP313 -Top FL | Partial Ocean •Pool•Gym•AC

Enjoy Partial Ocean Views & Moir Garden Views! A/C, Pool, Hot Tub and Gym

Enjoy Partial Ocean Views & Moir Garden Views! A/C, Pool, Hot Tub and Gym
Poipu
9.4 out of 10, Exceptional, (25 reviews)
"Clean, comfortable, excellent communication, and great location! We’d stay here again in a heartbeat."
United States
Kileigh S.
The price is AU$1,008
includes taxes & fees
5 May - 6 May
Enjoy Partial Ocean Views & Moir Garden Views! A/C, Pool, Hot Tub and Gym
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.
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 favourite 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 depend 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 AU$553 per night. Entering your travel dates in the search wizard might find you 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.