South Shore Vacation Rentals from $381: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for South Shore vacation rentals

1. Sheraton Kauai Resort Villas

Poipu

andrew

$321 nightly

Sep 1 - Sep 2

Total with taxes and fees

2. Marriott's Waiohai Beach Club

Poipu

Alenka

$503 nightly

Sep 12 - Sep 13

Total with taxes and fees

3. Pili Mai Family Condo 11J, Golf Course View, Grassy Area Around Lanai

Poipu

Mayte M

$746 nightly

Sep 6 - Sep 7

Total with taxes and fees

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

Poipu

Holly W.

$427 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

Poipu

Shanelle

$697 nightly

Aug 31 - Sep 1

Total with taxes and fees

6. Prince Kuhio 335 OCEANVIEW STUDIO

Poipu

Katherine B.

$400 nightly

Sep 2 - Sep 3

Total with taxes and fees

Beach nearby, sun loungers, beach towels

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

Poipu

Marie-Louise M.

$507 nightly

Sep 20 - Sep 21

Total with taxes and fees

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

Poipu

William N.

$522 nightly

Sep 4 - Sep 5

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Condos

Private vacation homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top South Shore Hotel Reviews

Castle Kiahuna Plantation & Beach Bungalows

10/10 Excellent

"Property has everything one needs to do own meals. Clean w/ Hawaiian motiff in rooms. Staff very helpful. 2nd stay here. Not sure what to do with trash- no instructions or obvious dumpsters nearby. took 2 days to figure out TV- probably operator challenged. Lots of options to watch- once I figured out how to get them....."

Luxury Poipu 4br Villa with AC Walk to the Beach! (224)

8/10 Good

"This property is in a terrific location that is very convenient to places like Brennecke and Poipu beaches. We walked to both multiple times over the course of our stay. All the other amenities of Poipu and Koloa are a short drive away. The owner was responsive, and the check in and out processes were given in sufficient time and simple to follow. The condo itself is perfect...for the right group. That 4th "bedroom" is actually an open loft area at the top of the stairs on the 2nd floor. It lacks the same privacy of an actual bedroom. Having stayed here, I think this would be a perfect fit for, say, two couples with two kids each. Each level would be very comfortable for such a group. For our party of seven adults, it was slightly less ideal, but the 28 year old who got the loft was good sport.The condo itself is in good repair but could use some minor TLC. There is noticeable and unattractive--we'll call it discoloration--on one of the vents in the bathroom and a similar item or two that could easily be remedied. They are adamant about no shoes inside (not unusual for Hawaii), but there's absolutely nowhere remotely private to place them outside. We carried ours in and put them on the porch. Overall, it was a comfortable condo in a great location. I wouldn't say it was quite the ideal fit for our group, but for others, it certainly could be."

Hilton Vacation Club The Point At Poipu Kauai

10/10 Excellent

"First time here and great place to stay. Came with my wife and four kids. Kids loved the pool, the grill was great and awesome outdoor area with gorgeous views. Room was just remodeled, great kitchen and two nice rooms. Would definitely stay again. Easy check in and plenty of parking. Great location. Close to many stores."

Koloa Landing Resort at Poipu, Autograph Collection

10/10 Excellent

"Absolutely Phenomenal resort! I was there celebrating my 50th birthday and they went above and beyond making my trip special! I even saw dolphins from our hotel room with an epic view of the ocean. I could not have asked for a better gift! We used the adults only pool, ate a couple of meals at the small restaurant on site, walked to the beach (so close), rented snorkel gear. We didn’t get a chance to use the transportation they offered to go to local spots, because we had our own car, but loved that they had that. Free parking too, that was wonderful! Tori was very sweet, helpful with great communication. Making my stay just perfect. I didn’t get a chance to get a spa treatment but I’m sure that would have been heavenly too Very grateful and will highly recommend Koloa Landing Resort!"

Charming 3BR Koloa Shore Cottage with ocean views and AC, sleeps 6 in Poipu

10/10 Excellent

"Only thing that would be nice is to have addtl trash bags as there were only 2. We had a couple that we used also. But great stay, beautiful location. We enjoyed being able to walk across the street and see the turtles. Plenty of room and property was in great shape. Thanks for hosting us. The additional bathroom and shower outside was great."

Find out more about South Shore

Everything you need to know about South Shore vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Shore vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Shore vacation 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 low season months. For more hustle and bustle, you may prefer to visit South Shore in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $381 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Shore rentals

At Expedia, we put the best South Shore vacation 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 vacation.

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.

South Shore Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for South Shore vacation rentals

1. Sheraton Kauai Resort Villas

2. Marriott's Waiohai Beach Club

3. Pili Mai Family Condo 11J, Golf Course View, Grassy Area Around Lanai

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

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

6. Prince Kuhio 335 OCEANVIEW STUDIO

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

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

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

10. Quiet Kiahuna plantation #88 , New Remodel with AC

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

12. Sheraton Kaua‘i Resort Villas (1BR)

13. South Kauai Tranquil Retreat w/ AC in Poipu

14. Poipu Pili Mai 4 Bedroom Condo with Ocean Views, Pool & Golf Course Access

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

16. Poipu Condo! Newly updated - Sleeps 5 - 5 minute walk to the beach!

17. Step to beach New Quiet Kiahuna Plantation Remodeled 2 bedroom condo with A/C

18. Hale Minoaka | Private Cottage w/ A/C & Bikes in Poipu Beach Estates

19. Kiahuna Paradise @ Poipu with 2 AC units Family size condo with patio

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

Find vacation rentals that suit your style

Top South Shore Hotel Reviews

Castle Kiahuna Plantation & Beach Bungalows

Find out more about South Shore

Explore a world of travel with Expedia

Expedia's Latest Trends

Go further with the Expedia app