A rocky shoreline with a sunset over the ocean.

South Shore Vacation Rentals

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Our top choices for South Shore vacation rentals

1. 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, (247 reviews)
"Great location. Perfect for our short stay."
United States
Heather A.
The price is CA $311
CA $730 total
includes taxes & fees
Oct 6 - Oct 7
Ocean-View Studio, Steps to Beaches, in Sunny Poipu

2. 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
9.2 out of 10, Wonderful, (127 reviews)
"A wonderful place to land very convenient to all the adventures the south had to offer. The space was clean and comfortable. Would stay here again!"
United States
Christine A.
The price is CA $170
CA $588 total
includes taxes & fees
Oct 6 - Oct 7
Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!

3. Cozy studio condo with AC and WiFi in charming Koloa/ Poipu

Cozy studio condo with AC and WiFi in charming Koloa/ Poipu
Poipu
10.0 out of 10, Exceptional, (5 reviews)
"Everything was great!"
United States
Jeff
The price is CA $185
CA $532 total
includes taxes & fees
Oct 6 - Oct 7
Cozy studio condo with AC and WiFi in charming Koloa/ Poipu

4. 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, (33 reviews)
"Absolutely perfect location! We loved it. Would stay again in a heartbeat."
United States
Tara P.
The price is CA $296
CA $1,033 total
includes taxes & fees
Oct 5 - Oct 6
Oceanview Penthouse Condo Just 50 Yards From the Beach! A/C, Pool, Hot Tub, Gym

5. 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, (204 reviews)
"Very easy instructions to enter and the villa had everything we needed. Great ocean view too!"
Australia
Annie B.
The price is CA $317
CA $947 total
includes taxes & fees
Oct 6 - Oct 7
Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!

6. Prince Kuhio 335 OCEANVIEW STUDIO

Prince Kuhio 335 OCEANVIEW STUDIO
Poipu
9.4 out of 10, Exceptional, (95 reviews)
"Great place. Will stay again"
United States
Matthew S.
The price is CA $185
CA $532 total
includes taxes & fees
Oct 6 - Oct 7
Prince Kuhio 335 OCEANVIEW STUDIO

7. Pili Mai Condo 1C, Spacious, AC, Great for Families and Friends!

Pili Mai Condo 1C, Spacious, AC, Great for Families and Friends!
Poipu
9.6 out of 10, Exceptional, (103 reviews)
"This property was lovely! The kitchen was well stocked, the pool was awesome, the location was perfect. We will definitely stay here again!"
United States
Janet C.
The price is CA $341
CA $1,249 total
includes taxes & fees
Oct 10 - Oct 11
Pili Mai Condo 1C, Spacious, AC, Great for Families and Friends!

8. An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.4 out of 10, Exceptional, (83 reviews)
"Property was comfortable, clean, and easy to find. Would stay here again. Host provided lots of extra amenities."
United States
Melissa C.
The price is CA $211
CA $635 total
includes taxes & fees
Oct 6 - Oct 7
An Affordable Alternative to Expensive Accommodations in Poipu

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

Quiet Kiahuna plantation #88 , New Remodel with AC
Poipu
10.0 out of 10, Exceptional, (36 reviews)
"Rental was clean with tons of kitchen supplies and extra linen for pull out sofa. Loved the wagon on the porch to take stuff down to the beach. Easy access to pool and beach. Wonderful gym amenities! "
United States
Melissa H.
The price is CA $398
CA $1,254 total
includes taxes & fees
Oct 10 - Oct 11
Quiet Kiahuna plantation #88 , New Remodel with AC

10. Ocean View & AC - 3 Min Walk To Poipu Beach - 100+ 5 Star Reviews

Ocean View & AC - 3 Min Walk To Poipu Beach - 100+ 5 Star Reviews
Poipu
10.0 out of 10, Exceptional, (125 reviews)
"The place was nice and close to the beach. Everything we needed was available and we had a great stay."
United States
Ryan D.
The price is CA $630
CA $839 total
includes taxes & fees
Oct 4 - Oct 5
Ocean View & AC - 3 Min Walk To Poipu Beach - 100+ 5 Star Reviews

11. 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
9.4 out of 10, Exceptional, (98 reviews)
"Loved this place! So clean and located just a couple minutes from the beach!! It was very quiet place and super clean! We absolutely loved staying here!"
United States
Ananiah
The price is CA $251
CA $1,060 total
includes taxes & fees
Oct 6 - Oct 7
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6

12. Charming apartment in delightful Koloa with fitness room, AC, WiFi

Charming apartment in delightful Koloa with fitness room, AC, WiFi
Poipu
9.6 out of 10, Exceptional, (13 reviews)
"Affordable beautiful place to stay. Easy access to several beaches and accommodations across the street. The pool across the street is nice as well and the host was responsive and helpful when we needed them. "
United States
Wade B.
The price is CA $321
CA $905 total
includes taxes & fees
Oct 6 - Oct 7
Charming apartment in delightful Koloa with fitness room, AC, WiFi

13. An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (69 reviews)
"We absolutely loved our stay at Cameron's place - Nestled in a chill resort area and easy access to a walking path to both nearby Shipwreck and Poipu beach areas (my fav part). Didn't use the pool or hot tub, but took advantage of the beach chairs and umbrellas provided. Thanks Cameron! Hope we get to visit again soon!"
United States
Zach W.
The price is CA $237
CA $669 total
includes taxes & fees
Oct 5 - Oct 6
An Affordable Alternative to Expensive Accommodations in Poipu

14. 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, (19 reviews)
"Nice unit in a great location. A couple of issues with bedding but the owner made it right. Would stay at this location again. The beach was great and loved the complimentary fitness club access and the nice assortment of restaurants nearby."
United States
Linda
The price is CA $370
CA $1,113 total
includes taxes & fees
Oct 5 - Oct 6
NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation

15. Luxury Ground Floor Condo Just 50 Yards From The Beach!

Luxury Ground Floor Condo Just 50 Yards From The Beach!
Poipu
9.8 out of 10, Exceptional, (49 reviews)
"Great location at our favorite beach on the island. Always nice getting to stay at kiahuna and this condo is great. Came as advertised and is steps from the water. Clean and well furnished. We had a great time. "
Canada
Tom C.
The price is CA $296
CA $1,035 total
includes taxes & fees
Oct 4 - Oct 5
Luxury Ground Floor Condo Just 50 Yards From The Beach!

16. South Kauai Tranquil Retreat w/ AC in Poipu

South Kauai Tranquil Retreat w/ AC in Poipu
Poipu
10.0 out of 10, Exceptional, (23 reviews)
"We loved our stay. Mahalo for all"
United States
Luiz
The price is CA $298
CA $858 total
includes taxes & fees
Oct 17 - Oct 18
South Kauai Tranquil Retreat w/ AC in Poipu

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

Kiahuna Paradise @ Poipu with 2 AC units Family size condo with patio
Poipu
9.8 out of 10, Exceptional, (32 reviews)
"Great location."
United States
Vivek
The price is CA $468
CA $1,320 total
includes taxes & fees
Oct 31 - Nov 1
Kiahuna Paradise @ Poipu with 2 AC units Family size condo with patio

18. 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, (144 reviews)
"The place was beautiful! And the owner is quick to respond with any questions. Definitely would stay again "
United States
Kathie R.
The price is CA $454
CA $1,109 total
includes taxes & fees
Oct 15 - Oct 16
Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!

19. An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (114 reviews)
"Had a great stay! We really liked the unit and the location. Everything was clean and comfy, and the host was super friendly. Would definitely stay here again."
United States
Myranda S.
The price is CA $278
CA $723 total
includes taxes & fees
Oct 28 - Oct 29
An Affordable Alternative to Expensive Accommodations in Poipu

20. 5 Beds Downstairs Corner Unit with AC, 3 Pools, 6 minutes to Beaches, Beach Cart

5 Beds Downstairs Corner Unit with AC, 3 Pools, 6 minutes to Beaches, Beach Cart
Poipu
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful stay!"
United States
jonathon y.
The price is CA $432
CA $1,110 total
includes taxes & fees
Oct 13 - Oct 14
5 Beds Downstairs Corner Unit with AC, 3 Pools, 6 minutes to Beaches, Beach Cart
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.
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Top South Shore Hotel Reviews

Find out more about South Shore

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Shore. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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