A rocky shoreline with a sunset over the ocean.

South Shore Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for South Shore holiday rentals

A nighttime pool area with a clear sky, a crescent moon, and a well-lit building with a pool.

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

Pili Mai Family Condo 11J, Golf Course View, Grassy Area Around Lanai
Poipu
9.8 out of 10, Exceptional, (91 reviews)
"Really enjoyed the property. Easy to access and depart. Loved Kauai! First time visit but not the last."
United States
Mayte M
The price is HK$2,087
HK$7,086 total
includes taxes & fees
24 Oct - 25 Oct
Pili Mai Family Condo 11J, Golf Course View, Grassy Area Around Lanai
A coastal residential area with houses, a tennis court, and a beach.

2. 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, (275 reviews)
"Wonderful property-wonderful hosts!"
United States
Anonymous traveller
The price is HK$3,130
HK$6,742 total
includes taxes & fees
10 Oct - 11 Oct
Coco Cottage at Poipu Beach - 2BR/2BA, Luxury Home
A nighttime pool area with a clear sky, a crescent moon, and a well-lit building with a pool.

3. 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
9.8 out of 10, Exceptional, (91 reviews)
"Perfect location beautiful property"
United States
Shanelle
The price is HK$1,687
HK$6,208 total
includes taxes & fees
30 Sept - 1 Oct
Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8
An aerial view of a resort with a large central pool, smaller pools, and lounge areas with sun loungers.

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

Poipu Pili Mai 4 Bedroom Condo with Ocean Views, Pool & Golf Course Access
Poipu
10.0 out of 10, Exceptional, (82 reviews)
"Janice and Brett were extremely accommodating and friendly. The condo has a wonderful view and is very conveniently located. We were a crew of 8 people and the space was great for that family size."
United States
Marjorie C.
The price is HK$5,452
HK$11,629 total
includes taxes & fees
7 Oct - 8 Oct
Poipu Pili Mai 4 Bedroom Condo with Ocean Views, Pool & Golf Course Access
A balcony with a view of the ocean, palm trees, and a purple orchid.

5. 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)
"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 HK$1,640
HK$3,721 total
includes taxes & fees
30 Sept - 1 Oct
Ocean-View Studio, Steps to Beaches, in Sunny Poipu
A poolside area with two cushioned chairs, a small table, and a pool with a metal ladder.

6. 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
9.8 out of 10, Exceptional, (84 reviews)
"The property was great, and Kevin was really good at sending info and responding to questions. Great location, and amazing amenities within the property area. Would definitely stay here again!!"
United States
Abe B.
The price is HK$1,569
HK$4,538 total
includes taxes & fees
8 Oct - 9 Oct
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
A resort pool with clear water, surrounded by a rocky landscape and a building with a thatched roof.

7. 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 HK$2,345
HK$6,701 total
includes taxes & fees
10 Oct - 11 Oct
Quiet Kiahuna plantation #88 , New Remodel with AC
A beach with clear turquoise water, a sandy shore, and lush green mountains in the background.

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

Hale Minoaka | Private Cottage w/ A/C & Bikes in Poipu Beach Estates
Poipu
9.8 out of 10, Exceptional, (151 reviews)
"Quiet, private, clean home! Have stayed here twice now and recommend it to anyone going to the island. Has everything you need for a comfy stay."
United States
Madison H.
The price is HK$2,188
HK$4,403 total
includes taxes & fees
11 Oct - 12 Oct
Hale Minoaka | Private Cottage w/ A/C & Bikes in Poipu Beach Estates
A balcony with a glass table holding fruits, a chair, and a view of the ocean and palm trees.

9. 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 HK$1,412
HK$3,262 total
includes taxes & fees
30 Sept - 1 Oct
Prince Kuhio 335 OCEANVIEW STUDIO
A thatched-roof structure with tables and chairs, surrounded by water and palm trees.

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

Step to beach New Quiet Kiahuna Plantation Remodeled 2 bedroom condo with A/C
Poipu
9.8 out of 10, Exceptional, (27 reviews)
"Great place, fantastic location!"
United States
Nick S.
The price is HK$3,522
HK$8,767 total
includes taxes & fees
17 Oct - 18 Oct
Step to beach New Quiet Kiahuna Plantation Remodeled 2 bedroom condo with A/C
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

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

Sheraton Kaua‘i Resort Villas (1BR)
Poipu
10.0 out of 10, Exceptional, (2 reviews)
"Our host was amazing and so responsive. The accommodations were beautiful and we were easily able to extend our stay. We loved it!"
United States
Rachel S.
The price is HK$3,718
HK$3,989 total
includes taxes & fees
12 Oct - 13 Oct
Sheraton Kaua‘i Resort Villas (1BR)
A coastal sunset view with palm trees and a beach.

12. Unaffected by Hurricane-Private 4 BR Luxury Home in Poipu - Sleeps 10 TVNC#1194

Unaffected by Hurricane-Private 4 BR Luxury Home in Poipu - Sleeps 10 TVNC#1194
Poipu
9.8 out of 10, Exceptional, (119 reviews)
"Location was great "
United States
Karen G.
The price is HK$5,883
HK$12,604 total
includes taxes & fees
12 Oct - 13 Oct
Unaffected by Hurricane-Private 4 BR Luxury Home in Poipu - Sleeps 10 TVNC#1194
A spacious living area with a sofa, chairs, a coffee table, and a TV. It features a balcony with a view of palm trees and the ocean.

13. 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 HK$1,751
HK$4,927 total
includes taxes & fees
4 Oct - 5 Oct
Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!
A tropical resort pool with a water slide, surrounded by lush greenery and palm trees.

14. *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.
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
A nighttime pool area with a clear sky, a crescent moon, and a well-lit building with a pool.

15. 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, (127 reviews)
"Great home, very clean, responsive host, and a perfect location!"
United States
Drew W.
The price is HK$2,774
HK$7,996 total
includes taxes & fees
12 Oct - 13 Oct
Pili Mai Family Condo 10B, 4 Bedrooms, 3.5 bath, AC Lanai Dining w/ Sunsets!
A tropical resort pool with a water slide, surrounded by lush greenery and palm trees.

16. *NEW Estate 5BR Retreat|Pool|AC & PickleBall

*NEW Estate 5BR Retreat|Pool|AC & PickleBall
Poipu
10.0 out of 10, Exceptional, (7 reviews)
"We loved this place. It was a wonderful place for all seven of us. The club house was a great place to end our day being lazy around the pool."
United States
Margaret G.
*NEW Estate 5BR Retreat|Pool|AC & PickleBall
A beach scene with palm trees, a building with a flat roof, and a grassy area with chairs.

17. 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, (143 reviews)
"Beautiful property, close to the beach. Air conditioning was a real plus. Our host provided lots of great ideas of things to do in the area."
United States
David M.
The price is HK$2,556
HK$5,845 total
includes taxes & fees
22 Oct - 23 Oct
Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!
A tropical resort pool with a water slide, surrounded by lush greenery and palm trees.

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

Poipu Condo! Newly updated - Sleeps 5 - 5 minute walk to the beach!
Poipu
9.6 out of 10, Exceptional, (36 reviews)
"We had a wonderful time on our trip and the place was perfect for us. Alex was awesome and super responsive and made sure we had a perfect stay. Thank you!!!"
United States
William P.
Poipu Condo! Newly updated - Sleeps 5 - 5 minute walk to the beach!
A resort with beachfront properties, a golf course, and lush greenery.

19. 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
NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation
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

Villas at Poipu Kai 3 bed/3 bath luxury villa with central air conditioning!

Villas at Poipu Kai 3 bed/3 bath luxury villa with central air conditioning!

10/10 Excellent
"We loved the ability to walk to Poipu beach and watch the Hawaiian sea turtles and Monk seals sunbathing. The villa is generously supplied with soap, coffee, laundry detergent, trash bags and other household items. The pool and hot tub are nice to use with the complimentary access. Beautifully decorated and maintained"
Emily W. 4-night trip
Posted 18 hours ago
Villas at Poipu Kai 3 bed/3 bath luxury villa with central air conditioning!

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