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South Shore Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for South Shore vacation rentals

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

Condo in Poipu

Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
9.6 out of 10, Exceptional, (77 reviews)
"Easy check in and check out. Great location, clean"
United States
PATRICK W.
The price is ￥36,347
￥129,175 total
includes taxes & fees
Feb 3 - Feb 4
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
Terrace/patio
500 feet to the 🌊, 1000 feet 🏝 and 🐢

Apartment in Poipu

500 feet to the 🌊, 1000 feet 🏝 and 🐢
9.8 out of 10, Exceptional, (21 reviews)
"Clean, comfortable, close to beach with turtles and monk seal!"
United States
Katherine M.
The price is ￥46,619
￥116,127 total
includes taxes & fees
Jan 15 - Jan 16
500 feet to the 🌊, 1000 feet 🏝 and 🐢
Property grounds
Quiet Kiahuna plantation #88 , New Remodel with AC

Condo in Poipu

Quiet Kiahuna plantation #88 , New Remodel with AC
10.0 out of 10, Exceptional, (30 reviews)
"Great property excellent communication by the owner very accommodating to allow an extra night last minute and very much appreciated. This unit had everything we needed, easy, walk to the beach, beautiful property grounds, and right across the street from our unit was the awesome coffee shop. I would definitely return again."
United States
tom
The price is ￥39,508
￥120,334 total
includes taxes & fees
Jan 19 - Jan 20
Quiet Kiahuna plantation #88 , New Remodel with AC
Pool
KP317-Private-3rdFl-Partial Ocean-Pool-Garden

Vacation Home in Poipu

KP317-Private-3rdFl-Partial Ocean-Pool-Garden
2.0 star property
The price is ￥42,668
￥121,449 total
includes taxes & fees
Jan 19 - Jan 20
KP317-Private-3rdFl-Partial Ocean-Pool-Garden
Interior
Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!

Condo in Poipu

Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!
10.0 out of 10, Exceptional, (124 reviews)
"Beautiful condo and wonderful location we had an amazing visit. "
United States
Denise B.
The price is ￥47,930
￥119,827 total
includes taxes & fees
Jan 27 - Jan 28
Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!
Pool
Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8

Condo in Poipu

Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8
9.6 out of 10, Exceptional, (80 reviews)
"This house was perfect for me and my family of 6, great location and lots of food and shopping within walking distance. House was very comfortable and beautiful, lots of room, great appliances and extras and the company was very accommodating to our needs and went above for us. Highly recommend for any family considering this location."
United States
tiffany m.
The price is ￥50,525
￥156,938 total
includes taxes & fees
Feb 1 - Feb 2
Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8
Property grounds
Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

Apartment in Poipu

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned
9.6 out of 10, Exceptional, (166 reviews)
"Loved the location. A peaceful & refreshing escape."
United States
Iris
The price is ￥31,448
￥62,689 total
includes taxes & fees
Jan 22 - Jan 23
Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned
Sun loungers, beach towels
Ukulele Oasis @ Kiahuna l AC l Family-Friendly l Beach Amenities l Ground Floor

Condo in Poipu

Ukulele Oasis @ Kiahuna l AC l Family-Friendly l Beach Amenities l Ground Floor
3.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Had all we could need and close to the beach!"
United States
Deepa B.
The price is ￥29,446
￥105,966 total
includes taxes & fees
Jan 27 - Jan 28
Ukulele Oasis @ Kiahuna l AC l Family-Friendly l Beach Amenities l Ground Floor
Dining
A/C • Pool/Spa • W/D • Walk to Poipu Beach 413, Spectacular Garden Oasis w/ W/D and AC, Pool

Apartment in Poipu

A/C • Pool/Spa • W/D • Walk to Poipu Beach 413, Spectacular Garden Oasis w/ W/D and AC, Pool
9.8 out of 10, Exceptional, (147 reviews)
"We had an awesome time! Pool and hot tub was great, met many fun people there. The beach was a short walk away and got to see the turtles! Location was close to stores and restaurants, and not too far from Waimea canyon."
United States
William M.
The price is ￥43,882
￥145,220 total
includes taxes & fees
Jan 15 - Jan 16
A/C • Pool/Spa • W/D • Walk to Poipu Beach 413, Spectacular Garden Oasis w/ W/D and AC, Pool
Outdoor pool
2/2 BEACHFRONT RESORT w AC, Poipu Beach - Kiahuna Garden View Condo, Pool/Gym

Condo in Poipu

2/2 BEACHFRONT RESORT w AC, Poipu Beach - Kiahuna Garden View Condo, Pool/Gym
9.8 out of 10, Exceptional, (80 reviews)
"Great family vacation "
United States
David P.
The price is ￥37,927
￥136,966 total
includes taxes & fees
Jan 16 - Jan 17
2/2 BEACHFRONT RESORT w AC, Poipu Beach - Kiahuna Garden View Condo, Pool/Gym
Property grounds
Air conditioned, Resort Location. Short Walks To Beaches & Restaurants

Apartment in Poipu

Air conditioned, Resort Location. Short Walks To Beaches & Restaurants
9.4 out of 10, Exceptional, (133 reviews)
"Nice place for our 5 day stay. Perfect size "
United States
Rachel C.
The price is ￥31,448
￥63,021 total
includes taxes & fees
Jan 20 - Jan 21
Air conditioned, Resort Location. Short Walks To Beaches & Restaurants
Outdoor dining
Kiahuna Paradise condo with A/C

Condo in Poipu

Kiahuna Paradise condo with A/C
9.6 out of 10, Exceptional, (5 reviews)
"Top notch, vacation rental."
United States
Bill G.
The price is ￥44,248
￥126,790 total
includes taxes & fees
Jan 20 - Jan 21
Kiahuna Paradise condo with A/C
Smart TV
1000 Feet to the 🏝

Condo in Poipu

1000 Feet to the 🏝
8.8 out of 10, Excellent, (14 reviews)
"Excellent stay, we appreciated the proximity to Seasport dive center for scuba diving adventures. We also highly enjoyed having a kitchen and quiet space to unwind."
United States
Charmaine R.
The price is ￥46,619
￥116,127 total
includes taxes & fees
Jan 15 - Jan 16
1000 Feet to the 🏝
Property grounds
An Affordable Alternative to Expensive Accommodations in Poipu

Vacation Home in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
9.2 out of 10, Wonderful, (104 reviews)
"Very thoughtful and helpful hosts. Comfortable furniture and close to many great places. "
United States
Don G.
The price is ￥30,579
￥73,653 total
includes taxes & fees
Jan 19 - Jan 20
An Affordable Alternative to Expensive Accommodations in Poipu
Interior
Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!

Condo in Poipu

Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!
9.8 out of 10, Exceptional, (191 reviews)
"Loved the location! Great stay!"
United States
Mary S.
The price is ￥42,526
￥113,657 total
includes taxes & fees
Jan 15 - Jan 16
Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!
Outdoor dining
Remodeled Family-Size Condo with Fantastic View of the Ocean and Pool

Condo in Poipu

Remodeled Family-Size Condo with Fantastic View of the Ocean and Pool
9.6 out of 10, Exceptional, (50 reviews)
"Check-in was easy, kitchen had everything we needed"
United States
Kevin F.
The price is ￥67,408
￥160,021 total
includes taxes & fees
Jan 15 - Jan 16
Remodeled Family-Size Condo with Fantastic View of the Ocean and Pool
Pool
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6

Condo in Poipu

Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
2.0 star property
10.0 out of 10, Exceptional, (58 reviews)
"The kitchen was well stocked and the amenities were great. Kevin was an amazing host. He responded to our messages right away. We had a wonderful vacation!"
United States
Lucia C.
The price is ￥41,878
￥110,901 total
includes taxes & fees
Feb 2 - Feb 3
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
On the beach
Enjoy Partial Ocean Views & Moir Garden Views! A/C, Pool, Hot Tub and Gym

Condo in Poipu

Enjoy Partial Ocean Views & Moir Garden Views! A/C, Pool, Hot Tub and Gym
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 ￥32,999
￥113,373 total
includes taxes & fees
Feb 9 - Feb 10
Enjoy Partial Ocean Views & Moir Garden Views! A/C, Pool, Hot Tub and Gym
Property grounds
Stunning Ocean View - Steps from the beach - Kahala 623

Condo in Poipu

Stunning Ocean View - Steps from the beach - Kahala 623
10.0 out of 10, Exceptional, (48 reviews)
"We had all we needed for our stay in this lovely condo. The lanai was our favorite place to relax and enjoy the birds, flowers and immense green lawns. "
United States
Robert L.
The price is ￥49,779
￥111,619 total
includes taxes & fees
Jan 18 - Jan 19
Stunning Ocean View - Steps from the beach - Kahala 623
Beach towels
BEAUTIFUL BREATH-TAKING Ocean Views w/ AC, Upscale Furnishing, & Art.

Condo in Poipu

BEAUTIFUL BREATH-TAKING Ocean Views w/ AC, Upscale Furnishing, & Art.
9.6 out of 10, Exceptional, (178 reviews)
"Lovely stay, GREAT location, very comfortable and as advertised!"
United States
Monica V.
The price is ￥59,893
￥138,995 total
includes taxes & fees
Jan 29 - Jan 30
BEAUTIFUL BREATH-TAKING Ocean Views w/ AC, Upscale Furnishing, & Art.
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

Koloa Landing Resort at Poipu, Autograph Collection

Koloa Landing Resort at Poipu, Autograph Collection

10/10 Excellent
"From the moment we arrived, the staff was welcoming and made us feel as if we were at home. The resort could not have been more beautiful, the room was spacious, beds comfortable, the kitchen was well stocked. We loved our stay and will be returning next year for sure. "
Caroline 7-night trip
Posted 2 days ago
Koloa Landing Resort at Poipu, Autograph Collection

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