South Shore Vacation Rentals

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Browse Select South Shore Vacation Homes

Our top choices for South Shore vacation homes

R413-Pool-Spa-Beach-Turtles-Ocean Access-w/d-A/C, Spectacular Garden Oasis w/ W/D and AC, Pool

9.8 out of 10, Exceptional, (145)
"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."
The price is CA $126
CA $929 total
includes taxes & fees
Sep 2 - Sep 3
R413-Pool-Spa-Beach-Turtles-Ocean Access-w/d-A/C, Spectacular Garden Oasis w/ W/D and AC, Pool

4 Star Beachfront Resort. AC. Lanai. Restaurant. Pool. Gym. Spa.

The price is CA $150
CA $645 total
includes taxes & fees
Sep 2 - Sep 3
4 Star Beachfront Resort. AC. Lanai. Restaurant. Pool. Gym. Spa.

An Affordable Alternative to Expensive Accommodations in Poipu

9.2 out of 10, Wonderful, (57)
"The property was excellent and the owner is a really helpful person."
The price is CA $204
CA $536 total
includes taxes & fees
Sep 2 - Sep 3
An Affordable Alternative to Expensive Accommodations in Poipu

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

9.8 out of 10, Exceptional, (20)
"Wonderful experience, would definitely stay again."
The price is CA $295
CA $927 total
includes taxes & fees
Sep 5 - Sep 6
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

An Affordable Alternative to Expensive Accommodations in Poipu

9.2 out of 10, Wonderful, (99)
"Great unit in a fantastic location!"
The price is CA $216
CA $571 total
includes taxes & fees
Sep 2 - Sep 3
An Affordable Alternative to Expensive Accommodations in Poipu

Great Rate Upgraded 4 Bedroom Luxury Poipu Home sleeps 10- Baby Beach TVNC#1194

9.0 out of 10, Wonderful, (6)
"This house is in great location while being well equipped with everything you need inside the house and for the beach!"
The price is CA $1,031
CA $2,294 total
includes taxes & fees
Sep 2 - Sep 3
Great Rate Upgraded 4 Bedroom Luxury Poipu Home sleeps 10- Baby Beach TVNC#1194

Cute 2BR Cottage w AC close to beaches

10.0 out of 10, Exceptional, (6)
"What a great little place! Split floor plan allows for the feeling of separate spaces with a communal kitchen. Patios and outdoor shower were perfect. Shampoo, conditioner and soaps provided were lovely, gentle, and smelled amazing. The pool was not located on site as you’d expect, but was about a half mile away or a ten minute walk. We did not end up utilizing the pool because of the distance. "
The price is CA $473
CA $1,429 total
includes taxes & fees
Sep 14 - Sep 15
Cute 2BR Cottage w AC close to beaches

Luxurious 4BR/3.5BA House: AC, Short Walk To Beach

10.0 out of 10, Exceptional, (17)
"Great location, lots of extra items including chairs, cart for the beach."
The price is CA $714
CA $1,922 total
includes taxes & fees
Sep 5 - Sep 6
Luxurious 4BR/3.5BA House: AC, Short Walk To Beach

Pili Mai 5L - 4 Bedroom Suite in Poipu Sleeps 8 AC, Pool, Fitness Center & More!

9.4 out of 10, Exceptional, (10)
"Great stay!"
Pili Mai 5L - 4 Bedroom Suite in Poipu Sleeps 8 AC, Pool, Fitness Center & More!

*NEW 7BD Farmhouse Estate |Pool, PickleB, Gym| AC

10.0 out of 10, Exceptional, (3)
"Great tume"
The price is CA $1,779
CA $3,962 total
includes taxes & fees
Sep 15 - Sep 16
*NEW 7BD Farmhouse Estate |Pool, PickleB, Gym| AC

Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194

9.8 out of 10, Exceptional, (112)
"Close to great snorkeling, boogie boarding beaches, & Very quiet community. Central location for excursions.Home was very clean and well stocked.It suited our three families very well"
The price is CA $1,031
CA $2,294 total
includes taxes & fees
Sep 2 - Sep 3
Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194

Luxury 3br Poipu Estates Home w Private Pool

9.8 out of 10, Exceptional, (32)
"Our all time favorite island, the house was perfect for our needs and would be great for 2 couples and children. Exactly as described peaceful, beautiful, private.."
The price is CA $1,180
CA $3,247 total
includes taxes & fees
Sep 14 - Sep 15
Luxury 3br Poipu Estates Home w Private Pool

5 Bed 3 Bath Home in Poipu Kai

10.0 out of 10, Exceptional, (26)
"Such a wonderful place for our family of 12 (6 kids, 6 adults). Short walk to the beach and the pool. Wonderful neighborhood. Felt very comfortable and safe there. We had everything we needed at the house to cook our meals. Would highly recommend."
5 Bed 3 Bath Home in Poipu Kai

Plantation-style home w Private Pool

9.4 out of 10, Exceptional, (22)
"This is a terrific property! The location is terrific, in a quiet subdivision near Poipu beach. Very easy to get to other island locations. The house is well-kept, full of amenities, everything works, the beds are comfortable. Check-in and check-out was very easy, the staff was very accommodating. Would not hesitate to stay here again."
Plantation-style home w Private Pool

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

The price is CA $356
CA $930 total
includes taxes & fees
Sep 10 - Sep 11
Charming apartment in delightful Koloa with fitness room, AC, WiFi

Fall special for months of October & November. See calendar

9.6 out of 10, Exceptional, (112)
"This home is incredible. It's beautiful, spacious, is in a perfect location to walk to the beach, and everything is well stocked and planned out inside. Can't wait to come back!"
The price is CA $412
CA $1,232 total
includes taxes & fees
Sep 4 - Sep 5
Fall special for months of October & November. See calendar

New Renovated April 2025 Charming Apartment In Delightful Kiahuna with AC,

The price is CA $405
CA $1,176 total
includes taxes & fees
Sep 29 - Sep 30
New Renovated April 2025 Charming Apartment In Delightful Kiahuna with AC,

4 Star Beachfront Resort. King Bed. Lanai. AC. Restaurant. Pool. Gym. Spa.

The price is CA $153
CA $611 total
includes taxes & fees
Sep 9 - Sep 10
4 Star Beachfront Resort. King Bed. Lanai. AC. Restaurant. Pool. Gym. Spa.

Ocean 500 Feet

9.0 out of 10, Wonderful, (2)
"the property was very clean and quiet. walk distance to the beautiful beach. "
The price is CA $618
CA $1,416 total
includes taxes & fees
Sep 2 - Sep 3
Ocean 500 Feet

Hale Huna - fully air conditioned 4 BD 4 BTH, short walk to beaches

10.0 out of 10, Exceptional, (110)
"Great location, close to the beach and pool"
The price is CA $909
CA $2,064 total
includes taxes & fees
Sep 2 - Sep 3
Hale Huna - fully air conditioned 4 BD 4 BTH, short walk to beaches
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

Find out more about South Shore

South Shore Vacation Homes information

Number of reviews
Accommodation
470 Vacation Homes
Lowest Price
CA $204
Highest Price
CA $204

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