Holiday Homes in South Shore

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Featured Holiday Homes in South Shore

An Affordable Alternative to Expensive Accommodations in Poipu

9.2 out of 10, Wonderful, (99)
"Great unit in a fantastic location!"
The price is NZ$680
includes taxes & fees
17 Aug - 18 Aug
An Affordable Alternative to Expensive Accommodations in Poipu

KP13-Beachfront-WD-Pool -Sunsets-2nd Floor

The price is NZ$1,061
includes taxes & fees
16 Aug - 17 Aug
KP13-Beachfront-WD-Pool -Sunsets-2nd Floor

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 NZ$1,255
includes taxes & fees
23 Aug - 24 Aug
R413-Pool-Spa-Beach-Turtles-Ocean Access-w/d-A/C, Spectacular Garden Oasis w/ W/D and AC, Pool

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

9.8 out of 10, Exceptional, (20)
"Wonderful experience, would definitely stay again."
The price is NZ$1,143
includes taxes & fees
22 Aug - 23 Aug
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠

9.6 out of 10, Exceptional, (17)
"We had a great stay. The house is very close to Poipu beach, and they provided all of the beach accessories we needed. The house had the basics and stayed cool in the evenings - we didn't even need to turn on the AC. We would definitely stay here again."
The price is NZ$952
includes taxes & fees
19 Aug - 20 Aug
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠

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

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 NZ$2,849
includes taxes & fees
25 Aug - 26 Aug
Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194

Brand New 4BR Poipu Beach Estates Home

10.0 out of 10, Exceptional, (2)
"A beautiful home! This home was well equipped for our family of 5 celebrating a milestone birthday. We rented bikes and were able to get around vehicle free to most places, beaches, town, shops, even early dinner. You won’t be sorry you chose this home ."
Brand New 4BR Poipu Beach Estates Home

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

10.0 out of 10, Exceptional, (3)
"The house was great for our entire family to stay. We were surprised with how much room we had given that the trip consisted of 12 of us in 4 separate family units. The house had everything we needed for supplies both whether we were at the house or at the beach. It was so close to several beaches and shopping. We couldn't be happier with our choice of accomodations."
*NEW 7BD Farmhouse Estate |Pool, PickleB, Gym| AC

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

10.0 out of 10, Exceptional, (15)
"Great location, lots of extra items including chairs, cart for the beach."
The price is NZ$2,739
includes taxes & fees
5 Sept - 6 Sept
Luxurious 4BR/3.5BA House: AC, Short Walk To Beach

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."
The price is NZ$3,542
includes taxes & fees
29 Aug - 30 Aug
5 Bed 3 Bath Home in Poipu Kai

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

The price is NZ$1,085
includes taxes & fees
25 Aug - 26 Aug
Charming apartment in delightful Koloa with fitness room, AC, WiFi

Ocean 500 Feet

9.0 out of 10, Wonderful, (2)
"the property was very clean and quiet. walk distance to the beautiful beach. "
Ocean 500 Feet

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

10.0 out of 10, Exceptional, (108)
"Great location, close to the beach and pool"
The price is NZ$2,490
includes taxes & fees
16 Aug - 17 Aug
Hale Huna - fully air conditioned 4 BD 4 BTH, short walk to beaches

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

The price is NZ$1,422
includes taxes & fees
19 Aug - 20 Aug
New Renovated April 2025 Charming Apartment In Delightful Kiahuna with AC,

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 NZ$1,500
includes taxes & fees
24 Aug - 25 Aug
Fall special for months of October & November. See calendar

Stunning 270° Hapuʻu Mtn Views • Walk to Beach • Pool • A/C • Sleeps 12 • Ocean

Stunning 270° Hapuʻu Mtn Views • Walk to Beach • Pool • A/C • Sleeps 12 • Ocean

As Seen on TV, Luxe Oceanview Villa, Heated Pool, Walk to Beaches

As Seen on TV, Luxe Oceanview Villa, Heated Pool, Walk to Beaches

Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi

9.4 out of 10, Exceptional, (122)
"Great place to stay. The kitchen was well equipped and great for our family. Would totally go there again!"
The price is NZ$1,019
includes taxes & fees
20 Aug - 21 Aug
Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi

Ocean & Golf Course Views / 2BR 2BA Princeville Townhouse / Walk to Beach / WiFi

9.8 out of 10, Exceptional, (24)
"Great spot. Beautiful sunsets. We thoroughly enjoyed our stay thank you"
The price is NZ$1,106
includes taxes & fees
25 Aug - 26 Aug
Ocean & Golf Course Views / 2BR 2BA Princeville Townhouse / Walk to Beach / WiFi
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