South Shore Vacation Rentals

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Browse Select South Shore Vacation Homes

3 bedrooms with baths, air conditioning and heated pool near Grand Hyatt.

9.2 out of 10, Wonderful, (76)
"Some items in the house need to be secured and could be dangerous for children staying in the home. It could also use a deep clean undwr/behind some of the furniture it was a great location with lots of stuff cclose by for stroller walking and we had lots of funin the pool! thhome. It could also ise some deep lwa. "
3 bedrooms with baths, air conditioning and heated pool near Grand Hyatt.

Private Ocean View Estate in Poipu with A/C, Jacuzzi, & Pool 5 min walk to beach

10.0 out of 10, Exceptional, (148)
"Better than the pictures! Comfortably accommodated two families of 5. Best stocked kitchen of any VRBO we've stayed at. Great ocean views and super short walk to the beach. I'd stay here again no question. "
Private Ocean View Estate in Poipu with A/C, Jacuzzi, & Pool 5 min walk to beach

Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park

10.0 out of 10, Exceptional, (270)
"It was our 4th time staying at the house and it was just as lovely as we remember. Clean, well maintained and soooo close to everything. "
Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park

LOCATION! LOCATION! LOCATION! Boogie Board at Brennecke's Beach!!!

10.0 out of 10, Exceptional, (94)
"The location of this house is absolutely perfect. Especially to take a toddler to the beach. We would love to come back sometime. "
LOCATION! LOCATION! LOCATION! Boogie Board at Brennecke's Beach!!!

Plumeria House, Poipu Beach, Koloa Home with a View

10.0 out of 10, Exceptional, (185)
"This property was perfect for our group of 8! Lots of space, clean and open layout, and great toys for the beach. Kitchen had ample room for our group and all the things to make perfect dinners. Would love to come back any day! "
Plumeria House, Poipu Beach, Koloa Home with a View

Beautiful Luxury Home, Walking Distance to Shops, Beaches & Fine Dining!

10.0 out of 10, Exceptional, (102)
"We had the best time. We loved the house and pool so much that we ended up spending majority of our time there. It was perfect for our family of 10 and was spotless upon arrival.The house was stalked with pool toys as well as beach toys and had more than we could have asked for"
Beautiful Luxury Home, Walking Distance to Shops, Beaches & Fine Dining!

PRIVATE HOME: 5 Min Walk to Beach, Pool & Tennis Courts

9.6 out of 10, Exceptional, (98)
"Nice place to stay, good location"
PRIVATE HOME: 5 Min Walk to Beach, Pool & Tennis Courts

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

9.6 out of 10, Exceptional, (18)
"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 CA $319
CA $774 total
includes taxes & fees
Aug 26 - Aug 27
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠

Honu La'e - 4 Bedroom, 4 Bath Ocean Front Vacation Home in Poipu with A/C

9.8 out of 10, Exceptional, (128)
"Very nice home w easy access to Poipu area and shops. Home was comfortable and front porch was perfect for sunsets. "
Honu La'e - 4 Bedroom, 4 Bath Ocean Front Vacation Home in Poipu with A/C

Private Guest Home / Stunning Location / Walk To Poipu Beach/ New AC and W/D

9.8 out of 10, Exceptional, (70)
"The house was in the perfect location. We had everything we needed for myself, my husband and our teen kids to enjoy a wonderful beach vacation. "
Private Guest Home / Stunning Location / Walk To Poipu Beach/ New AC and W/D

Luxury family friendly home within walking distance to Poipu Beach.

10.0 out of 10, Exceptional, (121)
"Our family thoroughly enjoyed our vrbo rental. The property is well maintained. We loved the short walk to the beach. "
Luxury family friendly home within walking distance to Poipu Beach.

Gorgeous Greenbelt! Home with beautiful mountain views & 5 min walk from beach!

9.2 out of 10, Wonderful, (98)
"This property had everything we needed and more! It is surrounded by the best beaches and in a safe neighborhood. We took walks to the beach every morning and evening. We got to watch the sea turtles come up on the beach to bask in the sunshine! Perfect experience!"
Gorgeous Greenbelt! Home with beautiful mountain views & 5 min walk from beach!

5 Bed/5 Bath Craftsman Home with large lanai, Central A/C. Close to Beach.

9.8 out of 10, Exceptional, (83)
"We thoroughly enjoyed our stay at this property. All of our family commented on how the house and its location were perfect. The kitchen was well equipped and the two dishwashers were very handy for our party of 9. We most certainly recommend this property."
5 Bed/5 Bath Craftsman Home with large lanai, Central A/C. Close to Beach.

Admired Poipu beach house in a perfect location, now a vacation home!

10.0 out of 10, Exceptional, (28)
"This place is fantastic. We stayed here for a month and loved every minute. The location of the home is perfect; central to other places to visit on the island, close to great restaurants, and a 2 minute walk to one of the best beaches on the island. Stand out items of the home are the large and comfortable lanai, the quality of the furnishings and cookware, the layout of the home, and the decor. The owner was very responsive and great to work with. We would go back to this rental in a...
Admired Poipu beach house in a perfect location, now a vacation home!

5 Star, Great for Families, 4BD w/AC, HTD Pool, Poipu Beach Athletic Club access

10.0 out of 10, Exceptional, (140)
"Perfect house to stay at on your family trip to Kauai. "
5 Star, Great for Families, 4BD w/AC, HTD Pool, Poipu Beach Athletic Club access

Hale Minoaka by Destination Kauai - Poipu Beach Estates Cottage with A/C

9.8 out of 10, Exceptional, (135)
"Overall a nice place and we loved the location! Clean and quiet property. It was wonderful to have a washer/dryer."
Hale Minoaka by Destination Kauai - Poipu Beach Estates Cottage with A/C

The Catbird Seat -Closest Vacation Home To Poipu Beach - 100 Ft Away!!! Pool!!

10.0 out of 10, Exceptional, (139)
"Always a pleasure to stay at Catbird Seat"
The Catbird Seat -Closest Vacation Home To Poipu Beach - 100 Ft Away!!! Pool!!

Leipiha ke Aloha - Steps Away from Poipu Beach with A/C!

10.0 out of 10, Exceptional, (20)
"We had an amazing stay at this incredible property. It is an unbelievable location and the home is really well designed. We loved staying here and would stay again!"
Leipiha ke Aloha - Steps Away from Poipu Beach with A/C!

Waiohai Beach House: Poipu Beachfront Estate

9.6 out of 10, Exceptional, (37)
"Absolutely perfect family gathering home! Everything was perfect for the ten of us. The open air home, views, seating all over, pool, beach, kitchen, beds….all as good as it gets!Thankful to have been able to be here together!"
Waiohai Beach House: Poipu Beachfront Estate

Five Bed, Five Bath Tropical Paradise With A/C, Hot Tub, & Beach Walk

9.4 out of 10, Exceptional, (43)
"Well supplied spacious house close to the beaches shops and restaurants. "
Five Bed, Five Bath Tropical Paradise With A/C, Hot Tub, & Beach Walk
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