Holiday Homes in South Shore

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in South Shore and around

HOME & GUEST HOUSE FOR PRICE OF 1 POIPU BEACH ESTATES 5 BR/ 5 BA WALK TO BEACH
Indoor pool, outdoor pool

HOME & GUEST HOUSE FOR PRICE OF 1 POIPU BEACH ESTATES 5 BR/ 5 BA WALK TO BEACH

9.8 out of 10, Exceptional, (194)
"Fully enjoyed"
HOME & GUEST HOUSE FOR PRICE OF 1 POIPU BEACH ESTATES 5 BR/ 5 BA WALK TO BEACH
3 bedrooms with baths, air conditioning and heated pool near Grand Hyatt.
Beach nearby, sun-loungers, beach towels

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

9.2 out of 10, Wonderful, (75)
"Perfect place for three couples"
3 bedrooms with baths, air conditioning and heated pool near Grand Hyatt.
Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops
Exterior

Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops

10.0 out of 10, Exceptional, (57)
"Excellent home for multiple family members "
Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops
Plumeria House, Poipu Beach, Koloa Home with a View
Exterior

Plumeria House, Poipu Beach, Koloa Home with a View

10.0 out of 10, Exceptional, (184)
"We had a great time! Wonderful house!"
Plumeria House, Poipu Beach, Koloa Home with a View
Hale Hapuna - Poipu's Best Ocean and Mountain Views
Dining

Hale Hapuna - Poipu's Best Ocean and Mountain Views

9.8 out of 10, Exceptional, (75)
"The house exceeded our expectations. It was spacious, well stocked and looked like it had recently been updated. We enjoyed the boogie boards, chairs, umbrellas and beach wagon. The outdoor showers were a plus. It was the perfect space for our family of 12. We plan to return. The property managers were responsive and easy to work with."
Hale Hapuna - Poipu's Best Ocean and Mountain Views
PRIVATE HOME: 5 Min Walk to Beach, Pool & Tennis Courts
Beach nearby, sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (97)
"Nice place to stay, good location"
PRIVATE HOME: 5 Min Walk to Beach, Pool & Tennis Courts
An Affordable Alternative to Expensive Accommodations in Poipu
Exterior detail

An Affordable Alternative to Expensive Accommodations in Poipu

9.2 out of 10, Wonderful, (56)
"The property was excellent and the owner is a really helpful person."
The price is €345
includes taxes & fees
20 Aug - 21 Aug
An Affordable Alternative to Expensive Accommodations in Poipu
Milo Hae Hale welcomes you to Beautiful Island of Kauai! Pet welcome ocean view
Terrace/patio

Milo Hae Hale welcomes you to Beautiful Island of Kauai! Pet welcome ocean view

9.8 out of 10, Exceptional, (38)
"John was an excellent host, he responded quickly to questions and we had everything we needed and more. The home and neighborhood are pristine. The pool and beautiful landscaping made for an excellent bonus as we enjoyed our coffee in the morning and swimming with the kids in the evening. All bedrooms have excellent A/C, the covered drive-thru driveway was awesome for close loading and unloading of luggage, plus it rained often and we could still access the vehicles without getting wet. We loved...
Milo Hae Hale welcomes you to Beautiful Island of Kauai! Pet welcome ocean view
Delightful Historic Cottage Steps from Poipu/Brennecke's Beaches A/C
Beach nearby, sun-loungers, beach towels

Delightful Historic Cottage Steps from Poipu/Brennecke's Beaches A/C

10.0 out of 10, Exceptional, (232)
"Our stay was perfect. Walking distance to one of the best snorkeling and swimming beaches on all of Kaua’i. Open kitchen area and adorable sunroom for afternoon naps. "
Delightful Historic Cottage Steps from Poipu/Brennecke's Beaches A/C
Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194
Beach nearby, sun-loungers, beach towels

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 €1,491
includes taxes & fees
25 Aug - 26 Aug
Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194
Private Ocean View Estate in Poipu with A/C, Jacuzzi, & Pool 5 min walk to beach
Interior

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

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

9.8 out of 10, Exceptional, (82)
"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.
Tiki Villa in Poipu 5 Bd/4Bth, Pool & AC Sleeps16
Interior

Tiki Villa in Poipu 5 Bd/4Bth, Pool & AC Sleeps16

Tiki Villa in Poipu 5 Bd/4Bth, Pool & AC Sleeps16
SPECTACULAR OCEANFRONT PENTHOUSE-Air Conditioned 3 Bedroom/3 Bathroom, Full Gym
Outdoor pool, a heated pool

SPECTACULAR OCEANFRONT PENTHOUSE-Air Conditioned 3 Bedroom/3 Bathroom, Full Gym

10.0 out of 10, Exceptional, (54)
"This was our second stay at this property. Great location, amazing view, and very comfortable. Perfect accommodations for our family."
SPECTACULAR OCEANFRONT PENTHOUSE-Air Conditioned 3 Bedroom/3 Bathroom, Full Gym
Poipu Beautiful Mountain View
Beach nearby

Poipu Beautiful Mountain View

9.6 out of 10, Exceptional, (30)
"All around great stay."
Poipu Beautiful Mountain View
Pane Road Hale, Quaint & updated for your comfort
Golf

Pane Road Hale, Quaint & updated for your comfort

10.0 out of 10, Exceptional, (57)
"Loved the stay - even learned to love the 3 am roosters crowing. Like a built in wake up call."
Pane Road Hale, Quaint & updated for your comfort
A/C Oceanfront View Of Poipu Beach.
On the beach, sun-loungers, beach towels

A/C Oceanfront View Of Poipu Beach.

9.8 out of 10, Exceptional, (133)
"Great house right by Poipu and Brennecke's beach. Outdoor shower is super nice for getting the sand off after playing in the waves all day. Close to lots of places to eat. House is well put together, AC works really well."
The price is €1,932
includes taxes & fees
17 Aug - 18 Aug
A/C Oceanfront View Of Poipu Beach.
Waiohai Beach House: Poipu Beachfront Estate
Pool

Waiohai Beach House: Poipu Beachfront Estate

9.6 out of 10, Exceptional, (35)
"Family had a fantastic time."
Waiohai Beach House: Poipu Beachfront Estate
Custom Home Walking Distance to the Grand Hyatt and Shipwreck Beach
Outdoor dining

Custom Home Walking Distance to the Grand Hyatt and Shipwreck Beach

9.8 out of 10, Exceptional, (44)
"This was a great spot. Convenient walk to the beach and loved all the beach supplies that were available. My family had a wonderful time!"
Custom Home Walking Distance to the Grand Hyatt and Shipwreck Beach
Beautiful Luxury Home, Walking Distance to Shops, Beaches & Fine Dining!
A heated pool

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

10.0 out of 10, Exceptional, (98)
"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!
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

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas

10/10 Excellent
"Such a beautiful and relaxing place to enjoy paradise"
Danielle 5-night trip
Posted 1 day ago
Sheraton Kauai Resort Villas