South Shore Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for South Shore vacation rentals

Property grounds

Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!

Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!
Poipu
9.0 out of 10, Wonderful, (105 reviews)
"Check in was clear and easy; condo was conveniently located to so much on the south shore! We especially loved walking to Baby Beach. The kitchen was well stocked, bed was very comfortable and the property was fun to explore. "
United States
Ashlee G.
$331 nightly
The price is $386
Apr 21 - Apr 22
Total with taxes and fees
Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!
Interior

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.4 out of 10, Exceptional, (74 reviews)
"Everything was as mentioned when we arrived. The room was inviting and had beach towels rolled on the bed along with a box of chocolate Macadamia nuts. Having the lanai kitchen area was a bonus as it was screened in and allowing the trade winds flow through the room. The host was responsive to our questions. Very satisfied!"
United States
Anonymous traveler
$410 nightly
The price is $479
Apr 27 - Apr 28
Total with taxes and fees
An Affordable Alternative to Expensive Accommodations in Poipu
Pool

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

Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
Poipu
9.4 out of 10, Exceptional, (85 reviews)
"Easy check in and check out. Great location, clean"
United States
PATRICK W.
$617 nightly
The price is $719
Apr 28 - Apr 29
Total with taxes and fees
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
Outdoor dining

Ocean-View Studio, Steps to Beaches, in Sunny Poipu

Ocean-View Studio, Steps to Beaches, in Sunny Poipu
Poipu
9.8 out of 10, Exceptional, (234 reviews)
"Place was quiet, clean and just right for our needs."
United States
Bryan D.
$397 nightly
The price is $464
Apr 26 - Apr 27
Total with taxes and fees
Ocean-View Studio, Steps to Beaches, in Sunny Poipu
Terrace/patio

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (65 reviews)
"Very easy to access the beach, and other amenities! "
United States
Sandra K.
$389 nightly
The price is $455
Apr 27 - Apr 28
Total with taxes and fees
An Affordable Alternative to Expensive Accommodations in Poipu
Outdoor pool

Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301

Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301
Poipu
10.0 out of 10, Exceptional, (12 reviews)
"Fantastic time!"
United States
Chris C.
$526 nightly
The price is $616
Apr 29 - Apr 30
Total with taxes and fees
Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301
Pool

Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6

Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
Poipu
10.0 out of 10, Exceptional, (69 reviews)
"Great place for families!"
United States
William N.
$522 nightly
The price is $611
Apr 22 - Apr 23
Total with taxes and fees
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
Pool

KP228 Garden View | Beach•Pool•Turtle•AC

KP228 Garden View | Beach•Pool•Turtle•AC
Poipu
9.6 out of 10, Exceptional, (12 reviews)
"KP228 was exactly as pictured in the photos, and also had a closetful of useful beach items for the guest to use (beach chairs, umbrellas, snorkel gear, etc.). Bed was very comfortable, and the A/C kept us cool throughout the house!"
United States
Kevin F.
$611 nightly
The price is $649
Apr 24 - Apr 25
Total with taxes and fees
KP228 Garden View | Beach•Pool•Turtle•AC
Interior

Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!

Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!
Poipu
9.8 out of 10, Exceptional, (196 reviews)
"The location is excellent. We walked five minutes and we're on Poipu Beach. "
United States
Sylvana B.
$518 nightly
The price is $606
Apr 25 - Apr 26
Total with taxes and fees
Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!
Dining

RE 413 | Walk to Poipu Beach • AC • Pool/Spa, Spectacular Garden Oasis w/ W/D and AC, Pool

RE 413 | Walk to Poipu Beach • AC • Pool/Spa, Spectacular Garden Oasis w/ W/D and AC, Pool
Poipu
9.8 out of 10, Exceptional, (150 reviews)
"Everything was accessible…clean and cheerful…we enjoyed our stay and definitely would return…"
United States
Judith S.
$741 nightly
The price is $779
Apr 21 - Apr 22
Total with taxes and fees
RE 413 | Walk to Poipu Beach • AC • Pool/Spa, Spectacular Garden Oasis w/ W/D and AC, Pool
A heated pool

Sheraton Kaua‘i Resort Villas (Studio)

Sheraton Kaua‘i Resort Villas (Studio)
Poipu
$450 nightly
The price is $453
May 12 - May 13
Total with taxes and fees
Sheraton Kaua‘i Resort Villas (Studio)
Dining

Makahuena 2-105 Partial Ocean View 2 Bedroom 2 Bath, Sleeps 6, Ground Floor

Makahuena 2-105 Partial Ocean View 2 Bedroom 2 Bath, Sleeps 6, Ground Floor
Poipu
9.2 out of 10, Wonderful, (7 reviews)
"Amenities were great. Condo was comfortable and very nice. We enjoyed our stay."
United States
Sheree A.
$538 nightly
The price is $627
Apr 21 - Apr 22
Total with taxes and fees
Makahuena 2-105 Partial Ocean View 2 Bedroom 2 Bath, Sleeps 6, Ground Floor
Exterior

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas
4.0 star property
Poipu
9.2 out of 10, Wonderful, (769 reviews)
"great location "
United States
Ronnie
$335 nightly
The price is $398
Apr 28 - Apr 29
Total with taxes and fees
Sheraton Kauai Resort Villas
Pool

Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8

Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8
Poipu
9.6 out of 10, Exceptional, (84 reviews)
"Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: GREAT PLACE TO STAY!"
United States
MELISSA L.
$702 nightly
The price is $818
Apr 26 - Apr 27
Total with taxes and fees
Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8
Sun loungers, beach towels

Penthouse Condo 100 Yards From The Beach! Includes A/C, Pool, Hot Tub and Gym

Penthouse Condo 100 Yards From The Beach! Includes A/C, Pool, Hot Tub and Gym
Poipu
9.6 out of 10, Exceptional, (40 reviews)
"My spouse and I stayed here for our honeymoon and we had a blast!"
United States
Hamzah Y.
$615 nightly
The price is $719
Apr 20 - Apr 21
Total with taxes and fees
Penthouse Condo 100 Yards From The Beach! Includes A/C, Pool, Hot Tub and Gym
Property grounds

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned
Poipu
9.6 out of 10, Exceptional, (173 reviews)
"Great location and stay."
United States
Juan
$340 nightly
The price is $398
Apr 20 - Apr 21
Total with taxes and fees
Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned
Property grounds

Quiet Kiahuna plantation #88 , New Remodel with AC

Quiet Kiahuna plantation #88 , New Remodel with AC
Poipu
10.0 out of 10, Exceptional, (33 reviews)
"The openness of the unit and the patio were great. The bed was super comfortable and the maid service was very good. The support staff were helpful and kind. "
Canada
Lori T.
$668 nightly
The price is $782
May 1 - May 2
Total with taxes and fees
Quiet Kiahuna plantation #88 , New Remodel with AC
Outdoor pool

Beachfront Condo Poipu Beach Amenities Galore

Beachfront Condo Poipu Beach Amenities Galore
Poipu
8.8 out of 10, Excellent, (68 reviews)
"Perfect spot best beach"
United States
Monia
$423 nightly
The price is $495
May 11 - May 12
Total with taxes and fees
Beachfront Condo Poipu Beach Amenities Galore
Outdoor dining

Ocean View & AC! 3 Min Walk To Poipu Beach!

Ocean View & AC! 3 Min Walk To Poipu Beach!
Poipu
10.0 out of 10, Exceptional, (114 reviews)
"Everything was as advertised. We had a great time. Thank you."
United States
Keri B.
$497 nightly
The price is $581
May 14 - May 15
Total with taxes and fees
Ocean View & AC! 3 Min Walk To Poipu Beach!
Property grounds

Air conditioned, Resort Location. Short Walks To Beaches & Restaurants

Air conditioned, Resort Location. Short Walks To Beaches & Restaurants
Poipu
9.4 out of 10, Exceptional, (144 reviews)
"Host was very responsive, great location, great room."
United States
Christopher C.
$340 nightly
The price is $398
Apr 20 - Apr 21
Total with taxes and fees
Air conditioned, Resort Location. Short Walks To Beaches & Restaurants
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

Ko'a Kea Resort on Po'ipu Beach

Ko'a Kea Resort on Po'ipu Beach

10/10 Excellent
"Beautiful resort. Small and quaint with direct access to the beach. "
Daria Ruth 7-night trip
Posted 4 hours ago
Ko'a Kea Resort on Po'ipu Beach

Find out more about South Shore

Everything you need to know about South Shore vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Shore vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Shore vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Shore vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Shore. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Shore in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $398 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Shore rentals

At Expedia, we put the best South Shore vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Shore rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Shore vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Shore. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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