South Shore Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for South Shore vacation rentals

2 outdoor pools

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas
4.0 star property
Poipu
9.2 out of 10, Wonderful, (786 reviews)
"Would visit again for sure "
United States
Milind
$300 nightly
The price is $356
May 26 - May 27
Total with taxes and fees
Sheraton Kauai Resort Villas
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)
"Location was perfect for 10 minute walk to convention at Grand Hyatt and beach. Never made it to the pool, not sure where it’s at. 2 minute drive to poipu beach where 20 large turtles were resting and beautiful sunset. The use of chairs, umbrella, ice chest and snorkeling gear was very convenient. "
United States
Charles
$413 nightly
The price is $482
May 18 - May 19
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, (86 reviews)
"This unit fit all of our needs regarding location, cleanliness, and amenities. I would 100% recommend this property to my friends and family and will revisit this if I'm in town in the future!"
New Zealand
Reservations G.
$608 nightly
The price is $710
May 17 - May 18
Total with taxes and fees
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
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
9.2 out of 10, Wonderful, (113 reviews)
"Loved the space and where it was located. Only thing that could be improved would be the communication of instructions and rules of the place."
United States
Ryan
$331 nightly
The price is $386
May 19 - May 20
Total with taxes and fees
Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!
Outdoor pool

KP169 Ground FL Beachside | Pool•AC•Ocean

KP169 Ground FL Beachside | Pool•AC•Ocean
Poipu
9.8 out of 10, Exceptional, (8 reviews)
"Great place for two people to enjoy Poipu beach. The condo was comfortable and had everything we needed. We slept well and "
Canada
Kerry B.
$534 nightly
The price is $561
May 16 - May 17
Total with taxes and fees
KP169 Ground FL Beachside | Pool•AC•Ocean
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.
$607 nightly
The price is $644
May 22 - May 23
Total with taxes and fees
KP228 Garden View | Beach•Pool•Turtle•AC
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, (235 reviews)
"We loved our stay and would look to stay here again in the future. It was very relaxing and close to everything we wanted to do "
United States
Lori
$428 nightly
The price is $501
May 22 - May 23
Total with taxes and fees
Ocean-View Studio, Steps to Beaches, in Sunny Poipu
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.
$630 nightly
The price is $739
May 14 - May 15
Total with taxes and fees
Quiet Kiahuna plantation #88 , New Remodel with AC
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, (13 reviews)
"Fantastic time!"
United States
Chris C.
$594 nightly
The price is $695
May 24 - May 25
Total with taxes and fees
Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301
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)
"I will definitely book here again! The place was perfect for my 19 year old daughter and I. It was clean, quiet and safe. Everyone was very friendly, and Cameron went above and beyond to answer any questions or provide assistance. Our new favorite place 😊"
United States
Jenifer
$402 nightly
The price is $470
May 20 - May 21
Total with taxes and fees
An Affordable Alternative to Expensive Accommodations in Poipu
On the beach, sun loungers, beach towels

Oceanview Penthouse Condo Just 50 Yards From the Beach! A/C, Pool, Hot Tub, Gym

Oceanview Penthouse Condo Just 50 Yards From the Beach! A/C, Pool, Hot Tub, Gym
Poipu
9.6 out of 10, Exceptional, (30 reviews)
"The property is beautiful and convenient to the beach"
United States
Rhonda
$614 nightly
The price is $719
May 28 - May 29
Total with taxes and fees
Oceanview Penthouse Condo Just 50 Yards From the Beach! A/C, Pool, Hot Tub, Gym
Property grounds

South Kauai Tranquil Retreat w/ AC in Poipu

South Kauai Tranquil Retreat w/ AC in Poipu
Poipu
10.0 out of 10, Exceptional, (21 reviews)
"Clean, well-appointed, convenient location, and excellent communication from host."
United States
Robert L.
$492 nightly
The price is $575
May 20 - May 21
Total with taxes and fees
South Kauai Tranquil Retreat w/ AC in Poipu
Outdoor pool

Kahala at Poipu Kai

Kahala at Poipu Kai
Poipu
9.6 out of 10, Exceptional, (137 reviews)
"Host was wonderful and responsive when needed. Place was centrally located to beaches and shopping. Local shops, golf and food very good."
United States
Terri B.
$451 nightly
The price is $528
May 20 - May 21
Total with taxes and fees
Kahala at Poipu Kai
Property grounds

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (109 reviews)
"Very nice hosts and a great place to stay "
United States
John H.
$407 nightly
The price is $476
May 14 - May 15
Total with taxes and fees
An Affordable Alternative to Expensive Accommodations in Poipu
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, (73 reviews)
"Great place for families!"
United States
William N.
$583 nightly
The price is $682
May 25 - May 26
Total with taxes and fees
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
Exterior

Marriott's Waiohai Beach Club

Marriott's Waiohai Beach Club
4.0 star property
Poipu
8.6 out of 10, Excellent, (189 reviews)
"Property is stunning…amazing beach, friendly staff"
United States
Jennifer
$405 nightly
The price is $481
May 26 - May 27
Total with taxes and fees
Marriott's Waiohai Beach Club
A heated pool

Sheraton Kaua‘i Resort Villas (Studio)

Sheraton Kaua‘i Resort Villas (Studio)
Poipu
$451 nightly
The price is $454
May 31 - Jun 1
Total with taxes and fees
Sheraton Kaua‘i Resort Villas (Studio)
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, (151 reviews)
"Everything was accessible…clean and cheerful…we enjoyed our stay and definitely would return…"
United States
Judith S.
$808 nightly
The price is $857
May 27 - May 28
Total with taxes and fees
RE 413 | Walk to Poipu Beach • AC • Pool/Spa, Spectacular Garden Oasis w/ W/D and AC, Pool
Outdoor dining

Step to beach New Quiet Kiahuna Plantation Remodeled 2 bedroom condo with A/C

Step to beach New Quiet Kiahuna Plantation Remodeled 2 bedroom condo with A/C
Poipu
9.8 out of 10, Exceptional, (24 reviews)
"Great place, fantastic location!"
United States
Nick S.
$893 nightly
The price is $1,047
May 19 - May 20
Total with taxes and fees
Step to beach New Quiet Kiahuna Plantation Remodeled 2 bedroom condo with A/C
Outdoor dining

Kiahuna Paradise condo with A/C

Kiahuna Paradise condo with A/C
Poipu
9.8 out of 10, Exceptional, (8 reviews)
"Our host was very kind and accommodating to our travel schedule! He responded quickly to our needs. Condo was extremely clean, nicely decorated, and in a wonderful area - the resort was beautiful with direct beach access, two breakfast cafes, and an area of shops/a grocery store! Def recommend! "
United States
Natalie P.
$676 nightly
The price is $793
May 14 - May 15
Total with taxes and fees
Kiahuna Paradise condo with A/C
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

Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai

Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai

10/10 Excellent
"Excellent clean condo with fantastic location. Was handy for Baby & Lawai beaches, etc. Quick drive to Poipu Shopping Village, the Shops at Kukui’ula, Koloa Shopping Village & Old Town which had great restaurants. Private & quiet view of the cove where could see the old turtle swimming from the Lanai."
Grant M. 3-night trip
Posted 2 days ago
Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai

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 $356 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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