South Shore Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for South Shore vacation rentals

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, (68 reviews)
"Good location! Great amenities! It had everything to make our stay comfortable. "
United States
Muna M.
$526 nightly
The price is $615
Apr 22 - Apr 23
Total with taxes and fees
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
Exterior

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas
4.0 star property
Poipu
9.2 out of 10, Wonderful, (765 reviews)
"great location "
United States
Ronnie
$335 nightly
The price is $398
Apr 15 - Apr 16
Total with taxes and fees
Sheraton Kauai Resort Villas
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, (231 reviews)
"Place was quiet, clean and just right for our needs."
United States
Bryan D.
$395 nightly
The price is $462
Apr 13 - Apr 14
Total with taxes and fees
Ocean-View Studio, Steps to Beaches, in Sunny Poipu
Interior

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.4 out of 10, Exceptional, (73 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 17 - Apr 18
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
9.6 out of 10, Exceptional, (84 reviews)
"Easy check in and check out. Great location, clean"
United States
PATRICK W.
$634 nightly
The price is $740
Apr 14 - Apr 15
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
9.0 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.
$345 nightly
The price is $402
Apr 14 - Apr 15
Total with taxes and fees
Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!
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, (32 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.
$646 nightly
The price is $756
Apr 14 - Apr 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, (11 reviews)
"Fantastic time!"
United States
Chris C.
$651 nightly
The price is $761
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
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)
"Location was great with easy access to the unit and easy access to the beach. It is one of the closer units to the beach and lake. Check in and check out process was really easy, and the unit had everything we needed. Would definitely stay here again."
United States
Guillermo R.
$543 nightly
The price is $571
Apr 13 - Apr 14
Total with taxes and fees
KP169 Ground FL Beachside | Pool•AC•Ocean
A heated pool

Sheraton Kaua‘i Resort Villas (Studio)

Sheraton Kaua‘i Resort Villas (Studio)
Poipu
$467 nightly
The price is $470
May 6 - May 7
Total with taxes and fees
Sheraton Kaua‘i Resort Villas (Studio)
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, (64 reviews)
"Very easy to access the beach, and other amenities! "
United States
Sandra K.
$400 nightly
The price is $468
Apr 15 - Apr 16
Total with taxes and fees
An Affordable Alternative to Expensive Accommodations in Poipu
Beach nearby, sun loungers, beach towels

NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation

NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation
Poipu
9.2 out of 10, Wonderful, (16 reviews)
"Convenient location near the beaches, very responsive owner, comfortable space. Would stay here again."
United States
Anush
$674 nightly
The price is $789
Apr 18 - Apr 19
Total with taxes and fees
NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation
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.
$671 nightly
The price is $719
May 5 - May 6
Total with taxes and fees
KP228 Garden View | Beach•Pool•Turtle•AC
Property grounds

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned
Poipu
9.6 out of 10, Exceptional, (172 reviews)
"Great location and stay."
United States
Juan
$339 nightly
The price is $397
Apr 20 - Apr 21
Total with taxes and fees
Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned
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, (107 reviews)
"Very nice hosts and a great place to stay "
United States
John H.
$332 nightly
The price is $389
Apr 16 - Apr 17
Total with taxes and fees
An Affordable Alternative to Expensive Accommodations in Poipu
Outdoor pool

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

🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠
Poipu
9.4 out of 10, Exceptional, (25 reviews)
"This is a great spot. We had two couples and two toddlers and it worked well. Space isn’t super friendly for toddlers but it was ok. It’s a short walk to the beach so we rented a beach wagon and that was super helpful with the little kiddos.The house has good AC units and comfy beds and an outdoor shower around the back of the houseGPS kind of leads you to the wrong driveway so you just gotta drive up the street a little bit and enter from the little cul de sac.Definitely would stay here again!"
United States
Evan R.
$489 nightly
The price is $572
Apr 14 - Apr 15
Total with taxes and fees
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠
On the beach, sun loungers, beach towels

Cozy 1-bedroom condo in beautiful Koloa with washer/dryer, AC fiber internet

Cozy 1-bedroom condo in beautiful Koloa with washer/dryer, AC fiber internet
Poipu
10.0 out of 10, Exceptional, (9 reviews)
"The home was perfect for our family of 4 to stay. Short 5 minute walk to the beach, quiet, conveniently located to restaurants and activities. The room was clean, ac was great! Kitchen was stocked well and it was nice to have a washer and dryer in the unit. The lawn area was great for the kids to play !"
United States
Krystal R.
$736 nightly
The price is $861
Apr 16 - Apr 17
Total with taxes and fees
Cozy 1-bedroom condo in beautiful Koloa with washer/dryer, AC fiber internet
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)
"Great location, easy check in, clean condo!"
United States
Komaki U.
$729 nightly
The price is $850
Apr 26 - Apr 27
Total with taxes and fees
Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8
Outdoor dining

Kiahuna Paradise condo with A/C

Kiahuna Paradise condo with A/C
Poipu
9.8 out of 10, Exceptional, (8 reviews)
"Top notch, vacation rental."
United States
Bill G.
$685 nightly
The price is $802
Apr 13 - Apr 14
Total with taxes and fees
Kiahuna Paradise condo with A/C
Pool

KP313 -Top FL | Partial Ocean •Pool•Gym•AC

KP313 -Top FL | Partial Ocean •Pool•Gym•AC
Poipu
10.0 out of 10, Exceptional, (46 reviews)
"It was a impeccably clean condo in a beautiful location. The listing description is 100% accurate. I had a great day and would love to stay again."
United States
Dave K.
$554 nightly
The price is $596
Apr 14 - Apr 15
Total with taxes and fees
KP313 -Top FL | Partial Ocean •Pool•Gym•AC
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

OCEANFRONT Ground Floor 2bd/2ba Unit with Amazing Ocean Views & A/C

OCEANFRONT Ground Floor 2bd/2ba Unit with Amazing Ocean Views & A/C

10/10 Excellent
"The oceanfront! Absolutely spectacular & immersive from the unit. Amazing location close to Spouting Horn, shopping area and Po’ipu resort area without being in the expansive resort land. Very well-appointed unit - plenty of good dishwares, cooking/cleaning supplies, beach wares, umbrella and friendly security/groundskeepers gave us local tips. Very comfortable beds. A few dated or damaged accesories, but understandable since there are so many amenities - impossible to keep up with the state of all of them."
Joy J. 3-night trip
Posted 21 hours ago
OCEANFRONT Ground Floor 2bd/2ba Unit with Amazing Ocean Views & A/C

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 $397 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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