Holiday Rentals in South Shore

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Our top choices for South Shore holiday rentals

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

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas
4.0 star property
Poipu
9.2 out of 10, Wonderful, (766 reviews)
"great location "
United States
Ronnie
The price is €339
includes taxes & fees
28 Apr - 29 Apr
Sheraton Kauai Resort Villas

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.
The price is €396
includes taxes & fees
18 Apr - 19 Apr
Ocean-View Studio, Steps to Beaches, in Sunny Poipu

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 traveller
The price is €432
includes taxes & fees
27 Apr - 28 Apr
An Affordable Alternative to Expensive Accommodations in Poipu

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.
The price is €613
includes taxes & fees
28 Apr - 29 Apr
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6

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

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.
The price is €647
includes taxes & fees
14 Apr - 15 Apr
Quiet Kiahuna plantation #88 , New Remodel with AC

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.
The price is €697
includes taxes & fees
4 May - 5 May
Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301

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.
KP169 Ground FL Beachside | Pool•AC•Ocean

Sheraton Kaua‘i Resort Villas (Studio)

Sheraton Kaua‘i Resort Villas (Studio)
Poipu
The price is €419
includes taxes & fees
27 Apr - 28 Apr
Sheraton Kaua‘i Resort Villas (Studio)

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.
The price is €402
includes taxes & fees
15 Apr - 16 Apr
An Affordable Alternative to Expensive Accommodations in Poipu

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

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.
The price is €645
includes taxes & fees
27 Apr - 28 Apr
KP228 Garden View | Beach•Pool•Turtle•AC

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
The price is €340
includes taxes & fees
20 Apr - 21 Apr
Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

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.
The price is €339
includes taxes & fees
16 Apr - 17 Apr
An Affordable Alternative to Expensive Accommodations in Poipu

🏝 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.
The price is €533
includes taxes & fees
26 Apr - 27 Apr
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠

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.
The price is €742
includes taxes & fees
26 Apr - 27 Apr
Cozy 1-bedroom condo in beautiful Koloa with washer/dryer, AC fiber internet

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.
The price is €702
includes taxes & fees
26 Apr - 27 Apr
Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8

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.
Kiahuna Paradise condo with A/C

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.
The price is €592
includes taxes & fees
26 Apr - 27 Apr
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

Find out more about South Shore

Everything you need to know about South Shore holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Shore holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Shore holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Shore holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Shore holiday rentals we have selected for you start as low as €339 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Shore rentals

At Expedia, we put the best South Shore holiday 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 holiday.

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.