South Shore Vacation Rentals

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Our top choices for South Shore vacation rentals

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas
4.0 star property
Poipu
9.2 out of 10, Wonderful, (788 reviews)
"Would visit again for sure "
United States
Milind
The price is CA $460
CA $546 total
includes taxes & fees
May 27 - May 28
Sheraton Kauai Resort Villas

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.4 out of 10, Exceptional, (75 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
The price is CA $241
CA $663 total
includes taxes & fees
May 30 - May 31
An Affordable Alternative to Expensive Accommodations in Poipu

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
The price is CA $140
CA $526 total
includes taxes & fees
May 20 - May 21
Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!

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
The price is CA $301
CA $680 total
includes taxes & fees
May 22 - May 23
Ocean-View Studio, Steps to Beaches, in Sunny Poipu

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, (74 reviews)
"Great place for families!"
United States
William N.
The price is CA $275
CA $841 total
includes taxes & fees
Jun 17 - Jun 18
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6

Pili Mai Family Condo 13F, Spacious 1st Floor Lanai,

Pili Mai Family Condo 13F, Spacious 1st Floor Lanai,
Poipu
9.8 out of 10, Exceptional, (63 reviews)
"Rating Details: The property manager was very 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: We absolutely loved staying here! It was clean, in a great location, and had a lot of space. We would absolutely stay here again."
United States
Jill C.
The price is CA $218
CA $988 total
includes taxes & fees
May 26 - May 27
Pili Mai Family Condo 13F, Spacious 1st Floor Lanai,

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.
The price is CA $259
CA $753 total
includes taxes & fees
May 20 - May 21
South Kauai Tranquil Retreat w/ AC in Poipu

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

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.
The price is CA $173
CA $676 total
includes taxes & fees
May 20 - May 21
Kahala at Poipu Kai

Quiet Kiahuna plantation #88 , New Remodel with AC

Quiet Kiahuna plantation #88 , New Remodel with AC
Poipu
10.0 out of 10, Exceptional, (34 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 CA $398
CA $1,104 total
includes taxes & fees
May 22 - May 23
Quiet Kiahuna plantation #88 , New Remodel with AC

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
The price is CA $229
CA $644 total
includes taxes & fees
May 24 - May 25
An Affordable Alternative to Expensive Accommodations in Poipu

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.
The price is CA $466
CA $1,136 total
includes taxes & fees
Jun 19 - Jun 20
Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301

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
The price is CA $556
CA $661 total
includes taxes & fees
May 26 - May 27
Marriott's Waiohai Beach Club

An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (110 reviews)
"Very nice hosts and a great place to stay "
United States
John H.
The price is CA $241
CA $660 total
includes taxes & fees
May 24 - May 25
An Affordable Alternative to Expensive Accommodations in Poipu

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 CA $205
CA $818 total
includes taxes & fees
May 22 - May 23
KP228 Garden View | Beach•Pool•Turtle•AC

Rare Find w/ 2 AC! Newly renovated condo #128, ground flr, 3-4 min walk to beach

Rare Find w/ 2 AC! Newly renovated condo #128, ground flr, 3-4 min walk to beach
Poipu
10.0 out of 10, Exceptional, (152 reviews)
"Kiahuna Resort is special. First, it's set on one of the most beautiful and easily enjoyable ocean beaches in the world. Second, the expansive grounds are lovely and very well maintained. There's probably not a bad unit in this resort - I've stayed in 4 over the last 42 years - so it probably comes down to price point, communication with owner, and standard of furnishings and decor. We have no complaints from this stay!"
Canada
Alan F.
The price is CA $408
CA $1,030 total
includes taxes & fees
Jun 4 - Jun 5
Rare Find w/ 2 AC! Newly renovated condo #128, ground flr, 3-4 min walk to beach

KP169 Ground FL Beachside | Pool•AC•Ocean

KP169 Ground FL Beachside | Pool•AC•Ocean
Poipu
9.8 out of 10, Exceptional, (8 reviews)
"We had a wonderful time steps to the ocean great views"
United States
Matthew H.
The price is CA $232
CA $864 total
includes taxes & fees
May 27 - May 28
KP169 Ground FL Beachside | Pool•AC•Ocean

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)
"We had a great time, loved the athletic club and beach access!"
United States
ryan z.
The price is CA $370
CA $1,076 total
includes taxes & fees
May 22 - May 23
NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation

500 feet to the 🌊, 1000 feet 🏝 and 🐢

500 feet to the 🌊, 1000 feet 🏝 and 🐢
Poipu
9.8 out of 10, Exceptional, (29 reviews)
"Great location and well furnished. Highly recommend."
United States
Robert
The price is CA $365
CA $967 total
includes taxes & fees
May 31 - Jun 1
500 feet to the 🌊, 1000 feet 🏝 and 🐢

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)
"The host, housecleaning services (they allowed us to put groceries into the refrigerator/freezer before the apartment was completely cleaned), intake at the main office, grounds, etc were all exceptional! Thank you for allowing us to stay in your wonderful apartment! Muc appreciated!"
United States
John M.
The price is CA $287
CA $990 total
includes taxes & fees
May 24 - May 25
Penthouse Condo 100 Yards From The Beach! Includes A/C, Pool, Hot Tub and Gym
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Shore. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.