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Our top choices for South Shore holiday rentals

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 £501
includes taxes & fees
28 Apr - 29 Apr
Pili Mai Family Condo 13F, Spacious 1st Floor Lanai,

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
The price is £358
includes taxes & fees
27 Apr - 28 Apr
An Affordable Alternative to Expensive Accommodations in Poipu

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)
"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 £368
includes taxes & fees
1 May - 2 May
Ocean-View Studio, Steps to Beaches, in Sunny 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, (12 reviews)
"Fantastic time!"
United States
Chris C.
The price is £608
includes taxes & fees
19 May - 20 May
Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301

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
The price is £536
includes taxes & fees
27 Apr - 28 Apr
Oceanview Penthouse Condo Just 50 Yards From the Beach! A/C, Pool, Hot Tub, Gym

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.
The price is £571
includes taxes & fees
26 Apr - 27 Apr
Pili Mai 3-Bedroom, 3 bath, A/C Condo unit 2L, Sleeps 8

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas
4.0 star property
Poipu
9.2 out of 10, Wonderful, (771 reviews)
"Great Stay! Friendly staff, very clean……"
United States
Alonzo
The price is £295
includes taxes & fees
30 Apr - 1 May
Sheraton Kauai Resort Villas

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.
The price is £582
includes taxes & fees
30 Apr - 1 May
RE 413 | Walk to Poipu Beach • AC • Pool/Spa, Spectacular Garden Oasis w/ W/D and AC, Pool

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, (109 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 £311
includes taxes & fees
7 May - 8 May
Waikomo Stream Villas 122 Fish Pond View, New AC, Walk to Beach and Shopping!

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 £531
includes taxes & fees
12 May - 13 May
KP228 Garden View | Beach•Pool•Turtle•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 £364
includes taxes & fees
13 May - 14 May
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
The price is £574
includes taxes & fees
28 Apr - 29 Apr
NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation

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
The price is £294
includes taxes & fees
10 May - 11 May
Bayview, Poipu, Koloa Hawaii "Torview" Air conditioned

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.
The price is £581
includes taxes & fees
1 May - 2 May
Quiet Kiahuna plantation #88 , New Remodel with AC

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.
The price is £452
includes taxes & fees
25 Apr - 26 Apr
Nihi Kai #403: Newly Remodeled in 2023, Full AC, Steps to Beach!

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.
The price is £330
includes taxes & fees
26 Apr - 27 Apr
An Affordable Alternative to Expensive Accommodations in Poipu

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.
The price is £428
includes taxes & fees
27 Apr - 28 Apr
Ocean View & AC! 3 Min Walk To Poipu Beach!

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.
The price is £506
includes taxes & fees
30 Apr - 1 May
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6

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

KP313 -Top FL | Partial Ocean •Pool•Gym•AC
Poipu
10.0 out of 10, Exceptional, (48 reviews)
"This was a very nice last minute stay. We enjoyed 2 nights at this property and it was perfect. Everything we needed for our stay and the host was very helpful! Thank you"
United States
Kara
The price is £474
includes taxes & fees
26 Apr - 27 Apr
KP313 -Top FL | Partial Ocean •Pool•Gym•AC

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
The price is £360
includes taxes & fees
11 May - 12 May
Beachfront Condo Poipu Beach Amenities Galore
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 £294 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.