Holiday Homes in South Shore

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for South Shore holiday homes

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 €412
includes taxes & fees
27 Apr - 28 Apr
An Affordable Alternative to Expensive Accommodations in Poipu

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 €382
includes taxes & fees
26 Apr - 27 Apr
An Affordable Alternative to Expensive Accommodations in Poipu

KP317 Third FL | Partial Ocean •Pool •Garden

KP317 Third FL | Partial Ocean •Pool •Garden
Poipu
10.0 out of 10, Exceptional, (2 reviews)
"Room was up to date and clean. Nice resort area close to beach. Would be nice to have small cooler and beach chairs for day trips."
United States
Joseph C.
KP317 Third FL | Partial Ocean •Pool •Garden

*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
Poipu
10.0 out of 10, Exceptional, (23 reviews)
"The property was great! Close enough to enjoy all the local activities but away from the crowds. "
United States
Jeff B.
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

🏝 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 €514
includes taxes & fees
25 Apr - 26 Apr
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠

Ocean 500 Feet

Ocean 500 Feet
Poipu
8.0 out of 10, Very good, (3 reviews)
"the property was very clean and quiet. walk distance to the beautiful beach. "
United States
Yuxia H.
The price is €888
includes taxes & fees
5 May - 6 May
Ocean 500 Feet

Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194

Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194
Poipu
9.8 out of 10, Exceptional, (116 reviews)
"The access to the beach and the amount of space the house has inside and out was amazing!"
United States
Andrea
Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194

Gorgeous Poipu Villa with Pool & Spa + Ocean Views

Gorgeous Poipu Villa with Pool & Spa + Ocean Views
Poipu
10.0 out of 10, Exceptional, (8 reviews)
"Amazing home. We loved our stay here. "
United States
ERIC K.
Gorgeous Poipu Villa with Pool & Spa + Ocean Views

*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC

*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC
Poipu
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC

Poipu 1940s Beach Cottage | Outdoor Showers

Poipu 1940s Beach Cottage | Outdoor Showers
Poipu
10.0 out of 10, Exceptional, (1 review)
The price is €1,153
includes taxes & fees
19 May - 20 May
Poipu 1940s Beach Cottage | Outdoor Showers

E Komo Mai

E Komo Mai
Poipu
9.6 out of 10, Exceptional, (121 reviews)
"Home was in a great location and plenty of room for our family. My only negative was it wasn’t very clean in some spots and a lot of the lights and fans didn’t work. I would stay here again. I enjoyed the beach gear provided and a huge washer and dryer! "
United States
Kylie H.
The price is €944
includes taxes & fees
2 May - 3 May
E Komo Mai

Kauai Oasis Luxe Ocean View, Pool SPA AC Sleep22

Kauai Oasis Luxe Ocean View, Pool SPA AC Sleep22
Poipu
10.0 out of 10, Exceptional, (2 reviews)
"Jasmine Villa was perfect for our family, spacious, clean, well appointed and attention to every detail one can imagine. Precision execution of amenities and cleanliness. Beautiful view and location. The owners care so much about the property it shows. "
United States
Kevin M.
Kauai Oasis Luxe Ocean View, Pool SPA AC Sleep22

Luxe Oceanview Getaway w/ Heated Pool & Epic Sunrise (As Seen on TV)

Luxe Oceanview Getaway w/ Heated Pool & Epic Sunrise (As Seen on TV)
Poipu
10.0 out of 10, Exceptional, (1 review)
"Nice property in a convenient location. Clean and well equipped. Owner, Ning, was very accommodative, over and above, very pleasant. Property manager, Evan, was excellent in taking care of our needs. The house has four proper bedrooms and allows up to 12 people. The fifth bedroom is really an enclosed patio/sunroom and okay for kids but not sleeping adults. We had 11 adults so a bit of a shuffle on sleeping arrangements. Otherwise, we had a great experience."
United States
Khashayar A.
The price is €2,267
includes taxes & fees
7 May - 8 May
Luxe Oceanview Getaway w/ Heated Pool & Epic Sunrise (As Seen on TV)

Poipu Kapili 54 - Air Conditioned OCEANFRONT Townhome - Can't beat our views

Poipu Kapili 54 - Air Conditioned OCEANFRONT Townhome - Can't beat our views
Poipu
10.0 out of 10, Exceptional, (137 reviews)
"Excellent Stay! The condo is beautiful! Fabulous kitchen, bedrooms and bathrooms. With the central a/c and fans the upstairs bedrooms stayed very cool which was so appreciated for sleeping. In many condos the bedrooms are always warm- not here! Other than our own food and drinks, we wanted for nothing as there were plenty of supplies provided. The pool area is beautifully landscaped and is very clean. We were impressed. From the condo’s lanai, the sunsets were awe inspiring and the...
United States
Denise J.
Poipu Kapili 54 - Air Conditioned OCEANFRONT Townhome - Can't beat our views

Sunny Poipu Beach House Near Grand Hyatt, Views, AC, Guest Favorite

Sunny Poipu Beach House Near Grand Hyatt, Views, AC, Guest Favorite
Poipu
10.0 out of 10, Exceptional, (223 reviews)
"Fabulous house and great location"
United States
Mary C.
Sunny Poipu Beach House Near Grand Hyatt, Views, AC, Guest Favorite

Stunning 270° Hapuʻu Mtn Views • Walk to Beach • Pool • A/C • Sleeps 12 • Ocean

Stunning 270° Hapuʻu Mtn Views • Walk to Beach • Pool • A/C • Sleeps 12 • Ocean
Poipu
10.0 out of 10, Exceptional, (1 review)
"We had the most wonderful stay with our family of eight, including two children age two and under. It was in a beautiful area, the amenities in the home allowed us to use the pool, the beaches, and to prepare meals with everything we needed.Evan, the property manager, was super to work with. He showed us everything we needed to know about the home, and gave us recommendations on the best beaches to go to with little ones. He was great with communications, always getting back to me promptly. ...
United States
Theresa H.
Stunning 270° Hapuʻu Mtn Views • Walk to Beach • Pool • A/C • Sleeps 12 • Ocean

*NEW 7BD Farmhouse Estate |Pool, PickleB, Gym| AC

*NEW 7BD Farmhouse Estate |Pool, PickleB, Gym| AC
Poipu
10.0 out of 10, Exceptional, (4 reviews)
"The farmhouse and cottage were lovely. The property fit our family perfectly and had everything we needed. Highly recommend!"
United States
Derrick F.
The price is €2,585
includes taxes & fees
8 May - 9 May
*NEW 7BD Farmhouse Estate |Pool, PickleB, Gym| AC

*NEW 2BD Luxe Beach Cottage |Pool PickleB Gym| AC

*NEW 2BD Luxe Beach Cottage |Pool PickleB Gym| AC
Poipu
6.0 out of 10, (1 review)
*NEW 2BD Luxe Beach Cottage |Pool PickleB Gym| AC

Cycle or Walk to Hanalei Bay

Cycle or Walk to Hanalei Bay
Hanalei
10.0 out of 10, Exceptional, (70 reviews)
"Great place close to beach! "
United States
Reagan S.
The price is €1,281
includes taxes & fees
30 Apr - 1 May
Cycle or Walk to Hanalei Bay

Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi

Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi
Princeville
9.4 out of 10, Exceptional, (129 reviews)
"This is a great place to stay, in a great area on the island. The condo had everything we needed, and is decorated nicely with Hawaiian charm. "
United States
Kevin M.
The price is €553
includes taxes & fees
28 Apr - 29 Apr
Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Shore Hotel Reviews

Find out more about South Shore

South Shore Holiday Homes information

Number of reviews
1,048
Accommodation
471 Holiday Homes
Lowest Price
€382
Highest Price
€2,585

Explore a world of travel with Expedia