Holiday Homes in South Shore

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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 AU$656
includes taxes & fees
18 May - 19 May
An Affordable Alternative to Expensive Accommodations in Poipu

*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 house was beautiful, the location was great! And getting to go to the athletic club was such a wonderful bonus. Would absolutely stay here again!!!"
United States
Camille H.
The price is AU$935
includes taxes & fees
8 May - 9 May
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

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 AU$658
includes taxes & fees
11 May - 12 May
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
9.6 out of 10, Exceptional, (27 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 AU$817
includes taxes & fees
14 May - 15 May
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠

KP317 Third FL | Partial Ocean •Pool •Garden

KP317 Third FL | Partial Ocean •Pool •Garden
Poipu
10.0 out of 10, Exceptional, (3 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.
The price is AU$985
includes taxes & fees
4 June - 5 June
KP317 Third FL | Partial Ocean •Pool •Garden

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 AU$1,404
includes taxes & fees
8 May - 9 May
Ocean 500 Feet

E Komo Mai

E Komo Mai
Poipu
9.6 out of 10, Exceptional, (122 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 AU$1,493
includes taxes & fees
10 May - 11 May
E Komo Mai

*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)
The price is AU$1,039
includes taxes & fees
12 May - 13 May
*NEW 2BD Luxe Beach Cottage |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 AU$1,609
includes taxes & fees
8 May - 9 May
Poipu 1940s Beach Cottage | Outdoor Showers

*NEW Estate 5BR Retreat|Pool|AC & PickleBall

*NEW Estate 5BR Retreat|Pool|AC & PickleBall
Poipu
10.0 out of 10, Exceptional, (6 reviews)
"We loved this place. It was a wonderful place for all seven of us. The club house was a great place to end our day being lazy around the pool."
United States
Margaret G.
The price is AU$2,223
includes taxes & fees
8 May - 9 May
*NEW Estate 5BR Retreat|Pool|AC & PickleBall

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, (224 reviews)
"Fabulous house and great location"
United States
Mary C.
The price is AU$1,622
includes taxes & fees
16 May - 17 May
Sunny Poipu Beach House Near Grand Hyatt, Views, AC, Guest Favorite

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, (117 reviews)
"The access to the beach and the amount of space the house has inside and out was amazing!"
United States
Andrea
The price is AU$2,294
includes taxes & fees
22 May - 23 May
Great Rates Private 4 BR Luxury Home in Poipu - Baby Beach Sleeps 10 TVNC#1194

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 AU$3,732
includes taxes & fees
30 May - 31 May
Luxe Oceanview Getaway w/ Heated Pool & Epic Sunrise (As Seen on TV)

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

*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC
Poipu
The price is AU$1,608
includes taxes & fees
22 May - 23 May
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC

*NEW 5BD Luxe Beach Estate |Pool, PickleB, Gym| AC

*NEW 5BD Luxe Beach Estate |Pool, PickleB, Gym| AC
Poipu
10.0 out of 10, Exceptional, (4 reviews)
"Love this house! We were able to separate between the main house and the cottage and have plenty of space for everyone. Awesome location too!"
United States
Brianna H.
The price is AU$2,807
includes taxes & fees
22 May - 23 May
*NEW 5BD Luxe Beach Estate |Pool, PickleB, Gym| AC

*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 AU$4,113
includes taxes & fees
8 May - 9 May
*NEW 7BD Farmhouse Estate |Pool, PickleB, Gym| AC

Honeymoon Cottage 1 Bed, 1 Bath with A/C, Steps to the Beach TVNC#5069

Honeymoon Cottage 1 Bed, 1 Bath with A/C, Steps to the Beach TVNC#5069
Anahola
10.0 out of 10, Exceptional, (2 reviews)
"What a delightful stay! Everything was perfect from the moment we arrived. The home was very clean and we were greeted with flowers and goodies! Such a nice touch! Location was perfect to get to everywhere we needed to go but the best part was the beach steps away. I was there every morning watching the sunrise and sipping my coffee and swimming everyday. It was a magical vacation, we’ll be back for sure."
United States
Sarah L.
Honeymoon Cottage 1 Bed, 1 Bath with A/C, Steps to the Beach TVNC#5069

Romantic Cottage, Private Acre of Paradise, View! Pool!

Romantic Cottage, Private Acre of Paradise, View! Pool!
Hanalei
9.6 out of 10, Exceptional, (108 reviews)
"Our stay was fantastic, the host with excellent guidance, prompt responses to inquiries , the property mgr. quick to respond to questions! We had an amazing stay and would highly recommend it, we will be coming back, we were mesmerized by the stars, geckos, frogs, sounds of birds, we felt like and were in paradise! Absolutely a 10 star retreat/escape!"
United States
Delilah T.
The price is AU$1,401
includes taxes & fees
12 May - 13 May
Romantic Cottage, Private Acre of Paradise, View! Pool!

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, (131 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 AU$842
includes taxes & fees
11 May - 12 May
Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi

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 AU$2,038
includes taxes & fees
16 May - 17 May
Cycle or Walk to Hanalei Bay
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

South Shore Holiday Homes information

Number of reviews
1,028
Accommodation
472 Holiday Homes
Lowest Price
AU$656
Highest Price
AU$4,113

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