Top 50 South Shore Vacation Rentals

Condos (1,430)
Houses (361)
Villas (103)
Golf rental (1,383)
Ocean view (722)
Beach view (562)

Explore a selection of South Shore vacation rentals

New executive Villa, 350 yards to beach, pool, hot tub, air cond...
Guests14
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$860 avg/night
5 beds
4 Bathrooms
Guests 14
112 reviews
Ocean-View Studio, Steps from Beaches!
Guests2
Studio
Bathroom1
Wonderful 4.8 / 5
$120 avg/night
Studio
1 Bathroom
Guests 2
21 reviews
BEST! Oceanfront - NEW A/C - Corner Unit - Ocean View from every...
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$275 avg/night
1 bed
1 Bathroom
Guests 2
32 reviews
Artist Retreat, Just 100 Steps from Poipu Beach!!!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.5 / 5
$155 avg/night
2 beds
1 Bathroom
Guests 4
55 reviews
Delightfully Renovated Historic Plantation Cottage Steps From...
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$295 avg/night
2 beds
1 Bathroom
Guests 4
44 reviews
POIPU Beach Plantation , 4br with POOL on 1/2 acre, steps to the...
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.9 / 5
$579 avg/night
4 beds
2 Bathrooms
Guests 10
45 reviews
Very PRIVATE BEACHFRONT condo in Poipu! End unit in single-level...
Guests4
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$425 avg/night
1 bed
1 Bathroom
Guests 4
7 reviews
Stunning New 2 Bedroom Luxury Cottage 300 feet from Poipu Beach...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$395 avg/night
2 beds
2 Bathrooms
Guests 4
59 reviews
LUXURY "SANDS" WITH A/C! CONTACT ME IF BOOKED FOR MY OTHER VRBO...
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$189 avg/night
1 bed
1 Bathroom
Guests 4
64 reviews
Prince Kuhio 205, Ocean View, Poipu area, sunny south shore
Guests4
Bedroom1
Bathroom1
Wonderful 4.6 / 5
$139 avg/night
1 bed
1 Bathroom
Guests 4
49 reviews
BEAUTIFUL, RELAXING POIPU CONDO ON THE BEACH. SUN, SURF, SNORKEL...
Guests4
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$205 avg/night
1 bed
1 Bathroom
Guests 4
36 reviews
South Shore Ocean View 1 BR Condo Ground Floor Poipu Sands #112...
Guests3
Bedroom1
Bathroom1
Wonderful 4.6 / 5
$177 avg/night
1 bed
1 Bathroom
Guests 3
50 reviews
Kiahuna Plantation #143 on Poipu Beach - New Low Rates
Guests4
Bedroom1
Bathroom1
Wonderful 4.6 / 5
$219 avg/night
1 bed
1 Bathroom
Guests 4
30 reviews
Across the street from beach
Guests2
Studio
Bathroom1
Wonderful 5 / 5
$135 avg/night
Studio
1 Bathroom
Guests 2
40 reviews
Dynamic Rental/Seasonal Rates/Refurbished in 2015
Guests4
Bedroom1
Bathroom1
Wonderful 4.4 / 5
$140 avg/night
1 bed
1 Bathroom
Guests 4
40 reviews
Beautiful Whitewater Views~ Steps to Poipu Beach~ Island Decor...
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$425 avg/night
3 beds
3 Bathrooms
Guests 6
38 reviews
Whitewater Views~ Steps to Poipu Beach~Tropical Decor throughout...
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$425 avg/night
3 beds
3 Bathrooms
Guests 6
38 reviews
Oceanfront, Palm Trees and the Beautiful Blue Pacific...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$275 avg/night
2 beds
2 Bathrooms
Guests 4
40 reviews
Beautiful New Plantation Style Cottage, Steps Away From Poipu Beach
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$360 avg/night
2 beds
2 Bathrooms
Guests 4
81 reviews
Incredible Oceanfront Views - 2 Bedroom/2.5 Bath - Air...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.2 / 5
$180 avg/night
2 beds
2 Bathrooms
Guests 4
21 reviews
Poipu Sands #426~2bd/2ba. Next to Hyatt/golf & easy walk to beach.
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$188 avg/night
2 beds
2 Bathrooms
Guests 6
51 reviews
15% OFF - LUXURY VILLA, Central A/C, 3 Suites, Pool/Spa, short...
Guests6
Bedrooms3
Bathroom1
Wonderful 5 / 5
$445 avg/night
3 beds
1 Bathroom
Guests 6
30 reviews
Beach Resort Condo Has Everything!
Guests4
Bedroom1
Bathroom1
Wonderful 4.5 / 5
$133 avg/night
1 bed
1 Bathroom
Guests 4
42 reviews
Perfect Location!! Short walk to beach, restaurants, pools and...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$223 avg/night
2 beds
2 Bathrooms
Guests 4
54 reviews
Makahuena 2202: Beautiful 3br condo, spacious inside, view, close...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.3 / 5
$179 avg/night
3 beds
2 Bathrooms
Guests 6
68 reviews
Large Poipu Kai Corner, Ground Floor, Quiet Condo With Relaxing...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$248 avg/night
2 beds
2 Bathrooms
Guests 6
34 reviews
Live On The Ocean While Exploring Idyllic Poipu, Points Beyond...
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$263 avg/night
1 bed
1 Bathroom
Guests 2
20 reviews
Amazing location for Family beach memories! Low Intro Rates!
Guests6
Bedrooms2
Bathroom1
Wonderful 4.4 / 5
$154 avg/night
2 beds
1 Bathroom
Guests 6
45 reviews
Luxurious Ocean View 3 Bedroom Condo with Large Pool, SPA and Lanai
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$150 avg/night
3 beds
2 Bathrooms
Guests 8
53 reviews
A/C in Bedrooms Now included in Summer Pricing!!!
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$233 avg/night
2 beds
2 Bathrooms
Guests 6
54 reviews
Unit 25, Ocean View, End Unit, Remodeled, Free Pool/tennis, Two...
Guests4
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$275 avg/night
1 bed
1 Bathroom
Guests 4
40 reviews
Intimate and Elegant Kiahuna Partial Ocean View
Guests4
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$232 avg/night
1 bed
1 Bathroom
Guests 4
36 reviews
Private Home Steps from Poipu & Shipwreck Beaches - New: A/C as of...
Guests7
Bedrooms3
Bathroom1
Wonderful 4.6 / 5
$372 avg/night
3 beds
1 Bathroom
Guests 7
29 reviews
Brand New Custom Plantation Cottage - Poipu Beach
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$405 avg/night
2 beds
2 Bathrooms
Guests 4
12 reviews
Condo Within Short 2 Minute Walk To The Best Beach In Sunny Poipu
Guests4
Bedroom1
Bathroom1
Wonderful 4.3 / 5
$155 avg/night
1 bed
1 Bathroom
Guests 4
16 reviews
Hale Mana Kai Poipu, Hawaii
Guests10
Bedrooms4
Bathrooms5
Wonderful 5 / 5
$833 avg/night
4 beds
5 Bathrooms
Guests 10
23 reviews
Deluxe Poipu Beach Oceanview -Park Next to Door! No Stairs! A/C!
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$199 avg/night
2 beds
2 Bathrooms
Guests 4
87 reviews
Luxury Air Conditioned 3BR Kauai Resort Condo
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.8 / 5
$260 avg/night
3 beds
3 Bathrooms
Guests 6
9 reviews
Kahala at Poipu Kai 932 - Tropical Resort Living on Kauai – 1BR/1BR
Guests4
Bedroom1
Bathroom1
Wonderful 4.6 / 5
$176 avg/night
1 bed
1 Bathroom
Guests 4
32 reviews
Ocean View At Kiahuna 2 Bedroom/2 Bath Newly Remodeled End Unit...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$400 avg/night
2 beds
2 Bathrooms
Guests 6
14 reviews
SPECIAL SUMMER/FALL SALE - Makahuena #4205 2BR/2BA OCEANFRONT GEM
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$175 avg/night
2 beds
2 Bathrooms
Guests 6
19 reviews
OCEANFRONT RESORT-Kiahuna Plantation 2BR/2BA - Poipu Beach Condo
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$313 avg/night
2 beds
2 Bathrooms
Guests 6
51 reviews
Kiahuna 1 - Single-story Beachfront Bungalow On Poipu Beach!
Guests4
Bedroom1
Bathrooms0
Wonderful 4.8 / 5
$415 avg/night
1 bed
0 Bathrooms
Guests 4
13 reviews
2 bedroom/2.5 bath of Absolutely Beautiful Expansive Views of the...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.7 / 5
$200 avg/night
2 beds
1 Bathroom
Guests 6
38 reviews
Kiahuna Plantation, Stunning View, Near Beach; Newly Renovated...
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$185 avg/night
1 bed
1 Bathroom
Guests 4
14 reviews
Kahala Poipu Kai 312 - Outstanding 2 Bedroom Condo Close to Poipu...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$166 avg/night
2 beds
2 Bathrooms
Guests 6
15 reviews
Gorgeous Remodeled Studio with Air Conditioning
Guests2
Studio
Bathroom1
Wonderful 4.9 / 5
$125 avg/night
Studio
1 Bathroom
Guests 2
68 reviews
Beach Bungalow With Full Ocean Views
Guests4
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$215 avg/night
1 bed
1 Bathroom
Guests 4
30 reviews
Ocean Front-Kuhio Shores-30 feet from water! Recently remodeled...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$321 avg/night
2 beds
1 Bathroom
Guests 6
49 reviews
Ocean View Kiahuna Plantation 2BR/2BA - Poipu Beach Condo Resort...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$320 avg/night
2 beds
2 Bathrooms
Guests 6
45 reviews

South Shore, Kauai, HI, USA Vacation Rentals

New executive Villa, 350 yards to beach, pool, hot tub, air cond...

Ocean-View Studio, Steps from Beaches!

BEST! Oceanfront - NEW A/C - Corner Unit - Ocean View from every...

Artist Retreat, Just 100 Steps from Poipu Beach!!!

Delightfully Renovated Historic Plantation Cottage Steps From...

POIPU Beach Plantation , 4br with POOL on 1/2 acre, steps to the...

Very PRIVATE BEACHFRONT condo in Poipu! End unit in single-level...

Stunning New 2 Bedroom Luxury Cottage 300 feet from Poipu Beach...

LUXURY "SANDS" WITH A/C! CONTACT ME IF BOOKED FOR MY OTHER VRBO...

Prince Kuhio 205, Ocean View, Poipu area, sunny south shore

BEAUTIFUL, RELAXING POIPU CONDO ON THE BEACH. SUN, SURF, SNORKEL...

South Shore Ocean View 1 BR Condo Ground Floor Poipu Sands #112...

Kiahuna Plantation #143 on Poipu Beach - New Low Rates

Across the street from beach

Dynamic Rental/Seasonal Rates/Refurbished in 2015

Beautiful Whitewater Views~ Steps to Poipu Beach~ Island Decor...

Whitewater Views~ Steps to Poipu Beach~Tropical Decor throughout...

Oceanfront, Palm Trees and the Beautiful Blue Pacific...

Beautiful New Plantation Style Cottage, Steps Away From Poipu Beach

Incredible Oceanfront Views - 2 Bedroom/2.5 Bath - Air...

Poipu Sands #426~2bd/2ba. Next to Hyatt/golf & easy walk to beach.

15% OFF - LUXURY VILLA, Central A/C, 3 Suites, Pool/Spa, short...

Beach Resort Condo Has Everything!

Perfect Location!! Short walk to beach, restaurants, pools and...

Makahuena 2202: Beautiful 3br condo, spacious inside, view, close...

Large Poipu Kai Corner, Ground Floor, Quiet Condo With Relaxing...

Live On The Ocean While Exploring Idyllic Poipu, Points Beyond...

Amazing location for Family beach memories! Low Intro Rates!

Luxurious Ocean View 3 Bedroom Condo with Large Pool, SPA and Lanai

A/C in Bedrooms Now included in Summer Pricing!!!

Unit 25, Ocean View, End Unit, Remodeled, Free Pool/tennis, Two...

Intimate and Elegant Kiahuna Partial Ocean View

Private Home Steps from Poipu & Shipwreck Beaches - New: A/C as of...

Brand New Custom Plantation Cottage - Poipu Beach

Condo Within Short 2 Minute Walk To The Best Beach In Sunny Poipu

Hale Mana Kai Poipu, Hawaii

Deluxe Poipu Beach Oceanview -Park Next to Door! No Stairs! A/C!

Luxury Air Conditioned 3BR Kauai Resort Condo

Kahala at Poipu Kai 932 - Tropical Resort Living on Kauai – 1BR/1BR

Ocean View At Kiahuna 2 Bedroom/2 Bath Newly Remodeled End Unit...

SPECIAL SUMMER/FALL SALE - Makahuena #4205 2BR/2BA OCEANFRONT GEM

OCEANFRONT RESORT-Kiahuna Plantation 2BR/2BA - Poipu Beach Condo

Kiahuna 1 - Single-story Beachfront Bungalow On Poipu Beach!

2 bedroom/2.5 bath of Absolutely Beautiful Expansive Views of the...

Kiahuna Plantation, Stunning View, Near Beach; Newly Renovated...

Kahala Poipu Kai 312 - Outstanding 2 Bedroom Condo Close to Poipu...

Gorgeous Remodeled Studio with Air Conditioning

Beach Bungalow With Full Ocean Views

Ocean Front-Kuhio Shores-30 feet from water! Recently remodeled...

Ocean View Kiahuna Plantation 2BR/2BA - Poipu Beach Condo Resort...