South Shore Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Dan Sherman

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top South Shore Vacation Deals

Price found within the past 48 hours. Click for updated prices.
2417 at Lihue Oceanfront Resort

2417 at Lihue Oceanfront Resort

3.5 out of 5
Price was CA $2,464, price is now CA $1,705 per person
CA $1,705
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lihue (LIH)
7/10 Good! (64 reviews)
Clean room

Reviewed on Jun 26, 2026

1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

5 out of 5
Price was CA $12,482, price is now CA $8,740 per person
CA $8,740
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lihue (LIH)
9.2/10 Wonderful! (368 reviews)
Amazing hotel and views. Breakfast and buffet delicious. Restaurant service was a bit lacking during meals. Pools are gorgeous and restaurant by pool was great

Reviewed on Aug 1, 2026

Kauai Inn

Kauai Inn

3 out of 5
Nawiliwili
Price was CA $2,598, price is now CA $1,832 per person
CA $1,832
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Lihue (LIH)
9.2/10 Wonderful! (1,419 reviews)

The Cliffs at Princeville by ResorTime

The Cliffs at Princeville by ResorTime

2 out of 5
Price was CA $3,569, price is now CA $2,669 per person
CA $2,669
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lihue (LIH)
8.8/10 Excellent! (39 reviews)
Amazing room!!! Great place to stay!!!

Reviewed on Jul 25, 2026

Kiahuna Plantation Resort Kauai by OUTRIGGER

Kiahuna Plantation Resort Kauai by OUTRIGGER

4 out of 5
Poipu
Price was CA $5,367, price is now CA $4,203 per person
CA $4,203
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Lihue (LIH)
8.4/10 Very good! (1,047 reviews)
Everything was perfect. I love the Plantation grounds, the gardens are so beautiful!

Reviewed on Aug 3, 2026

Where to stay in South Shore

Find the best South Shore areas and neighborhoods for the activities you enjoy most. Learn more about South Shore
A tropical beach with clear turquoise waters, palm trees, and a few buildings along the shore.

Poipu

8 out of top 10 points of interest in this area

Boasting high-end hotels, resorts, and two main shopping centers, Poʻipū offers a luxurious stay. Explore attractions like Allerton Garden, Mahaulepu Beach, and Spouting Horn for a memorable experience.

Find hotels in Poipu

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South Shore Hotel Deals

Koloa Landing Resort at Poipu, Autograph Collection

Koloa Landing Resort at Poipu, Autograph Collection

4.5 out of 5
2641 Poipu Rd Koloa HI
Fully refundableReserve now, pay when you stay
The price is CA $708 per night from Sep 1 to Sep 2
CA $708
CA $907 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,008 reviews)
"The best condominium and pool on the Island. Everything in Kōloa Landing from the staff, the spa, the beautiful resort…personified the Aloha spirit! Thank you for taking care of my family"

Reviewed on Aug 3, 2026

Koloa Landing Resort at Poipu, Autograph Collection
Grand Hyatt Kauai Resort and Spa

Grand Hyatt Kauai Resort and Spa

4.5 out of 5
1571 Poipu Road Koloa HI
The price is CA $1,427 per night from Sep 3 to Sep 4
CA $1,427
CA $1,786 total
Sep 3 - Sep 4
includes taxes & fees
Grand Hyatt Kauai Resort and Spa
Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas

4 out of 5
2440 Hoonani Road Koloa HI
Fully refundableReserve now, pay when you stay
The price is CA $402 per night from Aug 18 to Aug 19
CA $402
CA $477 total
Aug 18 - Aug 19
includes taxes & fees
Sheraton Kauai Resort Villas
See all 1,967 properties in South Shore
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular South Shore attractions

A tropical beach with palm trees, ocean waves, and people enjoying the beach.

Poipu Beach

9.4/10 (1,968 reviews)
Visit one of the world’s best beaches, with coves of white sand and clear water decorating the Sunny South Side.
See properties

Frequently asked questions

How much does a South Shore vacation package cost?
The cheapest South Shore vacation package is CA $1,705, so your dream escape can become a reality — without spending an arm and a leg. Bundle flights, hotels and car rentals to tailor a package suited to your traveling style.
How do I get a cheap travel package to South Shore?
Search for flights that fit your busy schedule, add a hotel to your booking and watch how much you save with a South Shore vacation package. It's as simple as that! From flights and hotels to rental cars and tours, Expedia makes traveling cheap and easy. And with more than 550 airlines and 1,000,000 hotels globally to select from, you'll never be short of choice.
Where should I stay in South Shore?
There aren't many better places to kick-start your South Shore break than in Poipu. Poipu Beach deserves a spot at the top of your sightseeing list here.
What are the top hotels in South Shore?
Sheraton Kauai Resort Villas and Hilton Vacation Club The Point At Poipu Kauai are a couple of great places to stay in Poipu. A must-visit on any good South Shore itinerary, we recommend taking the time to fully discover this impressive city.
How far in advance should I book my South Shore vacation?
To land rock-bottom prices, book as early as you can. Airlines usually start selling tickets, along with some of the lowest fares, nearly a year ahead of time. Hotels, activities and car rental should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway to South Shore, there are always lots of great bargains to be had on Expedia. Book your escape today!
What does an Expedia South Shore travel package include?
From airfares and hotels to car rentals, Expedia can help you craft a South Shore package that's ideal for you. Heading away for a week or two? Check out a rental car, hotel and flight bundle. If your break is short, a flight and hotel deal may suit you better. Activities can also be added once you've made your booking. Our travel packages make it easy to plan and save.
What should I know before booking a South Shore travel package?
Whether it's relaxation or adventure you're craving, a South Shore vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a South Shore Expedia vacation package?
You can, and with over 550 airlines to choose from all over the world, you have loads of choice. Look through the available options and see which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my South Shore vacation package?
Don't stress if you're rethinking your South Shore vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We know life can occasionally throw a spanner in the travel works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.