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.
Kauai Inn

Kauai Inn

3 out of 5
Nawiliwili
Price was CA $2,602, price is now CA $1,685 per person
CA $1,685
per person
Jan 16 - Jan 23
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lihue (LIH)
9.2/10 Wonderful! (1,438 reviews)

Timbers Kauai Ocean Club & Residences

Timbers Kauai Ocean Club & Residences

5 out of 5
Price was CA $10,837, price is now CA $7,060 per person
CA $7,060
per person
Jan 22 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Lihue (LIH)
9.6/10 Exceptional! (35 reviews)
Choose other resorts. The amenities for this resort are not worth the money. There is only one restaurant and its not open all the time. The beach is 1/2 mile walk. The beach is not just for this property but for many others. Staff is very friendly, but not much they can do about the issues.

Reviewed on Jun 17, 2026

1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

5 out of 5
Price was CA $7,647, price is now CA $5,143 per person
CA $5,143
per person
Jan 22 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Lihue (LIH)
9.2/10 Wonderful! (387 reviews)

Koloa Landing Resort at Poipu, Autograph Collection

Koloa Landing Resort at Poipu, Autograph Collection

4.5 out of 5
Poipu
Price was CA $4,126, price is now CA $2,921 per person
CA $2,921
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lihue (LIH)
9.6/10 Exceptional! (1,002 reviews)
.

Reviewed on Nov 2, 2026

Ko'a Kea Resort on Po'ipu Beach

Ko'a Kea Resort on Po'ipu Beach

4.5 out of 5
Poipu
Price was CA $5,411, price is now CA $4,028 per person
CA $4,028
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lihue (LIH)
9.4/10 Exceptional! (1,003 reviews)
Great option, love the small boutique size of the property vs many of the mega resorts in Hawaii.

Reviewed on Nov 2, 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 $733 per night from Nov 4 to Nov 5
CA $733
CA $936 total
Nov 4 - Nov 5
includes taxes & fees
9.6/10 Exceptional! (1,003 reviews)
"."

Reviewed on Nov 2, 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
Fully refundableReserve now, pay when you stay
The price is CA $796 per night from Nov 17 to Nov 18
CA $796
CA $1,037 total
Nov 17 - Nov 18
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Professional staff. Clean room. Relaxing atmosphere. Beautiful property."

Reviewed on Oct 31, 2026

Grand Hyatt Kauai Resort and Spa
Ko'a Kea Resort on Po'ipu Beach

Ko'a Kea Resort on Po'ipu Beach

4.5 out of 5
2251 Poipu Road Koloa HI
The price is CA $782 per night from Nov 20 to Nov 21
CA $782
CA $1,011 total
Nov 20 - Nov 21
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Great option, love the small boutique size of the property vs many of the mega resorts in Hawaii."

Reviewed on Nov 2, 2026

Ko'a Kea Resort on Po'ipu Beach
See all 1,987 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.
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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 $1,685, 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.

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