South Shore Vacation Packages

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Top South Shore Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Banyan Harbor Resort

Banyan Harbor Resort

3 out of 5
Nawiliwili
per person
Oct 1 - Oct 7
found 24 hours ago
Roundtrip flight included
Edmonton (YEG) to Lihue (LIH)
8.6/10 Excellent! (1,048 reviews)
Clean, friendly staff, walking distance to shopping

Reviewed on Jul. 16, 2025

1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

5 out of 5
per person
Oct 1 - Oct 7
found 24 hours ago
Roundtrip flight included
Edmonton (YEG) to Lihue (LIH)
9.2/10 Wonderful! (206 reviews)
Beautiful location nestled on a hill overlooking the bay. With amazing sunsets.

Reviewed on Jul. 18, 2025

Makai Club Resort

Makai Club Resort

3.5 out of 5
per person
Oct 1 - Oct 7
found 24 hours ago
Roundtrip flight included
Edmonton (YEG) to Lihue (LIH)
9/10 Wonderful! (358 reviews)
It’s absolutely beautiful the staff is amazing and kind. The stay was amazing everything to do with property went well and the staff being so friendly was the greatest it’s no fun dealing with ugly people and the property had none of this thankfully, Paul Acosta, from Austin,Texas

Reviewed on Jul. 17, 2025

Hanalei Bay Resort

Hanalei Bay Resort

3 out of 5
Save 100% on your flight
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lihue (LIH)
7.6/10 Good! (462 reviews)
The property is beautiful, the views are stunning, the pool is great, there are plenty of pickleball and tennis courts, there are restaurants available, and they provide rides to the nearest beach via golf cart. I also stayed at Marriot and Sheraton and I missed Hanalei Bay Resort the entire time I was at the other hotels. Definition of hidden gem.

Reviewed on Jun. 28, 2025

Timbers Kauai Ocean Club & Residences

Timbers Kauai Ocean Club & Residences

5 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lihue (LIH)
10/10 Exceptional! (31 reviews)
Wonderful! Highly recommend

Reviewed on Apr. 3, 2025

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
Poipu featuring a sandy beach, landscape views and tropical scenes

Poipu

8 out of top 10 points of interest in this area
4.5/5(29 area reviews)

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 $921 per night from Aug 17 to Aug 18
CA $921
CA $1,141 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"We live this place."

Reviewed on Jul. 17, 2025

Koloa Landing Resort at Poipu, Autograph Collection
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 $422 per night from Jul 26 to Jul 27
CA $422
CA $498 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (599 reviews)
"Easy acces yo parking lot"

Reviewed on Jul. 17, 2025

Sheraton Kauai Resort Villas
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 $922 per night from Aug 11 to Aug 12
CA $922
CA $1,178 total
Aug 11 - Aug 12
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"This was a beautiful resort. Have no complaints. Would stay here again."

Reviewed on Jul. 13, 2025

Grand Hyatt Kauai Resort and Spa
See all 1,963 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

Discover the most popular places to visit in South Shore

Poipu Beach which includes a beach

Poipu Beach

4.5/5(102 reviews)

Visit one of the world’s best beaches, with coves of white sand and clear water decorating the Sunny South Side.

Poipu Beach
Lawai Beach

Lawai Beach

5/5(4 reviews)

If a restful vacation is part of your travel plans, Lawai Beach might be the perfect place to seek out during your trip to Koloa. Discover the beautiful sunsets and shops in this romantic area.

Lawai Beach
Shipwreck Beach

Shipwreck Beach

4/5(3 reviews)

Why not spend a carefree afternoon at Shipwreck Beach during your travels in Koloa? Amble around this romantic area's seaside, or seek out the snorkeling spots.

Shipwreck Beach

Frequently asked questions

How much does a South Shore vacation package cost?
The cheapest South Shore vacation package is CA $1,457, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.