Romantic Vacations in South Shore 2026

Photo by Dan Sherman

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Flight and Romantic hotel deals in South Shore

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

OUTRIGGER Kauaʻi Beach Resort & Spa

CA $2,604

per person

Dec 26 - Dec 31

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Lihue (LIH)

8.4/10 Very good! (1,145 reviews)

1 Hotel Hanalei Bay

Save 100% on your flight

CA $4,855

per person

Dec 13 - Dec 18

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Lihue (LIH)

9.2/10 Wonderful! (384 reviews)

The place is beautiful but it was not a super clean resort. The rug was stained and the outside just felt dirty. Everything else was good

Reviewed on Oct 8, 2026

Koloa Landing Resort at Poipu, Autograph Collection

Poipu

Save 100% on your flight

CA $2,736

per person

Dec 3 - Dec 10

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Lihue (LIH)

9.6/10 Exceptional! (1,001 reviews)

We are so grateful that we decided to stay at this resort. Koloa Landing is absolutely stunning. We booked a three bedroom unit and it was perfect for our family.

Reviewed on Oct 11, 2026

Ko'a Kea Resort on Po'ipu Beach

Poipu

CA $3,524

per person

Dec 13 - Dec 18

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Lihue (LIH)

9.4/10 Exceptional! (1,001 reviews)

The staff were absolutely wonderful. We came on 10/1 so after the hurricane so the beach was closed but everything else was delightful

Reviewed on Oct 5, 2026

Timbers Kauai Ocean Club & Residences

Save 100% on your flight

CA $6,003

per person

Dec 13 - Dec 18

found 1 day ago

Roundtrip flight included

Edmonton (YEG) 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

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5* Romantic holidays in South Shore

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

1 Hotel Hanalei Bay

Save 100% on your flight

CA $4,855

per person

Dec 13 - Dec 18

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Lihue (LIH)

9.2/10 Wonderful! (384 reviews)

The place is beautiful but it was not a super clean resort. The rug was stained and the outside just felt dirty. Everything else was good

Reviewed on Oct 8, 2026

Timbers Kauai Ocean Club & Residences

Save 100% on your flight

CA $6,003

per person

Dec 13 - Dec 18

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Lihue (LIH)

9.6/10 Exceptional! (35 reviews)

Reviewed on Jun 17, 2026

Don't see what you're looking for?

See all available trips from Columbus to South Shore

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3 Night Romantic holidays in South Shore

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

The Cottages at Makai Club

CA $1,341

per person

Nov 23 - Nov 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Lihue (LIH)

No reviews

Grand Hyatt Kauai Resort and Spa

Poipu

CA $2,360

per person

Nov 23 - Nov 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Lihue (LIH)

9.4/10 Exceptional! (1,000 reviews)

The Royal Sonesta Kaua'i Resort Lihue

CA $1,747

per person

Jan 4 - Jan 7

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Lihue (LIH)

9.2/10 Wonderful! (1,351 reviews)

Amazing

Reviewed on Oct 12, 2026

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4 Night Romantic holidays in South Shore

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

Kauai Inn

Nawiliwili

CA $1,238

per person

Nov 19 - Nov 23

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Lihue (LIH)

9.2/10 Wonderful! (1,431 reviews)

Beautiful view

Reviewed on Oct 11, 2026

OUTRIGGER Kauaʻi Beach Resort & Spa

CA $1,330

per person

Nov 19 - Nov 23

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Lihue (LIH)

8.4/10 Very good! (1,145 reviews)

The Cottages at Makai Club

CA $1,306

per person

Dec 7 - Dec 11

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Lihue (LIH)

No reviews

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What are some of the benefits of booking a romantic South Shore vacation?

When booking a romantic South Shore vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Hawaii.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the South Shore destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in South Shore?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,238 and can enjoy savings of up to 27 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in South Shore?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout South Shore certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to South Shore.

Can I book a romantic South Shore vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your South Shore search.

Can I book a romantic trip to South Shore that is fully refundable?

Several romantic South Shore vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.