South Shore Vacation Homes

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Featured Vacation Homes in South Shore

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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.

Hotel Options in South Shore

    Koloa Landing Resort at Poipu, Autograph Collection

    Koloa Landing Resort at Poipu, Autograph Collection

    2641 Poipu Rd Koloa HI
    $549 nightly
    The price is $652 total per night from Jan 10 to Jan 11
    $652 total
    Jan 10 - Jan 11, 2026
    Total with taxes and fees
    9.4/10 Exceptional! (1,001 reviews)
    Grand Hyatt Kauai Resort and Spa

    Grand Hyatt Kauai Resort and Spa

    1571 Poipu Road Koloa HI
    $678 nightly
    The price is $805 total per night from Jan 10 to Jan 11
    $805 total
    Jan 10 - Jan 11, 2026
    Total with taxes and fees
    9.4/10 Exceptional! (1,004 reviews)
    Sheraton Kauai Resort Villas

    Sheraton Kauai Resort Villas

    2440 Hoonani Road Koloa HI
    $303 nightly
    The price is $360 total per night from Jan 3 to Jan 4
    $360 total
    Jan 3 - Jan 4, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (681 reviews)

South Shore Vacation Homes

Book vacation homes in South Shore
Next time you take a group getaway top South Shore, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of South Shore vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every South Shore vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in South Shore; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a South Shore rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to South Shore is sure to be a winner.

South Shore Vacation Homes essential information

Accommodation
462 Vacation Homes
Lowest Price
$360
Highest Price
$1,615
Popular accommodation
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠, Sunny Poipu Beach House Near Grand Hyatt, Views, AC, Guest Favorite, Large beautiful home with air conditioning! Walk to Beaches, Resort Pool, 4 Bed Poipu House, Guest House, Walk to Beach, Poipu Kai Pool, Large Lanai, Beach Toys, Wainani "Heated Pool, Hot Tub, Game Room & A/C", Delightful Historic Cottage Steps from Poipu/Brennecke's Beaches A/C, Luxury Poipu 4br Villa with AC Walk to the Beach! (224), Hale Ohana - Beautiful 'House of the Family' - Poipu Beach - sleeps 6, FULL OCEAN VIEWS Poipu Beach House, LOVELY lanai and A/C

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