South Shore Pet-friendly Holidays
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Price found within the past 48 hours. Click for updated prices.
Kiahuna Plantation Resort Kauai by OUTRIGGER
Poipu
€1,620
per person
19 Sept - 26 Sept
just found
Return direct flight included
Chicago (ORD) to Lihue (LIH)
8.4/10 Very good! (1,051 reviews)
Excellent property. Only thing I would note is that some of the kitchen tools were subpar. The blender top wouldn’t stay on, the can opener didn’t work at all, etc. Front desk very kind responsive, even let us check in early. Also, I’m pretty sure the unit they gave us wasn’t the one we thought we had rented based on Expedia photos, but it was still a great unit with a beach view.
Reviewed on 15 Aug 2026
Waipouli Beach Resorts & Spa Kauai by OUTRIGGER
Waipouli
€2,409
per person
19 Sept - 26 Sept
just found
Return direct flight included
Chicago (ORD) to Lihue (LIH)
8.8/10 Excellent! (1,001 reviews)
Nice garden and pool areas.
Nice bedrooms and bathrooms. Nice kitchen, but missing some essentials.
Had trouble picking up pool towels, as they were available only during a limited period during the day, even though the pool was open
Reviewed on 16 Aug 2026
Koloa Landing Resort at Poipu, Autograph Collection
Poipu
€2,258
per person
30 Sept - 7 Oct
found 21 hours ago
Return direct flight included
Chicago (ORD) to Lihue (LIH)
9.6/10 Exceptional! (1,008 reviews)
The place was so clean. From the amenities to our room. It was perfect. The front desk attendant Bree was so helpful and kind. Nikki at the bar made the entire stay.
Reviewed on 15 Aug 2026
Price found within the past 48 hours. Click for updated prices.
Timbers Kauai Ocean Club & Residences
€4,421
per person
30 Sept - 7 Oct
found 21 hours ago
Return direct flight included
Chicago (ORD) 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 17 Jun 2026
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