Koloa Winter Rentals & Holiday Homes

There are a lot of options in Koloa. If you plan on staying in the Koloa area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Koloa:

• Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park
• Poipu Bay Getaway - Poipu House - Saltwater pool, hot tub, AC!, Walk to Beach and Hyatt!
• A/C throughout spacious clean comfortable main floor condo with lush garden view
• Sunny Poipu Beach House Near Grand Hyatt, Views, AC, Guest Favorite
• Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai
• Ocean View 3BR at Makahuena | Lanai, Pool, AC
• LUXURY VILLA, 3 Private Suites, Pool/Spa, Gym, Central A/C, Beach
• Spectacular Floor-To-Ceiling Ocean View, Ground Floor For Direct Ocean Access!
• Regency 111 Defines Comfort & Spaciousness. Lovely Furniture & Furnishings
• Large Poipu Kai Condo with Air Conditioning in Perfect Location for Everything!

The average cost for winter rentals in Koloa is $916 per night. Pacificislands has a wide list of great winter places to stay near Koloa that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Koloa that allow you to bring your pet or dog:

• Fully Renovated Oceanfront with Air Cond. Ground Floor Unit with Spacious Lanai!
• Honu He'e Nalu - The Surfing Turtle - Ocean & Beachfront! Stunning Views!
• Kauai Pili Mai by Coldwell Banker Island Vacations
• The Catbird Seat -Closest Vacation Home To Poipu Beach - 100 Ft Away! Pool!

See all pet-friendly vacation rentals in Koloa on Pacificislands

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Koloa to find what works for you.

As of 2026, the data from Pacificislands shows that there are over 1870 private swimming pools or indoor pools accommodations near Koloa along with other great amenities.