What are the top rated Winter Rentals in Koloa?

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: <a href="/property/stunning-2-bedroom-luxury-cottage-300-feet-from-poipu-beach-park/HA-1213565510" class="class="static-page-link"">Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park</a> <a href="/property/poipu-bay-getaway-poipu-house-saltwater-pool-hot-tub-ac-walk-to-beach-and-hyatt/HA-3214298178" class="class="static-page-link"">Poipu Bay Getaway - Poipu House - Saltwater pool, hot tub, AC!, Walk to Beach and Hyatt!</a> <a href="/property/a-c-throughout-spacious-clean-comfortable-main-floor-condo-with-lush-garden-view/HA-321576524" class="class="static-page-link"">A/C throughout spacious clean comfortable main floor condo with lush garden view</a> <a href="/property/sunny-poipu-beach-house-near-grand-hyatt-views-ac-guest-favorite/HA-321356157" class="class="static-page-link"">Sunny Poipu Beach House Near Grand Hyatt, Views, AC, Guest Favorite</a> <a href="/property/ocean-front-condo-with-ac-watch-sea-turtles-from-our-lanai/HA-321328166" class="class="static-page-link"">Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai</a> <a href="/property/ocean-view-3br-at-makahuena-lanai-pool-ac/HA-3213554256" class="class="static-page-link"">Ocean View 3BR at Makahuena | Lanai, Pool, AC</a> <a href="/property/luxury-villa-3-private-suites-pool-spa-gym-central-a-c-beach/HA-1213722792" class="class="static-page-link"">LUXURY VILLA, 3 Private Suites, Pool/Spa, Gym, Central A/C, Beach</a> <a href="/property/spectacular-floor-to-ceiling-ocean-view-ground-floor-for-direct-ocean-access/HA-321326351" class="class="static-page-link"">Spectacular Floor-To-Ceiling Ocean View, Ground Floor For Direct Ocean Access!</a> <a href="/property/regency-111-defines-comfort-spaciousness-lovely-furniture-furnishings/HA-321879623" class="class="static-page-link"">Regency 111 Defines Comfort &amp; Spaciousness. Lovely Furniture &amp; Furnishings</a> <a href="/property/large-poipu-kai-condo-with-air-conditioning-in-perfect-location-for-everything/HA-3211019310" class="class="static-page-link"">Large Poipu Kai Condo with Air Conditioning in Perfect Location for Everything!</a>

How much does it cost to rent a place to stay near Koloa in the wintertime?

The average cost for winter rentals in Koloa is $905 per night. Bigislandhawaiirental 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.

Do you have any winter rentals in Koloa that are suitable for families?

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.

Are there winter accommodations in Koloa that have indoor swimming pools?

As of 2026, the data from Bigislandhawaiirental shows that there are over 1839 private swimming pools or indoor pools accommodations near Koloa along with other great amenities.

Winter Rentals in Koloa:【 GREAT PRICES 】

Fully Renovated Oceanfront with Air Cond. Ground Floor Unit with Spacious Lanai!

From US $427

10.0 (182 Reviews)

Condo

Fully Renovated Oceanfront with Air Cond. Ground Floor Unit with Spacious Lanai!

Air Conditioner
Parking
TV

Koloa Winter Rentals & Holiday Homes

Discover winter rentals Koloa - We found 1839 exact matches

When do you want to travel?