What are the top rated Winter Rentals in Kaunakakai?

There are a lot of options in Kaunakakai. If you plan on staying in the Kaunakakai area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Kaunakakai: <a href="/property/oceanfront-tropically-furnished-condo-comfy/HA-321309960" class="class="static-page-link"">Oceanfront-Tropically Furnished Condo-Comfy</a> <a href="/property/oceanfront-top-floor-molokai-condo-lush-east-end-location/HA-3214505781" class="class="static-page-link"">Oceanfront Top Floor Molokai Condo! Lush East End Location!</a> <a href="/property/spectacular-180-degree-oceanfront-view-wavecrest-resort-private-internet/HA-321768228" class="class="static-page-link"">Spectacular, 180 Degree, Oceanfront View! Wavecrest Resort. Private Internet!</a> <a href="/property/2bd-peace-paradise-molokai-1-5-bath-2-lanais-w-oceanview-grandeur-gorgeous/HA-3211923963" class="class="static-page-link"">2BD Peace &amp; Paradise MOLOKAI-1.5 bath/2 LANAIS w/Oceanview-Grandeur &amp; Gorgeous!</a> <a href="/property/amazing-waterfront-condo-with-ocean-views-shared-pool-balcony-grill/HA-3212273966" class="class="static-page-link"">Amazing waterfront condo with ocean views, shared pool, balcony, &amp; grill</a> <a href="/property/pu-u-o-hoku-is-true-to-its-hawaiian-name-which-means-hill-of-stars-surrounded-by-more-than-14-000-ac/HA-3214973572" class="class="static-page-link"">Pu&#39;u O Hoku” is true to its Hawaiian name — which means “Hill of Stars”— surrounded by more than 14,000 acres of protected land, immersed in the transcendent beauty of forest, sky, and ocean. The Ranch is a family-owned biodynamic and organic ranch a</a> <a href="/property/pool-access-ocean-view-molokai-shores-condo/HA-12120123060" class="class="static-page-link"">Pool Access: Ocean-View Molokai Shores Condo!</a> <a href="/property/charming-1st-floor-oceanfront-condo-with-shared-pool-tennis-courts-w-d/HA-3214728939" class="class="static-page-link"">Charming 1st floor oceanfront condo with shared pool, tennis courts &amp; W/D</a> <a href="/property/oceanfront-molokai-shores-condo-w-pool-access/HA-12120123057" class="class="static-page-link"">Oceanfront Molokai Shores Condo w/Pool Access!</a> <a href="/property/wavecrest-2-bdr-beautiful-ocean-view-ground-level-unit-with-washer-dryer/HA-3212699490" class="class="static-page-link"">Wavecrest 2 bdr beautiful ocean view ground level unit with Washer-Dryer.</a>

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

The average cost for winter rentals in Kaunakakai is $658 per night. Pacificislands has a wide list of great winter places to stay near Kaunakakai that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Kaunakakai that allow pets?

Yes, here are the top cottage/chalet rentals in Kaunakakai that allow you to bring your pet or dog: ‘Aloha Kai’ Oceanfront on Molokai, Top Floor, Modern, Peaceful Comfort, Pool Historical lodge at Pu'u O Hoku Ranch! Outdoor pool and farm-to-table meals! Modern Oceanfront W/Lanai and WiFi–Molokai Shores Oceanfront, AC!, king bed, kayaks, pickleball, and beach stuff all included! See all <a href="/all/usa/hawaii/kaunakakai/pet-friendly-rentals" class="class=&#34;static-page-link&#34;">pet-friendly vacation rentals in Kaunakakai</a> on Pacificislands

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

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

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

As of 2026, the data from Pacificislands shows that there are over 49 private swimming pools or indoor pools accommodations near Kaunakakai along with other great amenities.

Winter Rentals in Kaunakakai:【 GREAT PRICES 】

‘Aloha Kai’ Oceanfront on Molokai, Top Floor, Modern, Peaceful Comfort, Pool

From US $206

9.8 (81 Reviews)

Condo

‘Aloha Kai’ Oceanfront on Molokai, Top Floor, Modern, Peaceful Comfort, Pool

Parking
Pool
TV

Kaunakakai Winter Rentals & Holiday Homes

Discover winter rentals Kaunakakai - We found 49 exact matches

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