What are the top rated Winter Rentals in Kihei?

There are a lot of options in Kihei. If you plan on staying in the Kihei area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Kihei: <a href="/property/10-7-day-discount-kihei-1br-top-floor-split-ac-clean-free-wifi-turtles/HA-321589925" class="class="static-page-link"">10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!</a> <a href="/property/dazzling-ocean-view-modern-whole-house-ac-upgraded-glass-for-a-quiet-setting/HA-321454560" class="class="static-page-link"">Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting</a> <a href="/property/10-7-day-discount-kihei-studio-split-ac-clean-free-wifi-turtles/HA-321812407" class="class="static-page-link"">10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!</a> <a href="/property/stunning-views-from-only-double-lanai-penthouse-unit/HA-321698750" class="class="static-page-link"">Stunning Views from only double lanai Penthouse unit.</a> <a href="/property/5-star-reviews-all-remodeled-split-air-quiet-building-5-ocean-garden-view/HA-321600863" class="class="static-page-link"">5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!</a> <a href="/property/hotel-zoned-oceanfront-comfort-on-a-budget-2bed-2ba-condo-new-listing/HA-3214722797" class="class="static-page-link"">Hotel-zoned Oceanfront Comfort on a Budget 2bed 2ba condo - NEW LISTING!</a> <a href="/property/bingo-kkn-s-trophy-unit-deluxe-renovation-central-split-a-c-ground-floor/HA-321600143" class="class="static-page-link"">Bingo! KKN&#39;s TROPHY Unit! Deluxe Renovation, Central Split A/C &amp; Ground Floor.</a> <a href="/property/maui-paradise-beach-front-condo-w-ac-stunning-ocean-sunset-views/HA-321810572" class="class="static-page-link"">Maui Paradise – BEACH FRONT condo w/AC, Stunning Ocean &amp; Sunset Views!</a> <a href="/property/200-5-star-reviews-premier-front-row-sunset-views-1-of-largest-spacious-condos/HA-321448823" class="class="static-page-link"">200+ 5 Star Reviews, Premier Front-Row Sunset Views,1 Of Largest Spacious Condos</a> <a href="/property/hale-ili-ili-a-panoramic-oceanfront-unit-steps-from-charley-young-a-c/HA-321611274" class="class="static-page-link"">Hale Ili Ili #A, Panoramic Oceanfront Unit, Steps from Charley Young, A/C</a>

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

The average cost for winter rentals in Kihei is $611 per night. Pacificislands has a wide list of great winter places to stay near Kihei that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

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

Yes, here are the top cottage/chalet rentals in Kihei that allow you to bring your pet or dog: Ocean, mountain, pool views. Best location at The Banyan. Across from Kam2 beach Kihei Maui Island Style, Beach, Pool, Restaurants Kihei Gardens Estates Modern & Polished Oceanfront Vistas Ocean Front Penthouse Best View Most Amenities Fully Stocked Feels like home See all <a href="/all/usa/hawaii/kihei/pet-friendly-rentals" class="class=&#34;static-page-link&#34;">pet-friendly vacation rentals in Kihei</a> on Pacificislands

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

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

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

As of 2026, the data from Pacificislands shows that there are over 4904 private swimming pools or indoor pools accommodations near Kihei along with other great amenities.

Winter Rentals in Kihei:【 GREAT PRICES 】

Ocean, mountain, pool views. Best location at The Banyan. Across from Kam2 beach

From US $305

10.0 (219 Reviews)

Condo

Ocean, mountain, pool views. Best location at The Banyan. Across from Kam2 beach

Air Conditioner
Parking
Pool

Kihei Winter Rentals & Holiday Homes

Discover winter rentals Kihei - We found 4904 exact matches

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