What are the top rated Winter Rentals in Wailuku?

There are a lot of options in Wailuku. If you plan on staying in the Wailuku area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Wailuku: <a href="/property/amazing-oceanfront-condo-tropical-luxury-great-value-2-br-2-bath/HA-121976505" class="class="static-page-link"">Amazing Oceanfront Condo, Tropical Luxury, Great Value, 2 BR, 2 Bath</a> <a href="/property/beautifully-upgraded-beachfront-ground-floor-dream-vacation-118/HA-321718120" class="class="static-page-link"">Beautifully Upgraded, Beachfront, Ground Floor.Dream Vacation! #118</a> <a href="/property/in-the-center-of-it-all/HA-3213796078" class="class="static-page-link"">In the center of it all!</a> <a href="/property/beautiful-luxury-oceanfront-condo-grnd-floor-great-view-a-c-wi-fi-bdrm-view/HA-1213731387" class="class="static-page-link"">Beautiful Luxury Oceanfront Condo-Grnd Floor, Great View, A/C, Wi-Fi, BDRM View</a> <a href="/property/beautiful-beachfront-condo-oceanview-free-wi-fi-legal-rental/HA-32158258" class="class="static-page-link"">Beautiful BeachFront condo Oceanview Free wi-fi. Legal Rental</a> <a href="/property/today-tonight-turtles-turtles-turtles-n/HA-3211316102" class="class="static-page-link"">Today.Tonight.Turtles.Turtles.Turtles!n</a> <a href="/property/gorgeous-oceanfront-complex-on-maui-kanai-a-nalu-with-free-parking/HA-321382792" class="class="static-page-link"">Gorgeous Oceanfront Complex on Maui! Kanai A Nalu, with FREE parking!</a> <a href="/property/impeccably-remodeled-ground-floor-oceanfront-50-from-the-sea-turtle-sancuary/HA-3211485275" class="class="static-page-link"">IMPECCABLY REMODELED GROUND FLOOR OCEANFRONT - 50&#39; FROM THE SEA TURTLE SANCUARY!</a> <a href="/property/welcome-to-our-luxury-one-bedroom-eco-friendly-honeymoon-suite-condo/HA-32160550" class="class="static-page-link"">Welcome to our luxury one bedroom Eco-Friendly Honeymoon Suite condo.</a> <a href="/property/sea-la-vie-secluded-oceanfront-condo-magical-sunrise-romantic-honeymoon-getaway/HA-1219251645" class="class="static-page-link"">Sea La Vie Secluded Oceanfront condo, Magical Sunrise romantic honeymoon Getaway</a>

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

The average cost for winter rentals in Wailuku is $460 per night. Bigislandhawaiirental has a wide list of great winter places to stay near Wailuku that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

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

Yes, here are the top cottage/chalet rentals in Wailuku that allow you to bring your pet or dog: Romantic Beachfront Getaway Spectacular luxury , modern oceanfront condo Maalaea-Kihei ,Maui Maalaea Banyans by Coldwell Banker Island Vacations Oceanfront 3rd Floor Unit at Maalaea Kai Complex See all <a href="/all/usa/hawaii/wailuku/pet-friendly-rentals" class="class=&#34;static-page-link&#34;">pet-friendly vacation rentals in Wailuku</a> on Bigislandhawaiirental

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

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

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

As of 2026, the data from Bigislandhawaiirental shows that there are over 236 private swimming pools or indoor pools accommodations near Wailuku along with other great amenities.

Winter Rentals in Wailuku:【 GREAT PRICES 】

From US $479

9.6 (39 Reviews)

Condo

Romantic Beachfront Getaway

Air Conditioner
Parking
Pool

Wailuku Winter Rentals & Holiday Homes

Discover winter rentals Wailuku - We found 236 exact matches

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