Haleiwa Winter Rentals & Holiday Homes
Discover winter rentals Haleiwa - We found 184 exact matches
About Haleiwa Winter Rental on Big Island Hawaii Rental
Planning on a winter vacation in Haleiwa? Discover 184 places to stay in Haleiwa, for those traveling with their family, friends, in groups, or for a wedding retreat.
At Big Island Hawaii Rental, we have a wide range of listings for accommodations in Haleiwa, HI that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. Big Island Hawaii Rental winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Haleiwa winter accommodation starts at US $803, and the most popular properties in Haleiwa are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, Big Island Hawaii Rental will make your winter trip memorable.
Big Island Hawaii Rental offers a great deal for travelers planning on renting a place in Haleiwa, to enjoy these benefits and to book your winter vacation homes, go to Big Island Hawaii Rental filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Haleiwa and unlock even more amazing deals.
Frequently Asked Questions About Haleiwa Winter Rental
What are the top rated Winter Rentals in Haleiwa?
There are a lot of options in Haleiwa. If you plan on staying in the Haleiwa area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Haleiwa:
- Amazing Location & Beach. 200 plus 5-Star Reviews! Hot Tub, AC, 4 Bikes & More!
- Enjoy this Lovely Tropical Paradise!
- 1-Bed, 1-Bath - Walk to Beach.
- Private Tropical Paradise in the Heart of the North Shore - beachfront community
- Hale Laule'a North Shore Oahu Estate Walk to Sunset Beach! 1 booking per 30 days
- Luxury North Shore Beachfront - contact for details HI requires 1 renter/30 days
- Spacious Beachfront 6-bedroom on Breathtaking Sunset Beach
- PERFECT LOCATION BEACH FRONT INQUIRE special discounts reduced rates for october
- FANTASTIC apartment in charming Haleiwa with WiFi, AC beachfront
- North Shore Tropical Hale by Gather | Spacious w/Private Pool & Tropical Ga
How much does it cost to rent a place to stay near Haleiwa in the wintertime?
The average cost for winter rentals in Haleiwa is $803 per night. Bigislandhawaiirental has a wide list of great winter places to stay near Haleiwa that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Haleiwa that allow pets?
Yes, here are the top cottage/chalet rentals in Haleiwa that allow you to bring your pet or dog:
- Sunset Oceanfront Hale Kalea - Beach Cruisers!
- Waimea Bay Luxury Estate Views & Hot Tub
- Aloha Surf Cabin - Private Yard & Entrance!
- Beautiful "Beachfront" House on the Beach at Sunset Beach Paradise on the Beach
See all pet-friendly vacation rentals in Haleiwa on Bigislandhawaiirental
Do you have any winter rentals in Haleiwa that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Haleiwa to find what works for you.
Are there winter accommodations in Haleiwa that have indoor swimming pools?
As of 2026, the data from Bigislandhawaiirental shows that there are over 184 private swimming pools or indoor pools accommodations near Haleiwa along with other great amenities.
