Haleiwa Winter Rentals & Holiday Homes
Discover winter rentals Haleiwa - We found 208 exact matches
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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:
- Enjoy this Lovely Tropical Paradise!
- Walk to Pipeline Rocky Point and Waimea
- Haleiwa oceanfront inquiry special rate options
- ON THE SAND! Chuns Reef Beach House - Oceanfront Studio - A/C - Beach Toys
- Right on the Water, Newly Constructed Home!
- Sunset Beach. Relax! C&C LT rqmt. compliant. Fixed rental. Parking on-site.
- Gorgeous, Spacious, Ideal Family Vacation With 6 Ocean View Bedrooms!
- 1-Bed, 1-Bath - Walk to Beach.
- Beautiful North Shore Home at Ke Iki Beach. 30-day minimum bookings.
- Private Tropical Paradise in the Heart of the North Shore - beachfront community
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 $793 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 208 private swimming pools or indoor pools accommodations near Haleiwa along with other great amenities.
