Haleiwa Winter Rentals & Holiday Homes
Discover winter rentals Haleiwa - We found 201 exact matches
When do you want to travel?
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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:
- Amazing Location & Beach. 200 plus 5-Star Reviews! Hot Tub, AC, 4 Bikes & More!
- SUNSET BEACH FRONT LUXURY RENTAL WITH A/C. n72 JET JACUZI SPA COMING NOV/2025
- 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
- Sunset Beach. Relax! C&C LT rqmt. compliant. Fixed rental. Parking on-site.
- Right on the Water, Newly Constructed Home!
- Gorgeous, Spacious, Ideal Family Vacation With 6 Ocean View Bedrooms!
- ON THE SAND! Chuns Reef Beach House - Oceanfront Main House - A/C - Beach Toys
- 1-Bed, 1-Bath - Walk to Beach.
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 $806 per night. Pacificislands 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:
- Beautiful "Beachfront" House on the Beach at Sunset Beach Paradise on the Beach
- Waimea Bay Luxury Estate Views & Hot Tub
- Aloha Surf Cabin - Private Yard & Entrance!
- Sunset Oceanfront Hale Kalea - Beach Cruisers!
See all pet-friendly vacation rentals in Haleiwa on Pacificislands
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 Pacificislands shows that there are over 201 private swimming pools or indoor pools accommodations near Haleiwa along with other great amenities.
