Waimanalo Winter Rentals & Holiday Homes

There are a lot of options in Waimanalo. If you plan on staying in the Waimanalo area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Waimanalo:

• Waimānalo Beach Cottages 2 min walk to the beach!
• Hale Waimanalo Beachfront Home
• Family fun or just relax and say aaah! Max 6, 5 minute walk to Beach !
• Tropical Waimanalo Home
• Remodeled Beachfront Home w/Ocean views covered Lanai & AC - 15 min from Kailua

The average cost for winter rentals in Waimanalo is $1,109 per night. Pacificislands has a wide list of great winter places to stay near Waimanalo that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Waimanalo that allow you to bring your pet or dog:

• Hale Pohaku, Waimanalo - Lic.#1990/NUC-1689
• Beachfront Waimanalo Home with Pergola and Ocean Views
• Just a couple houses away from the nicest beach on the island.
• House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more

See all pet-friendly vacation rentals in Waimanalo on Pacificislands

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

As of 2026, the data from Pacificislands shows that there are over 29 private swimming pools or indoor pools accommodations near Waimanalo along with other great amenities.