Hawaii Winter Rentals & Holiday Homes

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

• Luxury Ocean Villa 217 at Turtle Bay! Ocean Front!
• Stunning Corner Villa, Ocean Views From Every Bed
• SALE June-Aug! Upgraded BeachFront Ocean View 3BR 2.5BA Villa 1734 sq.ft Floor 7
• SPECIAL PRICE THANKSGIVING November 23-30 nightly 525 ! Welcome the whales!
• 5-star. Rave reviews. Stunning lanai. Ocean & mountain views. Newly refurnished
• SPRING REDUCED! Villa 104 Ocean View Turtle Bay
• Luxury Golf Villa, Parking Lot Level Entrance, Best Location,Value, and View.
• Kolea - Stay with Us and Save! the Best Rates in Kolea!
• Luxury accommodations, discounted golf and beautiful sunsets year round.
• Oceanview Mauna Kea Luxury Villa - Private Pool & Spa - In-home Chefs Available

The average cost for winter rentals in Hawaii is $1,325 per night. Luxurysicilyvilla has a wide list of great winter places to stay near Hawaii 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 Hawaii that allow you to bring your pet or dog:

• Affordable 3 Bedroom Family Vacation Villa on the 9th Floor/Ocean View
• Kapalua Golf Villas 15P3-4
• Waikoloa Beach S C3 2 Bedroom Villa by RedAwning
• Beautiful Beach Villa in Oceanfront Resort

See all pet-friendly vacation rentals in Hawaii on Luxurysicilyvilla

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

As of 2026, the data from Luxurysicilyvilla shows that there are over 1294 private swimming pools or indoor pools accommodations near Hawaii along with other great amenities.