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:

• Hale Mauka Volcano Village Hawaii Volcanoes National Park
• Romantic & Breathtaking Oceanfront Kauai Condo
• Volcano Rainforest Estate & Lodge; 5 miles to National Park; Hot Tub; 3 BR/3 BA 11-3203 Huakai Street, Volcano, HI, 96785, US
• Hawaiian Charm.Just Steps From The Ocean.On Kauai's Sunny W Side * TVNC4216
• Oceanfront Home w/Private Pool. USA Military & Fire - Repeat Guest Discount!
• 'Aloha!' Perfect Location Near Beach & Turtle Bay Resort, File # 1990/NUC- 1964
• HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
• 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
• Private, ocean front home with private pool, Amazing place!
• Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park

The average cost for winter rentals in Hawaii is $800 per night. Thiscityknows 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:

• Ocean, mountain, pool views. Best location at The Banyan. Across from Kam2 beach
• Lahaina Oceanfront Estate-Main House
• Holualoa Inn
• Oceanfront Condo, 5G Wi-Fi, King Bed, Hot Tub/Pool, Free Parking

See all pet-friendly vacation rentals in Hawaii on Thiscityknows

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 Thiscityknows shows that there are over 30364 private swimming pools or indoor pools accommodations near Hawaii along with other great amenities.