Waikoloa Winter Rentals & Holiday Homes

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

• Updated 2 Bedroom Condo Walk to the Beach & Shops.
• Relax at our quiet remodeled end unit #601, tropical views and 95 golf!
• Steps to Beach Family Friendly in Private Setting Lots of Grass to Play On
• 🌺PARADISE AWAITS IN J4🌺’26 Hilton Pool Pass,⭐️Golf Discounts,BBQ, Beach Gear⭐️
• SPECIAL PRICE THANKSGIVING November 23-30 nightly 525 ! Welcome the whales!
• SPECTACULAR ! Ground Floor Condo Sleeps 5 Golf ,Tennis ,.Gym Pool, Jacuzzi
• DIRECT OCEAN FRONT/GROUND FLR, PANORAMIC DRS, 2 BED/2 BATH EN SUITES, DISCOUNTS
• Fairway Villas-2 Bed & 2 Bath
• Luxurious Oceanfront Escape Awaits – Stunning Views & Top-Floor Waikoloa Living!
• Salt Water Pool⛱️ Ocean View 🌊 Hualalai View🌋 140+ 5 Star Reviews 🌟

The average cost for winter rentals in Waikoloa is $591 per night. Bigislandhawaiirental has a wide list of great winter places to stay near Waikoloa 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 Waikoloa that allow you to bring your pet or dog:

• Waikoloa Beach Resort Hali'i Kai 7H Ocean View Private Club, Pool, Tennis/PB
• Hilton Pool Pass Included, Kolea - Luxe 2BR Villa Steps to Beach Pool HotTub Gym
• Villa Sea Renity
• Spectacular Beach Resort Condo with Amazing Views - Spacious Unit F-206

See all pet-friendly vacation rentals in Waikoloa on Bigislandhawaiirental

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

As of 2026, the data from Bigislandhawaiirental shows that there are over 1421 private swimming pools or indoor pools accommodations near Waikoloa along with other great amenities.