Winter is an ideal time to head to the Hawaiian Islands, especially if you’re trying to escape the cold. Though temperatures dip slightly during a Hawaiian winter, it still remains plenty warm to spend relaxing days on the beach and enjoy the many water- and land-based activities the island has to offer. With the scent of plumeria and ginger in the air, the rustle of the wind in the palms, and the gentle crash of the sea, the scents and sounds of a Hawaii winter fill your senses. Turn this winter into a tropical one when you spend it on the shores of a white sand beach in Hawaii. Our winter villas in Hawaii provide the perfect home base for your tropical hideaway!

Book Our Winter Rentals in Hawaii Below!


Luxurious Living in Hawaii

Enjoy unbeatable proximity to the ocean from our winter rentals in Hawaii. These accommodations offer all the best in both features and amenities, giving travelers the luxurious vacation they deserve. Whether your travel time is planned for a few days, weeks, or even the whole winter season, our Hawaii beach villa winter rentals have you covered. These well-equipped accommodations have all that is needed for enjoying daily life. Gather around the dining table in the morning and start the day off together with breakfast, easily prepared from the full kitchen. Ideal if you’ll be staying throughout the winter holidays, a full kitchen ensures you can still include all your favorite holiday recipes. Wrap up the most important meal of the day and sip your morning dose of caffeine before you’ve even left the privacy of your rental. These luxury villas are graced with an open floorplan, so the kitchen, dining area, and living room flow easily together, creating a seamless space for daily living or for enjoying a special holiday tradition. Most of our Hawaii beach villa winter rentals are situated along the island’s west coast, putting you in a spectacular setting to enjoy a fiery winter sunset. The sun sets only about one hour earlier during the winter months, leaving plenty of time to enjoy daytime winter activities and setting just in time for a spectacular light display during dinner. Grab dinner at one of the nearby Oahu restaurants or enjoy a quiet meal in with a view, sipping a cool beverage on the private lanai as the sun shines its last rays on the day. Beach vacations are meant for sharing with the ones you love. Our Hawaii beach villas can easily accommodate your loved ones, wrapping them in luxury. Most of our villas range from one to four bedrooms, offering a variety of square footage for your winter getaway. With comfortable furnishings and tropical touches throughout, these luxury accommodations offer the ideal mix of style and comfort. Spend this winter soaking up the sea, sand, and sun from a luxurious winter rental in Hawaii!

Winter Activities in Hawaii

Many of our Hawaii beach villa winter rentals are located on properties with onsite amenities, offering entertainment options for winter days when you don’t want to venture far. Lounge by the sparkling swimming pool, enjoy a beachfront family barbeque, soothe away the stress of daily life in the hot tub, or make it a day at the beach just steps from your door. Many of our winter villas in Hawaii offer beach gear such as chairs, umbrellas, and coolers, making it even easier to prepare for your winter day at the beach! While all of the water activities that normally make Hawaii such as great destination are still easily enjoyed during winter months, winter also brings with it a few additional possibilities that make the trip extra special. Winter in Hawaii coincides with whale watching season, providing the breathtaking opportunity to observe humpback whales in their natural habitat. The whale watching season ranges from December to April, and there are several tour operators that offer excursions to view these majestic creatures up close, often treating you to dolphin sightings along the way. Winter in Hawaii is also known for the giant waves that come to the north shore, bringing in big wave competitions and surfers from around the world. While you won’t want to try your own hand at surfing on the north shore during this time, watching locals and pros brave the huge waves is an amazing sight to see. If you’ll be celebrating the winter holidays on Oahu, the island comes alive with festivities that make this time extra special. Holiday markets pop up around the island, offering quality goods handmade in Hawaii perfect for giving or treating yourself. Holiday cruises and luaus offer a special new way to celebrate the holidays, while decorations and events around town still retain an element of tradition.

A Trusted Name in Hawaii Vacations

At Ola Properties, we offer upscale vacation rentals throughout West Oahu, Hawaii. Come experience the first-rate service that makes our company a vacation favorite!