Hawaii Winter Rentals | Escape the Cold to Tropical Paradise! | Ola Props

As winter draws near and cold weather threatens to descend, many find themselves longing for the warmth of summer. Especially in places where the cold seems to linger even into the beginning of spring, planning a warm-weather getaway can be the perfect way to break up those long winter months. Give yourself something to look forward to and consider Hawaii as your destination this winter! Check out our variety of Hawaii winter rentals today!

Book Our Hawaii Winter Rentals Below

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Relax in Hawaii This Winter

Pack your summer clothes and relax on the beach in Hawaii this winter! Most of our Hawaii snowbird rentals are situated close to the beach, so it’s easy to spend your days lounging in the sun. Whether you’re searching for a luxury condo, a romantic villa for two or a spacious townhouse for the whole family, you will find a variety of square footage options in our winter rental listings. Open-concept floorplans with full kitchens and spacious living rooms, spacious master suites, and an extended outdoor lanai are just a few of the features you will find in our Hawaii winter rentals. Many of our Hawaii snowbird rentals are situated on grounds that offer access to resort-like swimming pools, oceanfront lagoons, hot tubs, fitness centers, tennis courts, golf courses, shopping, dining, and more! It is easy to enjoy all the best in a Hawaii winter when so many amenities are right at your doorstep!

Features of Our Hawaii Winter Rentals

Catch a final glimpse of the ice, cold, and snow in your rearview mirror and welcome vistas filled with blue skies, lush greenery, and the endless turquoise of the ocean in Hawaii. The warmth and beauty that this island offers throughout the winter months will not disappoint. Whether you want to spend the entire winter season basking in the sunshine that Hawaii offers, or you simply want to get away for a time to escape the winter blues, our Hawaii winter rentals will provide a refreshing, relaxing space for bringing dreams of a tropical winter to life.

Leave behind the coats and thick layers in favor of packing your swimwear and favorite warm-weather outfits. Unpack and make yourself at home in the master bedroom of your Hawaii winter rental, where you will find a spacious dresser and closet. Stow away the luggage and embrace this beautiful location as home for the season! Our Hawaii winter rentals are offered in a variety of floorplans, with most offering 1-2 bedrooms. This makes them ideal for couples, small families, or a small group of friends traveling together. Stay rested and ready to embrace each day to the fullest from the comfort of the sleeping areas in these homes. High-quality linens are provided in both the bedrooms and bathrooms.

Especially when staying away from home for a season, you will want to select a vacation rental that access to in-unit amenities such as a full kitchen, washer, and dryer. You will be delightfully surprised at the high-quality kitchens found in these rentals, with spacious countertops, full-sized appliances, and all the cookware and flatware needed to create and enjoy meals in. This will take the burden off the budget and time constraint of eating out for every meal, offering a definite advantage. Not only are the kitchens in these rentals functional, but they also work together within a larger great room space to create a sense of home. Move easily between the kitchen and living room, where you will find a welcoming living space in which to spend your evenings. Relax with a movie enjoyed from the comfortable sofa or enjoy the last rays of sunlight streaming in through the oversized glass doors. Through the glass doors, an outdoor lanai provides yet another space for enjoying relaxing moments soaking up the warmth and beauty of your tropical surroundings.

Hawaii Winter Activities Near Our Hawaii Snowbird Rentals

Arriving in Hawaii during winter means that you’ll be just in time for whale watching season! Beginning in December, these majestic creatures arrive to the warm Hawaiian waters after migrating from Alaska. While you may be able to spot some spouts from the shoreline, the real thrill is getting out on the water to view them up close. Near our Hawaii winter rentals, several boat charters operate out of Ko Olina Marina, offering up the ultimate whale watching experience. Many whale watching tours also include other activities, such as snorkeling, dinner, or sunset viewing. This may very well be one of the most memorable activities you’ll experience while on the island!

Of course, even in winter, there is always the option to hit the beach in Hawaii! Warm weather and warm waters throughout the winter months mean that activities such as swimming, surfing, and boogie boarding are all readily accessible. Winter months offer the best of both worlds, with warm summer sunshine during the day and cool ocean breezes at night that keep things comfortable for relaxing and sleeping. With most of our Hawaii winter rentals situated along the west coast, you will enjoy front-row seats to fiery winter sunsets. Imagine spending the whole day on the beach, lazing in the shade, or getting active with many of the water sports available. Then when evening descends, wrapping up with towels and staying on the beach until the last light of the day fades with brilliant gold and pink splayed across the sky. The creation of cherished memories is inherent in a winter day in Hawaii!

Winter Festivities on Oahu

If your winter trip to Hawaii coincides with Christmas or New Year’s, there are plenty of additional festivities happening around the island to keep you in the holiday spirit. Santa visits, gift markets, parades, lights, and fireworks displays pop up all around the island, offering a variety of opportunities for participating in holiday celebrations. Twinkling palm trees and warm ocean breezes will most definitely make for a memorable holiday spent in the tropics, as will a dazzling fireworks display viewed along the waterfront to close out another great year.

If shopping is in the plans for your Hawaii winter getaway, options abound. Whether you need to pick up holiday gifts or just want to look your best for an evening out, you’ll find everything you need and want with Oahu shopping. When staying in one of our winter rentals near Ko Olina, shopping options are right onsite at Ko Olina Station and the Shops at Ko Olina. The town of Kapolei offers even more options, as do the bustling storefronts of Honolulu and Waikiki.

Brighten up those gray winter days with a trip to the tropical island of Oahu this winter!

Book Your Hawaii Winter Rental

Don’t let the lingering warmth of fall fool you… Those crisp fall days are soon to give way to the gray days of winter, and what better way to pass the lull of winter than with a warm-weather getaway! At Ola Properties, we specialize in vacation rentals situated across the western coast of Oahu, where sunny, summer-like days are perpetual. When you book with us at Ola Properties, you can rest assured that you are working with dedicated experts who are onsite and able to vet each property to ensure the high quality you desire in a Hawaii winter rental. Leave the ice and snow in your review mirror and escape to the beaches of Hawaii this winter! Browse our Hawaii winter rentals here.