Amazing Hawaii Vacation Rentals For Your Winter Escape

Say “aloha” to spending winter hiking and bird-watching in paradise. Homes & Villas by Marriott International offers several vacation rentals in the tropical paradise of Hawaii. And although winter — or hoolio, as its called in Hawaii — is the rainy season on the islands, it’s the most popular time to visit. Perhaps that’s because the average temperature at sea level is 78° Fahrenheit, which is much better than we can say for the weather on the mainland during January and February! From the Garden Isle of Kauai to the Valley Isle of Maui, we’ve rounded up the best vacation rentals in Hawaii to escape to this winter.

Big Island

Aptly dubbed the “Big Island,” as it is the largest island in the chain, the Island of Hawaii is a topographical wonder. Visitors can stroll green sand beaches, climb black volcanic boulders, view active lava flows, lose themselves in lush tropical forests, and explore majestic mountain ranges. Here are some great places to stay on the Big Island.

Homes & Villas by Marriott International

One-Bed, Two-Bath Villa With Yoga Studio

Prana is a unique a-frame villa tucked away on a lush property full of Balinese-style architecture called Ramashala in Pahoa, HI. The first floor is a yoga studio exclusively for guest use, while the living quarters are upstairs. With two California king beds, the one-bedroom, two-bath vacation rental can sleep up to four guests.

A covered balcony offers a peaceful place to enjoy your morning coffee. There’s a grill and picnic table on the covered patio where you can dine al fresco. Do note that this rental does not have air conditioning or TVs — a nice break for some, but something to consider.

Just a couple hundred yards away, you’ll find Kehena Beach, one of the world’s only black sand nude beaches. Keep an eye out for spinner dolphins, turtles, and whales. Other nearby attractions include Lava Tree State Monument, natural steam vents, and Hawai’i Volcanoes National Park.

Hawaii vacation rental with pool
Homes & Villas by Marriott International

Three-Bed, Three-Bath House With Pool

Situated along the sun-drenched Kohala Coast on the western side of the Big Island is the private, quiet community of KaMilo within the world-famous Mauna Lani Resort. Views of majestic mountains, a golf course, and a glimpse of the ocean surround this luxurious home.

Great for groups, this two-level, three-bedroom, three-bathroom home can accommodate up to 10 guests. Its master bedroom has a king-sized bed and has a walkout to the pool. The second bedroom has two full-sized beds, while the main-floor master has a queen-sized bed. There’s also a sleeper sofa in the family room. The hosts have thought of everything — even family essentials like a portable crib, high chair, baby monitors, and bed safety rails.

A large, sliding glass wall of windows opens up over 22-feet to one of the three lanais. This vacation rental home features a private pool as well as beach gear and bicycles. Enjoy access to Mauna Lani Resort’s private beach club and take advantage of the pools, hot tubs, recreation center, and more. Seven challenging golf courses lie within seven miles of this villa. You can even rent a golf cart to use during your stay.

Napua Restaurant is just a couple of miles away. A supermarket, coffee shops, eateries, boutiques, and more can be found a few minutes away at The Shops at Mauna Lani. Beach 69, Hapuna Beach, and Kauna’oa Beach (aka Mauna Kea Beach) and a few more of Hawaii’s most spectacular beaches are all just a short drive away.

View of ocean from Hawaii condo lanai
Homes & Villas by Marriott International

Two-Bed, Two-Bath Oceanview Condo

Hawaii is known for its breathtaking sunsets, and the wraparound lanai at this Oceanview Hideaway is the perfect place to watch the sun go down over the ocean. This spacious two-bedroom, two-bathroom condo can sleep up to six guests. Offering direct access to the lanai as well as ocean views, the primary suite has a California king bed. The guest room has a king-sized bed and there’s a queen sleeper sofa, too. Located on the top floor, this unit has central air-conditioning as well as an in-unit washer/dryer.

Part of the Kumulani vacation rental community, this condo is conveniently located by Mauna Kea Resort. For a $75 daily fee, you can take advantage of resort amenities, including two beautiful beaches, heated pools, hot tubs, two world-class golf courses, oceanside tennis courts, watersports lessons and rentals, fitness/yoga classes, a spa, and more. There are also shops and restaurants onsite.

Otherwise, there are more shopping and dining options and groceries available 7.5 miles away at The Shops at Mauna Lani. About 8.5 miles away, you’ll find even more shops, restaurants, and entertainment at Queen’s Marketplace.


With its forested mountains and fertile fields, it’s easy to see how Kauai earned its nickname, the “Garden Island.” But Hawaii’s oldest island is more than a lush landscape surrounded by a deep blue ocean. Waterfalls cascade over volcanic cliffs, creating rainbows that dance in the spray. Make your way to Waimea Town on the west coast to be treated to some of the most breathtaking gold, tangerine, and crimson sunsets you’ll ever witness. Lounge beneath coconut palms on the East Shore, or explore the romantic getaway’s string of seaside towns.

From helicoptering through emerald valleys and zip-lining through treetops to hiking to gushing waterfalls and zigzagging around imposing cliffs, Kauai is an amazing place for adventure. Here are some of the best vacation rentals in Kauai for an adventurous winter escape.

Tropical back porch of Kauai condo
Homes & Villas by Marriott International

Two-Bed, Two-Bath Condo

Take in lush mountain views from the lanai of this two-bedroom, two-bath condo. It is part of Princeville’s Pali Ke Kua resort, just up the road from Hanalei Bay. One king-sized bed and one queen-sized bed can sleep up to four guests. The ground-level unit opens out to an expansive green lawn, complete with tropical foliage. A shared pool and hot tub are just steps away. Pali Ke Kua also features its own paved path to Hideaway Beach.

View of ocean from Kauai condo
Homes & Villas by Marriott International

Two-Bed, Two-Bath Oceanfront Condo

This oceanfront escape on Kauai’s North Shore offers panoramic views of the water. At over 2,000-square-feet, the two-bedroom unit sleeps four. Its main bedroom comes with a luxurious ensuite bath, which features a Japanese soaking tub and an open shower room. Enjoy meals outside on the lanai. A telescope is provided so you can look for whales off the coast.

Part of the Puu Poa condo complex, this vacation stay includes access to a shared heated pool, tennis courts, and grills. A private trail leads to Hideaway Beach. Although it’s just a five-minute hike to the secluded sandy shore, there is a long stair path down from the bluff, which can be difficult for those with mobility issues. There’s also a two-mile walking path just outside the condo, which allows guests to explore the North Shore on foot.

Stroll next door to the five-star Princeville Hotel for breakfast or enjoy an elegant dinner overlooking Hanalei Bay at one of its award-winning restaurants. There’s also a world-class spa! Groceries can be found nearby at the Princeville Shopping Center. Nearby attractions include the world-famous Hanalei Bay (15-minute drive) and the Makai Golf Club. Activities include horseback riding on the beach, hiking to the beautiful Kalihiwai Falls, and snorkeling.

Hawaii vacation rental house interior
Homes & Villas by Marriott International

Four Bed, Four Bath Home

Dubbed the “Blue Hawaii House,” this four-bedroom, four-bathroom home features an enclosed lanai, wine fridge, and private hot tub. Are you in, or what? Tucked away on a quiet cul-de-sac, this magnificent home was custom-built by a contractor as his own personal residence, using the finest flooring, fixtures, and molding. A large, covered, screened-in lanai on the first floor can be accessed from the master bedroom. Soak your worries away in the master ensuite jacuzzi tub. There are three bedrooms upstairs — two with queen-sized beds and one with two twins. One guestroom comes with its own screened-in lanai. On the first floor, two futons in the den offer more places to crash.

A luxurious kitchen includes an instant hot water dispenser, gas cooktop, pot filler, and double ovens. There’s also a laundry room. Instead of A/C, it has an eco-friendly Island Cooling system that uses turbine fans.

This home’s oversized backyard has a shower built against a wall of lava rock and a grill under a covered shelter. Beyond the backyard lies a walkway that runs along the perimeter of a large park. Past the park is the public library as well as the Princeville Shopping Mall, where you can find restaurants, a grocery store, and convenience stores just a few minutes from the house. It’s also just a 10-minute walk to the pathway that leads to Anini Beach.


Known as the Valley Isle, Maui is the most visited of the Hawaiian Islands. From the deep blues of the ocean to the stark splendor of Haleakala’s volcano summit, it is easily one of the most stunning places to explore on Earth. Sweet scents of hibiscus and orchid flowers growing wild along the roadside fill the air of this lush, tropical locale. It is also home to such hidden gems as Molokini Crater, which offers some of the best snorkeling in North America. Here are some of the vacation rentals in Maui that Homes & Villas by Marriott International has to offer.

View of ocean from Hawaii condo
Homes & Villas by Marriott International

One-Bed, One-Bath Oceanview Condo

Wake up to views of the ocean and enjoy your coffee on the lanai to the soundtrack of waves. Located in the West Maui village of Kahana, this oceanview condo is conveniently positioned between the Kaanapali and Kapalua beach resorts. This cozy one-bedroom condo has a pull-out couch for extra guests and a washer and dryer. The resort features a heated pool in addition to beach access.

There are several places to eat close by, as well as a small market, coffee shop, brewery, and more. Shop for souvenirs in Lahaina, which is just a 10-minute drive away. Explore the island by bus, or hop a plane at the Kapalua airport to check out a neighboring island.

View of pool and ocean from Hawaii condo
Homes & Villas by Marriott International

Two-Bed, Two-Bath Oceanfront Condo

Tucked away in Kahana on West Maui’s coastline at the Hololani Resort, this oceanfront condo offers stunning sunset views, easy beach access, and a pool. This two-bedroom, two-bath unit can sleep up to six, with a queen bed in both bedrooms and a pull-out couch in the living room.

The Hololani Resort is surrounded by shops and restaurants, and Kapalua to the north and Ka’anapali to the south offer more variety. The sandy beach at Pohaku Park lies less than half a mile away. There’s no shortage of things to do. Explore Lahaina Town’s Front Street, hike coastal trails, and tee off at nearby courses.

Oceanfront villa vacation rentla from Homes & Villas by Marriott International
Homes & Villas by Marriott International

One-Bed, One-Bath Oceanfront Villa

Situated just steps away from the ocean, this two-level condo is part of Kapalua Bay Villas within the Kapalua Resort. It has only one bedroom, which features a king-sized bed that walks out to a private lanai.

If you get sick of the sand, you can always take a dip in one of the resort’s three swimming pools. A complimentary shuttle shuffles guests around Kapalua Resort’s golf courses, tennis courts, fitness center, shops, restaurants, and world-class spa. Since it is in one of Hawaii’s largest nature preserves, there are walking and hiking paths. Several bays and beaches, such as DT Flemming and Kapalua Bay, offer a place to snorkel, surf, or relax.

Browse the full inventory of available vacation rentals in Hawaii here!

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