Some destinations deserve a longer stay, and a little room for things to go off schedule. Hawaii is one of them.
A Thanksgiving dinner that runs late because the family stories came out. A beach morning run that turns into a day of tidepooling. Cousins who won’t leave the pool area, while adults chat over a breakfast that turns into brunch.
Nobody is checking the time because, for once, there is nowhere else everyone wants to be.
Hawaii lends itself to this kind of stay. And with a private home, there’s space for your whole group to enjoy it the ways they want.
The Maimon Group’s new Hawaii collection spans Oahu, the Big Island and Kauai, bringing families a fresh setting for Thanksgiving, the winter holidays and spring break, with the freedom to stay longer than a weekend and let the days take shape on their own.
3 Islands, 3 Ways to Settle In
We’ve curated our Hawaii collection across three islands that offer distinct experiences, fit for any personality or lifestyle. Our goal was range.
Oahu: Beach Mornings, City Within Reach
Oahu bridges the energy of Honolulu with the relaxed pace of its coastal communities, making it possible to spend mornings by the ocean and evenings at a dinner reservation downtown.
In Diamond Head, Kahala, and Portlock, oceanfront estates sit within established residential neighborhoods, with the city's restaurants and airport close by. Venturing out of the house won’t seem like a hassle, rather an easy outing requiring minimal coordination.
On the windward side, Kailua offers beach homes in a quieter coastal setting, similar to a remote spa retreat, where the day's biggest decision might be whether to stay on the sand a little longer.
For families who want ample time by the water without losing access to city life, Oahu offers a great balance.
Explore Honolulu vacation rentals or homes in Kailua-Kona when comparing destinations across the collection.
The Big Island: Resort Communities, Private Coastlines
The Big Island gives you room to think beyond the usual holiday itinerary. The landscape shifts from volcanic terrain to expansive coastlines, and the days can follow suit.
Our collection includes homes within the Hualalai, Mauna Lani and Mauna Kea resort communities, as well as private oceanfront properties along the Kona and Kohala coasts.
A home within this type of community combines the setting and amenities of resort living with the privacy of a residence of your own.
Along the coast, private estates offer space to gather and enjoy Pacific views without leaving the house, or embark on nearby nature excursions at your own pace.
The right choice depends on how your group prefers spending its days.
Explore Kailua-Kona vacation homes, or discover properties in Kamuela further inland.
Kauai: Fewer Plans, Longer Morning
Kauai’s South Shore suits families who want fewer plans and more quality time together.
There’s time for the beach, a meal that lasts hours, and an afternoon for exploring the island or staying close to the house. The pleasure is in having options without feeling obliged to use them all, and a private home that gives everyone somewhere to come back to.
And for a group whose calendars are usually crowded with school, work, and commitments, that freedom and slow pace isn’t only the point, but also the highlight.
Explore the Hawaii collection to discover Kauai vacation rentals in Koloa, and find a setting that suits your group, as well as your plans.
Thanksgiving in Hawaii: One Table, Everyone Together
Thanksgiving is one of those holidays when the guest list can span 3 generations, but the logistics can quickly take over. Grandparents want time to relax. Children have energy to spare. Someone has strong opinions about the cooking. And somehow, everyone needs to be fed at roughly the same time.
A private home gives the holiday a natural center: the kitchen. Family recipes make the journey, new dishes find their way onto the menu, and nobody has to surrender the entire afternoon to a restaurant reservation. There's a dining table where everyone can sit together, and separate bedrooms to recharge and rest once the day winds down.
The moments around the meal matter, too. Someone heads to the beach while preparations are underway. The children return hungry and conversation carries long after the plates are cleared. The holiday still has its familiar traditions, but the setting gives everyone more freedom in how they spend it.
Holiday weeks attract strong demand, particularly for larger homes that accommodate multiple generations. If you're considering Thanksgiving in Hawaii, inquire early to explore available properties and dates.
Explore our full Hawaii collection and inquire about your Thanksgiving stay.
Spring Break in Hawaii: Together, With Freedom Every Hour
Spring break plans typically involve more than a solo traveler.
Bring multiple families or groups on one trip and you'll quickly discover that everyone has a slightly different idea of a perfect day. Some are ready to head out early. Others prefer a slower morning. The children want to play, adults want quiet, and friend groups want the freedom to venture as they please.
A larger private home makes those differences easy to accommodate.
Depending on the property, homes in the collection sleep a dozen or more guests, with separate bedroom suites for privacy, and shared spaces for meals together, catching up on lost time. Families can spend the day side by side without having to follow the same schedule from morning to night.
That flexibility makes a difference over a full spring break. One afternoon might call for an outing and another is better spent at home. The island helps set the tone.
Oahu suits groups who want beaches alongside city conveniences. The Big Island offers expansive coastlines and resort communities, while Kauai lends is better for slower, nature-focused weeks.
If you're considering a mainland destination, Maimon Group also has options in Palm Springs and the surrounding desert. Our spring break guide to private luxury residences explores mainland alternatives for families planning a group getaway.
Los Angeles, Miami, and Now Hawaii
The Maimon Group’s story began in the hills above Los Angeles, where the collection first took shape along the California coast.
In 2026, the collection expanded east to Miami, bringing a new energy and a different kind of coastal experience. Now, with Hawaii joining the collection, the story continues west into the Pacific.
From California and Florida to the Hawaiian islands, our commitment to exceptional property quality, privacy and guest experience hasn’t wavered.
Three destinations, three distinct coastlines, and three very different ways to get away.
Los Angeles is known for its hillside estates, ocean views, and effortless connection to the best of Southern California. It was here that the collection established the character and standards it would become known for.
Miami brings a lively cultural calendar, with Art Basel Miami Beach drawing international attention to the city’s art scene in December. Our Art Basel Miami Beach luxury guide offers insight into planning a stay around Miami’s creative side.
Hawaii brings a different proposition: close-knit island communities, expansive coastlines and a setting that invites a longer stay. Across the 3 coasts, families have more ways to approach Thanksgiving getaways, school breaks, and extended time away.
Explore Los Angeles properties and Miami vacation homes alongside the Hawaii collection to compare what’s available for your next trip.
Planning Your Hawaii Stay
A few decisions make a meaningful difference when narrowing down your search:
- Start with your dates. Thanksgiving and winter holiday weeks attract strong demand, particularly for larger properties. Inquire early to compare availability.
- Think beyond a week. Some properties are offered as monthly stays, giving you the option to spend a whole winter in Hawaii rather than a single week.
- Choose the setting that suits your group. Consider Honolulu's established neighborhoods, a Big Island resort community or the slower pace of Kauai's South Shore.
- Ask about resort requirements. Homes within resort communities follow applicable rules, which may affect amenities and access. Our team can explain the relevant requirements before you book.
Your dates, group size and preferred setting help determine which properties are the best fit. Starting with those details gives you a clear way to compare the collection.
Find Your Home in Hawaii
Hawaii is now part of The Maimon Group collection, joining Los Angeles, Palm Springs, San Diego, and Miami, opening up new possibilities for families who want to spend more than a few days together on the islands.
Whether you're gathering 3 generations for Thanksgiving, bringing several groups together for spring break, or considering a longer winter stay, the appeal is the same: room for everyone to enjoy the trip in their own way, with plenty of reasons to come back together.
Explore the Hawaii collection or connect with our team to inquire about dates and find a setting for your stay.
