Luxury Vacation Rentals for Large Groups in Kailua
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 2 large group vacation rentals – enter your dates for availability.
Welcome to your large group retreat in Kailua
Planning a friends-and-family escape? Our luxury vacation rentals for large groups in Kailua bring everyone under one stylish roof with room to breathe and connect. Expect sunlit living spaces, island-chic interiors, and thoughtful layouts that keep conversation flowing from kitchen to lanai.
Each home features multiple primary suites for privacy, bunk or flex rooms for extras, chef-grade kitchens built for group cooking, and expansive outdoor areas for poolside lounging. Hotel-grade amenities meet private-home comfort, including ultra fast WiFi, dedicated workspaces, fitness areas, and 24/7 concierge service. Every Wander looks exactly like the photos and is pristinely cleaned, so coordinating a big group stays effortless.
Highlights in Kailua
Gather your group for unforgettable adventures on world-class beaches, scenic trails, and turquoise waters perfect for shared experiences.
Kailua Beach Park
Lanikai Beach
Lanikai Pillbox Hike (Ka'iwa Ridge Trail)
Mokulua Islands
Kaneohe Bay Sandbar
Ho'omaluhia Botanical Garden
Waimanalo Beach
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
Most popular amenities for large group vacation rentals in Kailua
More popular large group destinations near Kailua
Other popular amenities & vacation types in Kailua
Discover more large groups activities in Kailua
On Oahu’s windward side, Kailua pairs powder-soft beaches with relaxed elegance. Mornings glow over the Mokulua islets, trade winds keep the air crisp, and calm, reef-sheltered waters invite paddling, sailing, or a leisurely swim.
Beyond the shoreline, ridge trails deliver postcard views, while the town keeps a refined, beach-town rhythm with artisanal shops and open-air cafes. Days move at an easy pace, whether you are chasing sunrise, browsing the weekly market, or lingering over fresh island flavors. This is why Wander’s luxury vacation rentals in Kailua are the perfect choice, whether you are traveling for work or leisure.
FAQs: Vacation Rentals in Kailua
Why should I book a Wander in Kailua over other large group vacation rentals?
Wander offers a level of consistency and quality you won’t find with most large group vacation rentals.
Every home in Kailua delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?
Which are Wander’s most popular large group vacation rentals in Kailua?
Some of our most popular large group vacation rentals in Kailua include Wander Kailua Beachside, Wander Kailua Villa, and Wander Kailua Villa. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.
How many different large group vacation rentals does Wander have available in Kailua?
Wander offers 2 large group vacation rentals in Kailua, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.
What time is check-in and check-out at Wander’s large group vacation rentals in Kailua?
You can check-in to Wander large group vacation rentals in Kailua after 4.00pm and check-out before 10.00am.
Do Wander’s large group vacation rentals in Kailua have WiFi access?
Yes. Every Wander home in Kailua has ultra fast, reliable WiFi so you can stay connected throughout your stay.
What is Wander’s cancellation policy?
You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.