Luxury Vacation Rentals for Families 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 family vacation rentals – enter your dates for availability.
Welcome to family adventures in Kailua
Bring the whole crew to Wander's luxury family vacation rentals in Kailua, where five-star polish meets the comfort of a private home. Each residence is selected for style, space, and coastal serenity, so you can settle in the moment you arrive.
Think generous living areas, multiple king suites and playful bunk rooms, chef-ready kitchens, and fenced lawns made for downtime. Many homes feature private pools, ultrafast WiFi, dedicated workstations, and smart tech for easy routines. With pristine housekeeping, in-home laundry, baby gear by request, and 24/7 concierge support, family travel feels effortless from morning cartoons to lights-out.
Highlights in Kailua
Discover family fun on world-renowned beaches with calm, turquoise waters perfect for kids and a laid-back, welcoming town vibe.
Kailua Beach Park
Lanikai Beach
Lanikai Pillbox Hike (Kaiwa Ridge Trail)
Kayak to the Mokulua Islands
Kailua Farmers' Market
Ulupo Heiau State Historic Site
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 family vacation rentals in Kailua
More popular family destinations near Kailua
Other popular amenities & vacation types in Kailua
Discover more family fun in Kailua
On Oahu’s windward coast, Kailua pairs spectacular scenery with an easygoing pace. Powder-soft sand and glassy water curve along Kailua Bay, with steady trade winds and a reef that keeps the shoreline calm for family beach days.
Sunrise paints the Mokulua islets in pastel light, while afternoons invite coastal bike rides, tide pool wanders, or the famed pillbox hike for sweeping views. The town’s walkable center brings small-batch shops and a friendly, beach-forward rhythm, and Honolulu sits just across the Pali for quick access to culture and nightlife.
This harmony of nature, convenience, and calm is why Wander’s luxury family vacation rentals in Kailua are the perfect choice, whether you're traveling for work or leisure.
FAQs: Vacation Rentals in Kailua
Why should I book a Wander in Kailua over other family vacation rentals?
Wander offers a level of consistency and quality you won’t find with most family 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 family vacation rentals in Kailua?
Some of our most popular family 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 family vacation rentals does Wander have available in Kailua?
Wander offers 2 family 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 family vacation rentals in Kailua?
You can check-in to Wander family vacation rentals in Kailua after 4.00pm and check-out before 10.00am.
Do Wander’s family 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.