Luxury Vacation Rentals for Families in Kailua-Kona

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 34 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Kailua-Kona

Home in Kailua Kona

3 bedrooms•3.5 baths

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Home in Kailua Kona

3 bedrooms•3 baths

Home in Kailua Kona

3 bedrooms•2.5 baths

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Property in Kailua Kona

3 bedrooms•3.5 baths

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Home in Kailua Kona

3 bedrooms•3.5 baths

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Condo in Kailua Kona

3 bedrooms•3.5 baths

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Luxury

Property in Kailua Kona

4 bedrooms•4 baths

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Home in Kailua-Kona

3 bedrooms•2.5 baths

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Welcome to family adventures in Kailua-Kona

Make Kailua-Kona your family’s happy place with Wander. Our luxury family vacation rentals in Kailua-Kona blend hotel polish with the comfort and privacy of a beautifully designed home, so parents can relax and kids have room to spread out.

Enjoy hotel-grade amenities, ultra fast WiFi, fully equipped kitchens, and in-home laundry, all backed by pristine cleaning and 24/7 concierge support. Flexible sleeping arrangements and generous common areas make it easy to settle into a smooth routine from day one.

Choose a setting that fits your crew, from sunlit great rooms to breezy outdoor spaces for quality time together. This is family travel, elevated.

Available soon in Kailua-Kona

Apartment in Kailua-Kona

2 bedrooms•2 baths

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Iconic

Home in Kailua-Kona

5 bedrooms•6 baths

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Featured family vacation rentals in Kailua-Kona

Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths

Property in Kailua Kona

3 bedrooms•3 baths

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Property in Kailua Kona

3 bedrooms•3 baths

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Luxury

Home in Kailua Kona

4 bedrooms•4 baths

Luxury

Property in Kailua Kona

3 bedrooms•3.5 baths

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Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths

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Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths

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Property in Kailua Kona

3 bedrooms•3.5 baths

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Highlights in Kailua-Kona

Discover family fun in sunny Kailua-Kona, from snorkeling with sea turtles to exploring royal palaces and unique seahorse farms.

Kahaluʻu Bay

Magic Sands Beach Park

Ocean Rider Seahorse Farm

Huliheʻe Palace

Kamakahonu National Historic Landmark

Manta Ray Night Snorkel at Keauhou Bay

Kona Coffee Living History Farm

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Kailua-Kona

Home in Kailua Kona

3 bedrooms•3.5 baths

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Home in Kailua Kona

3 bedrooms•3 baths

Home in Kailua Kona

3 bedrooms•2.5 baths

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Property in Kailua Kona

3 bedrooms•3.5 baths

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Home in Kailua Kona

3 bedrooms•3.5 baths

New

Condo in Kailua Kona

3 bedrooms•3.5 baths

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Luxury

Property in Kailua Kona

4 bedrooms•4 baths

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Home in Kailua-Kona

3 bedrooms•2.5 baths

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View all homes

Most popular amenities for family vacation rentals in Kailua-Kona

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Discover more family fun in Kailua-Kona

On the leeward coast of Hawai‘i Island, Kailua-Kona pairs abundant sunshine with calm, crystal-clear water. Gentle mornings on protected bays, golden-hour strolls along Alii Drive, and big-sky nights create a rhythm that feels effortless for all ages.

The area layers natural beauty with rich Hawaiian history. Visit Hulihe‘e Palace in Historic Kailua Village, wander lava-born shorelines, and taste world-renowned Kona coffee at upland farms. Just offshore, manta rays glide at sunset for an unforgettable family memory.

For a trip that balances relaxation and discovery, Wander’s luxury family vacation rentals in Kailua-Kona are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Kailua-Kona

Why should I book a Wander in Kailua-Kona 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-Kona 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-Kona?

Some of our most popular family vacation rentals in Kailua-Kona include Piko Nani, Manukai Hale, and Kona Blue Vacations Holua Kai. 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-Kona?

Wander offers 34 family vacation rentals in Kailua-Kona, 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-Kona?

You can check-in to Wander family vacation rentals in Kailua-Kona after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Kailua-Kona have WiFi access?

Yes. Every Wander home in Kailua-Kona 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.