Luxury Vacation Rentals for Families in Kailua-Kona

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 44 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Kailua-Kona

Home in Kailua Kona property photo 1

Home in Kailua Kona

3 bedrooms•3.5 baths
New
Home in Kailua Kona property photo 1

Home in Kailua Kona

3 bedrooms•3.5 baths
3,368 US dollars for 3 nights•
New

~$295 less than other sites

Condo in Kailua Kona property photo 1

Condo in Kailua Kona

3 bedrooms•3.5 baths
7,096 US dollars for 5 nights•
New

~$625 less than other sites

Home in Kailua-Kona property photo 1

Home in Kailua-Kona

3 bedrooms•2.5 baths
1,968 US dollars for 3 nights•
New

~$170 less than other sites

Property in Kailua Kona property photo 1
Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths
15,223 US dollars for 5 nights•
New

~$1,350 less than other sites

Home in Kailua Kona property photo 1
Luxury

Home in Kailua Kona

4 bedrooms•3.5 baths
6,640 US dollars for 5 nights•
New

~$585 less than other sites

Property in Kailua Kona property photo 1
Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths
15,223 US dollars for 5 nights•
New

~$1,350 less than other sites

Home in Kailua Kona property photo 1

Home in Kailua Kona

3 bedrooms•3 baths
2,342 US dollars for 3 nights•

~$205 less than other sites

Welcome to family adventures in Kailua-Kona

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

Home in Kailua Kona property photo 1

Home in Kailua Kona

3 bedrooms•3.5 baths
3,368 US dollars for 3 nights•
New

~$295 less than other sites

Home in Kailua-Kona property photo 1

Home in Kailua-Kona

3 bedrooms•2.5 baths
1,968 US dollars for 3 nights•
New

~$170 less than other sites

Home in Kailua Kona property photo 1

Home in Kailua Kona

3 bedrooms•3 baths
2,342 US dollars for 3 nights•

~$205 less than other sites

Property in Kailua Kona property photo 1
Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths
9,127 US dollars for 3 nights•

~$810 less than other sites

Home in Kailua Kona property photo 1
Luxury

Home in Kailua Kona

5 bedrooms•6 baths
5,757 US dollars for 3 nights•
New

~$505 less than other sites

Condo in Kailua Kona property photo 1

Condo in Kailua Kona

3 bedrooms•3 baths
1,189 US dollars for 3 nights•
New

~$105 less than other sites

Condo in Kailua Kona property photo 1

Condo in Kailua Kona

2 bedrooms•2 baths
1,229 US dollars for 3 nights•
New

~$105 less than other sites

Home in Kailua Kona property photo 1

Home in Kailua Kona

3 bedrooms•2.5 baths
1,611 US dollars for 3 nights•
New

~$140 less than other sites

Featured family vacation rentals in Kailua-Kona

Property in Kailua Kona property photo 1

Property in Kailua Kona

3 bedrooms•3 baths
6,403 US dollars for 5 nights•
New

~$565 less than other sites

Property in Kailua Kona property photo 1

Property in Kailua Kona

3 bedrooms•3 baths
6,693 US dollars for 5 nights•
New

~$595 less than other sites

Property in Kailua-Kona property photo 1
Luxury

Property in Kailua-Kona

3 bedrooms•3 baths
6,694 US dollars for 5 nights•
New

~$595 less than other sites

Property in Kailua Kona property photo 1
Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths
13,881 US dollars for 5 nights•
New

~$1,230 less than other sites

Property in Kailua Kona property photo 1

Property in Kailua Kona

3 bedrooms•3 baths
6,575 US dollars for 5 nights•
New

~$585 less than other sites

Home in Kailua Kona property photo 1
Luxury

Home in Kailua Kona

3 bedrooms•3.5 baths
1,760 US dollars for 2 nights•
New

~$155 less than other sites

Home in Kailua-Kona property photo 1
Luxury

Home in Kailua-Kona

4 bedrooms•3.5 baths
10,794 US dollars for 5 nights•

~$960 less than other sites

Property in Kailua Kona property photo 1
Luxury

Property in Kailua Kona

3 bedrooms•3.5 baths
New

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 property photo 1

Home in Kailua Kona

3 bedrooms•3.5 baths
New
Home in Kailua Kona property photo 1

Home in Kailua Kona

3 bedrooms•3.5 baths
3,368 US dollars for 3 nights•
New

~$295 less than other sites

Condo in Kailua Kona property photo 1

Condo in Kailua Kona

3 bedrooms•3.5 baths
7,096 US dollars for 5 nights•
New

~$625 less than other sites

Home in Kailua-Kona property photo 1

Home in Kailua-Kona

3 bedrooms•2.5 baths
1,968 US dollars for 3 nights•
New

~$170 less than other sites

Property in Kailua Kona property photo 1
Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths
15,223 US dollars for 5 nights•
New

~$1,350 less than other sites

Home in Kailua Kona property photo 1
Luxury

Home in Kailua Kona

4 bedrooms•3.5 baths
6,640 US dollars for 5 nights•
New

~$585 less than other sites

Property in Kailua Kona property photo 1
Luxury

Property in Kailua Kona

4 bedrooms•4.5 baths
15,223 US dollars for 5 nights•
New

~$1,350 less than other sites

Home in Kailua Kona property photo 1

Home in Kailua Kona

3 bedrooms•3 baths
2,342 US dollars for 3 nights•

~$205 less than other sites

View all homes

Most popular amenities for family vacation rentals in Kailua-Kona

Ocean view (34)
Outdoor pool (39)
Jacuzzi (32)
Hot tub (32)
Heated pool (15)
Beachfront (5)
Waterfront (13)
Gym (20)
Sauna (1)
Outdoor shower (2)
Sound system (15)
Beach access (5)
Bbq area (40)
Beach essentials (2)
Balcony (35)
Beach umbrellas (1)

More popular family destinations near Kailua-Kona

Family vacation rentals in Waimea
Family vacation rentals in Kihei
Family vacation rentals in Koloa
Family vacation rentals in Princeville

Other popular amenities & vacation types in Kailua-Kona

Large group vacation rentals in Kailua-Kona
Beachfront vacation rentals in Kailua-Kona
Hot tub vacation rentals in Kailua-Kona
Private pool vacation rentals in Kailua-Kona
Discover more family fun in Kailua-Kona

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, Blue Hawaii, and 3BD Fairways Villa (104A) at Hualalai Resort. 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 44 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.