Luxury Vacation Rentals 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 9 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Kailua-Kona

Kailua-Kona, Hawaii

Wander Big Island Breeze

Next avail.

Dec 3 - Dec 4

Kailua-Kona, Hawaii

Wander Big Island Cove

Wander Big Island Garden

Next avail.

Dec 20 - Dec 21

Kailua-Kona, Hawaii

Wander Big Island Tides

Next avail.

Dec 6 - Dec 7

Kailua-Kona, Hawaii

Wander Big Island Escape

Next avail.

Dec 24 - Dec 25

Kailua-Kona, Hawaii

Wander Kona Bay Shores

Wander Big Island Bay

Next avail.

Feb 25 - Mar 2

Kailua-Kona, Hawaii

Wander Big Island Lush

Next avail.

Dec 9 - Dec 12

Welcome to Kailua-Kona

Set your stay on the sunny Kona Coast with Wander. Our luxury vacation rentals in Kailua-Kona pair crisp, contemporary design with island ease. Expect ocean-view lanais, private pools, and effortless indoor-outdoor living that brings the breeze inside.

Each home is professionally operated and pristine, with ultra fast WiFi, dedicated workstations, and hotel-grade linens. Enjoy dependable smart tech, gyms or fitness gear where available, and 24/7 concierge support. Photos match reality, so you can settle into a beautiful space for both focus and downtime. Everything you need, nothing you don't.

Destinations near Kailua-Kona

Popular vacation rentals in Kailua-Kona

Wander Kona Bay Shores

Wander Big Island Breeze

Next avail.

Dec 3 - Dec 4

Kailua-Kona, Hawaii

Wander Big Island Garden

Next avail.

Dec 20 - Dec 21

Kailua-Kona, Hawaii

Wander Big Island Escape

Next avail.

Dec 24 - Dec 25

Kailua-Kona, Hawaii

Wander Big Island Bay

Next avail.

Feb 25 - Mar 2

Kailua-Kona, Hawaii

Wander Big Island Cove

Wander Big Island Tides

Next avail.

Dec 6 - Dec 7

Featured vacation rentals in Kailua-Kona

Kailua-Kona, Hawaii

Wander Big Island Escape

Next avail.

Dec 24 - Dec 25

Kailua-Kona, Hawaii

Wander Big Island Garden

Next avail.

Dec 20 - Dec 21

Kailua-Kona, Hawaii

Wander Big Island Cove

Wander Big Island Bay

Wander Big Island Breeze

Next avail.

Dec 3 - Dec 4

Kailua-Kona, Hawaii

Wander Kona Bay Shores

Next avail.

Dec 3 - Dec 4

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Highlights in Kailua-Kona

Discover sunny Kailua-Kona, where historic Hawaiian sites meet world-famous coffee farms and vibrant coral reefs teeming with marine life.

Ali'i Drive

Hulihe'e Palace

Kamakahonu National Historic Landmark

Kahalu'u Beach Park

Magic Sands Beach Park

Kaloko-Honokōhau National Historical Park

Kona Coffee Living History Farm

Kealakekua Bay State Historical Park

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

Kailua-Kona, Hawaii

Wander Big Island Breeze

Next avail.

Dec 3 - Dec 4

Kailua-Kona, Hawaii

Wander Big Island Cove

Wander Big Island Garden

Next avail.

Dec 20 - Dec 21

Kailua-Kona, Hawaii

Wander Big Island Tides

Next avail.

Dec 6 - Dec 7

Kailua-Kona, Hawaii

Wander Big Island Escape

Next avail.

Dec 24 - Dec 25

Kailua-Kona, Hawaii

Wander Kona Bay Shores

Wander Big Island Bay

Next avail.

Feb 25 - Mar 2

Kailua-Kona, Hawaii

Wander Big Island Lush

Next avail.

Dec 9 - Dec 12

View all homes

Most popular amenities for vacation rentals in Kailua-Kona

Outdoor Dining Area (9)

Patio (8)

Beach Umbrellas (1)

Other popular amenities & vacation types in Kailua-Kona

Family vacation rentals 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 of Kailua-Kona

Located on the leeward side of Hawaiʻi Island, Kailua-Kona greets you with warm, dry days, cobalt water, and the rugged backdrop of Hualālai. Lava fields tumble to the shoreline, creating crystal-clear bays perfect for snorkeling, paddling, and sunset sailing. After dark, manta ray encounters at Keauhou are unforgettable.

Up mauka, family-run farms cultivate the world's most famous coffee along the fertile slopes, while historic Alii Drive fronts a lively waterfront. White-sand favorites like Maniniʻowali and Makalawena deliver that luminous, powdery glow, and Kaloko-Honokōhau preserves ancient fishponds and petroglyphs. This is why Wander's luxury vacation rentals in Kailua-Kona are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Kailua-Kona

Why should I book a Wander in Kailua-Kona over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most 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 vacation rentals in Kailua-Kona?

Some of our most popular vacation rentals in Kailua-Kona include Wander Kona Bay, Wander Kona Bay Shores, and Wander Big Island Breeze. 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 vacation rentals does Wander have available in Kailua-Kona?

Wander offers 9 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 vacation rentals in Kailua-Kona?

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

Do Wander’s 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.