Luxury Vacation Rentals 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 3 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Kailua

Luxury

Property in Kailua

5 bedrooms•5 baths

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Home in Kailua

5 bedrooms•4.5 baths

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Home in Kailua

5 bedrooms•5.5 baths

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Welcome to Kailua

Explore our collection of luxury vacation rentals in Kailua, where Wander pairs island calm with hotel-grade polish. Every home is professionally operated and exactly as pictured, so you can arrive confident and unwind instantly.

Choose from light-filled beachside retreats and ocean-view residences designed for both downtime and deep focus. Expect private pools or hot tubs, outdoor showers and lanais, chef-ready kitchens, plush bedding, and advanced smart home features. With ultra fast WiFi, dedicated workspaces, pristine cleaning, and 24/7 concierge service, your stay blends resort-level comfort with the privacy of a modern villa.

Destinations near Kailua

Featured vacation rentals in Kailua

Luxury

Property in Kailua

5 bedrooms•5 baths

New

Iconic

Home in Kailua

5 bedrooms•5.5 baths

New

All homes in Kailua

Luxury

Property in Kailua

5 bedrooms•5 baths

New

Home in Kailua

5 bedrooms•4.5 baths

New

Iconic

Home in Kailua

5 bedrooms•5.5 baths

New

View all homes

Highlights in Kailua

Discover pristine white-sand beaches, scenic coastal hikes, and a charming beach town atmosphere on Oahu's stunning windward coast.

Kailua Beach Park

Lanikai Beach

Lanikai Pillbox Hike (Ka'iwa Ridge Trail)

Mokulua Islands

Kailua Town

Waimanalo Beach

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.

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.

Most popular amenities for vacation rentals in Kailua

Other popular amenities & vacation types in Kailua

Private pool vacation rentals in Kailua

Large group vacation rentals in Kailua

Family vacation rentals in Kailua

Discover more of Kailua

On Oahu’s windward shore, Kailua pairs shimmering, reef-sheltered waters with a relaxed coastal pace. Sunrise paints Kailua Bay and the Mokulua islets in soft pastels, while the Koʻolau peaks frame miles of fine sand at Kailua and Lanikai Beaches.

Steady tradewinds invite paddling or sailing across the lagoon-blue shallows, and the Lanikai Pillbox trail rewards with sweeping island panoramas. The town brings a friendly, upscale vibe with independent shops and weekly markets, all without the crowds of Waikiki.

With natural beauty, calm energy, and effortless access to Oahu highlights, 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 vacation rentals?

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

Some of our most popular vacation rentals in Kailua include Kailua Beachside, Villa Hui Hou, and Kailua Beach Escape. 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?

Wander offers 3 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 vacation rentals in Kailua?

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

Do Wander’s 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.