Luxury Vacation Rentals for Large Groups in Hawaii

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 15 large group vacation rentals – enter your dates for availability.

Top-rated large group vacation rentals in Hawaii

Luxury

Property in Kailua

5 bedrooms•5 baths

New

Luxury

Home in Honolulu

4 bedrooms•4 baths

Home in Koloa

5 bedrooms•5 baths

New

Home in Kailua

5 bedrooms•4.5 baths

New

Luxury

Home in Koloa

5 bedrooms•5.5 baths

Luxury

Home in Koloa

4 bedrooms•5 baths

Luxury

Home in Koloa

6 bedrooms•6.5 baths

Luxury

Home in Koloa

4 bedrooms•4.5 baths

Welcome to your large group retreat in Hawaii

Bring everyone together with Wander’s luxury large-group vacation rentals in Hawaii. Set across Waimea, Koloa, Kailua-Kona, and Princeville, our private homes are designed for connection, comfort, and privacy for every guest.

Spread out with generous living areas, multiple primary suites, flexible sleeping arrangements, and indoor-outdoor spaces that make gathering effortless. Many homes include private pools and hot tubs, outdoor kitchens for grilling, and large dining areas, alongside chef-ready kitchens and stocked essentials for cooking as a team.

Every stay includes hotel-grade amenities, ultra fast WiFi, pristine cleaning, inspiring views, and 24/7 concierge. With consistent quality across all four locations, you can plan with confidence and give the whole group space to relax, work, and celebrate.

Available soon in Hawaii

Iconic

Home in Kailua-Kona

5 bedrooms•6 baths

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Featured large group vacation rentals in Hawaii

Luxury

Property in Kailua

5 bedrooms•5 baths

New

Home in Koloa

5 bedrooms•5 baths

New

Luxury

Home in Koloa

5 bedrooms•5.5 baths

Luxury

Home in Koloa

4 bedrooms•5 baths

Luxury

Home in Koloa

6 bedrooms•6.5 baths

Luxury

Home in Koloa

4 bedrooms•4.5 baths

Luxury

Home in Waimea

5 bedrooms•5 baths

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Iconic

Home in Kailua-Kona

5 bedrooms•6 baths

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Highlights in Hawaii

Gather your group for an unforgettable island adventure, with epic volcanoes, stunning beaches, and shared cultural experiences awaiting you.

Pearl Harbor National Memorial

Hawaiʻi Volcanoes National Park

Haleakalā National Park

Waikiki Beach

Nā Pali Coast State Wilderness Park

Polynesian Cultural Center

Road to Hāna

Waimea Canyon State 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 Hawaii

Luxury

Property in Kailua

5 bedrooms•5 baths

New

Luxury

Home in Honolulu

4 bedrooms•4 baths

Home in Koloa

5 bedrooms•5 baths

New

Home in Kailua

5 bedrooms•4.5 baths

New

Luxury

Home in Koloa

5 bedrooms•5.5 baths

Luxury

Home in Koloa

4 bedrooms•5 baths

Luxury

Home in Koloa

6 bedrooms•6.5 baths

Luxury

Home in Koloa

4 bedrooms•4.5 baths

View all homes

Most popular amenities for large group vacation rentals in Hawaii

Exercise equipment (2)

Beach essentials (3)

More popular large group destinations in Hawaii

Large group vacation rentals in Waimea

Large group vacation rentals in Koloa

Large group vacation rentals in Kailua-Kona

Large group vacation rentals in Princeville

Other popular amenities & vacation types in Hawaii

Family vacation rentals in Hawaii

Beachfront vacation rentals in Hawaii

Hot tub vacation rentals in Hawaii

Private pool vacation rentals in Hawaii

Discover more large groups activities in Hawaii

Hawaii blends dramatic natural beauty with an easygoing rhythm you feel from the first sunrise. The Island of Hawaii offers volcanic vistas and vast skies, while Kauai brings emerald valleys, rugged cliffs, and serene stretches of beach.

Trade winds keep days comfortable and evenings perfect for lingering outside. Coffee country, botanical richness, and star-filled nights set a memorable backdrop for time together, whether you are exploring coastal viewpoints or simply savoring the slow pace.

For reunions, team offsites, and milestone getaways, the islands make every moment feel special. This is why Wander’s luxury large-group vacation rentals in Hawaii are the perfect choice for work or leisure.

FAQs: Vacation Rentals in Hawaii

Why should I book a Wander in Hawaii over other large group vacation rentals?

Wander offers a level of consistency and quality you won’t find with most large group vacation rentals.

Every home in Hawaii 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 large group vacation rentals in Hawaii?

Some of our most popular large group vacation rentals in Hawaii include Kailua Beachside, Wailupe Seaside 4 Bedroom, and JC Surf House. 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 large group vacation rentals does Wander have available in Hawaii?

Wander offers 15 large group vacation rentals in Hawaii, 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 large group vacation rentals in Hawaii?

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

Do Wander’s large group vacation rentals in Hawaii have WiFi access?

Yes. Every Wander home in Hawaii 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.