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 28 large group vacation rentals – enter your dates for availability.
Hanalei, Hawaii
Wander Kauai Drift
Next avail.
Dec 12 - Dec 14
510
Princeville, Hawaii
Wander Kauai Paradise
Next avail.
Dec 12 - Dec 14
410
Princeville, Hawaii
Wander Kauai Retreat
Next avail.
Dec 15 - Dec 16
410
Waimea, Hawaii
Wander Big Island Falls
Next avail.
Dec 3 - Dec 4
510
Koloa, Hawaii
Wander Kauai Surf
Next avail.
Dec 3 - Dec 6
510
Waimea, Hawaii
Wander Big Island Estate
Next avail.
Dec 8 - Dec 10
410
Waimea, Hawaii
Wander Kamuela Bluffs
Next avail.
Dec 3 - Dec 6
410
Waimea, Hawaii
Wander Kamuela Vista
Next avail.
Dec 4 - Dec 5
510
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.
Kihei, Hawaii
Wander Maui Meadows
Next avail.
Mar 1 - Mar 6
410
4.8
Kailua-Kona, Hawaii
Wander Kona Bay Shores
Next avail.
Dec 3 - Dec 4
512
Waikoloa, Hawaii
Wander Waikōloa Beach
Next avail.
Feb 7 - Feb 15
516
5
Hanalei, Hawaii
Wander Kauai Drift
Next avail.
Dec 12 - Dec 14
510
Koloa, Hawaii
Wander Kauai Shores
Next avail.
Dec 3 - Dec 5
514
Koloa, Hawaii
Wander Kauai Oasis
Next avail.
Dec 16 - Dec 19
622
Koloa, Hawaii
Wander Kauai Sea
Next avail.
Jan 31 - Feb 10
411
Koloa, Hawaii
Wander Kauai Panorama
Next avail.
Dec 3 - Dec 6
615
Koloa, Hawaii
Wander Kauai Surf
Next avail.
Dec 3 - Dec 6
510
Hanalei, Hawaii
Wander Kauai Drift
Next avail.
Dec 12 - Dec 14
510
Koloa, Hawaii
Wander Kauai Pacific
Next avail.
Dec 11 - Dec 17
412
Kailua-Kona, Hawaii
Wander Big Island Cove
Next avail.
Jan 6 - Jan 11
414
Koloa, Hawaii
Wander Kauai Modern
Next avail.
Jan 24 - Jan 27
410
Waimea, Hawaii
Wander Big Island Retreat
Next avail.
Dec 11 - Dec 14
512
Waimea, Hawaii
Wander Big Island Estate
Next avail.
Dec 8 - Dec 10
410
Waimea, Hawaii
Wander Big Island Falls
Next avail.
Dec 3 - Dec 4
510
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.
All homes in Hawaii
Hanalei, Hawaii
Wander Kauai Drift
Next avail.
Dec 12 - Dec 14
510
Princeville, Hawaii
Wander Kauai Paradise
Next avail.
Dec 12 - Dec 14
410
Princeville, Hawaii
Wander Kauai Retreat
Next avail.
Dec 15 - Dec 16
410
Waimea, Hawaii
Wander Big Island Falls
Next avail.
Dec 3 - Dec 4
510
Koloa, Hawaii
Wander Kauai Surf
Next avail.
Dec 3 - Dec 6
510
Waimea, Hawaii
Wander Big Island Estate
Next avail.
Dec 8 - Dec 10
410
Waimea, Hawaii
Wander Kamuela Bluffs
Next avail.
Dec 3 - Dec 6
410
Waimea, Hawaii
Wander Kamuela Vista
Next avail.
Dec 4 - Dec 5
510
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.