Our research is editorially independent but we may earn a commission for purchases made through our links.

Top Oahu Vacation Rentals for Large Groups

Where do we even start when it comes to Oahu, Hawaii? A top spot for large group vacations, no matter whether that’s your extended family or all of your friends (or a little of both!), Oahu practically guarantees an incredible trip from the second you arrive in Honolulu. Maybe you’ll spend your time here surfing the waves or exploring the wonderful reefs, complete with snorkel or scuba diving gear. Perhaps you’re looking to enjoy a cocktail or two on Waikiki beach and soak up the sunshine. Or you could spend your time here exploring the island’s rich history and diverse terrain. When it comes to Oahu, there are so many fun things to do. Looking for the perfect spot to call home while you’re staying here? Read on for all of the best vacation rentals for large groups.

Kailua Beachfront Villa Kailua Beachfront Villa
Credit: Kailua Beachfront Villa by Airbnb.com

Kailua Beachfront Villa

This gorgeous pale yellow home seems to reflect the Hawaiian sunlight on a daily basis, just adding to your vacation glow. A dreamy Oahu rental with eight bedrooms and space for up to 14 guests, it’s ideal for family vacations, reunions, or anniversary celebrations where everyone can stretch out and relax. The best part about this Airbnb? Its incredible setting, with easy access for strolling along its six miles of white sand beach. Surf, swim, and snorkel every day or take a dip in the villa’s private pool. There are also two golf courses within ten minutes of the house.

Waialua Beachfront Home with 5 Bedrooms and 4 Baths Waialua Beachfront Home with 5 Bedrooms and 4 Baths
Credit: Waialua Beachfront Home with 5 Bedrooms and 4 Baths by Airbnb.com

Waialua Beachfront Home with 5 Bedrooms and 4 Baths

This Waialua beachfront home is one of the best places to stay on Oahu’s North Shore. Its stunning location means you’ll start each morning with unobstructed ocean views and the occasional marine animal swimming by. A picturesque family vacation rental with all of the trimmings, it’s a place you’ll check into and never want to leave. Wake up to the panoramic ocean magic on your own secluded estate just steps from the sandy beach and spend your days here chilling in the open-concept kitchen and living area with more of those stunning ocean views. Whether you’re planning on surfing, paddling, snorkeling, hiking, golfing, or watching whales breach, you’ll find it all here.

Designer Villa with Panoramic Ocean Views Designer Villa with Panoramic Ocean Views
Credit: Designer Villa with Panoramic Ocean Views by Airbnb.com

Designer Villa with Panoramic Ocean Views

With 4,500 square feet of space to relax and panoramic views of the grand mountains and the peaceful ocean as a backdrop, it’s hard to beat this magical villa. There’s space for a whole 16 guests at this spot, making it one of the largest private vacation rentals around, with endless space to enjoy all of the delights of Oahu. While it’s a large villa anyway, it’s one that appears even bigger thanks to its oversized windows and airy design. And, with a range of beds and amenities to suit guests of all ages, it’s well-equipped for visits with family members or friends.

Travel Deals

7-Day Tahiti Cruise w/ All-Inclusive Upgrade


Create the Ultimate Trip to Anchorage this Year


The Yucatan | Adults-Only All-Incl. Playa del Carmen

$95+ pp/pn

70% Off 2nd Guest | 5-Nt Riviera Maya Cruise w/ Tips


9-Day Best of Spain: Madrid to Barcelona Guided Tour


Air & 9-Day Wonders of Croatia Tour | Save $400


7-Day Introduction to Ireland Guided Tour w/ VIP Access


7-Day Exploration of Medieval Umbria | Save 50%


Air & 9-Day Islands of Croatia Tour | Save $400


Aer Lingus R/T Flights to Over 25 Top Europe Cities


Air & 11-Day Iconic Australia Vacation w/ 4-Star Hotels


8-Day Culinary Expedition in Morocco | 40% Off


8-Day Spain Culinary Adventure | 30% Off


Explore Anchorage's Local Flavor: Dining, Pubs, more


9-Day Private Chauffeur Ireland Vacation