Best Vacation Rentals Homes on Hilton Head for Big Groups

Planning a group trip to Hilton Head Island? Whether you’re reuniting with extended family, celebrating a milestone birthday, hosting a friends’ retreat, or organizing a multi-family vacation, finding the right rental home can make or break your experience. Fortunately, Hilton Head offers an incredible variety of large, well-appointed vacation properties designed with groups in mind—think expansive living areas, resort-style amenities, and plenty of beds for everyone.

In this roundup, we’ve handpicked some of the best vacation rental homes on Hilton Head for big groups. Each one offers a unique blend of comfort, convenience, and style—perfect for making lasting memories with the people who matter most. From oceanfront estates to private homes with pools and entertainment spaces, these rentals are equipped to handle your whole crew in luxury and ease.

Let’s dive in and explore the ultimate group-friendly getaways Hilton Head has to offer.

15 Flamingo Street – Hilton Head Island, SC

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Spacious, Stylish, and Just Steps from the Sand — Perfect for Multigenerational Gatherings

15 Flamingo Street is an upscale coastal sanctuary comprising 6 bedrooms, 5 full baths, and 2 half baths across nearly 5,000 sq ft. Designed with large groups in mind, the layout features four king suites—including one with a private balcony overlooking the ocean—a double‑bed room, and a bunk room, accommodating up to 18 guests comfortably. Elegant interiors and high-end finishes blend seamlessly with family-focused flexibility, offering smart‑lock entry, an elevator, central air, high‑speed Wi‑Fi, TVs in every bedroom, laundry facilities, and parking for six vehicles.

The heart of the home is an open‑concept living space featuring a chef’s kitchen with stainless steel appliances, a gas range, and ample prep space. Multiple gathering zones—including three living areas, two dining spaces, and a screened porch—provide flexibility for shared meals, quiet moments, or group socializing. For entertainment, the adjacent game room and a garage equipped with ping‑pong and foosball tables ensure guests stay engaged long after the sun sets, while an elevator makes the home accessible and convenient for all ages.

Outside, the property is a resort‑style escape: just 180 ft (about 40 yards) from the beach, the outdoor area includes a private heated pool (optional fee), hot tub, covered dining area with outdoor TV, gas grill, and an outdoor shower—ideal for alfresco meals or relaxing after the waves. Located within half a mile of Coligny Plaza’s shops and restaurants, this home delivers both serene coastal privacy and easy access to Hilton Head’s top attractions—making it a standout choice for family reunions, group retreats, or celebratory vacations where space, comfort, and location matter most.

Address: 15 Flamingo Street, North Forest Beach, Hilton Head Island, SC, 29928
Website: Beachside Gateway

2 Roadrunner – Hilton Head Island, SC

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Spacious, Well‑Equipped 6‑Bedroom Retreat with Pool, Spa & Easy Beach Access

Situated in the serene North Forest Beach neighborhood, 2 Roadrunner is a striking 6‑bedroom, 4.5‑bathroom home that accommodates up to 17 guests across its 3,150 sq ft footprint and two floors. The main floor brings family and friends together with dual living rooms and a central gourmet kitchen that flows into an elegant dining area with a table seating ten. With a king-bedded primary suite on the first floor and five more bedrooms upstairs—including three king rooms and two bunk rooms—each guest enjoys comfort and privacy. The home also features an elevator, central air conditioning, keyless entry, and a well-stocked kitchen with extras like dual coffee makers and mini‑fridges for convenience.

Outdoors, you’ll find a private pool and spa surrounded by a landscaped, fenced deck with lounge seating, an outdoor TV, and a covered porch—ideal for relaxation after a day at the beach, which is only about 300 ft away. The garage and driveway accommodate four cars and double as a game room, stocked with ping‑pong, foosball, and air‑hockey for group entertainment. Beach carts, bikes, and beach gear are provided, ensuring families and multi‑generational groups have everything they need for a seamless stay.

With glowing reviews praising the thoughtful, full‑service setup—“incredibly well‑stocked,” “listing is spot on,” and “worth every penny”—this property checks all the boxes for group comfort, convenience, and fun. Just a short drive or bike ride from Coligny Plaza and neighboring shops, restaurants, and biking trails, 2 Roadrunner delivers a tranquil, upscale escape with superb access to Hilton Head’s most vibrant spots.

Address: 2 Roadrunner St, North Forest Beach, Hilton Head Island, SC, 29928
Website: Beachside Getaway

67 Plantation Dr. – Hilton Head Island, SC

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6 Bedrooms, Private Pool, and Lush Golf Views in the Heart of Sea Pines

67 Plantation Dr is a beautifully renovated 6‑bedroom, 4.5‑bath retreat that sleeps up to 15 guests across approximately 3,670 sq ft of thoughtfully designed space. The main floor hosts four luxurious bedrooms including the expansive master suite with a king bed, daybed trundle, and spa-like bath, while upstairs an in-law suite above the garage offers two additional bedrooms, a living room with sleeper sofa, and its own full kitchen—ideal for families needing both togetherness and privacy.

The open-concept living area features large windows framing views of the 8th green and 9th tee of Harbour Town Golf Links, alongside a modern kitchen, dining area, and cozy family room with a 65″ smart TV and exposed beam ceilings. Outdoors, the private pool—measuring approximately 30×17 ft and available for heating—ushers you to a spacious deck overlooking the golf course and lagoon, complete with multiple seating zones for sunbathing or alfresco dining.

Just a short walk from Harbour Town and serviced by the Sea Pines trolley, this property blends resort-style amenities with accessible location—beach, golf, dining, and shopping are all close by. Equipped with Wi‑Fi, washer/dryer, parking for four vehicles, and updated furnishings throughout, 67 Plantation Dr delivers a peaceful, upscale base for multi-generational gatherings, golf outings, or family reunions—where space, comfort, and convenience come together beautifully. Let me know when you’re ready for the next property!

Address: 67 Plantation Drive, Sea Pines, Hilton Head Island, SC, 29928
Website: Beachside Getaway

49 Mooring Buoy – Hilton Head Island, SC

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Spacious Palmetto Dunes Retreat with Private Pool, Spa, and Prime Coastal Access

49 Mooring Buoy is an impressive 6-bedroom, 7-bath home spanning over 5,300 sq ft, located in the desirable Palmetto Dunes area. Ideal for large families or group retreats, this property sleeps up to 12 guests and features two master suites, panoramic views of the 17th hole of the Robert Trent Jones Golf Course, and serene lagoon vistas. Upon entry, guests are greeted by an expansive living room framed by large windows with direct glimpses of the pool deck, creating a bright, inviting atmosphere.

This residence offers a seamless blend of indoor and outdoor living. Inside, the layout includes a well-appointed kitchen, spacious dining and sitting areas, and multiple gathering zones to accommodate both socializing and quiet time. Outdoors, the private pool and spa can be heated (for an additional fee), while the surrounding deck is outfitted with lounge chairs and shaded seating—perfect for sunsoaked relaxation or evening get-togethers. With amenities like free Wi‑Fi, table tennis, laundry facilities, and on-site parking, this home is thoughtfully equipped for comfort and convenience.

Just a short 3–5 minute walk to the beach and within easy reach of Coligny Plaza, this property strikes an ideal balance between peaceful coastal seclusion and access to Hilton Head’s top attractions. Whether you’re planning a multigenerational family reunion, a group golf getaway, or a celebratory escape with friends, 49 Mooring Buoy offers the space, luxury, and location that make for unforgettable group vacations on Hilton Head.

Address: 49 Mooring Buoy, Hilton Head Island, SC, 29928
Website: Beachside Getaway

45 S Sea Pines Dr. – Hilton Head Island, SC

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Lagoon‑Front Luxury – Sea Pines’ Elegant 5‑Bedroom Retreat

45 S Sea Pines Dr is a freshly renovated 5‑bedroom, 5-bathroom haven that sleeps up to 16 guests—ideal for family reunions or celebratory getaways. Each bedroom boasts its own en‑suite, including a lavish master with king bed, soaking tub, and pool-facing views. The fifth bedroom is a flexible family-friendly bunk suite featuring twin-over-queen bunks, queen bed, and private bath—perfect for kids or extra guests.

The home’s interior is designed for both luxury and gatherings, with dual living rooms each equipped with large flat-screen TVs and a gourmet kitchen featuring Sub-Zero and Wolf appliances surrounding a spacious island. High-end renovations completed in spring 2025 ensure an upscale coastal atmosphere that complements the surrounding Lowcountry charm.

Outdoors, the private regulation-size pool (9×17 ft) and spa overlook the tranquil lagoon from an expansive deck, perfect for sun-filled lounging or al fresco dining. A screened porch, game room, air-conditioning, Wi‑Fi, laundry room, and elevator enhance the functionality and comfort for multigenerational stays. Located just a 5‑minute walk from South Beach and within biking distance of Harbour Town, this Sea Pines retreat offers resort-level privacy with premier access to Hilton Head’s best.

Address: 45 S Sea Pines Drive, Sea Pines, Hilton Head Island, SC, 29928
Website: Beachside Getaway

28 Pelican Street – Hilton Head Island, SC

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Stylish 5‑Bedroom Home with Private Pool & Spa in North Forest Beach

28 Pelican Street offers a stunning blend of refined architecture and relaxed coastal living. This spacious five-bedroom, five-and-a-half-bathroom retreat accommodates up to 12 guests and is styled with designer finishes that echo British West Indies and seaside influences. With an open foyer featuring curved wood ceilings, coffered and beamed accents, and a thoughtfully crafted layout, the home spans approximately 4,264 sq ft across two levels, including a 3–4 car garage and provisions for a future elevator.

Ideal for group living, the residence offers luminous indoor spaces with high-end flooring, tasteful molding, and functional bedrooms wired with modern comforts. Outdoors, guests can unwind in a private 14 × 22 ft heated pool and adjoining spa nestled under lush palms, accessed via a partially covered porch with lounge seating and a dining area. A seasonal free shuttle service, beach gear delivery, and proximity to Lowcountry Celebration Park and Coligny Beach Park—just steps away with public showers, paths, and playgrounds—ensure a seamless and enjoyable stay.

Whether planning a multigenerational vacation or a getaway with friends, this elegant Pelican Street home balances style, space, and location. The private pool and spa create a serene retreat, while indoor elegance and designer touches bring formality and comfort. And with the beach, bike paths, dining, and entertainment all within easy reach, this is one of Hilton Head’s best large-group escapes.

Address: 28 Pelican St, North Forest Beach, Hilton Head Island, SC, 29928
Website: Beachside Getaway

Set Sail on the Perfect Group Escape

When you’re traveling in a big group, choosing a vacation rental on Hilton Head Island isn’t just practical—it’s essential. These homes offer far more than just extra bedrooms: fully equipped kitchens, spacious living areas, private pools, and multiple bathrooms foster both togetherness and personal retreat. Splitting the cost across your group makes hosting luxe amenities and prime locations more affordable too, delivering value that hotels simply can’t match.

Beyond affordability, the experience is what truly elevates a group stay. Staying under one roof allows seamless bonding—from cooking meals together to late-night chats by the pool—without the hassles of coordinating separate rooms. Plus, being steps from beaches, bike trails, golf courses, and dining makes it easy to create group memories while still having the space to recharge. These Hilton Head rentals combine location, comfort, and convenience perfectly, ensuring your large-group getaway is as unforgettable as the company.