Sleeps up to 10
Ideal rental properties for large families & groups
Discover the perfect vacation rental on Hilton Head Island that comfortably accommodates up to 10 guests. Ideal for large families, groups of friends, or multi-generational trips, these rentals offer ample space and luxurious amenities. Enjoy fully-equipped kitchens, spacious living areas, multiple bedrooms, and beautiful outdoor spaces.
Located near Hilton Head's stunning beaches, world-class golf courses, and vibrant dining scene, these properties ensure a memorable and relaxing stay. Book your Hilton Head Island vacation rental today and experience the ultimate blend of comfort, convenience, and coastal charm, perfect for large gatherings and unforgettable vacations.
44 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
435 Captain\'s Walk overlooks the pool out to the ocean! Lots of recent updates!
435 Captain\'s Walk is a second-floor, 3-bedroom, 3-bathroom end unit that overlooks the pool and out to the ocean. A beautiful, updated villa with great views—you couldn\'t ask
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home is spacious and relaxing 3-bedroom home in the charming, gated community of Sea Pines. Open the door to experience a serene view of a private lagoon shaded by palm trees and live oaks dripping with Spanish moss. An abundance of natural sunlight stre
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home has been freshly updated with brand new exterior paint, kitchen countertops, renovated bedrooms and bathrooms, a new grill, and more exciting upgrades throughout! Photos have been updated to reflect these updates as of February 2026.
This pet-frien
36 Red Oak
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning oceanfront 3-bedroom villa is situated within the highly sought-after Captain\'s Walk complex in Palmetto Dunes. Palmetto Dunes is a premier resort community known for its pristine beaches, lush golf courses, and picturesque surroundings. This v
401 Captains Walk
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
With a scenic spot on the 11th hole, a private pool and spa to spend the day in, and spectacular views of the lagoon and golf course, this South Carolina home is the perfect vacation spot.
Vaulted ceilings make this property feel comfortably spacious, which
38 Stoney Creek Road | Carolina Getaway
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This Palmetto Dunes beach home features 4 bedrooms and is only a short walk to the beach—that is, if you ever want to leave this gem!
15 Sea Lane features a spacious open floor plan and plenty of natural sunlight! Unwind in the living room as you watch TV on
15 Sea Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
3 Bedroom Villa in Harbour Town Area, Newly Renovated, and Golf View. Gorgeous renovations in 2020 make this villa the right choice for you. As you enter, you are greeted with a two-story, open, and airy space. This open-concept living, dining, and kitchen ar
2371 Racquet Club
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2517 Windsor Place is a beautifully decorated villa with 3 bedrooms and 3 baths! Perfect for a golf getaway, family vacations, and couple retreats! This villa offers bedroom separation from the living and dining areas, allowing peaceful rest for those who ret
2517 Windsor II
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautiful oceanfront property features three spacious bedrooms, providing ample space for a relaxing and enjoyable stay. A gorgeous foyer with a spiral staircase ascends to a massive open floor plan with open living, dining, and kitchen areas with high-e
101 Seacrest
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
No details were missed in this amazing 3-bedroom Palmetto Dunes home. Amazing golf course views greet you as soon as you walk in the door. The large living room\'s main sitting area has a sleeper sofa, a loveseat, and a desk.
Heading further through this ho
10 Troon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Located in Palmetto Dunes and only a few minutes walk to the beach, this four bedroom home has all you need for the perfect stay on the island. 3 Cartgate offers four bedrooms and four and a half bathrooms, large spacious rooms, an open kitchen and private po
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
A stunning retreat in the heart of Palmetto Dunes, designed for relaxation and entertaining. Step into the bright and inviting living room, where floor-to-ceiling windows flood the space with natural light and offer serene views of the golf course. Comfortab
6 High Water
Tell us what you're looking for and someone will contact you with available options.