If you’re searching for the ultimate luxury escape on Hilton Head Island, look no further. This exclusive coastal haven is home to some of the most stunning oceanfront estates, private island retreats, and resort-style villas in the country. Whether you crave a sprawling beachfront mansion with a private pool and spa, a secluded getaway with its own dock and boat access, or a designer home packed with five-star amenities, Hilton Head delivers. From gourmet kitchens and infinity pools to private beach access and panoramic Atlantic views, these high-end rentals redefine vacation living. Here are the 10 most luxurious vacation homes on Hilton Head for 2025, each offering an unforgettable blend of elegance, comfort, and exclusivity. Please note: Clicking on the links will direct you to VRBO, and we may earn a commission if you book through these links.

• Bedrooms: 7
• Bathrooms: 8
• Sleeps: 14
• Average Price per Night: $4,567

Tucked away in the exclusive Gold Coast of Hilton Head Island, this stunning oceanfront estate offers direct beach access, private balconies with fireplaces, and breathtaking Atlantic views. Designed by an award-winning architect and updated in 2022, this 7-bedroom, 6,400 sq. ft. sanctuary blends grand gathering spaces with serene private retreats. Enjoy the chef’s kitchen, Sonos sound system, outdoor kitchen, heated pool and spa, and a charming lawn for badminton or yoga. Thoughtfully designed for families, the home includes built-in bunk beds, a play area, and two laundry rooms to handle all those beach towels with ease. Whether you’re sipping morning coffee by the waves, riding bikes along the shore, or dining alfresco under the stars, this estate offers the ultimate Hilton Head escape. Bonus perks include one free reservation at South Beach Racquet Club per week and proximity to Harbour Town, South Beach, and Bluffton’s charming historic district. Luxury, seclusion, and endless coastal beauty await.

• Bedrooms: 7
• Bathrooms: 8 Full & 2 Half
• Sleeps: 22
• Average Price per Night: $4,051

A true resort-style retreat, Southern Comfort offers unmatched oceanfront luxury in North Forest Beach. With 7 bedrooms, a massive private pool, hot tub, and multiple outdoor living spaces, this home is designed for relaxation and entertainment. Enjoy panoramic Atlantic views, a chef’s kitchen with dual appliances, and a stunning screened porch with a fireplace. The bunk room is a dream for kids, while the Turtle Watch deck provides breathtaking island views. Whether you’re lounging by the pool, grilling in the summer kitchen, or taking the private boardwalk to the beach, every moment here feels indulgent.

• Bedrooms: 7
• Bathrooms: 7
• Sleeps: 24
• Average Price per Night: $3,959

Nestled in the heart of Sea Pines Resort, this stunning oceanfront escape has been completely remodeled for the ultimate luxury beach retreat. Featuring seven bedrooms, seven baths, and breathtaking ocean views, this home offers double master suites, an oversized gourmet kitchen, and a private veranda with a fireplace and outdoor TV. The pool and spa overlook the Atlantic, with direct beach access just steps away. Enjoy floor-to-ceiling windows, a glass-enclosed Widow’s Walk for dolphin spotting, and easy access to Sea Pines’ world-class golf, dining, and bike trails. Perfect for family gatherings or group getaways, 23 Red Cardinal is a true coastal paradise!

• Bedrooms: 7
• Bathrooms: 10 Full & 3 Half
• Sleeps: 12
• Average Price per Night: $3,814

Nestled in Sea Pines, 24 Royal Tern is a masterpiece of coastal luxury, offering panoramic ocean views, an infinity pool, and private beach access. Every detail is curated for comfort, from the chef’s kitchen with double refrigerators and wine cooler to the elegant Great Room opening to a limestone fireplace on the oceanfront patio. With seven lavish bedroom suites, a media room, private office, and multiple outdoor spaces, this home blends classic Lowcountry charm with five-star amenities. Whether lounging by the pool or exploring Sea Pines’ golf courses, bike trails, and marinas, 24 Royal Tern delivers the ultimate beachfront retreat.

• Bedrooms: 7
• Bathrooms: 8 Full & 4 Half
• Sleeps: 26
• Average Price per Night: $3,705

For those seeking the ultimate secluded retreat, Buck Island is a rare gem—a 10-acre private island just off Hilton Head, accessible only by boat. This exclusive estate features a main house and guest house, offering luxury accommodations for up to 26 guests. Floor-to-ceiling windows frame the breathtaking water views, while the private pool, hot tub, and outdoor decks create a true paradise. A game lounge, gourmet kitchen, and spacious gathering areas make this an entertainer’s dream. Explore the island by golf cart, relax in the sun, or enjoy water adventures with private boat rentals. With a blend of high-end amenities and total privacy, Buck Island delivers an unforgettable island experience like no other.

• Bedrooms: 6
• Bathrooms: 8.5
• Sleeps: 14
• Average Price per Night: $3,624

Perched oceanfront in Sea Pines, 23 South Beach Lagoon is not just a vacation home—it’s a destination. Recognized as a VRBO Top Ten in America and featured on The Today Show, this sprawling luxury estate delivers an unparalleled coastal experience. With panoramic ocean views, a private heatable pool and spa, multiple decks for lounging and dining, and a lush lawn perfect for family games, every inch of this retreat is designed for relaxation. Inside, the home’s six en suite bedrooms, chef’s kitchen, and multiple gathering spaces make it an entertainer’s dream. Plus, with upcoming renovations in 2025, including a new kitchen, dining area, and primary bath, the luxury factor is only getting better. For those seeking the ultimate Hilton Head escape, 23 South Beach Lagoon is in a league of its own.

• Bedrooms: 6
• Bathrooms: 6
• Sleeps: 18
• Average Price per Night: $3,571

Set along the pristine shores of Palmetto Dunes, 8 Iron Clad is a 6,000-square-foot luxury retreat designed for those who want the best of Hilton Head Island. With six ocean-view bedrooms, an epic pool and spa, multiple living spaces, and a state-of-the-art kitchen, this home is built for relaxation and entertainment. Floor-to-ceiling windows frame the Atlantic, while a massive covered patio, a basketball hoop, cornhole, and ping pong bring the fun. The sprawling pool deck leads directly to the sand, offering unbeatable beach access. Whether you’re sipping coffee on the balcony at sunrise or watching the waves from the hot tub, 8 Iron Clad is pure oceanfront indulgence.

• Bedrooms: 6
• Bathrooms: 6.5
• Sleeps: 23
• Average Price per Night: $3,429

An exclusive beachfront estate in Sea Pines’ prestigious South Beach Lagoon, 33 S. Beach Lagoon is the epitome of Hilton Head luxury. Set on half an acre of lush gardens, this 7,530-square-foot retreat boasts breathtaking ocean views, soaring coffered ceilings, and custom iron railings that make a statement at every turn. With six spacious suites, multiple furnished patios, and a private pool and spa, this home is designed for unforgettable family gatherings and upscale entertaining. Direct beach access means long walks on the sand, while the Sea Pines Beach Club, world-class golf, and Harbour Town’s waterfront charm are just minutes away. 33 S. Beach Lagoon is where luxury meets Lowcountry tranquility.

• Bedrooms: 7
• Bathrooms: 7.5
• Sleeps: 18
• Average Price per Night: $3,206

This expansive oceanfront retreat is a dream destination on Hilton Head Island, offering unparalleled views of the Atlantic, a private pool and spa, and direct beach access. With 7 bedrooms, 7.5 baths, and a newly remodeled kitchen and baths, this 6,000-square-foot home was built for luxury and relaxation. The 28-foot-high great room, floor-to-ceiling windows, and a game room with a pool table and wet bar make this the ultimate space for family gatherings. Step onto the oceanfront deck, fire up the gas grill, and take in the coastal breeze, or unwind in the private sauna after a day of island adventures. A three-level elevator, an EV charger, and state-of-the-art entertainment systems throughout the home add to the convenience, making this a flawless Hilton Head getaway for up to 18 guests.

• Bedrooms: 9
• Bathrooms: 7.5
• Sleeps: 24
• Average Price per Night: $3,159

Tucked away on a quiet stretch of Hilton Head’s famed beaches, The Beach House at Sea Oak Lane delivers the ultimate coastal getaway with private beach access, multiple pools, a hot tub, and an outdoor cabana bar. Inside, expansive ocean views, a chef’s kitchen with Viking appliances, and multiple dining areas make it perfect for hosting large groups. Nine bedrooms, seven and a half bathrooms, and spacious suites ensure everyone has a relaxing retreat, while the media room, game center, shuffleboard, foosball, and air hockey keep the fun going. Whether lounging by the pool, sipping cocktails on a private balcony, or walking to nearby Coligny Plaza, this oceanfront oasis is designed for unforgettable memories. Sleeps 24 guests.