If you’re dreaming of a Hilton Head getaway filled with ocean breezes, private pools, and world‑class resort amenities, these exceptional vacation homes offer the perfect place to land. From oceanfront estates to spacious retreat‑worthy homes ideal for groups, each property delivers comfort, location, and unforgettable Lowcountry style.
Looking for the ultimate getaway? Destination Vacation has everything you could hope for! Book today!
In This Piece
- Spring Availability
- Summer Availability
- Ready to Book Your Hilton Head Escape?
- Frequently Asked Questions
Spring Availability
36 Ruddy Turnstone | Sea Pines
6 Bedrooms + Sleeper Den | 6.5 Bathrooms | Sleeps 14–16
An architectural showpiece, 36 Ruddy Turnstone is an oceanfront retreat designed for both relaxed beach days and memorable gatherings. Vaulted ceilings with custom beams, skylights, and walls of windows fill the home with warm natural light, while peaceful ocean views set the tone throughout. The main living and dining spaces are ideal for coming together after a day at the beach, complemented by a chef‑ready kitchen featuring double ovens, a gas range, wine cooler, and multiple prep areas.
Six spacious bedrooms provide privacy and comfort for everyone, including an expansive primary suite with oceanfront deck access. Outside, a private pool and spa overlook the Atlantic, complete with a shaded patio, grilling station, and a picturesque private beach walkway.
Featured Amenities
- Oceanfront location with private beach path
- Private pool & spa
- Furnished screened porch with ocean views
- Covered outdoor dining and grill station
7 Marsh Wren | Sea Pines
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5 Bedrooms | 5 Full & 2 Half Bathrooms | Sleeps 13–14
Just steps from the beach path, 7 Marsh Wren offers a refined yet welcoming coastal escape. This third‑row home features three distinct living areas—perfect for spreading out—along with a large kitchen that opens directly to a comfortable family room. The downstairs lounge includes a full bar and opens to the pool and covered veranda, making indoor‑outdoor living effortless.
With ensuite bedrooms, a private pool and spa, and a location that puts the beach within easy walking distance, this home balances resort convenience with at‑home comfort.
Featured Amenities
- Third‑row location on beach path
- Saltwater pool & outdoor spa
- Three spacious living areas
- Bar, covered veranda, and privacy fencing
206 N. Sea Pines Drive | Sea Pines
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7 Bedrooms | 8.5 Bathrooms | Sleeps 20
Ideal for family reunions, girls’ retreats, and corporate gatherings, this manor‑style estate delivers luxury on a grand scale. Set on a rare two‑acre lot, 206 N. Sea Pines Drive feels like a private resort with room for everyone to unwind, connect, and celebrate. The main home and guest house provide flexible sleeping arrangements, while high‑end finishes—including Thermador appliances and custom architectural details—elevate every space.
Amenities abound, from a home theater and recreation room to an infinity‑style pool, spa, and cabana bar. Guests also enjoy exclusive access to Atlantic Point community amenities just steps away.
Featured Amenities
- Perfect for large groups & special gatherings
- Infinity pool, spa & cabana bar
- Home theater & recreation room
- Access to Atlantic Point beach & courts
24 N. Live Oak | Sea Pines
4 Bedrooms | 3 Full & 2 Half Bathrooms | Sleeps 10
Completely renovated with a sophisticated coastal style, 24 N. Live Oak offers a relaxed escape overlooking the Atlantic Dunes golf course. This thoughtfully designed home features multiple living spaces, a gourmet kitchen, and a main‑level primary suite with direct access to the pool deck. A screened porch with grill and dining area creates an inviting spot to enjoy evening breezes.
Located just a short walk or bike ride from the beach, this home is ideal for families looking to balance tranquility with convenience.
Featured Amenities
- Private pool overlooking golf course
- Screened porch with grill & dining
- Gourmet kitchen & multiple living areas
- Easy walk or bike ride to beach
1907 South Beach Club | Sea Pines
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Waterfront living doesn’t get better than this. Situated directly across from South Beach Marina and the Salty Dog Café, 1907 South Beach Club places you at the heart of one of Sea Pines’ most iconic areas. The first‑floor villa captures stunning views of Calibogue Sound, with a private balcony perfect for spotting dolphins and seabirds.
A rare private staircase leads directly to the pool and beach access, making it easy to transition from coffee on the balcony to toes in the sand.
Featured Amenities
- Waterfront views of Calibogue Sound
- Steps to South Beach Marina Village
- Private staircase to pool & beach
- Walk‑in showers & private balcony
Summer Availability
37 Ruddy Turnstone | Sea Pines
6 Bedrooms | 6 Bathrooms | Sleeps 22
Designed for larger groups, 37 Ruddy Turnstone delivers oceanfront luxury with generous indoor and outdoor gathering spaces. The open floor plan showcases breathtaking views, while multiple living areas ensure plenty of room to relax. One of the largest pools on the island anchors the outdoor space, complemented by a spa and private boardwalk to the beach.
With bedroom layouts that easily accommodate extended families or group getaways, this home is ideal for those who want space without sacrificing style.
Featured Amenities
- Large oceanfront pool & spa
- Private beach path
- Media room & built‑in bar
- Multiple decks & covered patios
38 Canvasback | Sea Pines
6 Bedrooms + Sleeper Den | 7.5 Bathrooms | Sleeps 16–18
Crafted by a renowned local architect, 38 Canvasback blends refined design with laid‑back coastal living. Walls of windows frame sweeping ocean views, while expansive living and dining areas make hosting effortless. The upstairs veranda is a favorite gathering spot, offering panoramic views of both the pool and the Atlantic.
With a private boardwalk to the beach, multiple fireplaces, and a beautifully designed outdoor living area, this home provides a true oceanfront experience.
Featured Amenities
- Architect‑designed oceanfront home
- Private pool, spa & beach boardwalk
- Multiple living rooms & verandas
- Outdoor grill & covered porch
4 Lands End Court | Sea Pines
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3 Bedrooms | 3 Bathrooms | Sleeps 6
Charming and coastal, 4 Lands End Court is a waterfront cottage just steps from the beach and South Beach Marina Village. Bright interiors, colorful artwork, and peaceful water views create a relaxed atmosphere, while the sunny deck and all‑weather porch invite you to linger outdoors.
Guests also enjoy access to the community pool and easy walking distance to dining, shops, and water activities.
Featured Amenities
- Waterfront views of Braddock Cove
- Walk to beach & marina village
- Community pool access
- Sun deck & all‑weather porch
Ready to Book Your Hilton Head Escape?
Availability for spring and summer is limited, and these sought‑after Hilton Head vacation homes book quickly. Browse your favorite listings, secure your dates, and book direct with Destination Vacation to enjoy an unforgettable coastal getaway.
Frequently Asked Questions
Is Sea Pines open to the public?
Yes, Sea Pines Resort is open to the public, but it requires a parking pass that is $10.
Do these homes include beach gear or bike rentals?
Some stays include a VayK Life beach and bike gear credit, emailed after booking and valid for select rentals.