Vacation Single Family Homes Real Estate | Vacation Single Family Homes for Sale

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-502467 MLS

Carolina Club by Spinnaker - Hilton Head Island - 1 float week -You pick the week in advance and BOOK IT! VALUE here the 2026 maint. fee has been paid! The unit / townhome villa features two-bedrooms are suited for up to six people. This quiet townhome contains a fully equipped kitchen, washer and dryer, spacious dining and living area with entertainment center. You can also relax outside on the private deck.Hilton Head is truly a destination with a bit for everybody, relaxation, beaches, sport activities, bike trails, walking areas, shopping, evening fun just to name a few.Amenities are like two on-site pools, clubhouse, tennis courts, a playground, complimentary bicycle rental, children's activities and golf privileges at Golden Bear Course and more.Yearly maintenance fee is $1K.

200 Southwind Drive Unit # 225, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$450

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-501972 MLS

own week 24 of Hilton Head Island and never worry about booking again your fixed week is waiting for you. low maint. fee of 929.00 will reserve your 2bed 3bath villa with double bunk house room! 2 minute walk to coligny beach, and all it has to offer. Bring your toothbrush and shop at the piggly wiggly and enjoy your stress free week. (you can also stop in for a swim anytime of the year DAY PASS).

3 Avocet Road Unit 3214, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$29,900

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-501467 MLS

Great opportunity in the highly desired Brigantine Quarters behind the gates of Shipyard! With 13-weeks of annual usage, this 2 BR/2 BA second floor flat is on a rotating schedule and has an incredible long lagoon view. Your maintenance fee covers everything from taxes, insurance, to toasters! It's a great way to have a worry-free place at the beach. Two community pools (one heated seasonally) - plus allt he amenities that go along with Shipyard!

55 Barcelona Road Unit 274B, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$1,590,000

4 Beds ⋅ 4 Baths ⋅ 2,235 SqFt. ⋅ HILTONHEAD-500985 MLS

Location, location! Overlooking the 2nd fairway of the world-famous Harbour Town Golf Links, this beautifully renovated 4-bedroom, 4-bath home offers the perfect Sea Pines lifestyle. Enjoy front-row views of the Heritage Classic Golf Tournament right from your backyard. Walk around the corner to Sea Pines Center to for dinner. Walk to the Harbor Town Pool in 5 minutes. The Beach Club is reached in no time by hopping on the Trolley at the stop right around the corner; or take a bike on the leisure trails. Recently renovated from top to bottom, the home feels brand new with fresh paint, all-new trim, doors, flooring, lighting and new furniture throughout. The Chef's Kitchen features a brand-new GE gas range with a downdraft and a new GE Refrigerator; a new HVAC system plus all-new duct work provides year-round comfort. Each bedroom has its own full bath, creating the perfect setup for family and guests. Only used as a 2nd home right now, rental projections are $98,800/year. Whether this will be your primary home, vacation retreat, or rental investment, it has a winning combo of modern updates, timeless comfort, and one of the most desirable locations in Hilton Head.

11 Muirfield Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$3,999,999

6 Beds ⋅ 7 Baths ⋅ 3,097 SqFt. ⋅ HILTONHEAD-453418 MLS

Introducing an extraordinary 2026 brand new construction luxury residence at 71 Dune Lane. Perfectly positioned oceanside in the sought after North Forest Beach enclave. This 6-bedroom, 6.5-bath home, set within one of Hilton Head Island's most prestigious beach corridors, celebrates modern coastal living with ocean views, premium design, and thoughtful functionality. Architectural design by Neil Gordon with construction by Dan Anderson Construction, reflecting exceptional craftsmanship throughout. From the moment you enter, the home's open and luminous spaces flow naturally toward the Atlantic horizon. Entertain in style with a dedicated first-floor 2 car garage and additional entertainment space, resort-style relaxation with your heated pool and spa, and enjoy effortless access throughout the home by elevator. The expansive primary suites are thoughtfully oriented to capture sweeping ocean views, creating a serene retreat that epitomizes beachfront luxury. Sold fully furnished for your convenience. Whether you're looking for a primary residence, second home, or a powerhouse short term rental property, this home offers it all. An exceptional income producing property with over $325,000 in projected rental income. Vacation in your investment.

71 Dune Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,199,000

4 Beds ⋅ 4 Baths ⋅ 3,125 SqFt. ⋅ HILTONHEAD-500571 MLS

This sophisticated Marsh Island turn-key home offers a perfect floor plan and a gorgeous stunning marsh-wrapped view of the free-form pool with a large Stone Works designed surround. The numerous first-class updates in this home, its meticulous care, and only part-time occupancy by the owners add to its endless appeal. Enter into an atrium that opens to the great room and dining area with soaring ceiling, and the kitchen and breakfast area. This magazine-worthy kitchen offers extensive Poggen Pohl cabinets, SubZero refrigerator, Wolf Microwave and cook top, double ovens, Madagascar marble counters, and a laundry/pantry room with wine racks and a wine refrigerator. Also located on the first floor are a separate office and the primary suite. Over the garage is a large bonus room. Off the foyer soars a modern staircase and balcony with stainless handrails and balusters leading to the 3 guest rooms. There is a 220 volt EV charger in the garage. Enjoy the exclusive and coveted Marsh Island residential neighborhood, with close access to Sea Pines Country Club and all that Sea Pines offers.

2 Long Marsh Lane, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$7,995,000

7 Beds ⋅ 9 Baths ⋅ 7,311 SqFt. ⋅ HILTONHEAD-500493 MLS

Ringed by the quiet serenity of untouched maritime forest, 11 Headwaters Road is a 7,311 square foot, fully furnished, seven-bedroom, eight-and-a-half bath family compound consisting of a main house, guest house and carriage house set on more than 24 acres in the blissfully secluded Headwaters community of Palmetto Bluff. Throughout the estate grounds you'll find quiet waterside beauty, deep enchanting forests, lushly landscaped gardens, outdoor living, a private covered dock, and its heart, a family home for generations. The craftsmanship of Johnson-Dulaney builders paired with architectural brilliance from Wayne Windham to create grand sweeping spaces that give everyone room to come together, dotted with quiet retreats for soaking in the Lowcountry's grandeur. In the main house, a soaring two-story great room anchors the home with reclaimed pine floors running toward a dramatic tabby fireplace that stretches to exposed beams. These beams carry into the airy formal dining and down to the open kitchen. Centered on a broad quartz center island, its six-burner gas range and plentiful counterspace and nearby wine cellar allow for even the largest family dinners. The main houses second floor also houses a bedroom as well as a full guest suite flanking an elevated sitting room, while the first floor is given over to the sprawling primary suite. A long gallery hall, which terminates in a pair of spacious offices with private baths, also leads to this blissful oasis. Enjoying private access to the screened patio, the primary suite indulges with gorgeous views of the property and amenities for two dual walk-in closets, and his-and-hers en suite baths. Such space is necessary in a property like this, where guests from the main house, guest house and carriage house will come together. Situated above the sprawling garage, with room for four cars, the carriage house offers full apartment living with expansive living room, kitchen and full suite with private bath. Anchored by a spacious living room with kitchenette, the guest house offers three bedrooms with spacious closets, two of which share a jack-and-jill bathroom with the third being a full suite. A private enclave of ten family compounds overlooking the beautiful May River, the gated Headwaters community is the ultimate location for privacy and seclusion.

11 Headwaters Road, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$6,999,000

5 Beds ⋅ 6 Baths ⋅ 3,669 SqFt. ⋅ HILTONHEAD-500303 MLS

Welcome to your coastal sanctuary in Sea Pines Resort-an exquisite 2ND ROW new-construction home designed for luxury living and / or exceptional rental potential. This 5-bedroom, 5.5-bath masterpiece offers approximately 3,669 heated square feet of finely crafted space, perfectly positioned on a 2nd-row homesite with STRONG OCEAN VIEWS and effortless access to the wide white sand beaches of Hilton Head Island.From the moment you enter, a private elevator and light-filled foyer set the tone for a home that blends coastal elegance with modern comfort. The open-concept main level showcases a chef's kitchen with premium appliances, custom cabinetry, and a large island that flows seamlessly into the dining and living areas-ideal for entertaining large groups or enjoying intimate family gatherings. Expansive windows and glass doors draw your eye outward to the ocean and to the resort-style outdoor living spaces.Step outside to your private oasis: an infinity-edge pool and spa that appear to melt into the horizon, framed by a spacious covered lanai and multiple porches. Enjoy al fresco dining, lounging, or watching the sunset by the outdoor fireplace-this home was designed to embrace indoor-outdoor living at its finest. Just steps away, a convenient beach path delivers you onto one of Hilton Head's most beautiful stretches of sand.Each of the six bedrooms is thoughtfully appointed with its own en-suite bath, offering comfort and privacy for owners and guests alike. Multiple primary suites, generous bunk or guest rooms, and carefully planned bath layouts make this home ideal for multi-generational living or high-occupancy vacation rentals. The half bath is perfectly positioned for pool and common-area use.Every detail was considered for both luxury and durability: high-end finishes, impact-rated windows and doors, designer lighting, and a floor plan optimized for today's coastal lifestyle. Ample storage, a ground-level drop zone for beach gear, and flexible gathering spaces ensure that the home is as functional as it is beautiful.

18 Oyster Catcher Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$6,100,000

5 Beds ⋅ 5 Baths ⋅ 4,449 SqFt. ⋅ HILTONHEAD-500143 MLS

Welcome to 30 E Beach Lagoon, a stunningly remodeled Oceanfront home located on one of Sea Pines most prestigious streets. Rarely does a property blend luxury, charm, and location this seamlessly. Designed with timeless coastal elegance, this home offers an exceptional lifestyle, 5 bedrooms, 5 baths, and just steps from your private deeded beach access. Inside, soaring vaulted ceilings with exposed beams, a masonry brick fireplace, and wide-plank wood floors create a warm, inviting atmosphere. The kitchen features high-end natural wood cabinetry, sleek countertops, and stainless steel appliances ideal for entertaining or quiet mornings at home. The main house flows beautifully into a spacious living area filled with natural light, while the private, attached guest house offers flexibility for hosting friends or extended family. The primary suite features a private deck with peekaboo ocean views and easy access via the in-home elevator. Outside, enjoy your own private pool surrounded by lush, mature landscaping, creating a serene retreat that feels both secluded and coastal. The home also includes a two-car garage and has never been used as a rental, offering pristine condition and pride of ownership. Whether you're searching for a luxury second home or a high-performing short-term rental, 30 E Beach Lagoon delivers on all fronts location, design, and lifestyle all within the gates of Sea Pines Resort.

30 E Beach Lagoon Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,495,000

4 Beds ⋅ 5 Baths ⋅ 3,292 SqFt. ⋅ HILTONHEAD-453819 MLS

18 Lyonia Street is a new construction four-bedroom, four-and-a-half-bathroom contemporary Lowcountry style home and carriage house in the highly desirable Moreland Forest neighborhood of Palmetto Bluff. Situated around a grassy sun-kissed courtyard, and offering multiple screened porches, this home artfully blends the best of indoor and outdoor living. Crafted by Front Light Building Company from a Moser Design Group design, the home relishes in its openness immediately upon entry, with a foyer that opens to a massive screened-in porch with outdoor fireplace as well as to the central courtyard while breezing you into the open living spaces. Marked by crisp whites and sanded wood accents, this airy space incorporates a living room with gas fireplace, chef's kitchen with center island and custom hood over a five-burner gas range, and dining room that gazes out into the courtyard. Stretching away from this, a corridor draws past the butler pantry and powder room toward another porch at the rear of the property. The same scenic courtyard views that define the main living spaces also fill the indulgent primary suite, with floor-to-ceiling windows in the bedroom to soak them in. This expansive suite also incorporates a host of idyllic amenities, including a gorgeous walk-in closet, and spacious ensuite bath with his and hers vanities and wet room. On the second floor, a roomy flex space incorporates a full wet bar, anchoring a pair of second-story suites. In one suite, dual closets flank the entry to a private bath with tub and shower. In the other, a breezy sense of comfort drifts in from the private balcony, drawing sweet Lowcountry breezes into a space with private bath and walk-in shower. Situated above the two-car garage, the classic Lowcountry carriage house delights with its expansive floor plan, elevated village views and roomy private bath boasting a walk-in shower. Moreland Forest, Palmetto Bluff's new collection of homesites, features expansive homesites with a range of sizes located along the Inland Waterway, freshwater lakes, and parks. Strategically designed with wetlands and wildlife in mind, the community is also thoughtfully connected to first-class amenities via a network of trail systems. With preserved vistas, parkland green spaces, and proximity to amenities, Moreland Forest has endless appeal for residents of all ages.

18 Lyonia Street, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$3,390,000

4 Beds ⋅ 5 Baths ⋅ 3,100 SqFt. ⋅ HILTONHEAD-452729 MLS

SECOND ROW OCEANFRONT HOME IN THE SOUTH BEACH AREA OF SEA PINES PLANTATION is available to make your dreams come true!!! LOCATION! LOCATION! LOCATION! Living life in the Low Country only MINUTES away from our nationally recognized beach is now a REALITY! This custom built 2nd ROW OCEAN beauty has very close proximity to the beach & to the South Beach Marina area where your ultimate island experiences await. There are soooooo many direct views of the ocean from the multiple levels and balconies! All newly renovated coastal bathrooms give this home a current vibe! Fun local activities include biking, boating, dining, shopping, kayaking, dolphin watching, tennis, pickle ball & MORE! The cathedral ceilings in the living area, travertine floors & open concept living w/outside wrap-around balconies towards the ocean complement the Low Country lifestyle! The kitchen has a Viking stove, newer refrigerator, floating shelves, Italian imported marble countertops & a huge pantry! The entire lowest floor has as much space as you can imagine to store all your beach/pool/bikes and MORE!! During high season you can take the trolley anywhere in Sea Pines so you can park your car and never have to drive while you are visiting. The gorgeous pool has a spa with a water fountain and the pool also has had a heater added to it so you can swim in the pool year round! If you are looking for the perfect house in the PERFECT easy location....you have just found it!

4 Gadwall Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$4,250,000

6 Beds ⋅ 6 Baths ⋅ 6,000 SqFt. ⋅ HILTONHEAD-450230 MLS

Stunning deep-water residence in Sea Pines features a private, oversized dock with a boat lift, offering unparalleled waterfront access. Spanning nearly 6,000 square feet, the open floor plan showcases breathtaking, unobstructed water views. The entertainer’s dream kitchen boasts a 60” Viking gas range, double stainless steel refrigerator, walk-in pantry, and a striking 12-foot granite bar complete with a wine cooler and ice maker. The outdoor living space features a circular driveway with pervious pavers, a resort-style private pool and hot tub, and a fire pit—all set within over 3,000 square feet of beautifully designed patio space. OSCREA

25 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of DOT REAL ESTATE.

$3,395,000

5 Beds ⋅ 5 Baths ⋅ 3,879 SqFt. ⋅ HILTONHEAD-450364 MLS

Currently under construction crafted by Palmetto Bluff Builders, 32 Mallow Street will offer 5 beds and 5 baths among 3,879 of bespoke luxury finishes and architectural brilliance to take advantage of forest scenery. Soaring two-story windows in the great room look out toward protected wooded views, with outdoor living spaces that include a screened-in porch. A full Thermador appliance package in kitchen, with a large pantry and laundry. A full MIL suite in carriage house above the 2-car garage, along with three full suites and a primary with walk-in closets and a spacious bath. Located in Moreland Forest amid nature & amenities.

32 Mallow Street, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$4,099,000

4 Beds ⋅ 5 Baths ⋅ 3,135 SqFt. ⋅ HILTONHEAD-450899 MLS

This charming 4 bedroom, 4.5 bath cottage designed by Pearce Scott Architects sits along a private waterway accessible by bridge in the Montage Residences neighborhood. This turnkey residence is fully furnished with upscale furnishings inspired by the coastal setting and features Lowcountry detailing such as tabby stucco, standing seam metal roof, large screened porch, and a Carolina room. As part of the Montage Residences, homeowners enjoy the signature amenities of Montage Resorts with dedicated staff. This cottage is located across from Montage Inn and closely located to RT’s Market, The Wilson Lawn & Racquet Club, and Wilson Landing.

123 August Lane, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$4,600,000

4 Beds ⋅ 6 Baths ⋅ 6,042 SqFt. ⋅ HILTONHEAD-447864 MLS

This one-of-a-kind property is privately sited on almost an acre lot with panoramic marsh and water views providing the perfect backdrop for spectacular sunsets. Kermit Huggins, renowned architect, designed this property with 2 structures that harmoniously co-exist with their natural surroundings. Special features include new metal roof, hardwood flooring, pella windows/doors, renovated kitchen,& interior paint. The main house boasts an upper level luxurious owner suite & guest house has 2 en-suite bedrooms plus kitchenette. Incredible outdoor living with heated/chilled saltwater pool, expansive deck, and private dock. Waterfront Perfection!

29 Baynard Park Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,395,000

5 Beds ⋅ 4 Baths ⋅ 2,720 SqFt. ⋅ HILTONHEAD-447145 MLS

Sale subject to third-party/lender approval. Seller pursuing short sale. Property sold as-is. Folly Field Rental Machine built in 2019! Buxton Floorplan. Gated community only 10 minutes to the beach! This 5-bedroom, 4 full bath home has an open floor plan with a large kitchen, dining area, and living room with an attached screened porch! One bedroom furnished as a bunk room. The elevator takes you from the garage to all 3 floors above. Luxury Vinyl Plank (LVP) throughout. Private heated in-ground pool overlooking a brick paver patio and landscaped view. Sold fully furnished. Sleeps 18. Great opportunity for a primary home, secondary home, or investment property! Currently on the Short Term Rental Market.

101 Sandcastle Court, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$4,495,000

5 Beds ⋅ 6 Baths ⋅ 3,662 SqFt. ⋅ HILTONHEAD-446499 MLS

This new, five-bedroom, five-and-one-half-bath cottage by Palmetto Bluff Builders is in the Montage Residences neighborhood across the street from Montage Palmetto Bluff. Newly finished, this cottage maximizes its single story design with multiple indoor & outdoor living spaces & a detached carriage house. Exterior detailing, such as louvered shutters, tabby stucco and brick detail, and a metal roof add timeless appeal. As part of the Montage Residences, homeowners enjoy the signature amenities of Montage Hotels & Resorts with dedicated staff. This cottage has easy access to RT’s Market, Wilson Lawn & Racquet Club, and Wilson Landing.

130 August Lane, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$2,699,000

7 Beds ⋅ 8 Baths ⋅ 4,639 SqFt. ⋅ HILTONHEAD-440375 MLS

NOW SOLD FURNISHED! Welcome to your dream coastal retreat! This stunning NEW CONSTRUCTION home, JUST COMPLETED and STEPS TO THE BEACH offers an unparalleled blend of luxury and comfort in the heart of South Forest Beach. Spanning an impressive 4,639 square feet, this exquisite residence features 7 spacious bedrooms and 7.5 beautifully appointed bathrooms, making it the perfect getaway for families or groups seeking a memorable beach experience. As you step inside, youll be greeted by an open and airy floor plan adorned with luxurious LVP flooring throughout, providing both durability and elegance. The heart of the home is the expansive living area, complete with a cozy gas fireplace, perfect for those cooler evenings. The gourmet kitchen is a chef's delight, featuring top-of-the-line stainless steel appliances, an 11-foot bar with stunning quartz countertops, and a convenient butler's pantry. The adjacent wet bar, equipped with an ice maker and beverage fridge, ensures youre always ready to entertain.Each of the 7 bedrooms is a private sanctuary, with ample space and natural light. The bathrooms are equally impressive, showcasing custom tile work and granite countertops, ensuring a spa-like experience for you and your guests.Step outside to your own private oasis, where a large heated pool awaits, perfect for relaxing or hosting summer gatherings. The outdoor space is designed for enjoyment, with plenty of room for lounging and soaking up the sun.This home is equipped with a 3-stop elevator, making it accessible and convenient for all ages. The large garage provides ample storage for beach gear, bikes, and more, ensuring you have everything you need for your beach adventures.Located just steps from the pristine beach and a short bike ride to the vibrant Coligny Plaza and Celebration Park, this property offers the ultimate in convenience and leisure. There are several weeks already booked for the Summer. With short-term rental projections of up to $250,000, this home is not only a perfect personal retreat but also a lucrative investment opportunity. Don't miss your chance to own this exceptional property in one of the most sought-after locations on the island. Schedule your private tour today and experience the perfect blend of luxury, comfort, and coastal living!

110 Shell Midden Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.