Hilton Head Island Homes with Pool Association Amenities

Welcome to Hilton Head Island, South Carolina, a stunning coastal paradise nestled in Beaufort County. Renowned for its breathtaking beaches, lush landscapes, and vibrant culture, Hilton Head Island is a premier destination for those seeking a blend of relaxation and adventure. With over 12 miles of pristine shoreline, this island is perfect for sunbathing, water sports, and family-friendly activities.

The community is rich in recreational opportunities, boasting world-class golf courses, tennis facilities, and scenic bike trails that wind through the island's picturesque scenery. Nature enthusiasts will love exploring the island’s natural beauty, from the serene marshlands to the enchanting forests teeming with wildlife.

For those seeking a home in this idyllic setting, you’ll be pleased to discover a variety of properties featuring pool association amenities. Imagine stepping out of your beautifully designed home into your own private oasis, complete with a sparkling pool where you can unwind and soak up the sun. Many neighborhoods in Hilton Head Island offer pool association amenities, providing residents with access to community pools, clubhouses, and social events that foster a sense of belonging and camaraderie among neighbors.

Whether you’re looking for a vacation getaway or a permanent residence, Hilton Head Island offers a unique lifestyle that combines luxury, leisure, and natural beauty. Experience the charm of island living, where every day feels like a vacation. Come explore the homes available with pool association amenities and start your journey to paradise today!

Newest Hilton Head Island Homes with Pool Association Amenities

$295,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512265 MLS

Brand new HVAC and HW Heater! Welcome to this amazing unit in building 4, sold fully furnished and fully equipped with everything you need to start vacationing or renting. 2BD/2BA condo, ideally located just steps away from the beaches of Hilton Head. Top-floor unit complete with LVP floors and a spacious open-concept, making it an ideal residence or rental opportunity. Great rental history with a perfect set up for family vacations. Enjoy an array of incredible amenities, including indoor and outdoor pools, convenient beach access, tennis/pickleball courts, and a tropical beach bar. Additionally, numerous restaurants and shops are conveniently located nearby, ensuring the convenience and entertainment of island life. Don't miss the chance to see this exceptional condo today.

663 William Hilton Parkway Unit 4427, Hilton Head Island

Listing courtesy of Lowcountry Live Oak Realty.

$875,000

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512261 MLS

Beautifully RENOVATED and fully FURNISHED, this END UNIT villa at 27 Water Oak is ideally situated directly on the first fairway of the Robert Trent Jones Golf Course in the heart of Palmetto Dunes. Gorgeous NEW flooring throughout, HIGH END furnishings give the villa an elevated coastal feel that is fresh, sophisticated and inviting. The unique floor plan offers no steps to the front door, a first-floor primary suite, a powder room, and two spacious bedrooms, each with a private ensuite bath and deck. A generous LOFT provides flexible space for additional sleeping, a home office or extra living space. Enjoy expansive fairway VIEWS and sensational SUNSETS from the WRAPAROUND deck. The community pool is just across the street and the BEACH is a short walk away. Palmetto Dunes offers three championship golf courses, an 11-mile lagoon, world class tennis and pickleball, restaurants, a general store and the complimentary Dunes Buggy. Whether a place to call home, a weekend retreat or an investment opportunity, this exceptional villa is ready to be enjoyed from day one.

21 Haul Away Unit 27, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,150,000

4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511846 MLS

Rare Dolphin Head opportunity in Hilton Head Plantation. This 4BR/3BTH, 3357 SF home on a 0.42-acre homesite w/stunning lagoon views stretching to the 18th fairway of the Dolphin Head Golf Club-wide unobstructed views, gorgeous sunsets over the water, 50 year roof installed in 2014 and bright light/windows galore. This home was loved and lived in for 25 years. $10,000 seller credit toward updating. Buyers can move in with confidence. Clean stucco report and home inspection completed 7/7/2026. This is a true lagoon-fairway retreat minutes from groceries, Hospital Medical Pavilion, Schools, Spring Lake pool and tennis/pickle-ball and island beaches. HHP is voted over & over as "best community to live in" on the north end of Hilton Head Island.

11 China Cockle Way, Hilton Head Island

Listing courtesy of Charter One Realty.

$569,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511988 MLS

Welcome to the highly-desired St. Andrews Common community in world-renowned Palmetto Dunes Resort! This beautifully updated 2BD / 2BA villa offers a light, inviting retreat in one of Hilton Head Island's most ideal locations. The spacious layout provides plenty of room for both everyday living and entertaining, making this a perfect primary residence, second home, or turnkey investment opportunity. Offered fully furnished and ready to rent - having achieved nearly $45K in gross rentals just last year! Enjoy the peaceful surroundings of St. Andrews Common, complete with a community pool and picturesque lagoon and landscape views throughout the neighborhood. You'll have easy access to miles of pristine beaches, championship golf, tennis and pickleball, dining, shopping, biking, kayaking and everything that makes the Hilton Head lifestyle so special.

20 Queens Folly Road Unit 1659, Hilton Head Island

Listing courtesy of Maxey Blackstream Christie's International Real Estate.

$649,900

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511287 MLS

Moss Creek Lifestyle. Move-In Ready. Easy to Love. A rare opportunity to enjoy the Moss Creek lifestyle in a beautifully updated, move-in-ready home that is comfortable, manageable, and easy to love. Located in desirable Royal Pointe, this charming 3-bedroom, 2-bath home offers 1,822 sq. ft. with an open, inviting floor plan and numerous thoughtful improvements throughout. The remodeled kitchen features updated cabinetry, countertops, appliances and finishes and flows effortlessly into the dining and living areas-perfect for everyday living or entertaining. Updated flooring and fresh interior paint give the home a clean, current feel, while the spacious great room, vaulted ceiling and fireplace add warmth and character.The generous primary suite offers excellent closet space and an updated bath, while two additional bedrooms provide flexibility for guests, a home office or hobbies. Outside, enjoy a beautifully refreshed backyard, mature Lowcountry landscaping and private outdoor living space ideal for relaxing or entertaining. A spacious two-car garage provides additional storage and everyday convenience.For buyers looking to downsize, establish a Lowcountry second home or simply enjoy one of the area's most established private communities without taking on an oversized property, this one is especially compelling. Moss Creek offers two golf courses, clubhouse dining, marina and boating amenities, tennis and pickleball, fitness and swimming facilities, nature preserves and miles of leisure trails-all in an incredibly convenient location just before the Hilton Head Island bridge. Updated, well maintained and ready to enjoy from day one, 3 Royal Pointe Drive offers an exceptional combination of lifestyle, location and value.

3 Royal Pointe Drive, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$4,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512244 MLS

Shipyard 1st week full of June! maintence fee is less than 1200.00, so no more guessing, booking, and hoping it's a perfect spot to vacation. This can be your traditional week for life!

35 Egret Point Way Unit 4317, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$1,349,000

3 Beds ⋅ 4 Baths ⋅ HILTONHEAD-512177 MLS

Coastal luxury meets Lowcountry charm in this beautifully remodeled Huntington villa! Boasting 3 bedrooms and 3.5 bathrooms, this immaculate, never-rented property sits right across the street from the beach in the highly coveted Palmetto Dunes Resort. Inside, an open eat-in kitchen concept impresses with quartz countertops and stainless appliances, anchored by warm wood floors and elegant coastal décor. Unwind on the screened porch while gazing out at expansive water views. Living here unlocks a world-class lifestyle featuring three golf courses, premier tennis and pickleball facilities, miles of leisure trails, restaurants, shopping, a marina, and 3 miles of pristine beach. Offered entirely turn-key, this exceptional level of luxury adapts effortlessly to your lifestyle-whether as a primary residence, a seasonal retreat, or a lucrative addition to your investment portfolio.

80 Ocean Lane Unit 7619, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$845,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512238 MLS

Located in a great spot in Sea Pines, this 2 BD, 2 BA Lighthouse Road Villa is an end unit, providing extra privacy and a more open feel. One of the highlights is the large Carolina Room overlooking the peaceful landscape setting, giving you plenty of additional living space to enjoy year round. Inside, you'll find wood floors, a spacious great room with fireplace, and a kitchen with mostly new stainless steel appliances. Recent improvements also include a new washer and dryer, and HVAC system. Just a short walk or bike ride to Sea Pines Beach Club, Harbour Town, and Fraser's Tavern, the villa is being sold turn-key with a strong rental history.

11 Lighthouse Road Unit 24, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC.

$847,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512236 MLS

Imagine waking up on Hilton Head Island, grabbing your coffee, and taking a short stroll to one of the most beautiful beaches in America. This is the island lifestyle people dream about-and now it can be yours. Located in the desirable Beckingham section of Port Royal Village, this beautifully renovated 3-bedroom, 2.5-bath Hilton Head Island condo offers nearly 2,000 square feet of spacious coastal living just moments from Hilton Head Island's world-famous, award-winning beaches. Thoughtfully renovated and beautifully finished, this home combines the easygoing charm of the Lowcountry with the comfort and space of a full-time residence. The highly desirable first-floor primary bedroom makes everyday living effortless, while two additional bedrooms provide plenty of room for family, friends, or a home office. Outside, the large private patio creates your own peaceful retreat-perfect for morning coffee, evening cocktails, grilling after a day at the beach, or simply slowing down and enjoying the coastal air. Dedicated parking adds another layer of everyday convenience. Hilton Head Island was once again named America's Best Island by Condé Nast Traveler readers for the ninth consecutive year, and it doesn't take long to understand why. The island offers 250+ restaurants, more than 70 miles of leisure pathways, 19 public golf courses, incredible parks, boating, fishing, pickleball, tennis, shopping, and exceptional healthcare. Whether your perfect day means biking beneath moss-draped live oaks, playing a morning round of golf, spending the afternoon with your toes in the sand, or finishing the evening over fresh seafood and cocktails, Hilton Head Island makes everyday life feel a little more like vacation. With its generous size, renovated interior, first-floor primary suite, private outdoor living space, dedicated parking, and outstanding proximity to the beach, this Port Royal Village condo offers tremendous versatility. Make it your low-maintenance primary residence on Hilton Head Island, your family's second home at the beach, or take advantage of its great potential as a Hilton Head Island short-term vacation rental investment property. Some properties are simply a place to live. Others represent a completely different way of living. Schedule your private showing or video walkthrough today!

2 Wimbledon Court Unit 114, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$225,000

1 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512049 MLS

Welcome to cozy coastal living in the desirable Marshside community on the north end of Hilton Head Island! This well cared for, updated, and fully furnished 1 bedroom, 1.5 bathroom loft villa is move in ready and priced to sell. The main level offers an inviting living space featuring a cozy fireplace, a convenient half bath, and an updated kitchen equipped with stainless steel appliances. Upstairs, the spacious loft bedroom suite boasts a private full bathroom, a walk-in closet and beautiful sunrise views to start your morning right. Step out onto the back porch to relax and take in the tranquil marsh and landscaped views, perfect for watching local island wildlife. Additional features include an extra exterior storage closet for your beach gear. Residents of Marshside enjoy fantastic community amenities, including a pool, tennis courts, playground, and fitness center. Property is being sold AS-IS with seller to make no repairs (microwave and refrigerator water dispenser as-is; dispenser non-functional). Inspections are welcome.

5 Gumtree Road Unit L-18, Hilton Head Island

Listing courtesy of The Cox Team Brokered by EXP.

$32,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512232 MLS

Welcome to your coastal getaway! Own a deeded 2BR, 2BA quartershare at Brigantine Quarters in Shipyard. Enjoy 13 rotating weeks a year in this beautifully designed residence with vaulted ceilings and a large balcony with golf views. Prime weeks for 2027 include 4th of July and December 18th through New Year's Day 2028. This mini-resort includes tennis, pickleball, pools, a playground, and a private beach gate for BQ owners and guests. Maintenance fee covers appliances, furniture, maintenance upkeep, taxes, Shipyard fees, and more, ensuring a stress-free experience, ideal for personal use or rentals.

55 Barcelona Road Unit 242C, Hilton Head Island

Listing courtesy of The Homesfinder Realty Group.

$3,995,000

5 Beds ⋅ 7 Baths ⋅ HILTONHEAD-512060 MLS

Waterfront living in Wexford doesn't get much better than this and 20 Castlebridge Court offers the ONLY harborfront setting currently available in the community. Set directly on the harbor at the end of a private cul-de-sac, this five-bedroom residence combines exceptional outdoor living with one of the neighborhood's most desirable settings. A heated pool and spa, outdoor fire pit, built-in grilling station, and private dock make the most of life on the water. The spacious floor plan features a grand living room upon entry, adjacent dining room, a generous kitchen enhanced by Sub zero and Viking appliances, two stately gas fireplaces, bonus room, bunk room, three-car garage, and dedicated golf cart bay. The quality of construction does not go unnoticed with solid wood doors, plantation shutters, wide-planked hardwood floors, elevated lighting, and built-in features throughout. Then there is Wexford itself. Boasting a newly redesigned clubhouse with indoor/outdoor dining, community pool, exceptional Arnold Palmer Signature golf, active tennis community, pickle ball, a private marina, and the signature lock-controlled 37 acre inland harbour. The community truly is unlike anything else on Hilton Head Island and for someone looking for harborfront living within Wexford, there is only ONE.

20 Castlebridge Court, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

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