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

$729,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512327 MLS

Easygoing Oceanfront Escape at Beachwood Place. Enjoy easy island living in this charming second-floor, oceanfront villa at Beachwood Place. This two-bedroom retreat offers beautiful ocean and pool views, a private balcony, and the relaxed setting of a small, gated complex. Step outside and enjoy the beach just beyond your door, or take a short stroll or bike ride to the shops, restaurants, and lively atmosphere of Coligny Plaza. With its oceanfront location, convenient setting, and laid-back Lowcountry feel, this is a wonderful place to enjoy everything Hilton Head Island has to offer.

15 S Forest Beach Drive Unit 2G, Hilton Head Island

Listing courtesy of Century 21 Integra.

$59,000

HILTONHEAD-512326 MLS

Easy in-and-out location on C dock. Windmill Harbour is one of the most highly sought-after marinas on the entire east coast. Enjoy a 30' boatslip in a secure, locked marina, providing convenience and peace of mind with access to your vessel. The marina offers tide-free docking, controlled access, and immediate deep water once you have exited the lock system. If you would like fine & casual dining and social activities, the South Carolina Yacht Club is just steps away. Easy parking for non-residents. Seller is also selling the boat that is currently in the slip - boat price is $53,000.00

C53 Windmill Harbour Marina, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,650

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512324 MLS

Your Spicebush Fall Week 37 Awaits! Tucked within the heart of Hilton Head Island's prestigious Sea Pines community, this ownership places you just moments from the Sea Pines Beach Club and Plantation Club Golf Course. Perfectly situated, your Spicebush Week 37 offers effortless access to world-class golf, pristine beaches, waterfront dining, and the island's most celebrated events. Embrace coastal living at its best-start your mornings by the sea, unwind beneath golden sunsets, and savor the timeless charm of Sea Pines Resort. With refined, low-maintenance ownership, your annual island escape is always ready when you are.

124 N Sea Pines Drive Unit 582, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$1,500

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512325 MLS

Own Your Late Winter Escape! Make Hilton Head your tranquil tradition! Enjoy the islands serene off-season with deeded ownership of Week 8 at Swallowtail, nestled in the heart of Hilton Heads prestigious Sea Pines community. Perfectly positioned between the iconic Harbour Town Lighthouse and the Beach Club, this property places you steps from world-class golf, uncrowded beaches, waterfront dining, and early-spring cultural events. Experience coastal living at its most peaceful stroll mild, sunny beaches, sail into crisp sunset evenings, and savor the charm of Harbour Town without the crowds. With luxurious, low-maintenance ownership, your late-winter retreat is forever waiting.

70 Lighthouse Road Unit 2875, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$650,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512322 MLS

Location. Lifestyle. Condition. Value. 36 Ocean Breeze has it all! Discover an outstanding villa in a fantastic Forest Beach location, just a short stroll from Hilton Head Island's sugar-white sandy beach and the many shops, restaurants, and activities at Coligny Plaza. Add to that the year-round events at Lowcountry Celebration Park, including outdoor concerts by the Hilton Head Symphony Orchestra and a variety of festivals, and you have a location that makes enjoying the best of the island easy.36 Ocean Breeze is a totally updated three-bedroom, three-full-bath villa that truly feels like home. Updated from top to bottom, the villa features new flooring, new kitchen countertops and appliances, beautifully updated bathrooms, a new HVAC system, and much more. The floor plan is both comfortable and versatile, with a first-floor bedroom featuring bunk beds and two spacious bedrooms on the second floor. Step outside onto the back deck and enjoy a peaceful view overlooking a lagoon with a fountain-the perfect setting for morning coffee, an afternoon break, or an evening beverage after a day at the beach. Whether you're looking for a rental or a permanent home, or a second home at the beach, 36 Ocean Breeze offers an exceptional opportunity to own a beautifully updated villa in one of Hilton Head's most desirable locations. Great Location. Great Floor Plan. First-Class Condition. Outstanding Value. 36 Ocean Breeze has it all. Isn't it time for you to start making lasting beach‌‌‌‌‌‌‌‌‌‌‌‌ memories?

19 Lemoyne Avenue Unit 36, Hilton Head Island

Listing courtesy of Charter One Realty.

$459,600

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512283 MLS

Welcome to Treetops, ideally located in the heart of South Forest Beach just minutes from the beach, Coligny Plaza, Celebration Park, shopping, dining, and miles of Hilton Head Island bike paths. This 2-bedroom, 2.5-bath townhome-style villa features an updated kitchen, LVP flooring, and a new HVAC system. The main level offers comfortable living and dining areas, a convenient powder room, and a private patio for enjoying the outdoors. Upstairs, both bedrooms and full baths offer added privacy, along with access to an upper-level balcony. Ideally situated within the community, this villa is one of the closest units to the pool. Treetops offers multiple community pools and tennis courts and is a pet-friendly community that allows short-term rentals while also being home to many full-time residents. Enjoy the relaxed Lowcountry lifestyle from this convenient South Forest Beach location-perfect as a primary residence, second home, or Hilton Head getaway.

137 Cordillo Parkway Unit 6603, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$525,000

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512321 MLS

Opportunity to own a first-class villa in the heart of Forest Beach! Welcome to 1005 Tanglewood Villa, a beautifully updated 2-bedroom, 2-bath villa ideally located just a short distance from Hilton Head Island's sandy beaches, Coligny Plaza, Lowcountry Celebration Park, and the many attractions that make Forest Beach such a special place to own... As a second-floor villa, 1005 Tanglewood offers something truly special from its private balcony-a wonderful view overlooking the tranquil lagoon and fountain below. It is the perfect setting for morning coffee, an afternoon break, or relaxing after a day at the beach. Inside, this villa has been totally updated with quality finishes throughout. The flooring, kitchen countertops, appliances, and bathrooms have all been updated, creating a fresh and inviting coastal feel. The villa is offered with very nice furnishings, making it easy to envision as a turnkey second home or vacation rental. The complex also features a relaxing community pool, providing another place to unwind and enjoy the Hilton Head lifestyle. Whether you're looking for a successful short-term rental opportunity, a second home, or your own place at the beach where family and friends can gather and create lasting memories, 1005 Tanglewood Villa is an opportunity worth seeing. Come see why 1005 Tanglewood could be the perfect place to own your own piece of Hilton Head Island.

9 Tanglewood Drive Unit 1005, Hilton Head Island

Listing courtesy of Charter One Realty.

$417,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512313 MLS

Welcome to Admirals Row, a Hilton Head Island villa offering ocean views and resort-style living. This beautifully updated 2BD/2BA unit features NEW smooth ceilings throughout, sunrise views from the private balcony, and easy beach access. Enjoy a modern kitchen with granite countertops and stainless steel appliances. Sold FULLY FURNISHED and move-in ready! BEST PRICED UPDATED 2-BEDROOM in all of Beach & Tennis. Amenities include pools, restaurants, beach bar, bike rentals, tennis, and 12 brand-new pickleball courts. Great rental income potential!

40 Folly Field Road Unit 340, Hilton Head Island

Listing courtesy of Peirce Group Brokered by EXP Realty LLC.

$985,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512084 MLS

Welcome home to this beautifully maintained 3-bedroom, 3-bath residence offering exceptional curb appeal and a warm, welcoming atmosphere in the desirable Headlands section of Hilton Head Plantation. Perfectly positioned to enjoy picturesque golf views of the 18th hole of Bear Creek Golf Club, this move-in ready home has been lovingly cared for by its current owner. Inside, you'll find luxury vinyl plank flooring throughout most of the home, creating a seamless and stylish living space. The inviting living room features a cozy gas fireplace, while the kitchen is equipped with stainless steel appliances. The enclosed porch has been thoughtfully converted into an additional living space, providing even more room to relax, entertain, or simply enjoy the beautiful golf course views year-round. A brand-new HVAC system adds peace of mind, making this home as practical as it is inviting. Combining comfort, quality, and an outstanding location, this home is truly move-in ready and offers the perfect opportunity to enjoy the Hilton Head Plantation lifestyle. Virtually staged photos are meant to provide spatial information and decor inspiration. No structural modifications have been made.

5 Oyster Rake Court, Hilton Head Island

Listing courtesy of Collins Group Realty.

$1,095,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512031 MLS

Open ocean views, proven rentals, and Leamington prestige! 410 Barrington Court is a 2-bedroom / 2-bathroom villa with proven rental performance and projected annual gross rental revenue over $84K, offering a strong blend of income opportunity and second-home enjoyment within Palmetto Dunes Oceanfront Resort. Tucked in one of the most peaceful sections on Ocean Lane, the villa opens to an expansive private balcony designed for dining, lounging, and enjoying oceanfront views, with ocean views carried into both bedrooms. Consistently well maintained by the original owner, the villa features an ideal floor plan with spacious living and dining areas, bedrooms positioned on opposite sides for privacy, and a generous master suite with balcony access and a beautifully renovated walk-in shower. Recent improvements include all new LVP flooring, renovated bathrooms, fresh paint throughout including doors/trim/baseboards, HVAC (2020), dishwasher (2026), and new bedding (not pictured). Barrington Court offers an oceanfront pool and hot tub, pool pavilion with restrooms, grilling area, outdoor showers, covered parking, and designated owner storage locker in the garage for beach gear, golf clubs, and more-all set among beautiful lagoons, lush landscaping, and scenic walkways. Enjoy access to Palmetto Dunes' three miles of beach, tennis/pickleball, three golf courses, 11-mile lagoon system, trails, and dining, plus easy access across William Hilton Parkway to Shelter Cove Harbour & Marina for waterfront dining, shopping, watersports, seasonal activities and live entertainment.

77 Ocean Lane Unit 410, Hilton Head Island

Listing courtesy of Greenplate Group Brokered by eXp Realty.

$749,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512113 MLS

Enjoy coastal living in this beautifully updated 3-bedroom, 2.5-bath condo in Shipyard on Hilton Head Island. New windows and doors on the front of the condo add to the home's fresh, updated feel. The bright kitchen features white cabinetry, stainless steel appliances, a tiled backsplash, and a convenient breakfast/dining area. The spacious living room opens to a private patio and wooded surroundings, creating an inviting space to relax or entertain. The primary suite offers a generous bedroom, ceiling fan, and updated en-suite bath, while two additional bedrooms provide comfortable space for guests. Enjoy Shipyard amenities including a community pool, golf privileges, and easy access to Hilton Head's beaches.

90 Gloucester Road Unit 1003, Hilton Head Island

Listing courtesy of Peirce Group Brokered by EXP Realty LLC.

$299,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512308 MLS

Wake up to Lowcountry Beach living at its most effortless in this beautifully updated two bedroom, two bath villa at The Spa at Port Royal Sound, one of Hilton Head's most amenity rich resort communities. Step inside to an open living and dining layout anchored by warm and inviting LVP flooring that flows throughout the main living space. The dining area sits open to a fully renovated kitchen finished with crisp white cabinetry, granite countertops, subway tile backsplash, and a full suite of stainless steel appliances including refrigerator, range, and dishwasher. It's a kitchen built for both everyday living and easy entertaining.The primary suite offers a private retreat with an en suite bath featuring a sleek frameless glass shower enclosure and clean, modern finishes. The second bedroom and full bath provide comfortable flexibility for guests, family, or a home office setup, with the guest bath finished in a soothing sage green palette, a tub and shower combo, and elegant sconce lighting. A washer and dryer inside the unit add everyday convenience that's hard to find at this price point in a resort community. Just off the living area, a screened porch extends your living space outdoors, the perfect spot for morning coffee or an evening breeze, overlooking lush landscaping with tennis court views just beyond the tree line. Beyond the walls of this villa, The Spa at Port Royal Sound delivers a well appointed resort lifestyle: two outdoor pools, an indoor pool, hot tub, dry sauna, tennis and pickleball courts, hammocks, and community grilling areas, all just steps from your front door. Whether you're looking for a full time coastal residence, a second home, or a turnkey investment property, this villa offers the space, updates, and lifestyle amenities that make Hilton Head living so desirable. Don't miss this opportunity to own a move in ready two bedroom villa in one of the island's best priced resort communities.

239 Beach City Road Unit 3123, Hilton Head Island

Listing courtesy of EXP Realty LLC.

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