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

$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.

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.

$435,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512305 MLS

Welcome to a rare opportunity in South Forest Beach: a completely updated, open concept layout, turn-key 2-bedroom, 2-bath villa in the sought-after Dunes Villas community, just a short walk from Hilton Head Island's world-renowned beaches. This beautifully renovated upper-level end unit offers the ideal combination of coastal living, privacy, convenience, and investment potential. Thoughtfully updated throughout and sold fully furnished, the villa is ready to enjoy as a personal beach retreat, second home, or income-producing short-term rental. Dunes Villas offers a community pool and on-site parking, while its prime location places you within minutes of the beach, Coligny Plaza, restaurants, shopping, entertainment, and Hilton Head's extensive network of bike paths. With its turnkey condition, desirable 2-bedroom, 2-bathroom layout, pet-friendly appeal, and exceptional location in the heart of the island, this is a very rare opportunity to own a truly special Hilton Head property!

6 Woodward Avenue Unit I2, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$365,000

1 Beds ⋅ 1 Baths ⋅ HILTONHEAD-512279 MLS

Proven rental machine at The Spa on Port Royal Sound, generating approximately $52,000 in rental revenue last year! This 1BR/1BA villa offers sweeping sound views from the private balcony, along with a comfortable coastal interior featuring a king-size bedroom, en-suite bath with walk-in shower, well-equipped kitchen. The oceanfront community offers natural beach access, an observation pier, two outdoor pools, indoor pool, hot tub, dry sauna, fitness center, tennis and basketball courts, and multiple grilling and picnic areas. Enjoy beautiful sandy beaches and stunning sunrises just outside your door. With a strong rental history and an exceptional oceanfront setting, this is a turnkey opportunity for a second home or investment property on Hilton Head Island.

239 Beach City Road Unit 1203, Hilton Head Island

Listing courtesy of Coastal Luxury Real Estate.

$879,000

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512297 MLS

Welcome to effortless Lowcountry living in the desirable Club Course neighborhood of world-famous Sea Pines Resort. This beautifully maintained 3-bedroom, 2-bath Hilton Head Island home is light, bright, and move-in ready, offering the perfect combination of comfort, location, and island lifestyle. Thoughtful updates include new LVP flooring, fresh paint, updated primary bathroom, Trex decking, and a 2025 Trane HVAC system. The spacious back deck is ideal for outdoor dining, entertaining, or relaxing, while the large backyard offers space for a pool and for creating a private oasis. Located near the main gate of Sea Pines, this home provides quick and convenient access to everything Hilton Head Island has to offer while still enjoying the privacy and amenities of one of the island's most iconic communities. Sea Pines is home to three renowned public golf courses, miles of pristine beaches, numerous restaurants, Harbour Town, private owner and guest beach access at Tower Beach, and the exciting redevelopment of South Beach. From biking beneath moss-draped live oaks to golf, boating, dining, and days spent on the beach, the Sea Pines lifestyle is truly hard to beat. Hilton Head Island has also been recognized as the #1 Island in the U.S. for nine consecutive years, further reinforcing why so many people choose to call this special place home. Whether you're searching for a primary residence in Sea Pines, a Hilton Head Island second home, or a short-term rental investment / coastal getaway, this turnkey property is ready for its next owner. Move in, unpack, and start enjoying the Hilton Head Island lifestyle from day one. Schedule your in-person or live video walkthrough today.

157 Otter Road, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$265,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512267 MLS

This beautifully maintained 2-bedroom, 2-bathroom end-unit villa in the gated Woodlake Villas community offers added privacy and comfortable living. Enjoy an array of community amenities, including a pool, fitness center, tennis courts, and playground. Conveniently located near shopping, restaurants, gas stations, and everyday essentials, this villa offers both comfort and convenience. Whether you're looking for a primary residence, second home, or investment property, this is an excellent opportunity to enjoy low-maintenance living in a desirable community.

96 Mathews Drive Unit 218, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$395,000

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512148 MLS

Desirable and spacious 3-bedroom, 2-bath top-floor corner villa in the highly sought-after, beach-oriented Hilton Head Resort! With no neighbors above, this light-filled villa offers added privacy and beautiful lagoon, marsh, golf course, and tennis court views from the private balcony. The updated kitchen features white cabinetry, stainless steel appliances, granite countertops, and a convenient bar area with sink. Smooth ceilings and LVP flooring throughout create a clean, modern feel. Additional updates include a brand-new in-unit washer and dryer and new HVAC system. Hilton Head Resort offers an exceptional array of amenities, including two outdoor pools, an indoor pool, spa, sauna, jacuzzi, fitness room, and multiple tennis and pickleball courts. Enjoy seasonal dining at the main pool, plus convenient beach access via the private boardwalk with seasonal shuttle service, beach bar, and grill. Strong rental history makes this an excellent opportunity as a vacation getaway, investment property, or both!

663 William Hilton Parkway Unit 4420, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$760,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512291 MLS

Turnkey single-level 3-bedroom, 3-bath home blending Lowcountry charm and refined design on over 1/3 acre with peaceful views of Hilton Head Plantation's venerable Dolphin Head Golf Course. Reimagined from the studs in 2019, the light-filled layout with exposed wood beams, tray ceilings, tongue-and-groove accents, custom trim and premium fixtures throughout. The bright eat-in kitchen features Fantasy Brown dolomitic marble, Walker Zanger tile, soft-close cabinetry, high-end Bosch and GE Profile appliances including induction cooktop. Both the primary suite and sunken living room open to the tabby shell back patio with hot tub and grilling area. Inside, the woodburning fireplace and vaulted living room ceiling add warmth and character. Major systems replaced in 2019 include: new roof, energy-efficient windows, HVAC, ductwork, water heater, plumbing, wiring, new LVP, tile flooring and a refreshed garage with epoxy floors, craftsman-inspired lighting and carriage-style door. A short walk or ride to the clubhouse, Dolphin Cafe and Hilton Head Plantation's resort amenities. A beautifully upgraded retreat ready to welcome you home.

27 Pineland Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$199,000

HILTONHEAD-512270 MLS

Solitude on this remote street, yet a short path to amenities makes this the perfect blend of privacy and convenience on this meticulously maintained, oversized lot. Featuring immaculate stamped concrete pad and extensive landscaping, this site easily accommodates a 45-foot motorcoach. Priced unfurnished. Just steps from the pool, racquet sports, clubhouse, playground and laundry facilities. Beyond the front gates, enjoy convenient access to shopping, dining, the beach, bike paths and the town trolley. Experience the #1 Motorcoach Resort on the #1 island destination in America - an exceptional blend of lifestyle and investment.

133 Arrow Road Unit 81, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

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