Hh Resort/Four Seasons Homes with Pickleball Association Amenities

Welcome to HH Resort/Four Seasons, a hidden gem nestled in the beautiful Hilton Head Island, South Carolina. This charming subdivision is situated in the heart of Beaufort County, offering residents a perfect blend of coastal living and vibrant community spirit. With its lush landscapes and stunning natural surroundings, HH Resort/Four Seasons is an idyllic retreat for families, retirees, and everyone in between.

One of the standout features of this remarkable community is its commitment to an active lifestyle, highlighted by the exclusive Pickleball Association amenities. Whether you're a seasoned player or a newcomer eager to learn, the pickleball courts provide an inviting atmosphere to enjoy this fast-growing sport. Engage in friendly matches with neighbors, participate in organized tournaments, or simply hone your skills in a supportive environment. The sense of camaraderie cultivated here is unmatched, making it easy to forge lasting friendships.

In addition to pickleball, residents can take advantage of beautifully landscaped parks, walking trails, and other recreational facilities that promote an active lifestyle. The nearby beaches, world-class golf courses, and an array of dining and shopping options further enhance the appeal of this community.

Homes in HH Resort/Four Seasons are designed with comfort and style in mind, showcasing a variety of architectural styles that cater to diverse tastes. With spacious layouts, modern amenities, and a focus on outdoor living, these homes are perfect for those seeking a peaceful yet vibrant community.

Experience the best of Hilton Head Island living at HH Resort/Four Seasons, where every day feels like a vacation. Come and discover the perfect place to call home!

Newest Hh Resort/Four Seasons Homes with Pickleball Association Amenities

$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.

$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.

$245,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512100 MLS

Welcome to this light and bright 2-bedroom, 2-bath villa in Hilton Head Resort Villas, one of Hilton Head Island's most sought-after direct beach access communities. Perfectly positioned in the heart of the island, this turn-key villa offers an ideal blend of lifestyle, convenience, and strong short-term rental potential. Enjoy direct beach access via a private boardwalk, making beach days effortless for owners and guests alike. Inside, the villa features an updated kitchen with stainless steel appliances, modern finishes, and updated lighting throughout, creating a fresh, coastal feel that's both inviting and functional. The open layout maximizes natural light, making this villa feel comfortable and welcoming from the moment you step inside. Hilton Head Resort Villas is renowned for its resort-style amenities, including indoor pools and a Jacuzzi, two outdoor pools with a poolside bar, tennis courts, a sauna, fitness center, game room, and 24-hour security gate. Whether you're relaxing poolside, heading to the beach, or enjoying the on-site amenities, everything you need is right at your doorstep. This villa also shines as an investment property, with recent gross rental income of approximately $40,000, making it an excellent option for buyers seeking a proven short-term rental on Hilton Head Island. Equally appealing as a second home, the location offers quick access to shopping, dining, golf courses, and all the island has to offer. Offered fully turn-key, this is a rare opportunity to own a Hilton Head Island beach villa that delivers on lifestyle, income, and long-term value.

663 William Hilton Parkway Unit 3417, Hilton Head Island

Listing courtesy of EXIT Hilton Head Realty.

$369,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511958 MLS

Featuring captivating 120 degree views of the Atlantic ocean, Folly Field estuary, and the 10th fairway of the Robert Trent Jones Course at Palmetto Dunes, this immaculately renovated 4th-floor villa marries modern comfort with timeless coastal charm. Recent updates include a new water heater, range/oven, fresh paint, ceiling fans, paneling removed, and contemporary furnishings. Hilton Head Resort is a 24-hour gated community, and is renowned for its amenities including direct beach access via an elevated marsh boardwalk, complementary seasonal shuttle, two outdoor pools, one indoor pool, a hot tub, sauna, steam room, a running track, six lighted tennis/pickleball courts, gym, atrium, grilling/picnic area, an on-site seasonal restaurant/bar, the iconic Coco's Beach Bar featuring dune-side sand volleyball courts, and elevator access. Combining undeniable short-term rental appeal with true ROI potential, this unique villa represents a rare opportunity to acquire a turnkey two-bedroom ocean view condo on Hilton Head Island for under $400k.

663 William Hilton Parkway Unit 2402, Hilton Head Island

Listing courtesy of FATHOM REALTY.

$259,990

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511405 MLS

Recently refreshed with fresh paint and stylish new furnishings, this ocean-oriented 2-bedroom villa is truly turnkey and ready to enjoy. Whether you're searching for a personal vacation getaway, an income-producing investment, or the perfect combination of both, 4104 Hilton Head Resort presents an exceptional opportunity. With existing reservations already in place, this villa offers immediate rental income potential while giving future owners the flexibility to enjoy everything Hilton Head Island has to offer. Located within the gated Hilton Head Resort community, owners and guests enjoy an impressive collection of resort-style amenities, including indoor and outdoor pools, tennis courts, a fitness center, game room, private beach access, and Coco's on the Beach. Conveniently situated near championship golf courses, shopping, dining, and miles of pristine beaches, this low-maintenance villa makes island living effortless. Whether you're expanding your investment portfolio, purchasing your own coastal retreat, or seeking a property that offers the best of both worlds, this beautifully updated villa delivers outstanding value in one of Hilton Head Island's most amenity-rich beach communities.

663 William Hilton Parkway Unit 4104, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$399,500

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511307 MLS

Lowest-Priced 3-Bedroom Condo on Hilton Head Island. Turnkey Short-Term Rental Steps from the Beach. Discover the most affordable 3-bedroom villa on Hilton Head Island, a rare opportunity for investors and vacation home buyers alike. This spacious 3-bedroom, 2-bathroom condo sits just steps from the beach and Coco's oceanfront restaurant and bar. Completely transformed with stylish laminate flooring, smooth ceilings, and updated tile showers, it offers a fresh, modern feel throughout. Sold fully furnished with in-unit laundry, the villa is entirely move-in ready, whether for guests or your own getaway, and comes with a proven short-term rental history that helps generate income to offset ownership costs. Residents also enjoy a gated, resort-style community with 24/7 security, a fitness center, indoor track, indoor pool and spa, game room, pickleball, an on-site restaurant, six tennis courts, and two outdoor pools. With unbeatable amenities and a price point unmatched on the island, this villa won't last. Schedule your showing today.

663 William Hilton Parkway Unit 3321, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$299,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511168 MLS

Beautifully Renovated 2-Bedroom Villa with Direct Pool Views - Closest Building to the Beach! This is the beach getaway you've been waiting for! This stunning, fully renovated 2-bedroom villa at Hilton Head Resort offers a beautiful direct view of the heated outdoor pool from your front porch. No detail has been overlooked in this top-to-bottom renovation. Upgrades include shiplap accent walls, stylish barn doors, smooth ceilings, new ductwork, luxury vinyl plank flooring with a coastal feel, recessed lighting, closet lighting, all-new ceiling fans and light fixtures, a completely remodeled kitchen with new cabinetry, countertops, and appliances, plus beautifully updated bathrooms. The primary bath even features a lighted makeup magnifying mirror for added convenience. Sold fully furnished, this villa is truly turnkey - start enjoying it immediately after closing, whether as your personal beach retreat or a vacation rental investment. Hilton Head Resort offers an outstanding lineup of resort-style amenities, including: 7-minute walk to the beach or seasonal golf cart shuttle service. Poolside restaurant just downstairs. Oceanfront bar and grill. Indoor heated pool. Two outdoor pools, including another heated pool just outside your kitchen window! Indoor 1/10th mile jogging track, Hot tub, sauna, and steam room. Tennis and pickleball courts, Beach volleyball, Fitness center, Kiddie pool and Picnic area with BBQ grills. Whether you're looking for a second home, investment property, or both, this beautifully updated villa combines an unbeatable location, exceptional amenities, and true move-in-ready convenience. Come experience everything this incredible property and The Hilton Head Resort have to offer!

663 William Hilton Parkway Unit 1223, Hilton Head Island

Listing courtesy of Hilton Head Isl Realty.

$325,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511159 MLS

Welcome to Unit 4129 at Hilton Head Resort, a beautifully furnished 2-bedroom, 2-bath villa offering the perfect blend of comfort, convenience, and resort-style living. This turnkey property features durable tile and laminate flooring throughout, making it ideal as a primary residence, vacation getaway, or investment property.The fully equipped kitchen boasts granite countertops, maple cabinetry, and a cozy dinette area for casual dining. Have peace of mind knowing the HVAC was just replaced 2023! The villa is being sold fully furnished and includes TVs in every room, a sleeper sofa for additional guests, and everything needed to begin enjoying the coastal lifestyle immediately.Relax on the private covered porch overlooking the outdoor tennis courts and swaying palm trees-a peaceful setting to enjoy your morning coffee or unwind after a day at the beach.Hilton Head Resort offers an exceptional array of amenities, including private beach access via a scenic boardwalk or complimentary golf cart shuttle, six free tennis courts, two outdoor pools, an indoor heated pool, indoor hot tub, sauna, steam room, fitness center with Nautilus equipment, indoor running track, badminton, volleyball, picnic areas, bicycling, and nearby surfing opportunities. Owners and guests also enjoy the oceanfront cabana and Coco's on the Beach, the resort's popular beachfront bar and grill. Free Wi-Fi is available throughout the resort. Ideally located just minutes from Palmetto Dunes, Shelter Cove, championship golf, shopping, dining, entertainment, and all that Hilton Head Island has to offer, Unit 4129 is your opportunity to own an affordable slice of paradise with outstanding rental potential.

663 William Hilton Parkway Unit 4129, Hilton Head Island

Listing courtesy of Family Tides Real Estate LLC.

$275,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-510822 MLS

This TURN-KEY, top-floor 2-bedroom, 2-bath villa at Hilton Head Resort offers one of the best ocean-side values on Hilton Head ... thoughtfully renovated with new LVP FLOORING, SMOOTH CEILINGS, an UPGRADED KITCHEN, quality furnishings, a NEW HVAC in 2020, and a brand-new tiled kitchen backsplash ... the baths feature floor-to-ceiling tile, giving the villa a clean, updated feel throughout ... enjoy a convenient building location with tennis and pickleball courts just below the front porch, BBQ grills and picnic space just out back, and an outdoor pool just down the hall at ground level ... bring your furniture, decorations, or rental setup and start enjoying an easy beach getaway from day one ... Hilton Head Resort is a gated community known for direct beach access by scenic marsh boardwalk with seasonal shuttle, two outdoor pools, one indoor pool, running track, tennis courts, sauna, jacuzzi, fitness room, atrium, beach bar, restaurant, and volleyball ... just steps to the ocean and a short bike ride to Shelter Cove Marina & Towne Centre.

663 William Hilton Parkway Unit 4432, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$279,999

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-510133 MLS

Just a short walk from the beach, this turnkey top-floor 2BR/2BA villa offers a bright coastal interior, a rare private screened-in rear balcony, and a proven short-term rental history exceeding $30,000 annually. Backed by a 4.97-star Airbnb rating, Guest Favorite designation, and Superhost status, this property delivers privacy, enjoyment and return-making it the ideal Hilton Head getaway or investment opportunity.Fully furnished and vacation-ready, the bright coastal-inspired interior is highlighted by LVP flooring, smooth ceilings, recessed lighting, and an open-concept layout that flows seamlessly from kitchen to living area. The kitchen features quartz countertops, modern fixtures, and a functional design suited for both everyday use and high-volume vacation rental stays.The screened-in rear balcony offers a quieter, more private outdoor space than typical units in the community, enhancing guest experience and overall rental desirability.A comfortable primary suite includes a private en-suite bath, while the guest bedroom is thoughtfully configured with a bunk bed and full-size bed to maximize flexibility for families and rental use.Stroll down the scenic marsh boardwalk leading directly from the resort to the Atlantic shoreline and the iconic Coco's Beach Bar. Located in Hilton Head Resort, a gated oceanfront community on Hilton Head Island, residents and guests enjoy resort-style amenities including three pools (two outdoor and one indoor), six lighted tennis courts, a fitness center, indoor running track, and on-site dining options. An exceptional opportunity to own a proven income-producing vacation rental and private beach getaway!

663 William Hilton Parkway Unit 4431, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$258,900

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-509246 MLS

This unit located in the oceanfront complex of Hilton Head Resort was remodeled by Hilton Head Builders and is well-established on the short-term rental market. A 2-bedroom, 2-bath condo offering the perfect blend of comfort and investment potential. Features include a full size kitchen with island, spacious bedrooms, updated furnishings, and a tankless water heater, all contribute to a clean, comfortable, and turnkey experience. Hilton Head Resort is a gated oceanfront community offering direct beach access and an impressive lineup of resort-style amenities, including an oceanfront tiki bar, fitness center, three pools (two outdoor and one indoor), tennis courts, bike rentals, and more. Its unique combination of indoor and outdoor amenities, paired with easy beach access, makes Hilton Head Resort one of Hilton Head Island's most appealing year-round short-term rental destinations.

663 William Hilton Parkway Unit 3317, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$295,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-508845 MLS

Come to Hilton Head Island for the beaches, sunshine and great restaurants. Our 2 bedroom/2 bath updated beach condo on the first floor includes many amenities for your vacation enjoyment. The beach is just a short boardwalk away or take the free golf cart shuttle. New HVAC in 2022 and a total remodel in 2018 with granite countertops, new floors, cabinets and showers. Comes fully furnished with a king size bed, a queen size bed, sofa and two smart tvs- 60" and 42". Just bring your toothbrush and family. The Resort is a complete beach resort with many amenities: an indoor pool and hot tub, sauna, two outdoor pools, six tennis courts, indoor running track, fitness room, private boardwalk - to ocean beach approximately 5 minute walk, and oceanfront bar and grill - Cocos. The Beach Bear and poolside bar offer drinks and food for adults and children. It's also a mini convenience store. Great mid island location on main bike path close to Whole Foods and Kroger with Starbucks.

663 William Hilton Parkway Unit 2121, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

Start Your Search

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.