Holiday Homes Real Estate

Welcome to Holiday Homes, a charming subdivision nestled in the heart of Hilton Head Island, South Carolina. This picturesque community is the perfect blend of tranquility and vibrant coastal living, making it an ideal destination for families, retirees, and anyone seeking a serene escape.

Holiday Homes offers a variety of thoughtfully designed properties, each showcasing unique architectural styles that reflect the island’s coastal charm. With lush landscaping and well-maintained streets, this subdivision creates a warm and inviting atmosphere. Residents enjoy access to a variety of amenities, including community parks, playgrounds, and walking trails that encourage an active lifestyle.

One of the most appealing aspects of Holiday Homes is its proximity to Hilton Head Island's stunning beaches. Just a short drive away, you’ll find miles of pristine coastline, perfect for sunbathing, swimming, and enjoying water sports. The area is also home to world-class golf courses, tennis clubs, and a variety of dining and shopping options, ensuring that residents have everything they need right at their fingertips.

The community is well-connected, offering easy access to major roads and local attractions, while still maintaining a sense of seclusion. With its friendly neighbors and strong sense of community, Holiday Homes is not just a place to live; it’s a place to create lasting memories.

Whether you're looking for a permanent residence or a vacation getaway, Holiday Homes in Hilton Head Island promises a lifestyle filled with relaxation, adventure, and the beauty of coastal living. Come discover your dream home in this idyllic subdivision today!

Newest Listings in Holiday Homes

$2,295,000

7 Beds ⋅ 5 Baths ⋅ HILTONHEAD-509321 MLS

Brand-new 7-Bedroom, 4.5 Bath Hilton Head Island home with private pool, and elevator to all floors. This spacious luxury home features 10-foot ceilings on the main level, and in the primary suite, 9-foot ceilings upstairs, wide-plank flooring, a hand-hewn exposed beam ceiling from reclaimed wood, an electric fireplace, and a grand staircase with a chandelier. The chef's kitchen includes quartz countertops, built-in wine chiller, Forno gas double oven and stove, Forno double refrigerator/freezer combo, stainless appliances, and oversized island. Dual sliders open from the living room to a huge covered balcony. The home offers two laundry areas, a first-floor primary suite with dual vanities, four bedrooms upstairs, two additional garage-level bedrooms, and an oversized garage. Enjoy an in-ground private pool, large side yard, and generous spacing from neighboring homes. Ideal as a primary residence, second home, or investment property. Listed price is for the real property only. Turnkey Pottery Barn furniture package available for separate purchase by bill of sale.

37 Oleander Street, Hilton Head Island

Courtesy of RE/MAX Island Realty

$955,000

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-508893 MLS

Nestled just steps from the ocean, this charming beach cottage offers the perfect blend of coastal comfort and relaxed seaside living. Three bedrooms and two full baths plus a huge kitchen, breakfast room and light-filled great room. A huge laundry room/mud room is great for extra storage. A one-car carport keeps your car out of the sun. The massive backyard is fenced and has an oversized deck with a hot tub, a sandy area great for your hammock, and a storage shed. The impressive live oak tree welcomes you as you drive up. With sunlit interiors, breezy open spaces, and thoughtfully curated décor inspired by the ocean, the cottage creates a warm and inviting weekend getaway or permanent beach home. Spend mornings on the back deck enjoying a cup of coffee, afternoons spent on sandy beaches, and evenings under stunning coastal sunsets. Whether you're seeking a peaceful getaway or a memorable beachside escape, this cottage provides a cozy haven where every day feels like a vacation. Folly Field is a quaint community just a short stroll to Nalas Beach Bar, a short bike ride to Shelter Cove, and all of its fun spots (restaurants, shopping, nightlife, and waterfront activities). This home has been lovingly updated and you will be totally impressed!

8 Azalea Street, Hilton Head Island

Courtesy of Charter One Realty

$2,295,000

7 Beds ⋅ 5 Baths ⋅ HILTONHEAD-506962 MLS

35 Oleander Street, Hilton Head Island

Courtesy of RE/MAX Island Realty

$1,799,999

4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-452326 MLS

Stunning Custom-Built 4-Bedroom Home in Prime Folly Field, Hilton Head - Steps from the Beach. Discover your dream coastal retreat in the highly desirable Folly Field neighborhood of Hilton Head Island. This exceptional custom-built 4-bedroom (plus unique loft), 3-bath home offers 2,523 square feet of timeless elegance and modern luxury on a generous lot. Just a short 7-10 minute stroll to Folly Field Beach Park, this property delivers the perfect blend of beach access, privacy, and investment potential. Step inside to an inviting open-concept floor plan flooded with natural light. Soaring vaulted ceilings and a dramatic wall of windows frame the gorgeous great room, creating an airy, spacious feel ideal for relaxing and entertaining. The chef's dream gourmet kitchen features elegant marble countertops, high-end stainless steel appliances (including a premium Bertazzoni range, Bosch, and Blomberg), and beautiful custom stone and tile work. Charming barn doors, a step-down living area, and an expansive balcony add character and functionality. Bonus First-Floor Apartment: This home includes a completely separate 1-bedroom, 1-bath apartment with its own full kitchen and private lanai - offering two distinct living/rental units for the price of one. Whether you're looking for a primary residence, second home, or turnkey investment, the strong short-term rental demand in Folly Field makes this a high-performing opportunity.

9 Mimosa St, Hilton Head Island

Courtesy of Charter One Realty

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.

This information is deemed reliable, but not guaranteed. Neither the Lowcountry Regional MLS, nor the listing broker, nor their agents or subagents are responsible for the accuracy of the information. The buyer is responsible for verifying all information. This information is provided by the Lowcountry Regional MLS for use by its members and is not intended for use for any other purpose.