Luxury rentals in Chatham County

Villa in Hilton Head Island

A tranquil pool is surrounded by a paved patio, featuring a tanning shelf and a small waterfall. Lush greenery offers privacy, while scenic golf-course views extend beyond the property. Sunlight filters through leafy trees, creating a serene outdoor setting.

Stoney Creek

Sunshine gleams on the greens just outside this golf-course-view hideaway on Hilton Head Island. From the front, it brims with traditionally inspired bungalow style; in back, there’s a laid-back outdoor entertaining area facing the fairways. Walk to the Harbour Town lighthouse and marina for shopping and dining in a quaint setting or bike to the beach on the Atlantic side of the island. The villa’s backyard is laid out around a piano-shaped pool with a tanning shelf and waterfall. Spend the afternoon splashing here, taking breaks to sip lemonade in the shaded sitting area or catch highlights on the outdoor TV. Then heat up the barbecue for dinner at the alfresco table and a marshmallow roast in the firepit, and finish the evening with a little friendly competition around the pool table in the games room. The golf-course views are the focal point of the U-shaped great room and its slide-away glass-door wall leading to the porch. But even non-players will appreciate the soft mint-and-cream sitting area, the farmhouse-style dining table, and the breakfast bar lining the fully equipped kitchen. This villa is a half-mile walk from Harbour Town, where you can find one-of-a-kind art in the galleries, dine on fresh seafood and steaks, climb the classic red-and-white-striped lighthouse, and set off on fishing charters or dolphin-spotting tours from the marina. Cycle to the beach on the provided beach-cruiser bikes or take the Sea Pines trolley over. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Dual vanity, Walk-in closet, Television • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Dual vanity, Television • Bedroom 3: 2 Double size bunk beds, Jack & Jill bathroom shared with bedroom #4, Shower/bathtub combo, Dual vanity, Television • Bedroom 4: Queen size bed, Jack & Jill bathroom shared with bedroom #3, Shower/bathtub combo, Dual vanity, Television • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower, Dual vanity, Walk-in closet, Television FEATURES & AMENITIES • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

An inviting outdoor space features a spacious pool surrounded by multiple lounge chairs. Tall trees provide natural shade, while the warm glow of sunset enhances the serene atmosphere. A decorative sculpture stands prominently, adding an artistic touch to the landscape.

5 out of 5 average rating, 6 reviews

8 Heritage

Welcome to your home away from home in charming Hilton Head. Inside, earthy tones and wicker accents are set ablaze with natural light. Effortlessly transition from the contemporary indoors to the sprawling outdoor area which features plenty of space for al fresco dining and lounging under the sun. The spacious pool awaits to envelope you in a refreshing plunge. Stargaze with a glass of champagne. Copyright © Luxury Retreats. All rights reserved.

A spacious living area is designed with two brown armchairs and light-colored sofas, complemented by a decorative coffee table. A modern fireplace is positioned beneath a large window, providing views of the outdoors, while wooden beams adorn the ceiling, enhancing the room's character.

5 out of 5 average rating, 5 reviews

1872 Beachside Tennis Villa

Surrounded by lush vegetation on Hilton Head Island, this cozy residence features a superb blend of sun and shade. From the tiled terrace, steps lead into the turquoise pool. The heart of the village is a brief bike ride away. Discover waterfront restaurants, unique shops, and activities for the whole family. A 5-minute stroll is all it takes to sink your toes into the toasted sand at the beach. Copyright © Luxury Retreats. All rights reserved.

Apartment in Hilton Head Island

1875 Beachside Tennis Villas

Welcome to BESTNEST/Luxe: An Elevated Experience in Vacationing, and the Luxe property at 1875 Beachside Tennis Villas at South Beach in Sea Pines. Enjoy the ultimate in vacation rental accommodations on Hilton Head Island, featuring a carefully curated collection of homes and villas, chosen with the discerning traveler in mind, fabulously stocked, outfitted, and equipped, and supported by your personal property concierge, available 24/7.

A spacious backyard is highlighted by a private swimming pool surrounded by lounging chairs. Shade is provided by patio umbrellas, and lush green landscaping enhances the serene atmosphere. The two-story villa, framed by trees, features a wraparound deck with steps leading down to the pool area.

74 Baynard Cove

The perfect destination for family fun, this Hilton Head Island villa has space for 10 and easy access to the bike paths that connect you to the beach, marina, and more within a short ride. When you’re not out at the beach, enjoy the spacious swimming pool at home in the private backyard. For dinner, dine alfresco on the screened porch or head to nearby restaurants around the marina. Copyright © Luxury Retreats. All rights reserved.

A spacious living room features a light-colored sectional sofa with decorative pillows. A coffee table with a decorative plant sits in front, while a relaxing area rug lays on the wooden floor. A flat-screen television is mounted above the white fireplace, and an open staircase is visible.

Sound Villa

You won’t have any trouble finding the beach at this luxurious Hilton Head Island townhouse, just walk outside and follow the path. Actually, it’s even easier. Just look out the window or off the back deck! You’re also steps from the community pool. When you’re not lounging in the spacious living room at home, check out the nightlife at the bustling South Beach Marina Village. Copyright © Luxury Retreats. All rights reserved.

A spacious living area is illuminated by natural light from large windows that overlook the lush greenery outside. Soft, neutral-toned furnishings, including a sectional sofa and two armchairs, are arranged around a modern coffee table, creating a welcoming space for relaxation and gathering.

5 out of 5 average rating, 6 reviews

26 Tupelo Road

Capturing views of the golf course, this Hilton Head Island home is perfect for exciting, multi-family vacations. The guest house adds a little extra privacy, as do the mature trees surrounding the backyard’s pool and hot tub. When you’re ready to explore, ride the nearby bike paths to the South Beach Marina Village or the beach. Both only take a few minutes. Copyright © Luxury Retreats. All rights reserved.

Apartment in Hilton Head Island

1879 Beachside Tennis Villas

Welcome to the BESTNEST at 1879 Beachside Tennis Villas in Sea Pines (247 South Sea Pines Drive). Beautifully renovated with an open living plan and gorgeous ocean view. 1879 Beachside Tennis is a wonderfully comfortable villa and we have filled it with every amenity we appreciate when we vacation. The sweeping view of the Atlantic Ocean, to the Calibogue Sound and to Daufuskie Island is simply sublime.

Home in Hilton Head Island

2628 Calibogue Club

Welcome to BESTNEST/Luxe: An Elevated Experience in Vacationing. Our NEW BESTNEST/Luxe property at 2628 Calibogue Club in Sea Pines is a super stylish 3BR/3 BA townhome, just fully renovated with new and fabulous furnishings. Our philosophy is that your vacation experience should be completely comfortable and consistently amazing. Cleanliness is one of our hallmarks and we take clean seriously.

Home in Hilton Head Island

Private Island in Hilton Head, Events & Poolside

Sleeps 26 on your own private island! Buck Island is an exclusive 10-acre retreat off Hilton Head featuring two homes. The main house offers 5 master suites sleeping 10, plus a guest house sleeping 16. Perfect for large groups seeking total privacy, comfort, and adventure. Enjoy a true private island experience with unmatched, easy access—seclusion without sacrificing convenience.

Home in Hilton Head Island

A spacious living area is illuminated by natural light from large windows and features a high brick fireplace as a focal point. Comfortable seating is arranged around a decorative rug, complemented by an entertainment unit and access to the outdoor space.

4th Row beach home with screened porch & pool

This stunning 4th row Sea Pines home has soaring ceilings and beautiful high-end furnishings to truly create a luxurious feel, all while making guests feel right at home. 5 bedrooms all with their own ensuite bathrooms offer plenty of space for 16 guests!

Apartment in Hilton Head Island