Luxury rentals in Chatham County

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Top-rated luxury vacation rentals in Chatham County

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Luxe

A wooden two-story cottage is surrounded by palm trees and lush foliage. The spacious outdoor area includes a swimming pool and multiple loungers arranged on the stylish stone pool deck, providing a serene setting for relaxation.

Villa in Hilton Head Island

Sea Pines Oceanfront

Palms and pines shade this classic beachfront cottage at Hilton Head’s Sea Pines. Shiplap walls, beamed ceilings, heart-pine floors, and wicker furniture are constant—and charming—reminders that you’re on the ocean, while a recent renovation brought in state-of-the-art appliances and an open modern layout. Cross the pool courtyard to the beach or take the trolley into town. Start the day with coffee and sunrise views on the screened-in porch, then move to a lounger by the private pool or an Adirondack chair that’s practically set on the sand. Finish a day at the beach with a waterfront dinner, served fresh from the barbecue at the alfresco table on the back porch. Beamed ceilings, crisp white walls, and pine floors lend Carolina charm to the open-plan great room on the home’s top floor. Gather on the slipcovered sofas, seat 10 to 12 in wicker chairs around a pine and zinc dining table, and perch at the breakfast bar in the fully equipped kitchen. Downstairs, you’ll find an inviting den stocked with board games and a TV. The ocean front pool has been refreshed with new tile and a new sandstone pool deck with 10 chic sling loungers. The adjoining lower patio has been enhanced with deep seating and an outdoor ping pong table, providing shady diversions for hot summer afternoons. A new dune deck with seating and outdoor shower connects the pool to the sand via a shapely new boardwalk over the dunes. And just above the pool deck, serious golfers and putt-putt enthusiasts alike will enjoy a new 4-hole putting green with ocean views. Not only is this villa right on the beach, its Sea Pines location puts you a short drive from a kid-friendly beach park with a splash pad. It’s also an easy drive to the golf course and about 10 minutes to shopping and dining in downtown Hilton Head. Or take one of the area’s trolley services to the picturesque Harbour Town marina. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with rain shower, Dual vanity, Television, Direct access to balcony, Ocean view • Bedroom 2: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television, Direct access to balcony • Bedroom 3: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television, Direct access to pool • Bedroom 4: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television, Direct access to garden • Bedroom 5: King size bed, Ensuite bathroom with rain shower, Television, Direct access to pool FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • Screened porch STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • Tennis at The Sea Pines Tennis Center or The South Beach Racquet Club • Boating, fishing, and crabbing at two different Marinas • Horseback riding and animal petting farm • More under “Add-on services” below

Luxe

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.

Villa in Hilton Head Island

5 out of 5 average rating, 3 reviews

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

Luxe

A spacious living area features comfortable seating arrangements, including a light-colored sofa and accent chairs. A wooden coffee table sits center, while built-in shelving displays decorative items. Large sliding doors offer a view of the outdoor area, enhancing the room's airy feel.

Place to stay in Hilton Head Island

103 Governors

Just a short drive from the beach, this luxurious Hilton Head Island villa is the perfect home base for your next family getaway or golf vacation. When you’re not out exploring the coast or checking out the sights in South Beach Marina Village, gather your group in the extra-spacious screened porch for a night of good fun and fresh air. If you fancy a dip, your private pool is just in the backyard. Copyright © Luxury Retreats. All rights reserved.

Luxe

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.

Place to stay in Hilton Head Island

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.

Luxe

A spacious living area features light-colored sofas positioned around a wooden coffee table. A large decorative bowl rests atop the table. Soft lighting from two lamps enhances the airy feel, while the high ceiling and open layout contribute to a bright atmosphere.

Place to stay in Hilton Head Island

29 South Beach

The beach is a 3-minute stroll away from this Hilton Head escape. Inside, soaring ceilings create an airy ambiance alongside plump furniture and a creamy color palette. Soaring trees cast dappled shadows on the terrace. Up for a challenge? Try a ping-pong tournament. A pool entices you in for a cooling dip. Hop on a bike and head into the village for shopping, dining, and activities for everyone. Copyright © Luxury Retreats. All rights reserved.

Luxe

A bright living area features a combination of leather armchairs and a spacious sectional sofa, complemented by a wooden coffee table. A fireplace sits below a wall-mounted television. Large windows offer views of the water, while an open kitchen area is visible in the background.

Place to stay in Hilton Head Island

5 out of 5 average rating, 3 reviews

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.

Luxe

A modern living area features two light-colored sofas arranged around a glass coffee table. A spacious kitchen with white cabinetry and stainless steel appliances can be seen in the background. Soft lighting creates a welcoming ambiance throughout the open layout.

Place to stay in Hilton Head Island

South Beach Villas

Wake up each morning to the sound of palm trees rustling in the fresh sea breeze. Start your day with coffee on the porch while you relax in a sun chair. If you’re feeling more energetic, take that coffee for a stroll along the sandy beach, it’s just 50 meters from your back porch. If you feel like a swim, grabbing dinner, or checking out some luxury yachts, head for South Beach Marina Village. Copyright © Luxury Retreats. All rights reserved.

Luxe

A spacious villa is situated steps from the beach, featuring large windows that reflect a vibrant sunset. The outdoor area includes a patio with lounge chairs and a pool, offering a relaxing atmosphere amid lush landscaping.

Home in Hilton Head Island

23 South Beach Lagoon

With private access to the beach and incredible ocean views, this villa is Hilton Head Island’s finest rental. Perfect for large families, this villa has space 14, an elevator that stops on every floor, and lots of outdoor space for the kids. On sunny afternoons, the pool is the spot. In the evening, move over to the hot tub and watch the stars come out. There’s also tennis and golf nearby. Copyright © Luxury Retreats. All rights reserved.

Luxe

A private backyard features a spacious swimming pool surrounded by a sunbathing area, equipped with lounge chairs. Lush greenery and mature trees provide shade and enhance the natural setting, while a portion of the house with a deck is visible in the background.

Place to stay in Hilton Head Island

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.

Luxe

A spacious living room is adorned with neutral-toned furnishings and a large coffee table. A bright blue floral artwork complements the white brick fireplace, while natural light streams in through large windows. The open layout connects to a well-equipped kitchen visible in the background.

Place to stay in Hilton Head Island

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.

Luxe

A private pool is framed by a spacious patio with lounge chairs and a dining area. Tall trees provide shade, while the villa's modern architecture is complemented by large windows reflecting natural light.

Place to stay in Hilton Head Island

Merganser Court

Steps from the beach walk, this Hilton Head Island villa will have you on the sand in minutes. When you’re not splashing around in the ocean, enjoy the relaxing, private pool at home or a shared community pool nearby. In the evening, gather around the alfresco dining table for a family dinner, or use the bike paths to ride around and check out the restaurants nearby. Copyright © Luxury Retreats. All rights reserved.

Luxe

A spacious living area is furnished with soft seating options, including a light-colored sofa and two accent chairs. Natural light enters through glass doors, while neutral tones and a textured rug create a calming ambiance. A coffee table and decorative accessories add to the inviting space.

Place to stay in Hilton Head Island

5 out of 5 average rating, 4 reviews

44 Heritage

Set alongside the 11th tee box of the famous Harbour Town Links, this exclusive villa on Hilton Head Island is the perfect home base for your next golf vacation or family getaway. When you’re not out on the golf course, take a refreshing dip in the South Beach community pool or head down to the sandy beach. In the evening, check out South Beach Marina Village. Copyright © Luxury Retreats. All rights reserved.