Luxury rentals in Hilton Head Island

Find and book unique accommodations on Airbnb

Top-rated luxury vacation rentals in Hilton Head Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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 multi-level coastal home is shown, featuring a blend of pale blue and beige exterior. Lush landscaping surrounds the entrance, and palm trees provide a tropical vibe. The driveway is paved with stones, leading to garage doors on the ground level.

Villa in Hilton Head Island

4.88 out of 5 average rating, 26 reviews

Bradley Circle

Triple Cleaned, New construction home! This 7,200sf Beach home is the PERFECT rental for any occasion; weddings, family vacation, reunions, etc. A 2 minute walk to the beach, beautiful views and plenty of living space! The home is located in Bradley Beach area of Hilton Head Island. The home has four covered balconies, an infinity pool, two living rooms, 10 bedrooms and a private elevator. Whether you're planning a family vacation, wedding, or corporate retreat, this home will fit your needs.

Luxe

The exterior of a grand beach home features multiple levels, arched balconies, and elegant columns, surrounded by lush palm trees. The pale stucco facade is complemented by a multi-gabled roof, with scenic ocean views in the background, enhancing the home's coastal charm.

Home in Hilton Head Island

31 Singleton, Pool, Pickleball, Views, Free Golf

31 Singleton Beach Place on Hilton Head Island epitomizes luxury living. This 5,500+ sq. ft. pristine beach home features 6 spacious bedrooms and 9 beautifully designed bathrooms, offering a combination of high-end finishes and sophisticated decor. Enjoy expansive oceanfront views and direct beach access just steps away. Relax by the private pool, sunbathe on the deck, or soothe yourself with the calming sounds of the waves. This home offers the perfect setting for relaxation and recreation.

Luxe

The living area features a light-filled space with large glass windows that open to views of the garden. A circular coffee table made of natural wood is central, surrounded by two light-colored sofas with soft cushions. A round mirror and a stylish light fixture accent the room.

Home in Hilton Head Island

5 out of 5 average rating, 6 reviews

100 Fairway Lane: Sea Pines

Welcome to all NEW BESTNEST/Luxe: An Elevated Experience in Vacationing, and our newest Luxe property at Unit 100 Fairway Lane Villas in Sea Pines. (200 Fairway Lane for mapping) 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.

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

5 out of 5 average rating, 3 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.

Luxe

A spacious living area features two light-colored couches, adorned with orange accent pillows, arranged around a wooden coffee table. A large glass vase sits atop the table. Natural light floods the room, highlighting the airy atmosphere created by the high ceilings.

Place to stay in South Beach

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 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.

Place to stay in South Beach

5 out of 5 average rating, 5 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 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.

Place to stay in South Beach

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 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.

Place to stay in South Beach

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 South Beach

5 out of 5 average rating, 3 reviews

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 highlighted by large windows that allow natural light to brighten the room. Comfortable seating is provided by two armchairs and a sofa, complemented by textured poufs. A neutral area rug anchors the space, enhancing the overall relaxed ambiance.

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.

Luxe

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.

Place to stay in Hilton Head Island

5 out of 5 average rating, 4 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.