Luxury rentals in Hilton Head Island

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Top-rated luxury vacation rentals in Hilton Head Island

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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 Sea Pines

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

4.92 out of 5 average rating, 25 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

A spacious patio area is viewed, featuring multiple lounge chairs arranged on well-manicured grass. The villa is characterized by large glass doors that open to the outdoor space, with a gas grill positioned nearby among lush surrounding greenery.

Home in Sea Pines

5 out of 5 average rating, 5 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

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 Sea Pines

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

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, 4 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 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 Sea Pines

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 dining area features a large wooden table surrounded by four chairs and a bench. Two pendant lights hang above the table, illuminating the warm wood floors. The open layout connects to a modern kitchen in the background, enhancing the light and airy feel.

Place to stay in Sea Pines

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.

Luxe

A bright living area features high ceilings and large windows allowing natural light to fill the space. A neutral-colored sectional sofa and armchair are arranged around a light rug. The modern fireplace is complemented by a sleek television and artwork, enhancing the room's contemporary design.

Place to stay in Sea Pines

21 Shell Ring

Set alongside the waterways of Hilton Head Island, this stylish villa enjoys 2 master suites and works great for couples vacationing together. Nearby, you’ll have access to the shared community pool, and the beach trolley is just a 3-minute drive from home. Back home, you’ll love looking out over the water while barbecuing and dining alfresco on the patio. Copyright © Luxury Retreats. All rights reserved.

Luxe

The exterior of the three-story estate showcases elegant architectural details with grand columns and multiple balconies. A spacious driveway leads to a garage with three doors, framed by lush greenery and palm trees.

Home in Hilton Head Island

14 Collier, Free Golf, Oceanfront, Pool

Welcome to 14 Collier Beach, Hilton Head Island! This stunning oceanfront estate boasts a state-of-the-art chef's kitchen, open-concept living, and dining area, leading to an oceanfront pool and deck. With a luxurious master suite, private boardwalk to the beach, and garage-level bar area, it's the ultimate retreat. Book now for an unforgettable vacation experience!