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 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

4.92 out of 5 average rating, 24 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 Beach, Pool, Ping Pong, 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

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 Hilton Head Island

5 out of 5 average rating, 4 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

The exterior view of the house is presented with a two-story design and large windows. A spacious pool features lounge chairs arranged around its perimeter. Surrounding greenery adds to the inviting setting, with a patio area visibly equipped for outdoor relaxation.

Home in Hilton Head Island

4 Brigantine, 2nd Row, Pool, Free Golf, Elevator

Welcome to 4 Brigantine, your perfect family vacation home! With 6 bedrooms, each with a full bath, and ocean views from the second-floor living area, relaxation awaits. Enjoy an elevator, oversized pool, and beach access just across the street. The large pool area offers ample seating, while the deck features a grill for outdoor dining. Plus, enjoy rocking chairs and fans on all porches. Book now for up to $1000 in FREE activities and experience coastal luxury!

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 South Beach

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

The exterior of the vacation rental features a green façade complemented by white accents. A circular brick pattern adorns the driveway, leading to a garage on the left. Lush greenery surrounds the property, and steps lead up to a welcoming front entryway.

Home in Hilton Head Island

18 Sand Dollar, Oceanfront, Hot Tub, Free Golf

Welcome to 18 Sand Dollar, Hilton Head Island! This impressive vacation rental features 7 bedrooms, 7 bathrooms, and an open-concept floor plan, ensuring a memorable stay. Enjoy family fun with the pool table, ping pong, and Foosball table upstairs, while the massive pool deck with a private pool is perfect for relaxation. Book now for up to $1000 in FREE activities with every reservation!

Luxe

The exterior of a custom-built home showcases a covered deck, accessible via a set of stairs, and features lush landscaping. A putting green is present in the front yard, complemented by colorful plantings and a driveway. The home is situated in a scenic neighborhood.

Home in Hilton Head Island

3 Shore Crest, Chefs Kitchen, Game Room, Free Golf

3 Shore Crest Lane, Hilton Head Island. This custom-built 5-bedroom home in Burkes Beach offers luxury amenities including a chef's kitchen, sunroom, covered deck, pool table, private pool, and outdoor kitchen. With easy beach access and nearby amenities, it's the perfect vacation getaway. Plus, every reservation includes up to $1000 in FREE activities for an unforgettable experience.

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!