Sea Pines Rentals

Discover the timeless beauty and recreational opportunities of Sea Pines with Island Rentals of Hilton Head. Located on the southern tip of Hilton Head Island, Sea Pines is known for its scenic landscapes, pristine beaches, and abundance of outdoor activities.

Our Sea Pines vacation rentals offer a range of accommodations to suit every traveler’s needs, from charming cottages nestled among towering pines to luxurious oceanfront estates. Each rental is equipped with modern amenities and is just moments away from Sea Pines’ iconic attractions.

Explore over 15 miles of leisure trails on foot or bike, play a round of golf at one of three world-class courses, or relax on the sandy shores of Sea Pines Beach. Visit Harbour Town to see the iconic Harbour Town Lighthouse and enjoy waterfront dining and boutique shopping.

Whether you’re planning a family vacation, a romantic getaway, or a golf retreat, Sea Pines offers something for everyone. Experience the natural beauty and leisurely pace of Sea Pines with Island Rentals of Hilton Head. Book your vacation rental today and start creating unforgettable memories on Hilton Head Island!

49 properties available

Welcome to 28 Gunnery Lane, a beautifully appointed 3-bedroom, 2-bathroom home nestled in the heart of Sea Pines. This inviting island retreat offers the perfect blend of comfort, space, and amenities – ideal for your next Hilton Head getaway. With 150 feet of lagoon frontage and water views from nearly every window, this home is designed to immers

Proudly hosted by Island Rentals of Hilton Head. Just a five-minute walk to the beach, this beautifully maintained Lighthouse Road Villa offers the perfect Sea Pines getaway. Overlooking the 10th fairway of the Atlantic Dunes Golf Course, this spacious two-story villa is ideally located near the Sea Pines Beach Club, providing easy access to the is

8 Lighthouse Road Villas

Proudly hosted by Island Rentals of Hilton Head, this beautifully renovated Caravel Court villa offers a truly iconic Sea Pines experience with breathtaking views of the Harbour Town Lighthouse and the sparkling waters of the Calibogue Sound. Located in the heart of Harbour Town, this one-bedroom retreat is ideal for couples or a small family seeki

Proudly hosted by Island Rentals of Hilton Head, 1425 South Beach Villas is a coastal retreat designed for guests who crave sun, sand, and the soothing rhythm of the ocean. Ideally located in the iconic South Beach area of Sea Pines, this spacious villa offers the perfect blend of comfort, style, and unbeatable proximity to the shoreline, making it

1425 South Beach Villas

6 Cannon Row, Sea Pines Private Home, New Private Pool Basic Features: - 2121 sq. ft. - 3 bed, 2 Bath - 2 Kings, 2 Twins, 2 Bunk Beds - TV/DVD player in living room - Fireplace (For Decorative Purposes Only) - Gas Grill - Huge back deck with lagoon view - WiFi - 1 Hour free tennis daily at South Beach Racquet Club - 1 Car pass into Sea Pines - 4 F

Proudly hosted by Island Rentals of Hilton Head, 157 N. Sea Pines Drive is a stunning Sea Pines retreat perfectly positioned along the 17th tee of the Atlantic Dunes Golf Course. With tranquil lagoon views, a private pool, and an unbeatable central location, this home offers the ideal blend of relaxation, recreation, and classic Hilton Head Island

HOT 33

Proudly hosted by Island Rentals of Hilton Head. Nestled in the heart of Sea Pines Resort, this charming 2-bedroom, 2-bath villa at Plantation Club offers a prime location midway between Harbour Town and the Sea Pines Beach Club, two of Hilton Head\'s most beloved attractions. With one king bed and two full-size beds, the villa provides comfortable

Proudly hosted by Island Rentals of Hilton Head. Discover your ideal Sea Pines retreat in this beautifully appointed home, blending tasteful features with upscale furnishings for an unforgettable stay. This centrally located property in Greenwood Forest offers three bedrooms, two bathrooms, and a lofted fourth sleeping area, comfortably accommodati

Proudly hosted by Island Rentals of Hilton Head, this beautifully secluded 4-bedroom, 3-bath retreat in Sea Pines offers the perfect blend of comfort, space, and Lowcountry charm. Nestled among lush landscaping and scenic lagoons, this inviting family home features a spacious open floor plan with a large living room designed for gathering—complete

HOT 38

Proudly hosted by Island Rentals of Hilton Head. Welcome to this beautifully remodeled home in the private Greenwood Forest community, offering a serene retreat within the heart of Sea Pines Plantation. This 3-bedroom, 2-bath home features a king bed, queen bed, and a full/twin bunk bed, comfortably accommodating families or groups seeking a peacef

Proudly hosted by Island Rentals of Hilton Head, 525 Plantation Club Villas is an absolutely gorgeous, single-level retreat perfectly situated within the prestigious Sea Pines community. Overlooking the lush fairways of the Atlantic Dunes Golf Course, this villa offers a serene setting where sweeping golf views create a relaxing Lowcountry backdrop

525 Plantation Club Villas

Proudly hosted by Island Rentals of Hilton Head, this bright and beautifully updated home is nestled in the desirable Lawton Woods section of Sea Pines, offering the perfect balance of central convenience, privacy, and Lowcountry serenity. Thoughtfully designed to sleep 8–10 guests, the home features three bedrooms and two fully remodeled bathrooms

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