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!

51 properties available

Proudly hosted by Island Rentals of Hilton Head, this coastal-chic Sea Pines villa offers the perfect blend of relaxation, comfort, and adventure in one of Hilton Head Island\'s most sought-after destinations. Nestled in a peaceful corner of Sea Pines Resort, this beautifully appointed one-bedroom, one-bathroom villa invites you to start each day w

Proudly hosted by Island Rentals of Hilton Head, this inviting three-bedroom, two-bathroom home is nestled within the prestigious Sea Pines community and offers a relaxing blend of comfort, space, and Lowcountry charm. Designed for easy coastal living, the home features an open-concept layout with a light-soaked living room, decorative fireplace, a

Proudly hosted by Island Rentals of Hilton Head, 25 Wildwood offers the perfect blend of comfort, style, and convenience in the desirable Greenwood Forest neighborhood of Sea Pines. This contemporary coastal retreat features 3 bedrooms and 2 bathrooms, comfortably sleeping up to 9 guests. With polished wood floors, chic décor, and abundant natural

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

HOT 273

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 beautiful Sea Pines home offers a spacious, single-level layout designed for comfort and relaxation. Each bedroom features premium bedding, stylish furnishings, and large flat-screen TVs, with an additional TV located on the screened porch for outdoor entertainment. The fully equipped kitchen bo

Proudly hosted by Island Rentals of Hilton Head, this incredible Sea Pines retreat has undergone extensive updates for 2025 and offers an exceptional setting for large families or groups vacationing together. Thoughtfully designed with both a five-bedroom main house and a two-bedroom attached guest house, the property comfortably sleeps up to fourt

Proudly hosted by Island Rentals of Hilton Head, this inviting 2-bedroom, 2-bath villa in the heart of Sea Pines offers the perfect blend of comfort, convenience, and coastal charm. Sleeping up to six guests, this spacious retreat is ideal for families or small groups looking to experience all that Hilton Head Island has to offer. Located just a sh

478 Plantation Club Villas

Proudly hosted by Island Rentals of Hilton Head, this inviting Lighthouse Tennis Villa offers an exceptional blend of space, comfort, and classic Hilton Head charm in the largest one-bedroom floor plan within the community. Vaulted ceilings and tasteful décor define the open living area, which features two sofas, including a queen sleeper, and open

2375 Lighthouse Tennis Villas

Proudly hosted by Island Rentals of Hilton Head, this beautifully updated one-bedroom villa offers the perfect blend of coastal comfort and relaxing island charm. Bright, airy, and thoughtfully designed, this inviting retreat is ideal for couples, small families, or friends looking to experience the best of Hilton Head Island. The villa features a

Proudly hosted by Island Rentals of Hilton Head, this spacious maritime forest retreat offers the perfect setting for an unforgettable island escape. With approximately 3,000 square feet of living space, this beautifully designed home features 4 bedrooms, 4 bathrooms, and comfortable accommodations for up to 10 guests. Thoughtfully appointed with T

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

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