Sea Pines Vacation Rentals

Located on the southern end of Hilton Head, Sea Pines is a classic resort community known for its natural beauty, quiet beaches, and family-friendly atmosphere. Guests enjoy easy access to golf, tennis, bike trails, Harbour Town, and plenty of space to relax or explore. host2coast offers a variety of Sea Pines vacation rentals, perfect for couples, families, or group getaways.


🏖️What You'll Love About Sea Pines: 

  • Easy access to Harbour Town, South Beach Marina, and the Sea Pines Beach Club 
  • Miles of bike-friendly trails through shady oak canopies 
  • Championship golf and tennis facilities 
  • Quiet neighborhoods with natural surroundings 
  • Family-friendly dining, shopping, and local events 

Stay in the heart of Hilton Head’s most iconic resort and enjoy the charm, beauty, and convenience of Sea Pines. Browse vacation rentals today and start planning your Lowcountry escape.

Sea Pines Vacation Rentals in Hilton Head Island

SEA PINES: Visitor Information 

TRANSPORTATION: Sea Pines Trolley


Properties Available 83 properties available
Your Hilton Head Island vacation should be nothing less than spectacular and 8 Dewberry Lane nestled in the heart of Sea Pines Resort gives you that and more! Community pool and tennis court included! This beautiful vacation “home away from home” comfortably accommodates a family or group of 8 and is located just a short walk or bike ride to the
Hot HOT 130
8 Dewberry Lane
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 4.9 (52)
Step into pure Lowcountry luxury at 4 Jessamine Place - where resort-style living and coastal charm unite. This extraordinary retreat immediately captivates with its grand architecture, expansive windows glowing at sunset, and a secluded backyard designed for unforgettable moments. With its lush palms, sparkling waters, and sleek, modern finishes,
Hot HOT 112
4 Jessamine Place
House
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half baths
Guests 9 guests
Rating 5 (1)
Welcome to 1764 Bluff Villas, a beautifully renovated coastal retreat nestled in the heart of the renowned Sea Pines Resort on Hilton Head Island. This tastefully designed villa combines relaxed seaside charm with elevated modern finishes, offering a turnkey living experience just steps from the beach, marina, shops, and dining! Step inside and fe
Hot HOT 106
1764 Bluff Villas
Villa
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (3)
"This villa in the South Beach area has it all. Great location and amenities. Can’t wait to go back!" We love when our guests are delighted with this villa and leave such great reviews! This is definitely something special and you are just steps from the beach! We know you and your family will want to make this your island vacation home away from h
Hot HOT 126
1736 Bluff Villas
Villa
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (38)
Lovely Single-level End-unit Villa with Pool, Tennis, and Pickleball exclusive to complex. Great convenient location! Just a short half-mile walk to the world-renowned Harbour Town. Explore its shops, restaurants, and beautiful sunset views over Calibogue Sound. Also, the villa is just minutes away from The Shops at Sea Pines. Take the free trolley
Hot HOT 103
2373 Racquet Club
Villa Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (22)
Inside, the home unfolds into a bright and welcoming great room where floor to ceiling windows and vaulted ceilings flood the space with natural light. Plush seating and a smart TV make it easy to unwind after a day spent on the course or by the shore. The full kitchen is a chef’s dream, featuring gleaming custom countertops and a complete suite of
Hot HOT 112
10 Piping Plover
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.9 (29)
Plan the family reunion at 1714 Bluff Villa, a beachy and bright 3rd floor villa just perfect for a family or group of 10! Located just a short walk from the beach on the Calibogue Sound in Sea Pines, this 3-bedroom, 2-bath villa features an open plan with plenty of room to enjoy family game or movie night. The open living space includes a large
Hot HOT 113
1714 Bluff Villas
Villa
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (63)
Make your Hilton Head vacation dreams come true at 1 Willow Oak West! This recently renovated 3 bedroom and 3 full bathroom home is situated in the heart of Sea Pines. It has easy access to the endless bike paths that Hilton Head has to offer and is equidistant to Harbour Town, and the Sea Pines Beach Club. Also, strong Wi-Fi makes this the perf
Hot HOT 95
1 Willow Oak West
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (27)
Welcome to your Hilton Head Island retreat at 503 Plantation Club, a luxurious villa designed to provide the perfect blend of comfort and elegance. This stunning two-story villa features three spacious bedrooms, accommodating up to six guests with ease. The master suite boasts a king-sized bed, while the two guest rooms offer a queen bed and two do
Hot HOT 88
503 Plantation Club
Villa Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half baths
Guests 6 guests
Rating 4.8 (25)
Our guests absolutely love 1614 Port Villa and here are some reasons why, taken from their reviews - "Great location!" "It is a quick walk to the tennis courts, Salty Dog, and the beach." "Good to have 3 levels to spend time together or divide up." "The early morning view from the back patio is majestic." "You can’t beat seeing dolphins every day!"
Hot HOT 125
1614 Port Villas
Villa Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 4.9 (45)
Here comes the sun, doo-doo-doo-doo, do come and stay at the one and only Beatles-Themed vacation rental on Hilton Head Island! 24 Water Oak Lane, or the "Here Comes the Sun" home is nestled in a quiet corner of Sea Pines Resort and is just a short 15-minute bike ride to the best beach Hilton Head Island has to offer as well as the Harbour Town Yac
Hot HOT 116
24 Water Oak
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (45)
* Palmetto Dunes is a gated community in which every vehicle must have a gate pass for entry. One gate pass is included with your reservation at the time of booking. If you require additional passes, please request the exact number needed to ensure they are prepared in advance. Each pass has a fee of $45. All gate passes must be picked up at the ho
Hot HOT 110
101 Fairway Lane Villas
Villa Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (11)

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At host2coast, we manage a wide selection of quality Hilton Head Condo Rentals and Hilton Head Island House Rentals across the island’s most popular resort communities, including Sea Pines, South Forest Beach, Palmetto Dunes, and beyond.

Vacation Perks

From private pools and fully equipped kitchens to our collection of Hilton Head oceanfront rentals, host2coast offers vacation homes and villas that fit every style and budget. Each of our Hilton Head rentals is designed with comfort and convenience in mind, so you can focus on making memories that last.

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About this page: Content created and regularly reviewed to reflect host2coast’s local expertise and commitment to guest satisfaction.

Do I need a gate pass to enter Sea Pines?

Yes. Sea Pines is a gated community and requires either a gate pass (for vehicles) or appropriate entry authorization. Your host2coast pre-arrival email will explain how your pass is handled. For community access info and fees, see the Sea Pines CSA website.

Source: Sea Pines CSA

How close are Sea Pines rentals to Harbour Town and the Beach Club?

Most Sea Pines homes and villas are a short bike ride or drive to Harbour Town and the Sea Pines Beach Club. Exact distance varies by neighborhood; use the map on each listing to check walk/bike times. Seasonal trolley service may also operate within Sea Pines.

Is there a trolley or shuttle inside Sea Pines?

Sea Pines typically offers a seasonal trolley with stops at popular points like Harbour Town, South Beach Marina, and the Beach Club. Schedules and routes can change by season.

What are typical HOA/community rules in Sea Pines (parking, beach access, bikes)?

Sea Pines observes community rules for parking, beach access, quiet hours, and bike path use. Most rules are guest-friendly but enforced for safety and conservation. Always review your rental’s house rules and posted signage within the community.

Community reference: Sea Pines CSA

When is sea turtle nesting season on Hilton Head, and are there beach rules I should know?

Turtle nesting season generally runs May–October. Please fill in any beach holes, remove items from the beach at night, and keep lights off the beach after dark to avoid disorienting hatchlings. Local beach ordinances apply to all visitors.

Beach regulations: Town of Hilton Head Island

What amenities are common in host2coast’s Sea Pines rentals?

Most homes and villas include full kitchens, Wi-Fi, streaming-ready TVs, outdoor living spaces, and parking. Many offer extras like private pools, golf/lagoon views, or bike friendly locations. Use filters on the Sea Pines page to sort by bedroom count, pool, and view.

What’s the best time of year to visit Sea Pines?

Spring and fall bring mild weather, lighter crowds, and excellent biking. Summer is peak season with full amenities and family activities. Winter offers lower rates and a quieter island experience, great for golf getaways and long weekends.

Content created and regularly reviewed to reflect host2coast’s local expertise and commitment to guest satisfaction.