Sea Pines Vacation Rentals: 2026 Harbour Town Traditions & The Lowcountry Canopy

Boardwalk to the beach from a Sea Pines vacation rental in Hilton Head
In Sea Pines, the real island pace is found under the shade. Most of our neighbors know that the most efficient way to see the area isn't by car, it's via the trails that wind through the Lowcountry canopy. We focus on residences tucked away under the moss-draped oaks, providing a natural cooling effect while you pedal to the beach or the forest preserve. Whether you are staying in a villa near the sand or a condo on the golf course, our goal is to help you throw the keys on the counter the moment you arrive and not touch them again for a week.

If you’re planning on taking in the Harbour Town traditions, do what we do: take the bike. You’ll bypass the parking crowds at the lighthouse and ride straight to the pier for the sunset over the Calibogue Sound. We’ve curated a collection of villas and homes specifically for their proximity to these leisure paths, ensuring your morning coffee or evening dinner is just a short ride away under the trees. When you book your stay direct with us, you’re talking to neighbors who live here and know exactly which paths offer the most shade and which docks have the best view of the fleet coming in.


Properties Available 7 properties available
Unparalleled Location & Scenic Views at 1102 Harbour South Club Villa!Wake up to the charm of Harbour Town and unwind with breathtaking sunset views from the screened-in porch. Just a short stroll away, you'll find the iconic Harbour Town Marina, the Harbour Town Clubhouse, world-class golf courses, boutique shopping, and gourmet dining. (*Maximum
1102 Harbour South Club Villa Harbour Town
Villa -
$112 - $2,400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Welcome to 20 Willow Oak Road!Luxury Golf Course Retreat with Private Pool & Spa in Sea Pines ResortDiscover the perfect blend of tranquility and recreation in this newly remodeled 4-bedroom, 3-bath home, nestled in the heart of Sea Pines Resort. Boasting 2,396 sq. ft. of upscale living space, a brand-new private pool and hot tub, and breathtaking
Hot HOT 20
Spacious Pet Friendly Home Sea Pines Golf Views
House - Pet Friendly
$324 - $1,069 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.7 (30)
Welcome to Your Perfect Sea Pines Getaway – A Hilton Head Island Retreat! Nestled in the heart of The Sea Pines Resort, this spacious 3-bedroom villa offers stunning fairway and lagoon views, beach access just across the street, and all the comforts of home. Whether you’re planning a family-friendly vacation or a golfer’s retreat, this villa is the
Fairway One Villa Golf Lagoon Views Walk to Beach Club
Villa -
$171 - $552 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (12)
Welcome to Your Hilton Head Island Escape – A Perfect Coastal Retreat in Sea Pines Resort! Discover the ideal location for relaxation and recreation at our beautifully remodeled 3-bedroom, near-beach villa in the exclusive Sea Pines Resort. This spacious and thoughtfully designed home offers all the comforts of an upscale getaway, paired with the e
Spacious 3BR Villa Plantation Club Sea Pines
Villa -
$171 - $552 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (18)
Welcome to 528 Plantation Club Villa – Your Perfect Sea Pines Retreat! Located in the heart of Sea Pines Resort, this third floor updated villa offers the ideal combination of comfort, convenience, and leisure. Whether you’re looking for a peaceful getaway or an action-packed vacation, this 2-bedroom villa is your perfect island escape.Villa Highli
Sea Pines Plantation Club Villa Pool Beach
Villa -
$87 - $281 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.8 (8)
Welcome to Harbourwood Villa ~ Your Ultimate Retreat on the Harbour Town Golf Links!Prime Location with Stunning Golf Views & Steps to Harbour TownNestled along the 9th fairway of the world-renowned Harbour Town Golf Links, this 2-bedroom, 2-bathroom villa offers the perfect blend of relaxation and recreation. Whether you're sipping your morning co
Harbourwood Villa 150 Golf Views of Harbour Town
Villa -
$93 - $1,500 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (5)
Welcome to 5 Bald Eagle – Sea Pines ResortGorgeous 4th-Row Ocean Home with Private Pool, Steps from the Beach! Escape to paradise at this newly remodeled 5-bedroom, 5-bathroom home, perfectly located just steps from Hilton Head Island’s most beautiful beaches. Nestled in the exclusive Sea Pines Resort, this spacious and luxurious retreat is designe
Direct Beach Path Pool Near The Salty Dog Cafe
House -
$387 - $1,277 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 4.5 (28)

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