5 Br Private Vacation Home Vacation Rental In Hilton Head Island, South Carolina

Welcome to the Sea Pines Escape at 39 Oak Court—an upscale 5-bedroom, 5.5 bathroom retreat in Hilton Head Island's exclusive Sea Pines Resort. This fully renovated luxury home offers the perfect blend of modern coastal design, spacious indoor comfort, and resort-style outdoor living—perfect for your next family vacation or group getaway!

Enjoy a private pool, always-heated standalone spa, Carolina room with bar, custom outdoor shower, elevated tiled dining deck, and rocking-chair front porch, all surrounded by lush tropical landscaping and privacy in a quiet Sea Pines cul-de-sac. You're just minutes from pristine beaches, Harbour Town, Coligny Plaza, South Beach Marina, tennis, pickleball, horseback riding and world-class golf —accessible by bike or trolley.

Meticulously Maintained Cleanliness:
• Guests consistently praise the home's immaculate condition
• It's maintained to the highest standards between every stay

Stylish, Spacious and Comfortable Interiors:
Step into vaulted ceilings, bright open living spaces, and designer furnishings. The main living room offers plush seating and a large Roku Smart TV, seamlessly connected to the dining area and chef’s kitchen. The fully-equipped kitchen features quartz countertops, Café appliances, dual sinks, a gas range, and an oversized island with barstools—great for entertaining! Enjoy a movie or watch the big game in the separate media room upstairs.

Sleeps 12 in Total Comfort:
• 3 King Bedrooms, 1 Queen Bedroom, 1 Room with 4 Twins
• 2 Queen Sleeper Sofas (office + media room)
• 3 ensuite bathrooms, hallway bathroom, 2 half baths, pool bathroom, plus a private outdoor shower

Each bedroom is a cozy, inviting retreat and includes:
• Roku Smart TV, premium linens, plush comforters, pillow-top mattress, ceiling fan, individual A/C and Heat, and ample closet/dresser space

Work-from-Home Friendly:
• Dedicated office with desk, chair, and Roku TV
• Additional desk setup in private upstairs bedroom
• High-speed WiFi

Has a decorative only fireplace.

RESORT-STYLE OUTDOOR LIVING
Guests love the private and fully integrated outdoor areas!

Carolina Room (Covered & Poolside):
• Bar area with seating for 8, sink, full fridge/freezer
• 2 deep seating sofas, outdoor Roku TV, ceiling speakers, fans, and ambient lighting

Private Pool and Heated Spa:
• Underwater bench seating and integrated outdoor Roku TV
• Adirondack chairs and chaise loungers for the sun seekers
• Spa always heated (free), and ready year-round
• Luxury pool bathroom with shower, towels, bench, storage
• Free pool heat June-August. Pool heat available during other months for an additional $100 per night plus a $50 set-up fee.

Custom Outdoor Shower:
• Rainfall head, handheld wand, excellent water pressure with instant hot water, fully enclosed

Tiled Dining Deck:
• Dining for 10, Weber gas grill
• Overlooks pool and yard; connected to kitchen for seamless indoor-outdoor flow

Front Porch:
• Rocking chairs, ceiling fans, coastal charm —perfect for morning coffee or evening wine

Bonus Amenities:
• 4 free adult bikes, 10 beach chairs, pool towels/toys/floats
• 9 Roku Smart TVs, free Spectrum cable, free WiFi, 2 full size washer/dryer sets
• Board games, garage and breezeway storage, parking for 3–4 vehicles

Incredible Sea Pines Location:
• Walk or bike to Sea Pines Beach Club, Harbour Town, Coligny Plaza, and more
• Minutes to grocery stores, restaurants, shopping, golf, pickleball and nature trails
• 2 blocks from bike path entrance

Perfect For:
• Family and group vacations
• Golf getaways
• Snowbird retreats
• Remote work trips
• RBC Heritage lodging
• Year-round enjoyment

What Guests Love Most:
• “We loved the outside space and the pool!”
• “Super clean, incredibly comfortable, and beautiful.”
• “Close to everything—beach, golf, dining.”
• “One of the top houses we’ve rented by far!”
• “A home away from home.”

* All Reservations made for a duration of 1 month (28 Days) or longer are non refundable. Travel Insurance is highly recommended.

HHI STR Permit #075146

Located by the sea, this vacation home is in Sea Pines, a neighborhood in Hilton Head Island. Shelter Cove Harbour and Palmetto Dunes Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Coligny Beach and Sea Pines Forest Preserve. Looking to enjoy an event or a game while in town? See what's happening at Van Der Meer Tennis Academy or Van Der Meer Tennis Center. Fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and horse riding nearby.