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Holiday rentals in Sea Pines

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Top-rated holiday rentals in Sea Pines

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Guest favourite
A serene walking path is surrounded by lush greenery, featuring a sandy surface framed by overhanging branches and foliage. Sunlight filters through the leaves, casting soft shadows on the ground. The path leads deeper into the natural landscape, inviting exploration.
Flat in Hilton Head Island
4.88 out of 5 average rating, 49 reviews

New! 1 BD APT~Beach Access~NICE!

Time for a peaceful beach trip! Just minutes to the beach, private 1 bedroom apt that is all new inside! Park outside your door! King bedroom with lots of storage & TV. Large bathroom with tile shower! Living Room has 50" Smart TV and access to a front patio. There is a kitchenette that has a Keruig, microwave/air fryer, refrigerator and table and chairs. Central air conditioning makes it comfy! Great S Forest Beach Location! End of owners home, but private entrance. No kids, sorry. 1 car only.

Top guest favourite
An airy living space is highlighted by soft white sofas and a large rug featuring ocean-themed designs. A ceiling fan hangs above, while natural light floods in through expansive glass doors. The room includes a cozy fireplace and a wooden coffee table in the center.
Home in Hilton Head Island
5 out of 5 average rating, 26 reviews

Sal and Babs Sea Pines Sanctuary

Nestled along the picturesque coastline of Sea Pines on Hilton Head Island, the beachside area of this premier community offers an idyllic retreat by the sea. Residents and visitors alike are treated to expansive views of the Atlantic Ocean, with pristine sandy shores inviting leisurely walks, sunbathing, and water activities. Sea Pines is a sanctuary where the sounds of waves crashing and seabirds calling create a soothing backdrop for relaxation. With easy access to the beach from various poin

Top guest favourite
A wooden boardwalk leads through grassy dunes towards the beach. The path extends toward the calm ocean, under a gray sky. Soft sand is visible at the boardwalk's end, inviting guests to access the beachfront.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 334 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled just last year! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve!

Guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 7 reviews

Harbour Town Villa: Sleeps 6-Perfect for Families

Welcome to your serene retreat in the heart of Sea Pines Resort. This minimalistic 2-bedroom, 2-bath villa offers a peaceful escape just steps from the iconic Harbour Town Golf Links and Racquet Club. Ideal for families and couples, the villa is a short stroll from the Harbour Town Lighthouse, boutique shops, and waterfront dining. Whether you're sipping coffee on the private balcony or unwinding after a day of exploration, this villa is your perfect home base for a relaxed Hilton Head getaway.

Top guest favourite
A spacious deck features a circular fire pit surrounded by four wooden adirondack chairs with cushions. A striped pouf adds comfort to the area. Scenic sunset views over the beachfront landscape create a serene backdrop.
Chalet in Hilton Head Island
4.98 out of 5 average rating, 108 reviews

180º Ocean Views, Treehouse "Siren's Lookout"

Waterfront and sunset views abound in this unique "treehouse", with 360 degree views. On Deer Island, just steps from the Harbour Town Lighthouse, known for its' large-boat marina, restaurants, shops and Golf Club, host of the RBC Heritage Classic, PGA Tour Event. Enjoy all the amenities of Sea Pines, including the South Beach Marina, Sea Pines Beach and Salty Dog Cafe, only 3 miles away, serviced by trollies & bike paths. Enjoy the sunset seated around the firepit. Gas grill with a view

Guest favourite
A sunlit living area features large windows providing views of the surrounding greenery. A comfortable sofa sits opposite a white coffee table, complemented by a stylish armchair and a small workspace with a wooden desk. Light wooden flooring enhances the vibrant atmosphere.
Apartment in Hilton Head Island
4.86 out of 5 average rating, 50 reviews

SeaPines - Walk to beach, Remodeled, Pet friendly

Beautifully renovated in modern beach style! With beautiful new flooring throughout, new furniture, linens and updated baths, this stylish coastal villa is just waiting for you to relax and enjoy all of Sea Pines and HHI. From the stunning kitchen to the thoughtful dedicated workspace and expanded patio with grill, this two bedroom, two bath villa comfortably sleeps six adults. This property is pet friendly, yet clean and well appointed, and offers one of the best locations in Sea Pines.

Guest favourite
A large, colorful turtle sculpture is seen in a natural outdoor setting. The turtle features a intricately designed shell in earthy tones and vibrant blue flippers, perched on a textured rock with white, oval shapes resembling eggs located at its base.
Flat in Hilton Head Island
4.94 out of 5 average rating, 118 reviews

KING BED!Ocean View, Free Bikes Poolside 3rd Floor

Pack your flip-flops and get ready for fun—this sunny poolside villa on Hilton Head Island is your ticket to the ultimate coastal escape! Just steps from the beach and the refreshing Atlantic breeze, this vibrant retreat serves up the perfect mix of relaxation, adventure, and ocean views. Start your day with coffee on the balcony, soak up the sun by the pool, then hop on one of our free bikes to cruise the island like a local! The perfect getaway starts right here!

Top guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 107 reviews

5 Star Location-Pool, Walk to Dining/Shops/Marina

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

Guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 9 reviews

Sea Pines Top-Floor Villa | Golf & Wooded Views

Stay where the pros play! Perfectly situated for the Heritage Golf Tournament, this renovated top-floor villa overlooks lush fairways and peaceful woods. The modern interior boasts taupe tile backsplashes and speckled granite throughout. Sea Pines’ famous bike paths are right outside your door, leading you to pristine beaches and luxury shopping. Experience elevated HHI living with contemporary amenities and the quiet privacy of a top-floor treetop location.

Superhost
Home in Hilton Head Island
5 out of 5 average rating, 4 reviews

Lovely & Secluded Sea Pines Retreat on Hilton Head

4 Pine Court, This spacious 3 bedroom, 2 bath ranch home is nestled on a private cul-de-sac, providing a peaceful and secluded getaway. With sleeping accommodations for up to 8 guests and a screened porch for relaxing, this rental is the perfect retreat. The outdoor living area boasts a grilling area, ideal for hosting a family barbecue. Located just minutes from the beach and Sea Pines amenities, this rental provides both convenience and relaxation.

Top guest favourite
The bungalow is nestled among lush greenery and tall trees, surrounded by a natural environment. Palm leaves frame the structure, and a small deck is visible at the front, inviting warmth and privacy in this woodland setting.
Bungalow in Hilton Head Island
4.95 out of 5 average rating, 119 reviews

Closest to Beach Path, Screened Porch, 1 dog ok

Wonderful Single Sea Pines Bungalow for 2 people. Walk 5 min on beach path. Excellent location; ride bikes to Harbor Town, Beach Club, Coligny Plaza, No elevator or parking lots! Grill out on deck. 50" TV ; screened-in porch. Walk to best beach on island, no hotels. Swimming pool onsite. Equipped Kitchen with Cooktop, Dishwasher, Refrigerator. We allow 1 dog.. under 30lbs. 4 night min bookings.

Superhost
A tranquil evening scene is captured at the marina, showcasing boats illuminated by soft blue lights. The sky transitions from dark blue to warm orange and gold at the horizon, with the Lighthouse standing tall in the background.
Apartment in Hilton Head Island
4.9 out of 5 average rating, 10 reviews

Ketch Studio - an iTrip Hilton Head Home

With its breathtaking views of the Harbour Town Yacht Basin and Lighthouse, Ketch Studio is the ideal getaway retreat in Sea Pines Resort for a couple or individual that wants to get away, relax and unwind. From inside the unit or on the Juliet balcony, you can watch the boats come and go from the harbour or catch a gorgeous sunset over Daufuskie Island.

Popular amenities for Sea Pines holiday rentals