Holiday rentals in Sea Pines

5 out of 5 average rating, 15 reviews

Beachfront Dream, Luxury Condo

Your perfect oceanfront vacation! This beautifully designed condo offers breathtaking ocean views, direct access to the sandy shore, and all the comforts of home. Wake up to the sound of waves and enjoy your morning coffee on the private balcony overlooking the water. This beautiful home features: 5 full bathrooms, 8 total beds amongst 3 Bed Rooms and 2 additional sleeping rooms one with a Murphy queen size bed and the other with pull out full size bed. Book your stay today! Permit#: 076342

FamilyLocationOutdoor spaces

5 out of 5 average rating, 19 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.

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Superhost

A private outdoor oasis features a gently curving pool surrounded by a smooth concrete deck. Four lounge chairs are arranged on the patio, nestled under the shade of large trees. Lush greenery and palm trees frame the serene setting, creating a tranquil atmosphere.

4.83 out of 5 average rating, 12 reviews

32 Plantation Dr @ Sea Pines | Heated Private Pool

Indulge in sophisticated coastal living at 32 Plantation Drive, nestled within the tranquil ambience of Sea Pines Resort. Embrace Lowcountry charm in its finest with its serene lagoon views and meticulously crafted design where every detail is thoughtfully curated. Venture out to the private FREE heated pool and explore the resort's many offerings—from Harbour Town and Lawton Stables just stone's throw away to world-class amenities like tennis and golf. Ready to enjoy & relax? Learn more below!

LocationFamilySleep quality

A spacious living area is furnished with a blue sectional sofa and a coffee table. Soft lighting is provided by two lamps on either side of the sofa. A large patio door opens to an outdoor seating area, allowing natural light to fill the room.

5 out of 5 average rating, 20 reviews

Renovated 1BR HHI – Walk to Beach & Salty Dog Café

Welcome to your home away from home on Hilton Head Island! Stay steps from the beach in this newly renovated 1-bedroom villa with all new furnishings. It is the perfect blend of comfort, convenience, and coastal charm. Nestled just a short walk from the beach and the famous Salty Dog Café, you're in the heart of Sea Pines fun with dining, shopping, biking, pickleball and sun-soaked relaxation right at your doorstep, not to mention nearby access to some of the state’s most iconic golf courses.

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Superhost

5 out of 5 average rating, 3 reviews

Family Memories Are Made Better at Deer Run

Relax with the whole family at this private and adorable 3 Bedroom, one level home just a short bike ride to the beach! Nature surrounds you in the secluded fenced in backyard setting with heated walk-in pool, and spa. This spacious home includes large bedrooms, Open living room with fireplace, and bedrooms. Prepare your family meals in the fully equipped kitchen, dine in or walk out walk-out to the screened porch perfect for family gatherings and memories to last a lifetime. Permit # 32403

FamilyBack gardenPool

5 out of 5 average rating, 28 reviews

Harbour Town Marina Studio | Walk to Lighthouse

Cozy, bright penthouse studio with direct views of the Harbour Town Marina, just steps from the lighthouse, shops, dining, and golf. The space features a comfortable sleeping area with king bed, sitting space, kitchenette, and full bath with tub/shower combo. Enjoy the small private balcony, perfect for morning coffee or evening sunsets over the marina. Ideal for 1–2 guests looking to enjoy the Harbour Town lifestyle in Sea Pines. Located on the fourth floor with convenient elevator access.

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The exterior of the house presents a modern coastal design, featuring a spacious deck with multiple seating areas, a large umbrella, and a grassy surrounding. Large glass doors invite natural light into the interior while a BBQ grill is visible on the deck.

5 out of 5 average rating, 44 reviews

New Sea Pines Remodel Close To Beach

This stunning, newly remodeled getaway offers a modern coastal vibe with an open and airy floor plan that features two spacious king Master en-suites and an additional bedroom with two full beds - sleeps up to eight. Enjoy views of the famed Harbour Town Golf Links and breathtaking sunsets right from the back deck! Add in the chef's kitchen, access to a community pool, tennis and pickleball and The Pines is the perfect vacation destination for families seeking a luxury Hilton Head escape!

FamilyLocationBiking

5 out of 5 average rating, 15 reviews

Sea Pines Villa: Pool, Tennis & Golf

This renovated 1-bedroom villa in Sea Pines offers comfort and convenience just steps from shops, dining, and bike rentals. Enjoy a plush king bed, memory foam sleep sofa, sleek walk-in shower, Smart TVs, a private deck, and a fully equipped kitchen with washer/dryer. Relax by the sparkling pool, play free tennis on-site, or bike to Harbour Town and the Beach Club. With the seasonal trolley nearby, every island adventure is at your fingertips. One small dog (under 25 lbs)- $230 pet fee.

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Guest favourite

A spacious living area is furnished with a light gray sofa and two striped armchairs. Natural light filters through the sliding glass doors, which lead to a balcony. Two framed landscape images are displayed on the wall, complemented by a neutral area rug and a ceiling fan.

4.87 out of 5 average rating, 62 reviews

SeaPines - Pool Free Bikes, Walk to Beach, Pets OK

Located in central SeaPines, this beautiful two bedroom in Plantation Club offers a perfect home to stay comfortably and still be close to the best things Sea Pines HHI has to offer. This spacious villa now welcomes your small dog to the trip. A fully equipped, newly renovated kitchen allows guests to cook their favorite meals right at home even while on vacation. On the third floor of the mid-rise, take in the stunning golf view off the veranda or enjoy exploring on the free bikes.

LocationFamilyNearby

5 out of 5 average rating, 125 reviews

5 Star Location-Harbourtown-Walkable Area

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.

LocationFamilyQuiet

A red and white striped lighthouse is visible, surrounded by boats docked in a harbor. A multi-storied building with a sloped roof stands in the background, complementing the maritime setting under a partly cloudy sky.

5 out of 5 average rating, 49 reviews

Harbour Town Lighthouse & Sunset Views | Sea Pines

Enjoy direct Harbour Town lighthouse, yacht basin, and Calibogue Sound views from our beautifully updated Sea Pines condo. Located in Ketch Court, this cozy coastal retreat puts you steps from Harbour Town dining, shopping, sunsets, bike paths, golf, and the marina. Perfect for couples, golfers, or a small family looking for one of Hilton Head’s most iconic locations. Come relax and unwind and take in all that Harbour Town has to offer!

FamilyLocationCleanliness

A modern living area features a gray sofa adorned with decorative pillows, complemented by a round wicker coffee table. Light fills the space through large windows, with a balcony view visible in the background. A flat-screen TV and lamps enhance the inviting ambiance.