Holiday rentals in Sea Pines

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Top-rated holiday rentals in Sea Pines

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Top guest favourite
The outdoor space features a shimmering pool surrounded by a spacious deck. Lounge chairs and a dining table are arranged for relaxation and enjoyment. A large umbrella provides shade, and a decorative swan float adds a playful touch to the calm waters.
Home in Hilton Head Island
5 out of 5 average rating, 32 reviews

Marsh Views | Pool, HotTub, Game Room&Pet Friendly

Welcome to The Heron Hideaway- your Luxury Hilton Head Getaway. Stay Lowcountry in this exclusively designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from SeaPines Beach Club and 6 mins from the Harbourtown Golf Links. Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, pool access, HarbourTown Lighthouse, & most importantly- the beach!

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

Top guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 25 reviews

Sea Pines Hut, 5-min Stroll to Ocean, Dog Friendly

Ocean, serene, luxury! Awaken your senses in this cottage surrounded by natural beauty of pines, pond, and blue herons. 5 min walk to Sea Pines pristine beach. 2-mile bike to the beach club and Nature Reserve full of wildlife. Luxurious interior and cozy outdoor porch, plush king bed, queen sofa bed sleep 4. cathedral ceiling, dog friendly, free bikes, beach chairs and cart, perfect for couples, solo travelers, or small families looking to create a luxurious Hilton Head Island experience.

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.

Top guest favourite
A private pool area is nestled among lush greenery and towering trees. Sun loungers are arranged around the pool, providing a tranquil setting. A secure fence surrounds the pool, enhancing privacy and safety in this serene outdoor environment.
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
An open-concept living area features a beige sofa with decorative pillows and a light-colored armchair. A wooden coffee table rests on a neutral-toned rug, while a round mirror adorns the wall. Light streams through sliding glass doors, illuminating the space and leading to the kitchen.
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, 3 reviews

Charming Lagoon view Townhome near Harbor Town

With a picturesque lagoon view this two-bedroom townhome is perfect for getting away from the every hustle. Spacious living area to relax and enjoy the peaceful settings of the lagoon on the back patio. Two well appointed bedrooms upstairs each with their own full bath and TV's. Walking distance to the Harbor Town Golf Club and Tennis courts as well as the Harbor town to shop, eat and enjoy the beautiful sights of the marina.

Superhost
Aerial view captures the scenic beachfront, showcasing two pools surrounded by palm trees. Lounge chairs are arranged around the pools, while the sandy beach leads to the ocean in the distance. The serene landscape includes well-maintained greenery and pathways leading to the beach.
Apartment in Hilton Head Island
4.71 out of 5 average rating, 7 reviews

Marriott's Monarch at Sea Pines 2BD

Marriott's Monarch at Sea Pines is located along six oceanfront acres within Hilton Head Island's renowned Sea Pines Plantation - a natural beauty framed by spectacular scenery. This beautiful vacation ownership resort embraces the natural setting and offers an idyllic location and exceptional amenities. With privileged access to the adjacent Sea Pines Beach Club, you can make golf and tennis part of your day as well.

Top guest favourite
The unique structure features floor-to-ceiling windows, allowing natural light to illuminate the interior. Surrounded by tall pine trees, the exterior showcases a blend of green tones. An inviting deck area includes seating options, creating a perfect spot to unwind in nature.
Home in Hilton Head Island
4.99 out of 5 average rating, 82 reviews

Harbour Town Treehouse | Deer Island | Sea’Forever

Please see our almost 1000 5-star reviews at our other properties. Enjoy unbelievable tranquility high in the Sea Pines tucked away on Deer Island next to Harbour Town. Walk to the shops, restaurants, entertainment, and the Yacht Basin in just minutes. Feed the deer from your hand while you connect with nature. The Sea Loft is just one house away from the Turtle Trail that winds along the marshlands.

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.

Top guest favourite
A cozy balcony setting is pictured, featuring comfortable seating and a view of the scenic marina. The iconic Harbour Town Lighthouse stands in the background, accompanied by moored boats and lush greenery along the waterfront. Bright blue skies enhance the tranquil atmosphere.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 23 reviews

MyStay at 1027 Caravel Ct.-Lighthouse View & Pool!

Harbour Town villa with direct views of the iconic lighthouse and marina. This updated 2BR retreat features luxury vinyl flooring, stainless steel kitchen, private balcony, and elevator access. Walk to dining, shopping, golf, and the Harbour Town Pool. Located inside gated Sea Pines with two gate passes included. Premier views, unbeatable location, elevated MyStay hospitality. Sleeps 6.

Superhost
A private pool is surrounded by a screened lanai, offering a serene space for relaxation. Wooden lounge chairs are positioned comfortably beside the pool, providing a tranquil view of the lush greenery outside. Sunlight reflects off the water's surface, enhancing the inviting scene.
Home in Hilton Head Island
5 out of 5 average rating, 7 reviews

Island Getaway - an iTrip Hilton Head Home

Stop your search and reserve your dates now for this incredible vacation home tucked away on a quiet & peaceful cul-de-sac within the Greenwood Forest community of Sea Pines Resort! This beautifully renovated & decorated home features a private pool (which can be heated for an additional fee) and a flowing, open floor plan layout with all the rooms located on the same floor.

Popular amenities for Sea Pines holiday rentals