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Resort holiday rentals in Hilton Head Island

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Top-rated resort rentals in Hilton Head Island

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An expansive outdoor pool area is surrounded by palm trees and colorful umbrellas, creating a vibrant atmosphere. A fountain is centrally located in the pool, with guests enjoying the water. The ocean is visible in the background, complemented by the resort's modern architecture.
Resort in Hilton Head Island

Marriott’s Grande Ocean

FIND TRANQUILITY AT OUR BEACHFRONT HILTON HEAD RESORT Perfectly located on the oceanfront in Hilton Head Island, SC, Marriott's Grande Ocean is a premium vacation ownership resort. Embark on a family vacation or trip with friends at our resort brimming with modern amenities. Enjoy access to three outdoor pools, an indoor pool, a fitness center, whirlpool spas, bocce ball, shuffleboard, a putting green, nature trails, a seasonal kid's camp, on-site dining, and of course, the beach.

A bright living area features a light-colored sofa, a dining table with blue chairs, and a chair in a blue pattern. Large glass doors offer views of the ocean and lead to a balcony with seating. Natural light fills the space through sheer curtains.
Resort in Sea Pines

Marriott Monarch Condo Sea Pines April 5-12 only

Marriott Monarch at Sea Pines on Hilton Head Island framed by six oceanfront acres and gated within the renowned Sea Pines Plantation community. Many family and children amenities including a heated outdoor lap pool, children's splash pad, whirlpool spa and direct beach access. Energize at the fitness center, rent a bicycle or delight in exclusive access to the tennis courts at neighboring Sea Pines Beach Club. Complimentary WiFi, parking and an outdoor grill and firepit.

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The resort pool area is surrounded by palm trees and lounge chairs, with shaded cabanas offering relaxation spots. The expansive pool glistens under the sunlight, complemented by the modern architecture of the buildings in the background.
Resort in Hilton Head Island

Hilton Ocean Oak Charming 2 Bedroom

We are able to offer reservations in weekly increments with arrivals and departures on Saturdays only. Paying homage to the sweeping landscape of grand live oaks that dot Hilton Head Island, Ocean Oak Resort by Hilton Grand Vacations Club is a new oceanfront property offering the best of low country luxury located within minutes of the exceptional golf and tennis, nature excursions, boating and beach activities, and wealth of restaurants this barrier island is known for.

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A wooden boardwalk leads to a serene beach, flanked by tall grasses under a clear sky at sunset. A bicycle is parked on the right side, showcasing a basket attached to the front, inviting exploration of the nearby coastline.
Resort in Sea Pines

Heritage Club, Hilton Head, SC 2-Bedroom

Ask about OUR Fall Special... Hilton Head Island is part of the Lowcountry region in the U.S. state of South Carolina. It's known for Atlantic Ocean beaches and golf courses. The Harbour Town Lighthouse and Museum marks the southwest tip. The Coastal Discovery Museum features heritage buildings, trees, and themed gardens. Between the island and mainland, the Pinckney Island National Wildlife Refuge salt marsh hosts deer, alligators, and birds.

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Aerial view of the Marriott's Grande Ocean resort captures lush landscaping and multiple buildings, framed by winding pathways. The sandy beach and gentle waves are visible under a colorful sunset, creating a serene coastal atmosphere.
Resort in Hilton Head Island

Marriott's Grande Ocean 2BR Villa Ocean View

Experience coastal luxury at Marriott's Grande Ocean, perfectly positioned on Hilton Head Island's pristine beachfront. This premier resort offers direct access to miles of sandy beaches and Atlantic waters. Features multiple pools, hot tubs, and seasonal activities. Minutes from world-class golf courses, tennis courts, and cycling paths. Perfect location for exploring the island's natural beauty, upscale dining, and shopping at Coligny Plaza.

An aerial view of a wide sandy beach is shown, bordered by gentle ocean waves. Beachfront buildings are visible amidst lush greenery in the background, providing a sense of spaciousness. The scene captures people enjoying the beach, highlighting the natural beauty of the location.
Resort in Sea Pines

2Br Marriott Monarch at Sea Pines 4/13-4/20

Oceanfront Luxury at Marriott’s Monarch at Sea Pines RBC Heritage Week 4/13-4/20 Experience the ultimate Hilton Head Island getaway at Marriott’s Monarch at Sea Pines, a premier beachfront resort nestled within the prestigious Sea Pines Plantation. Set on six lush oceanfront acres, this tranquil retreat offers spacious 2-bedroom, 2-bath villas—each 1,200 sq. ft.—designed for comfort and convenience

A spacious studio layout is shown, featuring a comfortable sofa and armchair, with natural light filtering through large windows. The sleeping area contains a cozy bed with a headboard. A small dining table and a kitchenette are visible, providing a functional living space.
Resort in Palmetto Dunes

1 Large BDR Studio Near the Beach

The Village at Palmetto Dunes is a beautiful natural setting just a quick walk from Hilton Head Island's famous beaches. Guests can relax at the Dunes House Beach Club. The Village community amenities include a heated pool, hot tub, playground, waterside picnic tables, and BBQ grills.

An inviting entrance features a large covered porch supported by elegant wooden beams. Surrounding greenery provides a relaxing atmosphere, while the multi-story building showcases a combination of balconies and large windows that enhance the exterior appeal.
Resort in Sea Pines

Harbour - 2 Bedroom Condo

Waterfront Villa + Pool & Marina Access — Hilton Head (Harbour Club) Wake to marsh breezes, sip coffee on the balcony, stroll to the marina for a waterfront lunch, hit the pool or spa, then cook dinner in your full kitchen and relax with sunset views — a laid-back island escape.

The image showcases the Marriott Grande Ocean resort located along a sandy beach. The building's architecture is visible against a backdrop of green trees, with guests gently strolling along the shoreline. The ocean waves lap at the shore, reflecting a clear blue sky.
Resort in Hilton Head Island

2 Star Marriott Grande Ocean

Discover the beauty and relaxation of Hilton Head Island at the Marriott Grande Ocean. Situated on the island’s stunning coastline, this oceanfront resort offers the perfect blend of luxury, comfort, and adventure, making it an ideal destination for families or couples.

The image captures an oceanfront view, showcasing a multi-story building adjacent to a sandy beach. Lush green landscaping features palm trees and shrubs, enhancing the coastal setting under a clear blue sky with gentle waves lapping at the shore.
Resort in Sea Pines
5 out of 5 average rating, 4 reviews

Marriott's Monarch - 2 Bedroom

Spacious Family Villa w/ Pool & Resort Perks — Orlando, FL 🌴 Start with coffee on your balcony, enjoy a lazy morning swim or resort pool time, cook a home‑style lunch in your kitchen, relax in comfort and plan your Orlando adventure — easy, cozy, flexible stay.

An inviting oceanfront pool area is surrounded by palm trees and lounge chairs. The midrise building is visible in the background, with outdoor seating areas nearby. Soft lighting enhances the tranquil ambiance as evening approaches, reflecting off the water's surface.
Resort in Hilton Head Island

Ocean Oak Resort - 2 Bedroom Condo

Seaside Family Suites with Ocean Views & Pool – Hilton Head Island Wake to moss-draped live oaks and salt air, enjoy breakfast in your bright condo, lounge by the zero-entry pool, stroll to the beach, then unwind on your balcony under southern skies.

The image captures a calm swimming pool area featuring a large gazebo at its center. Surrounding palm trees and multiple lounge chairs create a relaxed atmosphere. An apartment building can be seen in the background against a clear sky, adding to the scenic environment.
Resort in Hilton Head Island

Barony Beach - 2 Bedroom

Oceanfront Paradise – Pools, Beach Access & Tropical Views - Hilton Head Island Wake to Caribbean breezes, enjoy breakfast on your balcony, stroll to the beach, relax by the pool, explore local dining, then watch a stunning sunset over the ocean.

Popular amenities for resort rentals in Hilton Head Island

Quick stats about resort rentals in Hilton Head Island

  • Total holiday rentals

    Explore 70 holiday rentals in Hilton Head Island

  • Nightly prices starting at

    Hilton Head Island holiday rentals start at £67 per night before taxes and fees

  • Verified guest reviews

    Over 30 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    70 of Hilton Head Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hilton Head Island rentals

  • 4.8 Average rating

    Hilton Head Island stays are highly rated by guests – averaging 4.8 out of 5!

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