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Resort holiday rentals in Hilton Head Island

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Top-rated resort rentals in Hilton Head Island

Guests agree: these resort rentals are highly rated for location, cleanliness and more.

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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 Grand 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.

Resort in Hilton Head Island

Family friendly resort, minutes from beach!

Stay in a spacious apartment nearby the beach, with all the comforts of home. 3 bedroom, 3 bathroom apartment with full kitchen, living room, dining area. Wifi, washer & dryer. Gym/fitness center on site. Family friendly resort, plenty of on-site and nearby activities, minutes from the beach. Kayaking, golf, biking, on-site pools, hot tubs, lazy river. Resort activities. Fun, relaxing getaway for all ages. Nearby activities, restaurants & nightlife.

Superhost
A large pool area is surrounded by tropical landscaping, featuring a winding lazy river and a splash pad. Loungers with vibrant umbrellas are arranged around the pool, and the resort building rises in the background against a clear sky.
Resort in Hilton Head Island

Charming two bedroom at Bluewater Resort

We are able to offer reservations in weekly increments with arrivals and departures on Saturdays only, The interiors of this unit will make you feel like you're in Key West instead of being located on Hilton Head's beautiful Intracoastal Waterway. You will be amazed at the stunning 'Low Country' sunsets. The helpful staff (seasonal) at the Activity Center can help you plan golf as well as the many other things offered on Hilton Head Island.

Superhost
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.

Superhost
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

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

An aerial view showcases the resort nestled among lush greenery, with clear waters of the harbor in the background. The property features multiple levels, complemented by landscaped surroundings and a small pool area visible on-site, providing a serene escape near the water.
Resort in Sea Pines

2 Br Marriott Harbour Club

Located in a prime area with stunning views of the harbor, this property offers a serene and exclusive atmosphere, perfect for those seeking a tranquil escape or a sophisticated retreat. The spacious and elegantly appointed villas provide the ultimate in convenience, featuring full kitchens, private balconies, and home-like amenities, allowing guests to feel both pampered and at ease.

The image showcases a large swimming pool surrounded by lounge chairs and umbrellas. A multi-story building is visible in the background, framed by palm trees and greenery. The atmosphere appears inviting for relaxation and leisure.
Resort in Hilton Head Island

Surfwatch - 2 Bedroom

This charming resort's seaside setting, comfortable accommodations and fine amenities are sure to impress. With its private oceanfront location, Marriott's SurfWatch offers scenic views of the Atlantic and rolling sand dunes. Nearby, enjoy golf, tennis and miles of trails for hiking and biking.

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 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.

The image captures a serene pool area surrounded by palm trees, with lounge chairs and umbrellas positioned around the water. The multi-story building is visible in the background, illuminated slightly by the evening sky transitioning into twilight.
Resort in Hilton Head Island

Ocean Oak Resort - 2 Bedroom Premier - Ocean Front

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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