Resort vacation rentals in Hilton Head Island

A serene pond reflects the nearby resort buildings, surrounded by lush green trees. Wooden decks extend into the water, providing spaces for relaxation. The architecture features a charming gazebo-style structure with a peaked roof, enhancing the natural beauty of the surroundings.

Marriott SurfWatch Two Bedroom Villa. Book Now!

Reservations are available in weekly (7 night) increments with arrivals and departures on Thursdays, Fridays, Saturdays, and Sundays only. Welcome to Marriott's SurfWatch on the charming island of Hilton Head, South Carolina. Here you’re surrounded by ocean views, delicate sea-green marsh grasses, rolling sand dunes, and refreshing sea breezes. This 31-acre resort puts you in touch with nature, and the limitless leisure activities that make Hilton Head Island a popular destination.

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.

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.

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.

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.

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.

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.

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.

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 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.

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.

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.

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 expansive outdoor pool is surrounded by lounge chairs and palm trees, reflecting evening lights. The sleek, multi-story building provides a modern backdrop, while the pool's gentle curves invite relaxation. Umbrellas offer shaded seating areas for comfortable enjoyment.

Ocean Oak Resort - 2 Bedroom Plus - Partial Ocean

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.

4.29 out of 5 average rating, 7 reviews

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.

The living area features a green sofa with decorative pillows, complemented by an accent chair and a coffee table. Large glass doors open to a balcony, allowing natural light to fill the space. A framed landscape artwork hangs on the wall.

Resort in Shelter Cove

Harbour Point At Shelter Cove - 2 Bedroom Condo

Waterfront Villas with Pool & Marina Access — Hilton Head (Harbour Point) Wake to serene marsh and marina views, enjoy coffee on your balcony, stroll to the waterfront, lounge by the pool, or explore nearby shops and golf courses before sunset.

A clear blue pool is surrounded by a spacious deck featuring several lounge chairs. The pool area is flanked by palm trees and a three-story building with balconies, reflecting a relaxing outdoor environment.

Resort in Shelter Cove

Sunset Pointe At Shelter Cove - 2 Bedroom

Sunny Lagoon‑View Villa with Pool & Kitchen – Hilton Head, SC Wake with marsh breezes, stroll through palm‑lined paths, sip coffee on your balcony, hit the pool or beach nearby, grill dinner on resort BBQ, then unwind by a fire‑pit under stars.

Popular amenities for Hilton Head Island resort rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly resort rentals

Barony Beach - 2 Bedroom

5 out of 5 average rating, 4 reviews

Marriott's Monarch - 2 Bedroom

Ocean Oak Resort - 2 Bedroom Plus - Partial Ocean

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.

Charming two bedroom at Bluewater Resort

A spacious outdoor pool area is surrounded by lounge chairs and umbrellas in a vibrant blue. The building stands nearby, featuring multiple floors with balconies. Lush greenery and palm trees provide a natural backdrop, enhancing the inviting atmosphere of the resort.

Surfwatch - 2 Bedroom

A large swimming pool is surrounded by lush landscaping and palm trees. Poolside seating is provided with green umbrellas shading lounge chairs. A gazebo stands in the center of the pool, and the sky above features soft colors as the sun sets.

Marriott's Barony Beach - Stunning Two Bedroom!

Marriott SurfWatch Two Bedroom Villa. Book Now!

Aerial view of Marriott's Grande Ocean resort showcases its proximity to the beach and a large, sandy coastline. The sunset casts warm colors over the landscape, while lush greenery and several buildings are visible, along with outdoor pools and a serene pathway leading to the shore.

Marriott's Grande Ocean 2BR Villa Courtyard View

Resort rentals with a pool

Barony Beach - 2 Bedroom

5 out of 5 average rating, 4 reviews

Marriott's Monarch - 2 Bedroom

Charming two bedroom at Bluewater Resort

Surfwatch - 2 Bedroom

Marriott's Barony Beach - Stunning Two Bedroom!

Marriott SurfWatch Two Bedroom Villa. Book Now!

Marriott's Grande Ocean 2BR Villa Courtyard View

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.

Hilton Ocean Oak Charming 2 Bedroom

Resort rentals with a gym

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.

2 Br Marriott Harbour Club

An aerial view of the resort reveals multiple buildings with blue roofs surrounded by lush greenery. A swimming pool is centrally located, featuring lounge chairs placed along the edge. The serene landscape blends natural elements with modern architecture.

Relaxing & Spacious Beach Villa

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.

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

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.

Surfwatch - 2 Bedroom

A tranquil outdoor pool area is situated in front of a multi-story building. Lounge chairs are arranged around the pool, which is surrounded by palm trees and greenery. The clear sky and water create a serene environment, perfect for relaxation.

Resort in Shelter Cove

Sunset Pointe At Shelter Cove - 2 Bedroom

Marriott's Grande Ocean 2BR Villa Courtyard View

The image captures a serene beach scene during sunset, showcasing gentle waves lapping against the shore. Soft colors reflect on the water's surface, while clouds are softly illuminated by the fading sunlight, creating a tranquil atmosphere.

2Br MVC Barony Beach Club

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.