Hilton Head, SC 2+ Bedroom Vacation Rentals

Fiddlers Cove 2KOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor a coveted top-floor location, set amid the gorgeously maintained grounds of Fiddler’s...

Golfmaster J2Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the best of Hilton Head Island from this impressive condo located in the gated community of...

This centrally located Plantation Club three bedroom villa is a short walk to the impressive SeaPines Beach Club and Golf Clubhouse. Striking updates in 2022 include new carpeting, furnishings, sliding glass doors, screened porch refurbishment and...

You'll be glad you and your family chose this sizable five bedroom home with four full baths and two half-baths! The entire home has many upgrades and has been attractively decorated with comfort and the beach in mind. The kitchen is handsome and...

Feel Coastal Luxury at 180 Olive Shell Court – Your Hilton Head Island RetreatWelcome to your dream vacation hideaway on elegant Hilton Head Island – consistently ranked the #1 island in the U.S. by Travel + Leisure readers for its pristine...

Seascape 3227: Stylish Tri-Level Townhome – Just a 5-Minute Stroll to the Beach!Book Direct for the Finest Prices & Feel!Professionally managed by Vacation Time of Hilton Head, Seascape 3227 promises a seamless booking experience and a stay...

The Cottages 30Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'A modern island escape awaits at this condo at the Cottages. Located in the resort community of...

***Please use the "Contact Host" located under Check Availability for any reservation questions that you may have.Most high-demand season weeks are offered on a Friday, Saturday, and Sunday check-in & out with SEVEN NIGHT INCREMENTS. HOWEVER, we may...

Sea Pines Resort 01Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make your next coastal hideaway a breeze when you stay at this Hilton Head Island resort...

Unwind and Unwind at This Elegantly Updated 2 Bedroom, 2 Bathroom Vacation Rental on Hilton Head Island.Escape to this newly refreshed, coastal inspired getaway, where modern comfort meets tropical appeal. Located in a relaxing area with vistas of...

This amazing home has something to offer everybody with its four bedrooms and four bathrooms, private pool and spa. The kitchen is huge and features ample storage and prep space, stainless steel appliances, island cooktop and bar seating for two. ...

Forest Beach Villas 405Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'The worries of everyday life aren't allowed here on Hilton Head Island, so slip into...

Villamare 1410Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make your next trip to Hilton Head Island an exceptional one by staying in this gorgeous home in...

You'll savor this handsome two bedroom villa located in Queens Grant Village within the heart of Palmetto Dunes. This Queens Grant villa is centrally located, providing very painless access to the Palmetto Dunes Tennis Center, Robert Trent Jones...

Hilton Head Resort 1108Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to a delightfully updated two-bedroom, two-bath condo located in the serene...

Stunning coastal chic two bedroom two bathroom villa! Come and relax in this newly modernized and decorated 1st floor villa in Palmetto Dunes Oceanfront Resort within the Centre Court complex. Savor peaceful mornings on the porch overlooking the...

Sealoft 2055Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'A lofted villa in a canopy of trees where the windows are the walls is waiting to welcome you to...

Feel true island luxury in this delightfully remodeled four bedroom, five bathroom lagoon-front getaway, ideally positioned on one of the widest stretches of the breathtaking 11-mile lagoon system in Palmetto Dunes. Just a short walk to Palmetto...