Hilton Head, SC 2+ Bedroom Vacation Rentals

Coastal CharmOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located on the 1st Tee of the Clipper Course in Shipyard Plantation, this impressive French...

Shorewood 311Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'At this Hilton Head condo, you can take a dip in the seasonally-heated, shared pool, walk on the...

2nd Row Ocean! 5 Bedrooms, 4 Full baths, 2,500sq.ft. Next to Sea Pines Ocean gate.You will definitely fall in adore with this charming South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row to the...

The ideal Hilton Head vacation starts with finding the ideal Hilton Head vacation rental! Consider it done when you book this 4 bedroom, 4 bath bright and sunny home, located in Hilton Head Island’s Shipyard less than a mile from the beach.To the...

Tennismaster 303Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please note the Tennismaster pool is closed as of 9/25/2025. Renovations will begin...

Plantation Club 486Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to Plantation Club 486 and experience the casual lifestyle of Hilton Head Island...

Seascape Villas 3043Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Serenity awaits you at this comfortable 1100 sq. ft. home on South Forest Beach Drive at...

Ocean Breeze 37Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Pack your favorite swimsuits and get ready for unlimited fun in the sun here on Hilton Head...

Mooring BuoyOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please read our important pool heat information to help you have the best vacation possible!*This...

Queens Grant 768Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Swim at the shared pool, bicycle along a path that winds its way through the plantation, or...

Feel coastal luxury in this refreshed 2 bedroom, 2 bathroom villa, where every detail has been thoughtfully curated for your comfort. Wake up to pretty oceanfront vistas, ideal for appreciating your morning coffee or evening beverages. Inside...

Managed professionally by Vacation Time of Hilton Head, our oceanfront complex is charmingly booked directly through our website.Welcome to 23 Beach Villas: Your Oceanfront Oasis!!Exciting News: Our Sensational New Swimming Pool is Now Open!Discover...

Ketch Court 824Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ketch Court 824 is conveniently located in the heart of Sea Pines. This newly updated villa...

Island Club 1401Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This two-bedroom, two-bath oceanview condo is great for families or other gatherings...

Calibogue Club 2630Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Centrally located in Sea Pines Resort, this townhouse style condo has been completely...

OCEANFRONT DOLPHIN WATCH! This handsome villa has been completely re-decorated by a professional designer! The view is spectacular. You will be able to watch dolphins play all day in this charming condominium! Savor a grand, unobstructed view of...

Golfmaster D2Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Slip into the island mindset with nautical decor, a cavernous layout, lagoon vistas, and all of...

2 Oyster Catcher | 2 Minute Walk to the Beach *4 Bedrooms | 4 Bathrooms*Sleeps 10*2 Kings, 2 Twins, 1 Queen, Queen Sleeper Couch*6 SMART TVs | DVD | Alexa | Wi-Fi | Keurig*Guest Has Use of the Garage *Two Master Suites*5th Row Ocean Home*Private...