Hilton Head, SC 2+ Bedroom Vacation Rentals

Summary:Sealoft 2042The Space:Appreciate lush surroundings in a striking treehouse that offers all of the amenities of modern life along with close by fishing areas, beaches, rivers, and the ocean. You'll be well-served by this Sea Pines treehouse...

Summary:Island Club 5501The Space:This fifth-floor, oceanfront Island Club villa is a prime hideaway for your next oceanside vacation. Each guest has access to the complex’s many recreational facilities, including the shared pool/hot tub complex...

Summary:Pools • Tennis • Private Beach Access • Hilton Head IslandThe Spa on Port Royal Sound | Unit 1218The Space:Feel the ideal blend of coastal serenity and resort-style amenities in this handsome ocean‑view condo at The Spa on Port Royal...

Summary:Fiddlers Cove 17KThe Space:Welcome to Fiddler's Cove Beach & Racquet Club, a gorgeous condo complex located mid-island in Hilton Head, SC, just a few hundred yards from the pristine beach. This gated community offers a ideal blend of...

14 Collier Beach, Hilton Head Island is a striking oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grille. The home features a extravagant master suite...

Located at the end of the street with direct beach path access from the pool, just 2 mins. from the gorgeous beaches of Palmetto Dunes, this home offers a great space for your next hideaway! Savor countless sunny days by the pool and calming...

**New Bonus Room Off of the Pool and Updated Bathrooms!!**44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a enormous 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the...

This gorgeously modernized 3-bedroom, 3-bathroom oceanfront condominium, located on the 4th floor, was completely refreshed in April 2026 and offers a fresh, modern coastal getaway with all-new furnishings and finishes throughout.The open-concept...

Welcome to this cavernous three-bedroom Queens Grant villa, appealingly located right on the first hole of the esteemed Robert Trent Jones Oceanfront Golf Course. Ideal for families or groups, this villa offers comfort combined with gorgeous vistas...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.435 Captain's Walk overlooks the pool out to the ocean! Lots of recent updates!435 Captain’s Walk is a second-floor, 3-bedroom, 3-bathroom end unit that...

Summary:Courtside 83The Space:Your dream Hilton Head escape awaits at this 2BR/2.5BA townhome! Located in the Courtside Villas community, you can walk to the soft sand and rolling Atlantic waves in just a few mins.. Return to dip in the two shining...

This Hilton Head gorgeous two bedroom, two bath plus additional twin room villa has exceptional vistas of the George Fazio golf course! The kitchen is completely equipped featuring new stainless steel appliances and granite countertops. The...

You'll be glad you chose this marvelous two bedroom villa with its freshly refreshed kitchen, floor, beds, linens and furnishings! The floor has been updated throughout the entire villa. The beds in both the primary and guest bedrooms are new...

Summary:Fiddlers Cove 6iEscape to Hilton Head Island and savor the ideal combination of beachside convenience, resort amenities, and laid-back coastal comfort. Located within the gated Fiddler's Cove Beach & Racquet Club community, this inviting...

You'll appreciate the privacy and updates in this cavernous end unit in Wildwood Spa, a private little neighborhood just ten mins. on foot to the Sea Pines Beach Club. This Premier Property features two bedrooms and an added loft area with a trundle...

The Windsor Place condominium is attractively decorated villa having four bedrooms and four baths! This condominium has been newly refreshed with new lighting, bathrooms, paint and floor!Being one of the bigger units in Windsor Place makes this...

This striking modernized 3 bedroom oceanfront villa is for those who want to feel like they are always on the beach. As you enter the villa, you will look out toward the beach under a massive oak tree and you will know you have found one of the...

Summary:Colonnade Club 204The Space:This condo provides simple access to a hot tub and pool. Savor the delightfully landscaped grounds from the outside patio area that features a rustic, wooden foundation and a table with numerous patio chairs.The...