Hilton Head, SC 5+ Bedroom Vacation Rentals

This amazing near ocean home in the heart of Palmetto Dunes is brand new to the rental market for summer 2024! With only a 5 min. walk to the beach, private pool, private dock, and a fantastic layout for families, this is sure to be a new favorite...

You can practically feel the sand between your toes! This Palmetto Dunes island beauty is at the end of the beach path, so you’re just a few flip-flops or barefoot steps to the ocean and fun in the sun. The first-floor living area has a handsome...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This impressive 5-bedroom, 5.5-bathroom home is located in the heart of North Forest Beach. Ideally located, it features direct access to the pristine sandy...

9 Sandy Beach Trail, Hilton Head Island. Welcome to your bespoke-constructed vacation home! This striking property features an open-concept layout with the kitchen, living, and dining areas facing the pool, creating a seamless indoor-outdoor...

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

3 Port Au Prince is a outstanding 5 bedroom, 3.5 bath, pet friendly home located in the gated community of Shipyard Plantation. The entirely equipped kitchen has granite countertops, new range, island that seats 3, and breakfast table for six...

Sandcastle 97Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.Step inside to an impressive, upsized entryway that immediately sets the tone for this exceptional home. The huge entrance features a sweeping spiral staircase...

Treat your family with this immense five bedroom home located oceanfront on Catboat Lane within Palmetto Dunes Oceanfront Resort! The gourmet chef's kitchen will be entirely-equipped with everything you'll need to prepare a meal for your entire...

Cartgate 21Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Freshly updated, cavernous home with six bedrooms and five baths that accommodates up to 16 people...

This new, 5 bedroom, 5 ½ bath, home is a ideal fit for extended families, or as a multi-family vacation residence. Feel absolute luxury and convenience in this pretty professionally decorated coastal beach home. As a guest at Serenity Now you are...

True Southern Living at its best! This gorgeous Sea Pines home with an open floor plan, ideal indoor/outdoor living, tons of natural sunlight, and steps to the world-famed sandy beaches of Hilton Head, this home is a true gem! Coming soon!!!*New...

High Water 9Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An broad luxury home in Palmetto Dunes, High Water 9 features a single-level layout with seven...

Bradley Beach Road EstateOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Offering a memorable, family-friendly, coastal escape, this charming home is located...

Come appreciate this enormous five bedroom and five bathroom home located on Palmetto Dunes' 11-mile lagoon system! Located within the heart of Palmetto Dunes Oceanfront Resort, this home has been attractively decorated throughout with wood floor...

Tucked away just four rows from the ocean and directly across from a beach access path, this roomy 5 bedroom, 4 bathroom home offers the ideal blend of comfort, privacy, and unbeatable location.As you enter, you’re greeted by an open floor plan...

Welcome to your dream vacation home located in the heart of Palmetto Dunes Oceanfront Resort. This delightfully appointed 5-bedroom, 4.5-bath offers the ideal blend of coastal appeal, modern comfort, and outdoor serenity ideal for creating memorable...

4 Surf Watch Way is a gorgeous 6-bedroom, 5.5-bathroom, pet friendly home accommodating up to 16 guests and making it ideal for family get-togethers or huge gatherings. Outside, a magnificant deck overlooks the pool and spa, with a entirely fenced...