Hilton Head long-term rentals

With a fully-furnished monthly rental, South Carolina’s coastal beauty is yours to explore.

View from a balcony at a Hilton Head rental.
Vacation Rentals for Road Trip: Hilton Head, SC

A long-term vacation to look forward to

Receive a discounted rate on many of our monthly rentals (displayed at check-out) and reductions in our usual fees. We also allow for partial payment if you book at least 45 days ahead of time. Call (888) 257-7970 for additional information about long-term bookings.

Plus, enjoy peace of mind with our simple cancellation policy and optional travel insurance.

Call us to learn more >

cartoon design of a home.
Vacation rentals in Hilton Head, SC

Sun, sand, and Southern charm

Unwind and explore along beautiful Hilton Head Island. Book a long-term rental along the coast and revel in ocean views, world-class golf courses, fresh seafood, scenic walking trails, and 12 miles of shoreline. Hilton Head Island is well-known as a favorite summer playground, but the fun doesn’t end when the season does. Snowbirds, couples, and families flock to these stunning shores for a change of scenery with remote work and schooling. Gather together in a fully furnished monthly rental and let your adventure begin.

Oceanfront vacation rental in Hilton Head with pools.

FEATURED HHI LONG-TERM RENTAL

Dune Lane 105

Save your spot by the beach in this spacious and stunning crowd-pleaser. Located on a scenic oceanfront just two miles from Coligny Beach Park, this family home boasts two wraparound decks, an elevator, a luxurious outdoor pool, and a private boardwalk to the beach. Between boogie boarding at the beach or lounging by the pool, there’s something the whole family is sure to love.

Browse long-term rentals by neighborhood

Find a HHI community that fits like a glove for your extended stay. Reserve your beach house rental before they book up.
The interior of a maritime themed vacation rental in Hilton Head, SC.

FEATURED UNIQUE MONTHLY HILTON HEAD RENTAL

Sealoft 2042

Make it a winter to remember with a treehouse vacation rental. Located just a short distance from nearby beaches, rivers, and fishing areas, you’ll have no trouble getting out to adventure or relax along the waves. Book this dog-friendly stay and bring the whole family out for some quality time by the ocean, whether playing fetch in the waves or hitting the nature trails.

Monthly resort condos in Hilton Head

Barking allowed at these long-term vacation homes

Your four-legged friends want a vacation too. Book a pet-friendly monthly rental and bring your dog along for twice as much fun by the beach.

The pool area of a pet-friendly vacation rental in Hilton Head, SC.

FEATURED PET-FRIENDLY VACATION HOME WITH A PRIVATE POOL

Gloucester 36

Your private slice of paradise awaits. Feel right at home in this family-sized pet-friendly retreat. Spend the day exploring all that HHI has to offer, then return to your vacation rental for more fun, between dinners on the outdoor patio, quality time on the screened porch, a dip in the swimming pool, and drinks at the pool bar.

MONTHLY RENTALS WITH POOLS

Dive into relaxation

The beach is nice, but sometimes there’s no substitute for poolside lounging. Float, swim, or play your way with access to a pool on your extended stay vacation.

The backyard of a vacation rental in Hilton Head, SC with a pool.

FEATURED LONG-TERM RENTAL WITH PRIVATE POOL

Dunes House

If easy living is the name of the game, this beachfront home is your ace in the hole. Spacious and beautifully designed, you can come together with family for big breakfasts in the fully-equipped kitchen or lounge around across the outdoor deck, pool, hot tub, or the beach just a few steps away. Treat your loved ones to a new favorite tradition with a long-term vacation rental on Hilton Head Island all winter long.

Long-term rentals perfect for golfing

Can’t get enough time on the greens? Spend your beach trip or snowbird vacation putting away on expertly-groomed fairways waiting just beyond your front door.

Long-term rentals perfect for fishing and boating

Make it easy to enjoy fishing, water sports, or a simple day on the water. The open sea (and waterways) await at these fully furnished long-term rentals on Hilton Head Island.

Long-term beach houses steps from the shore

Vacation to the fullest with the ocean just beyond your front door. Grab a monthly beach house rental and savor a quick commute to fishing, kayaking, and water activities.

HHI long-term rental FAQ

In many cases, yes. If your reservation is eligible for a discount, you’ll see that reflected in the price when you book. Our long-term reservation sales specialists can also help answer any questions about discounts. Call (888) 257-7970) or email snowbirdreservations@vacasa.com.

You don't have to pay all at once. In fact, you’ve got a couple of different options to pay in installments. First, you can make monthly payments (over 3, 6, or 12 months) on most reservations through our partnership with Affirm. It’s easy, too—just select “Pay later with Affirm” when completing your vacation purchase.

If you book at least 45 days before your trip, your other option is to split your trip into just two payments. If the cost of your reservation is between $2,000 and $9,999, 50% is due at the time of booking. If the cost of your reservation is over $10,000, 25% is due at the time of booking. If you choose to make two payments, you must make your second payment 30 days before the start of your trip.

Vacasa offers snowbird rentals across South Carolina’s coast, Hilton Head Island included. Find the perfect vacation rental for your trip when you add the snowbird-friendly filter to your search.

Find hundreds of long-term, snowbird, and monthly rentals on Hilton Head Island by adding the snowbird-friendly filter to your search.

Hilton Head Island makes for a great winter escape, with plenty of activities for all ages. With its year-round mild temperatures, beach activities, fishing, and water sports are always in season. Through the fall and winter, Hilton Head also enjoys several seafood festivals and holiday events, like the Hilton Head Island Seafood Festival. The island is a popular retreat for golfers who prefer to play year-round, as well as families and couples looking to spend time outdoors.

Long-term rental inspiration