Monthly and Winter Rentals in Hilton Head, SC

How Hilton Head Island Long-Stay Rentals Work

Winter rentals on Hilton Head Island, SC, are the same furnished homes and villas that rent by the week in summer. From fall to spring, when weekly demand drops, companies open them to stays of a month or more at a lower monthly rate. Most name a season: Sunset Rentals rents monthly from October 1 to April 1, host2coast gives its monthly discount from October through February, and Vacation Time of HHI’s snowbird dates for 2026-27 run November 1 to March 20. A few homes rent by the month all year.

The monthly rate usually starts at 28 to 30 nights, and it is rarely shown online: most companies quote a long stay by phone. What it covers varies. Dwell’s monthly rate includes utilities, Wi-Fi and departure cleaning, while Vacation Time’s leaves out departure cleaning, taxes and fees, and bills electricity over $100 a month. Payment and cancellation terms are stricter too: Island Rentals of Hilton Head makes any booking of 28 days or more non-refundable, and Five Star Properties asks for 120 days’ notice to cancel a monthly stay. Book Hilton Head snowbird rentals early: many snowbirds rebook the same home every year, so the best homes for January and February go first.

Winter 2026-27 Monthly Rentals: Windows and Minimums

The monthly season opens in the fall. Sunset Rentals starts renting by the month on October 1, host2coast’s monthly discount runs from October, and Vacation Time of HHI’s snowbird stays begin November 1 and end March 20. The two HHI.com partners, Island Rentals and Coastal Vacations, take stays of a month or longer and quote them by phone. Most companies start the monthly rate at 28 to 30 nights.

Windows and minimums come from each company’s own long-stay page. Many snowbirds rebook the same home year after year, so January and February go first: call early, ask for the total with every tax line, and see what to ask before you book. Companies not listed may still take a long stay; find them all in the rental company directory. Rent by the month and not listed here? Get in touch.

Stay 90 Days and Skip the 10% Tax

Rentals shorter than 90 days in a row carry 10% in taxes: 7% to South Carolina and 3% to the Town. Book 90 nights or more and neither applies, which saves about $100 on every $1,000 of rent. Ask the company to show the tax lines on your quote.

Where a Month-Long Stay Is Allowed

The resort areas that rent by the week also rent by the month. Some private, residential communities bar any lease shorter than 90 days or six months, whatever the Town allows.

Monthly Stays Allowed

Book a month or the whole winter.

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Sea Pines

Homes and villas here are rented by the week and by the month; several island companies list Sea Pines homes for monthly stays, including one in Harbour Town.

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Palmetto Dunes

Oceanfront villas in Palmetto Dunes turn up in several companies’ monthly and winter collections, from Windsor Place to Hampton Place.

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Forest Beach

The condos and homes around Coligny and North Forest Beach are in companies’ snowbird lists, a walk or a bike ride from shops and restaurants.

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Folly Field

Oceanfront villas at Sea Cloisters, on the beach at Folly Field, are in one company’s monthly collection.

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One month minimum

Moss Creek

Just over the bridge, off the island. Rentals must run at least a month, so confirm the current minimum with the association.

90-Day Minimum

Plan on a full season, three months or more.

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Sun City Hilton Head

In Bluffton, not on the island. Every lease must run at least 90 days, and tenants must meet the community’s age rule.

Six-Month Minimum

Not an option for a winter month; these suit a long-term lease.

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Hilton Head Plantation

Leases must run at least six months unless the board approves otherwise, so a winter month is not an option.

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Indigo Run

Every lease must run at least six months, with no subletting.

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Long Cove

The covenants bar leases shorter than six consecutive months without the association’s written permission.

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Windmill Harbour

Homes can’t be rented for less than six consecutive months.

Hilton Head Winter Rentals: What the Season Is Like

Winter is the island’s quiet season, not a closed one. Afternoons are mild, nights are cool, and the beaches and bike paths are yours. The ocean is too cold for most swimmers, so a winter rental is about walks, golf, bikes and long dinners rather than days in the water. Hurricane season ends on November 30. Here are the averages for a snowbird season; the Hilton Head weather guide has every month.

Dogs get the beach to themselves too: from Oct 1 to Mar 31, the Town allows them on the sand at any hour, on a leash or under voice control (see the dog-friendly beaches guide, and the dog-friendly rentals page for homes that take them). It is oyster season, with the island’s seafood markets at their best, and Shelter Cove Harbour marks the holidays with A Coastal Christmas.

Before You Book a Hilton Head Snowbird Rental

Staying Six Months or Longer?

Past a season, you are looking for a lease, not a vacation rental: an unfurnished or furnished home for six or twelve months, through a long-term rental company. That side of the market, including the communities that only allow six-month leases, is on the Hilton Head long-term rentals page.

Try the Island Before You Buy

A winter month is the cheapest way to test a move. Rent in the area you like, shop and drive the way you would live here, then see what a year on the island costs.

Moving to Hilton HeadSave

Taxes, insurance, flood zones and what each part of the island costs, for a winter renter thinking about buying.

More Ways to Plan a Long Stay

Hilton Head Vacation RentalsSave

Hilton Head vacation rentals: beach houses, condos and villas by beach area and complex, who manages them, dog-friendly homes, and how renting works.

Hilton Head Vacation Rental CompaniesSave

Hilton Head rental companies grouped by what each rents, from resort programs to Sea Pines specialists, with phone numbers and links to each one.

Dog-Friendly Vacation RentalsSave

Pet-friendly rentals in Hilton Head: which communities and complexes allow dogs, the beach leash rules by season, and companies with pet filters.

Long-Term Rentals on Hilton HeadSave

Hilton Head long term rentals: houses, villas and condos for rent by the year, the local companies that rent them, and what to ask before you sign.

Hilton Head Weather by MonthSave

Hilton Head weather by month: average highs, lows, rainfall and ocean temperature for all 12 months, plus the live forecast, hurricane season and swim months.

Dog-Friendly BeachesSave

Every Hilton Head beach is dog-friendly, but leash rules change by season and hour — plus a no-dog zone near Fish Haul Creek. Here’s exactly when and where.

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