Monthly and Winter Rentals in Hilton Head, SC
Hilton Head monthly rentals, for a month or the whole winter: who offers them, and the rules and taxes that change at 30 and 90 days.
Companies Offering Hilton Head Island Winter Rentals
These are the island rental companies that say, on their own sites, that they offer Hilton Head monthly rentals or rent for the winter. Each card has what the company publishes about long stays and a button to that page; the name opens its profile here. The companies marked HHI.com partner are listed first.
Coastal Vacation Rentals
Offers seasonal snowbird rentals of 28 days or longer in homes and villas across the island. It quotes rates by phone.
Island Rentals
Takes stays of a month or longer. Its rental policies make any booking of 28 days or more non-refundable, so it recommends travel insurance for a long stay.
Keeps a snowbird rentals search on its site. It doesn't publish monthly rates or a minimum stay, so ask when you call.
Lists the homes and villas that allow monthly stays and suggests October through March for them. Quotes for a long stay come by phone.
Between the Rentals
Its homepage invites snowbird bookings. It doesn't publish monthly rates or a minimum stay.
Specializes in monthly winter rentals, from one-bedroom villas to pet-friendly homes, and says some extended-stay discounts are only given by phone.
Treats 27 nights or more as a long stay, with the final payment due 90 days before arrival.
Any stay of 30 nights or more gets its monthly rate, which includes utilities, Wi-Fi and departure cleaning. It will extend a stay at the same rate if the home is free.
Takes monthly reservations on stricter terms: cancel at least 120 days before check-in, and shorten a stay at least 90 days out.
Has a monthly rentals collection of villas and homes from one to seven bedrooms, in Sea Pines, Palmetto Dunes and Folly Field.
Says many of its guests stay two weeks or a month in the spring and winter. It doesn't publish monthly rates.
Has a winter monthly rentals search and runs a discount on stays of 28 nights or more. Check its current dates before you book.
Searches monthly, snowbird and extended winter stays online, and shows the full total with taxes and fees before you book.
Gives its monthly discount on any stay of more than 28 days between the start of October and the end of February.
Publishes a list of its snowbird rentals, and one Harbour Town home in Sea Pines rents by the month all year, at a discount for four weeks or more.
Recommends a month or longer in the fall, winter and spring, and has a search for monthly stays.
Takes monthly rentals. Its policies say a monthly stay may carry a monthly usage fee.
Its rental search has a filter for snowbird-friendly homes. It doesn't publish monthly rates.
Rents homes and villas by the month from October 1 to April 1. Monthly quotes are by phone.
Its national snowbird program discounts many monthly stays, reduces some fees, and names Hilton Head among its winter destinations.
Posts winter and monthly specials on individual homes, including discounts on long stays in January and February.
Rents snowbird stays of 30, 60 or 90 days, November 1 to March 20 for the 2026-27 winter. Guests pay electricity over $100 a month, and the monthly rate leaves out departure cleaning, taxes and fees.
The other companies in the rental company directory don’t publish monthly terms online, which doesn’t mean they won’t take a long stay: call and ask. A rental company that offers monthly stays and isn’t listed here can get in touch through HHI.com.
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.
The Rules That Change at 30 and 90 Days
Two lines matter on a long stay. The Town of Hilton Head Island’s short-term rental ordinance defines short-term as less than 30 days, for condos, villas and houses alike (not timeshares or hotels), so a stay of a month or more falls outside it. The taxes change at 90 days. South Carolina charges 7% on accommodations rented for less than 90 consecutive days (5% sales tax and 2% accommodations tax), and the Town adds 3% (a 1% accommodations tax and a 2% beach preservation fee) on stays shorter than 90 days. Past 90 consecutive days, neither applies: Island Time Hilton Head says as much on its monthly stays page. Ask the company to show every tax line on your quote.
| Length of stay | Town short-term rental rule | Accommodations taxes |
|---|---|---|
| Under 30 nights | A short-term rental under the Town’s ordinance | State 7% and Town 3% apply |
| 30 to 89 nights | Not a short-term rental under the ordinance | State 7% and Town 3% still apply |
| 90 nights or more in a row | Not a short-term rental under the ordinance | Neither the state nor the Town tax applies |
Sources: the Town’s short-term rental FAQ and accommodations tax page, and the South Carolina Department of Revenue’s accommodations tax page.
Where a Month-Long Stay Is Allowed
The resort areas that rent by the week also rent by the month. The private, residential communities are another matter: several bar any lease shorter than six months, whatever the Town allows. Each rule below comes from that community’s own page on this site.
Sea Pines
Homes and villas here are rented by the week and by the month; several companies above list Sea Pines homes for monthly stays, including one in Harbour Town.
About Sea PinesPalmetto Dunes
Oceanfront villas in Palmetto Dunes turn up in several companies’ monthly and winter collections, from Windsor Place to Hampton Place.
About Palmetto DunesForest 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.
About Forest BeachFolly Field
Oceanfront villas at Sea Cloisters, on the beach at Folly Field, are in one company’s monthly collection.
About Folly FieldMoss Creek
Just over the bridge, off the island. Rentals must run at least a month, so confirm the current minimum with the association.
About Moss CreekSun 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.
About Sun City Hilton HeadHilton Head Plantation
Leases must run at least six months unless the board approves otherwise, so a winter month is not an option.
About Hilton Head PlantationIndigo Run
Every lease must run at least six months, with no subletting.
About Indigo RunLong Cove
The covenants bar leases shorter than six consecutive months without the association’s written permission.
About Long CoveWindmill Harbour
Homes can’t be rented for less than six consecutive months.
About Windmill HarbourHilton 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.
| Month | Average high | Average low | Rain | Ocean |
|---|---|---|---|---|
| November | 70°F | 49°F | 2.6 in | 66°F |
| December | 63°F | 43°F | 3.1 in | 58°F |
| January | 60°F | 40°F | 3.4 in | 53°F |
| February | 63°F | 42°F | 3.2 in | 56°F |
| March | 69°F | 48°F | 3.9 in | 62°F |
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
The monthly rate, in writing
Most companies quote long stays by phone. Ask for the total for your dates, with cleaning, fees and every tax line.
Utilities
Some include them and some cap them: one company charges for electricity over $100 a month. Ask what the rate covers.
Cancellation terms
Long stays often have stricter rules, from non-refundable bookings to a 120-day cancellation window. Price in travel insurance.
Cleaning and linens
A weekly rental is cleaned once, at the end. For a month or more, ask whether a mid-stay clean or linen change is included or extra.
A heated pool
Many complex and private pools are seasonal, and some homes heat theirs only for a fee. Ask what is open in the months you are there.
Pets and the pass
Check the home’s pet rule, and in a gated community ask how a long-stay guest gets a gate pass for the whole stay.
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.
Frequently Asked Questions
Can you rent a vacation home on Hilton Head by the month?
Yes. Many island rental companies rent homes and villas by the month, mostly from fall through early spring. Sunset Rentals, for one, rents monthly from October 1 to April 1, and Vacation Time of HHI rents snowbird stays of 30, 60 or 90 days from November 1 to March 20 for the 2026-27 winter.
How many nights count as a monthly rental?
It depends on the company. Dwell gives its monthly rate on any stay of 30 nights or more, Coastal Vacation Rentals and host2coast start at 28 days, and Coastal Home and Villa treats 27 nights or more as a long stay.
Do you pay tax on a monthly rental in Hilton Head?
Yes, if the stay is shorter than 90 days in a row. South Carolina charges 7% (5% sales tax and 2% accommodations tax) and the Town of Hilton Head Island adds 3% (a 1% accommodations tax and a 2% beach preservation fee). A stay of 90 consecutive days or more is outside both.
Is a monthly rental a short-term rental under the Town’s rules?
No. The Town’s short-term rental ordinance defines short-term as less than 30 days, and it covers condos, villas and houses. It does not apply to timeshares or hotels.
Which Hilton Head communities don’t allow monthly rentals?
Hilton Head Plantation, Indigo Run, Long Cove and Windmill Harbour require leases of at least six months, and off the island Sun City Hilton Head requires 90 days. Moss Creek, just over the bridge, allows rentals of a month or more.
What is the weather like on Hilton Head in the winter?
Mild. January, the coolest month, averages highs near 60°F and lows near 40°F, and the ocean is in the low 50s, so the beach is for walks rather than swims. By March, afternoons average about 69.
Can I bring a dog on the beach in the winter?
Yes. From October 1 to March 31 the Town allows dogs on the beach at any hour, on a leash or under voice control. The rental home sets its own pet rule.
More Ways to Plan a Long Stay
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 rental companies grouped by what each rents, from resort programs to Sea Pines specialists, with phone numbers and links to each one.
Pet-friendly rentals in Hilton Head: which communities and complexes allow dogs, the beach leash rules by season, and companies with pet filters.
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 month: average highs, lows, rainfall and ocean temperature for all 12 months, plus hurricane season and the best time to visit.
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.
Keep exploring
Windsor Court at Palmetto Dunes: two five-story buildings just past the south gate, next to Hampton Place, with a pool, hot tub and private boardwalk.
Barrington Arms at Palmetto Dunes: one- to three-bedroom villas right next to the shared oceanfront pool, with a boardwalk to the beach.
Places to stay on Hilton Head Island: how resorts, hotels, rentals, timeshares and RV sites compare, plus Sea Pines vs Palmetto Dunes.
Hilton Head vacation rentals: beach houses, condos and villas by beach area and complex, who manages them, dog-friendly homes, and how renting works.
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