Second Homes · Hilton Head Island & the Lowcountry

Second Homes on Hilton Head Island

Hilton Head Island draws out-of-state buyers who want more than a vacation property — they want a residence that holds its value in a supply-constrained coastal market and delivers a particular quality of experience when they are here. COAST brokered by eXp Realty represents buyers in this market every week, and the questions that determine a successful purchase run deeper than square footage.

A second home on Hilton Head Island occupies a distinct category. It is not a speculative trade and not a primary residence — it is an asset that must perform on two axes simultaneously: as a property that appreciates in a barrier-island market where new land supply is structurally constrained, and as a place that delivers on the experience that brought you here in the first place. Buyers who arrive with a clear sense of how they intend to use the property — and how often — make faster, better decisions.

The island organizes itself into a set of master-planned communities and beachside neighborhoods, each with its own ownership rules, amenity access, and short-term rental posture. Those differences are material. A property in Sea Pines and a property in Hilton Head Plantation may sit a few miles apart and yet represent entirely different ownership frameworks. Understanding that structure before you begin your search is not a courtesy — it is the difference between closing on the right property and spending eighteen months learning the market the hard way.

Second Homes · Hilton Head Island & the Lowcountry

Second Homes on Hilton Head Island

Where Second Homes Concentrate on Hilton Head Island

The island's second-home inventory divides along two broad lines: resort communities and beachside neighborhoods. Sea Pines Resort — the island's largest master-planned community — encompasses Harbour Town, South Beach Marina, and a substantial collection of oceanfront and lagoon-side properties at the island's southern end. Palmetto Dunes Oceanfront Resort, situated mid-island, includes oceanfront homes, an interconnected lagoon system, and villa complexes that have drawn second-home buyers for decades. Shipyard, a central gated community, offers golf, a beach club, and a large inventory of townhomes and villas.

Forest Beach, the un-gated neighborhood surrounding Coligny Beach Park, offers a different character: oceanfront single-family homes and condominium buildings with fewer HOA layers and broader flexibility for owners who intend to rent. Folly Field, a mid-island beachside neighborhood, draws buyers with a similar profile. For those whose priority is residential lifestyle over rental income, communities such as Hilton Head Plantation, Long Cove Club, Indigo Run, Wexford, and Windmill Harbour offer golf, marina, and club amenities within a quieter ownership posture — these communities have chosen to restrict short-term rentals, which shapes who buys there and why.

Short-Term Rental Rules: What Every Buyer Must Verify

Hilton Head Island operates a two-layer regulatory framework for short-term rentals. The first layer is the community. Approximately 70% of the island sits within master-planned communities whose governing documents either permit or prohibit rentals of fewer than 30 days. Sea Pines Resort, Palmetto Dunes, Shipyard, Forest Beach, and Folly Field are among the communities where short-term rentals are permitted, subject to the applicable community rules. Hilton Head Plantation, Indigo Run, Long Cove Club, Palmetto Hall, Port Royal Plantation, Wexford, and Windmill Harbour restrict short-term rentals — minimum lease terms of 90 days to six months apply in those communities.

The second layer is the Town of Hilton Head Island STR permit program, which applies island-wide regardless of community. As of 2026, the Town charges $150 per bedroom per year for an annual STR permit, and a separate Town business license is required in addition. Operators must collect and remit South Carolina accommodations tax, state sales tax, Town accommodations tax, and a Beach Preservation Fee — a total estimated tax stack of roughly 9 to 13 percent of gross rental revenue, filed quarterly with the Town's Revenue Services Office. Critically, STR permits are non-transferable and property-specific: a buyer cannot inherit the seller's permit and must apply anew after closing, which affects first-year rental timing. Buyers considering a rental-income strategy should factor all of these costs into their pro-forma before submitting an offer.

The Ownership Considerations That Define the Purchase

Beyond rental rules, second-home buyers on Hilton Head Island should understand how community amenity access is structured. In resort communities like Sea Pines and Palmetto Dunes, owners pay a community services assessment or resort fee that funds beach access, security, and amenity infrastructure. Golf club membership, deep-water dock rights, and marina slip access may be governed by separate waiting lists or purchase agreements that are distinct from the base property transaction. A property in Harbour Town's marina village carries a different set of considerations than a lagoon-front villa in Palmetto Dunes — the physical setting, the price tier, and the ownership structure all interact.

Property type matters as well. Oceanfront single-family homes, oceanfront condominiums, lagoon-front homes, and golf-course-adjacent properties each carry different insurance profiles, HOA structures, and long-term maintenance obligations. South Carolina's coastal location means flood zone determination and wind and flood insurance costs are material line items in any ownership budget. Out-of-state buyers accustomed to inland insurance markets routinely underestimate this expense. Accurate quotes from an insurer familiar with Lowcountry coastal properties should be obtained before going under contract — not after.

How COAST Brokered by eXp Realty Represents Second-Home Buyers

COAST brokered by eXp Realty was founded in 2022 by Rick Saba and Tristan O'Grady — two of Hilton Head Island's established producers — on the eXp Realty platform. Since then, the team has closed $958 million in volume across 1,334 transactions and holds the #1 ranking among eXp teams in South Carolina by volume. Its founding agents represented the $12.5 million closing at 15 Bald Eagle Road in Sea Pines, among the highest residential transactions in Hilton Head Island history. The eXp Luxury network COAST anchors has set multiple top-tier benchmarks across the island.

For an out-of-state buyer, that depth of local transaction history matters. COAST agents navigate community-specific nuances — which neighborhoods are active in the short-term rental market, where HOA rules have shifted recently, where supply is thinnest relative to demand — with the working knowledge that comes from representing buyers in this market week to week. The buyer representation process begins with a structured consultation that accounts for intended use, rental income requirements, community preferences, and financing structure, then maps those inputs to the inventory that actually fits — not simply what happens to be available.

The Market · June 2026

What Hilton Head Island, SC homes are selling for

$1,055,000median sale price · single-family homes112 days on market · 97.1% of list price · 231 sold
$515,000median sale price · villas & condos146 days on market · 96.2% of list price · 431 sold

Source: Hilton Head Area Association of REALTORS® — published June 2026 market report.

Questions

Answered

Can I rent my second home on Hilton Head Island as a short-term rental?
It depends on the community where the property is located. Roughly 70% of the island sits within master-planned communities that either permit or prohibit short-term rentals. Sea Pines Resort, Palmetto Dunes, Shipyard, Forest Beach, and Folly Field are among the communities that allow short-term rentals. Hilton Head Plantation, Indigo Run, Long Cove Club, Palmetto Hall, Port Royal Plantation, Wexford, and Windmill Harbour restrict short-term rentals, with minimum lease terms of 90 days to six months. On top of community rules, the Town of Hilton Head Island requires a separate annual STR permit and business license for any rental of fewer than 30 days.
What does the Town of Hilton Head Island STR permit cost, and what else is required?
As of 2026, the Town charges $150 per bedroom per year for an annual STR permit, plus a separate Town business license. Operators must also collect and remit South Carolina accommodations tax, state sales tax, Town accommodations tax, and a Beach Preservation Fee — an estimated total of 9 to 13 percent of gross rental revenue — filed quarterly with the Town's Revenue Services Office. STR permits are property-specific and non-transferable: a buyer must apply for a new permit after closing rather than inheriting the seller's existing permit.
Which Hilton Head Island communities allow short-term rentals, and which prohibit them?
Communities where short-term rentals are generally permitted include Sea Pines Resort, Palmetto Dunes Oceanfront Resort, Shipyard, Forest Beach, and Folly Field — though buyers should verify the specific covenants for any individual property, as sub-community rules can differ. Communities that restrict short-term rentals include Hilton Head Plantation, Indigo Run, Long Cove Club, Palmetto Hall, Port Royal Plantation, Wexford, and Windmill Harbour, where minimum lease terms of 90 days to six months apply. This distinction is foundational to any second-home purchase decision and should be confirmed in writing during due diligence.
What are the main second-home communities to consider on Hilton Head Island?
The most established second-home communities include Sea Pines Resort (the island's largest planned community, encompassing Harbour Town and South Beach Marina), Palmetto Dunes Oceanfront Resort (mid-island, with oceanfront homes and a lagoon system), Shipyard (central, with golf and beach club access), Forest Beach (un-gated, surrounding Coligny Beach Park), and Folly Field (a mid-island beachside neighborhood). Residential communities including Long Cove Club, Indigo Run, and Wexford attract buyers seeking a golf and club lifestyle with a quieter ownership posture.
How does flood and wind insurance work for a second home on Hilton Head Island?
Coastal properties on Hilton Head Island carry flood and wind insurance requirements that vary by flood zone designation, proximity to the shoreline, and construction type. The insurance cost can be a significant annual ownership expense, and out-of-state buyers accustomed to inland markets routinely underestimate it. Accurate quotes from an insurer with Lowcountry coastal experience should be obtained before making an offer — this is a line item that belongs in the financial analysis, not in the closing-cost review.
What HOA fees and community assessments should I expect when buying a second home on Hilton Head Island?
Most communities on Hilton Head Island charge a community services assessment or HOA fee that funds security, common-area maintenance, and amenity infrastructure — in resort communities like Sea Pines and Palmetto Dunes, these fees can be substantial and are separate from any individual condominium or villa HOA dues. Golf club membership, marina slip access, and deep-water dock rights may involve separate purchase agreements or waiting lists. Before evaluating any property's net cost of ownership, buyers should obtain a full accounting of all recurring costs: community assessments, club dues, STR permit fees, insurance, and applicable town taxes.
Is Sea Pines a good location for a second home on Hilton Head Island?
Sea Pines Resort is the island's largest and most recognized planned community, with a substantial inventory of oceanfront, lagoon-front, and golf-course properties as well as the established Harbour Town marina and South Beach Marina areas. Short-term rentals are permitted for most properties within Sea Pines, making it a common choice for buyers who want the option of rental income. Certain residential sub-neighborhoods within the community enforce stricter covenants, so buyers should review the governing documents for any specific property under consideration. COAST brokered by eXp Realty closed the $12.5 million sale of 15 Bald Eagle Road in Sea Pines — among the highest residential transactions in Hilton Head Island history.
How does COAST brokered by eXp Realty help out-of-state buyers purchase a second home on Hilton Head Island?
COAST brokered by eXp Realty begins with a structured buyer consultation to clarify intended use, rental income goals, community preferences, and financing approach — then matches those parameters to the inventory that fits, including the specific communities, property types, and price tiers that align with the buyer's situation. The team has closed $958 million in volume and 1,334 transactions since 2022, holds the #1 ranking among eXp teams in South Carolina by volume, and includes agents whose day-to-day practice is representing buyers in Hilton Head Island's second-home market.

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Whether you are evaluating an oceanfront property in Sea Pines, a lagoon-front villa in Palmetto Dunes, or a Forest Beach home with a rental history, COAST brokered by eXp Realty brings the local transaction depth to represent your interests with precision. Contact the COAST team to begin a conversation about second-home ownership on Hilton Head Island.

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