Hilton Head Island, SC
Luxury golf and beach island - premium repeat visitor market
Hilton Head Island is the most upscale STR market in South Carolina, combining 12 miles of beach, 24 golf courses, and a gated resort infrastructure that attracts a high-income, repeat-visitor demographic. The island's Sea Pines, Palmetto Dunes, and Shipyard Plantation communities are particularly popular STR markets with strong HOA-managed amenity access.
Across 97 active STR-viable listings analyzed this month, Hilton Head Island shows a 2.2% median cap rate at a $950K median list price, 40% occupancy, and $272/night. That ranks #46 of 57 markets in STRROI's live ranking. At typical prices, cash flow is tight: most listings only pencil out with a large down payment, a below-list purchase, or above-market nightly rates.
Hilton Head Island real estate market right now
As of October 16, 2026, STRROI is tracking 97 homes for sale in Hilton Head Island that could run as short-term rentals, at a median list price of $950,000. The middle half are priced between $559K and $2.5M. That works out to a median of $551 per square foot for a typical 1,822 square foot home. Homes here have been on the market 82 days on average, shorter than the 101 days typical across the 56 markets in STRROI's ranking, so well-priced homes here tend to go quickly. 34 of them were listed in the last 30 days.
These numbers cover the homes for sale STRROI analyzes as potential short-term rentals in Hilton Head Island, mainly ZIP 29928. They are not every home sale in the area, so they can differ from MLS-wide figures. Month-by-month price history starts Oct 2026 and fills in as the market is re-checked each month.
What's for sale in Hilton Head Island right now
Of the 97 homes for sale we analyzed in Hilton Head Island, 10 (10%) project positive monthly cash flow with 20% down at a 7.5% rate, and none rate Buy or better on STRROI's 1-10 scale. 2-bedroom homes are the most common (34 for sale, median $584K). Returns are strongest in 1-bedroom homes at a 3.0% median cap rate, and weakest in 5+ bedroom homes at 1.0%. By property type, townhouses lead at a 3.0% median cap rate across 15 listings.
- Weak: 14
- Avoid: 83
| Beds | For sale | Median price | Cap rate |
|---|---|---|---|
| 1 | 4 | $413K | 3.0% |
| 2 | 34 | $584K | 2.9% |
| 3 | 23 | $975K | 2.3% |
| 4 | 19 | $2.5M | 1.3% |
| 5+ | 17 | $5.0M | 1.0% |
| Type | For sale | Median price | Cap rate |
|---|---|---|---|
| Single-family homes | 41 | $2.6M | 1.5% |
| Condos | 41 | $638K | 2.8% |
| Townhouses | 15 | $609K | 3.0% |
Top-ranked homes for sale in Hilton Head Island this month
Scored 1-10 against real Airbnb comps. Addresses, photos and the full underwriting are in the app.
- #1Weak · 4/102 bd · 2 ba condoZIP 29928 · listed at $4K
- Cap rate
- 244.5%
- Cash flow
- +$793/mo
- Nightly
- $160 at 40%
- #2Weak · 4/103 bd · 3 ba condoZIP 29928 · listed at $28K
- Cap rate
- 56.1%
- Cash flow
- +$1,153/mo
- Nightly
- $231 at 40%
- #3Weak · 4/102 bd · 2 ba townhouseZIP 29928 · listed at $25K
- Cap rate
- 39.9%
- Cash flow
- +$691/mo
- Nightly
- $169 at 40%
How Hilton Head Island compares
Hilton Head Island ranks #16 of 21 Southeast markets in STRROI's live ranking; St. Augustine leads the region with a median cap rate of 5.7%. Its 2.2% cap rate is 0.7 points below the 2.9% median across all 57 ranked markets, and its $950K typical list price is pricier than the Southeast median of $633K.
| Rank | Market | Cap rate | Typical price |
|---|---|---|---|
| #40 | Destin, FL | 2.4% | $515K |
| #42 | Asheville, NC | 2.3% | $750K |
| #43 | Anna Maria Island, FL | 2.2% | $3.5M |
| #46 | Hilton Head Island, SC | 2.2% | $950K |
| #47 | Sarasota, FL | 2.1% | $1.2M |
| #49 | Miami Beach, FL | 1.8% | $2.4M |
| #50 | Charleston, SC | 1.8% | $2.5M |
Rank is national, by median cap rate across active STR-viable listings. Cash flow uses STRROI's default financing assumptions. See the full ranking
Estimated Annual Performance
* Estimates based on market averages. Individual property performance varies. Always run a full underwriting analysis.
Why Investors Choose Hilton Head Island
Hilton Head Island STR investing, answered
Is Hilton Head Island, SC a good short-term rental market?
Hilton Head Island is a Southeast STR market with a 2.2% median cap rate, 40% annual occupancy, and $272/night across STR-viable listings, based on 97 active listings. It ranks #46 of 57 markets by median cap rate in STRROI's live ranking. This month none of its 97 homes for sale rate Buy or better.
What is the average Airbnb occupancy rate in Hilton Head Island?
STR-viable properties in Hilton Head Island average about 40% occupancy across the year. Peak season is Mar - May (golf), June - Aug (beach). Occupancy here reflects availability-adjusted booking performance, not raw calendar occupancy, so it represents what a full-time operated rental can realistically achieve.
How much do short-term rentals earn in Hilton Head Island?
At $272/night and 40% occupancy, a typical Hilton Head Island STR grosses roughly $39,513 per year before expenses, leaving an estimated $23,708 in net operating income. Across analyzed listings the median cap rate is 2.2%. Individual results depend on property, amenities, and management.
What types of properties work best for STR in Hilton Head Island?
Among homes for sale right now, 1-bedroom homes post the strongest median cap rate by size (3.0%), and townhouses lead by property type (3.0%). With guests, the best-performing STR types here are Villa, Single Family, Condo, Golf Course Home. Matching the local guest profile and the amenities that drive bookings matters more than raw square footage.
How many homes for sale in Hilton Head Island cash flow as an Airbnb?
10 of 97 STR-viable listings (10%) project positive monthly cash flow after the mortgage, assuming 20% down at a 7.5% rate on a 30-year loan. The top-ranked listing this month is a 2-bedroom condo in ZIP 29928 listed at $4K, projecting a 244.5% cap rate and +$793 a month.
What is the median home price in Hilton Head Island, SC right now?
The median list price of the 97 homes for sale STRROI tracks in Hilton Head Island is $950,000, and the middle half are priced between $559K and $2.5M. The median price per square foot is $551. These are homes that could run as short-term rentals, mainly ZIP 29928, not every sale in the area. Against a 2.2% median cap rate, that price level sets the return baseline you'd underwrite against.
How long do homes stay on the market in Hilton Head Island?
Homes for sale in Hilton Head Island have been listed 82 days on average, shorter than the 101 days typical across the 56 markets in STRROI's ranking, so well-priced homes here tend to go quickly. 34 of them were listed in the last 30 days.
Market averages, not guarantees. Cap rates, occupancy, and nightly rates are market-wide averages based on active STR listings and historical data. Individual property performance depends on location, amenities, management, and listing quality. Always run a full underwriting analysis before purchasing.Stats sourced from 97 active listings · last updated Oct 16, 2026
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