Real Estate Investment Properties for Sale in Hilton Head Island, SC

Looking for investment property in Hilton Head Island, SC with high ROI ?

Explore a variety of short-term homes & houses in Hilton Head Island, SC. Invest wisely with VRBO & Hilton Head Island, SC Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Hilton Head Island, SC

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
40 Folly Field Road #B114 Hilton Head Island, SC Experience coastal living at its finest in this prime 1-bed, 1-bath condo at the highly so...	1 beds \| 1 baths \| 540 sq.ft.	$320,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 1.05% Airbnb Rental Income: $708 Traditional Rental Income: $883 Airbnb ROI: -0.55% Traditional ROI: 1.05%
66 Timber Lane Hilton Head Island, SC Value priced, updated/superbly maintained residence with charming curb appeal and lagoon v...	3 beds \| 4 baths \| 2,898 sq.ft.	$699,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 2.39% Airbnb Rental Income: $1933 Traditional Rental Income: $2968 Airbnb ROI: 0.02% Traditional ROI: 2.39%
245 Fort Howell Drive Hilton Head Island, SC Welcome to this charming and well maintained one level 3-bedroom, 2.5-bathroom home, locat...	3 beds \| 3 baths \| 2,174 sq.ft.	$879,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.63% Airbnb Rental Income: $null Traditional Rental Income: $1891 Airbnb ROI: N/A Traditional ROI: 0.63%
40 Folly Field Road #130 Hilton Head Island, SC Great opportunity on first floor villa at the beach! Neutral tones and coastal vibes, this...	2 beds \| 2 baths \| 996 sq.ft.	$409,000	Airbnb cash on cash: -3.71% Traditional cash on cash: -0.8% Airbnb Rental Income: $571 Traditional Rental Income: $1403 Airbnb ROI: -3.71% Traditional ROI: -0.8%
28 Lenora Drive Hilton Head Island, SC MOTIVATED SELLERS!!! Beautifully updated and thoughtfully designed, this spacious 3-bedroo...	3 beds \| 3 baths \| 3,174 sq.ft.	$1,075,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.87% Airbnb Rental Income: $948 Traditional Rental Income: $2528 Airbnb ROI: -1.06% Traditional ROI: 0.87%
18 Sandpiper Street Hilton Head Island, SC Located in North Forest Beach on Hilton Head Island, this 7th-row beach home offers the ra...	3 beds \| 2 baths \| 1,666 sq.ft.	$1,375,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.34% Airbnb Rental Income: $2165 Traditional Rental Income: $2146 Airbnb ROI: -0.07% Traditional ROI: 0.34%
1 Gloucester Road #J-2 Hilton Head Island, SC 3BR 3BA well maintained end unit villa. Spacious & inviting living & dining areas with a v...	3 beds \| 3 baths \| 2,000 sq.ft.	$749,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.3% Airbnb Rental Income: $2165 Traditional Rental Income: $2637 Airbnb ROI: 0.84% Traditional ROI: 2.3%
6 Richfield Way Hilton Head Island, SC Lightly lived in patio home in sought after Indigo Run. 4BR -3.5BA; split bedroom plan wit...	4 beds \| 4 baths \| 2,432 sq.ft.	$899,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 1.79% Airbnb Rental Income: $2573 Traditional Rental Income: $2903 Airbnb ROI: 0.66% Traditional ROI: 1.79%
3 Craven Place Hilton Head Island, SC Beautiful ocean-side custom home in Port Royal, fully remodeled in 2018 and in excellent c...	3 beds \| 3 baths \| 2,438 sq.ft.	$1,625,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.02% Airbnb Rental Income: $1232 Traditional Rental Income: $2486 Airbnb ROI: -1.07% Traditional ROI: 0.02%
20 China Cockle Lane Hilton Head Island, SC New Price! An exceptional opportunity to own a beautifully updated coastal retreat just st...	4 beds \| 4 baths \| 3,962 sq.ft.	$1,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.75% Airbnb Rental Income: $null Traditional Rental Income: $3310 Airbnb ROI: N/A Traditional ROI: 0.75%
61 Tucker Ridge Court Hilton Head Island, SC Welcome to 61 Tucker Ridge and "Palmetto Hall"! This 4 bedroom/3.5 bath home with gorgeous...	4 beds \| 4 baths \| 2,519 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.97% Airbnb Rental Income: $null Traditional Rental Income: $2892 Airbnb ROI: N/A Traditional ROI: 1.97%
6 Audubon Place Hilton Head Island, SC Newly rebuilt down to the studs in the gated oceanfront community of Port Royal - set on a...	3 beds \| 2 baths \| 1,635 sq.ft.	$949,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 0.51% Airbnb Rental Income: $1232 Traditional Rental Income: $1629 Airbnb ROI: -0.39% Traditional ROI: 0.51%
11 Muirfield Road Hilton Head Island, SC Location, location! Right on the 2nd fairway of the world-famous Harbour Town Golf Links, ...	4 beds \| 4 baths \| 2,066 sq.ft.	$1,649,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.16% Airbnb Rental Income: $2018 Traditional Rental Income: $2731 Airbnb ROI: -0.65% Traditional ROI: 0.16%
8 Old Fort Way Hilton Head Island, SC Perfectly located near the Country Club of Hilton Head, a boat club, and the back gate of ...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,395,000	Airbnb cash on cash: -1.45% Traditional cash on cash: -0.02% Airbnb Rental Income: $948 Traditional Rental Income: $2447 Airbnb ROI: -1.45% Traditional ROI: -0.02%
116 Dune Lane Hilton Head Island, SC Beautifully renovated second-row beach home at 116 Dune Lane in North Forest Beach, Hilton...	4 beds \| 3 baths \| 2,564 sq.ft.	$3,199,000	Airbnb cash on cash: -0.95% Traditional cash on cash: -1.02% Airbnb Rental Income: $4116 Traditional Rental Income: $3050 Airbnb ROI: -0.95% Traditional ROI: -1.02%
5 Misty Morning Drive Hilton Head Island, SC Overlooking the 7th tee box of Bear Creek Club, this 3BR/3BA home is designed to impress f...	3 beds \| 3 baths \| 2,505 sq.ft.	$989,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.42% Airbnb Rental Income: $948 Traditional Rental Income: $2484 Airbnb ROI: -0.63% Traditional ROI: 1.42%
7 Lavender Circle Hilton Head Island, SC Welcome to 7 Lavender Circle, a beautifully designed residence located in the desirable Si...	3 beds \| 4 baths \| 3,116 sq.ft.	$1,099,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.38% Airbnb Rental Income: $1908 Traditional Rental Income: $2879 Airbnb ROI: -0.06% Traditional ROI: 1.38%
77 Ocean Lane #117 Hilton Head Island, SC Experience effortless oceanfront luxury in this impeccable 1 BR, 1.5 BA villa, perfectly p...	1 beds \| 2 baths \| 862 sq.ft.	$785,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 0.61% Airbnb Rental Income: $653 Traditional Rental Income: $1685 Airbnb ROI: -1.21% Traditional ROI: 0.61%
6 Village N Drive #59 Hilton Head Island, SC Beautifully updated first floor condominium offering gorgeous water views and effortless i...	2 beds \| 2 baths \| 1,183 sq.ft.	$679,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 0.89% Airbnb Rental Income: $656 Traditional Rental Income: $1648 Airbnb ROI: -1.15% Traditional ROI: 0.89%
1 Gloucester Road #E-2 Hilton Head Island, SC Nestled in the gated Shipyard community of Golfmaster II, the fully furnished, beautiful 3...	3 beds \| 3 baths \| 2,000 sq.ft.	$775,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 1.91% Airbnb Rental Income: $2165 Traditional Rental Income: $2607 Airbnb ROI: 0.54% Traditional ROI: 1.91%
50 Ocean Lane #110 Hilton Head Island, SC 110 Abbington - A Legacy Property! (New photos coming soon)Some properties are simply mean...	3 beds \| 3 baths \| 1,098 sq.ft.	$1,299,000	Airbnb cash on cash: -0.85% Traditional cash on cash: -0.18% Airbnb Rental Income: $1372 Traditional Rental Income: $1764 Airbnb ROI: -0.85% Traditional ROI: -0.18%
40 Folly Field Road #A209 Hilton Head Island, SC Welcome to the ultimate beachside getaway on Hilton Head Island! This beautifully renovate...	1 beds \| 1 baths \| 592 sq.ft.	$315,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.66% Airbnb Rental Income: $708 Traditional Rental Income: $1051 Airbnb ROI: -0.53% Traditional ROI: 1.66%
30 N Forest Beach Drive Hilton Head Island, SC Welcome to 30 N Forest Beach Drive, a spectacular coastal retreat located in the highly so...	4 beds \| 4 baths \| 2,326 sq.ft.	$2,600,000	Airbnb cash on cash: -0.56% Traditional cash on cash: -0.52% Airbnb Rental Income: $3882 Traditional Rental Income: $3148 Airbnb ROI: -0.56% Traditional ROI: -0.52%
141 Lamotte Drive #H1 Hilton Head Island, SC This first-floor 2BR/2BA villa in Palmetto Commons presents a compelling long-term investm...	2 beds \| 2 baths \| 985 sq.ft.	$259,999	Airbnb cash on cash: -0.27% Traditional cash on cash: 3.85% Airbnb Rental Income: $719 Traditional Rental Income: $1421 Airbnb ROI: -0.27% Traditional ROI: 3.85%
663 William Hilton Parkway unit: 4205 Hilton Head Island, SC Income producing from day one, 4205 Hilton Head Resort presents a rare opportunity to secu...	2 beds \| 2 baths \| 831 sq.ft.	$275,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.77% Airbnb Rental Income: $912 Traditional Rental Income: $1365 Airbnb ROI: -0.3% Traditional ROI: 2.77%
663 William Hilton Parkway #3321 Hilton Head Island, SC Investor's Dream on Hilton Head Island! This fully furnished & renovated 3BR/2BA villa is ...	3 beds \| 2 baths \| 1,186 sq.ft.	$415,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 1.22% Airbnb Rental Income: $1105 Traditional Rental Income: $1662 Airbnb ROI: -1.17% Traditional ROI: 1.22%
32 Compass Point #32B Hilton Head Island, SC Stunning Broad Creek, Calibogue Sound, and sunset views from one of the best marsh, creek,...	3 beds \| 2 baths \| 1,602 sq.ft.	$599,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 1.84% Airbnb Rental Income: $2393 Traditional Rental Income: $1996 Airbnb ROI: 1.49% Traditional ROI: 1.84%
239 Jonesville Road Hilton Head Island, SC Deepwater tidal dock with long marsh views! Phenomenal newer-style home offering 4 bedroom...	4 beds \| 4 baths \| 2,578 sq.ft.	$1,490,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 0.47% Airbnb Rental Income: $2641 Traditional Rental Income: $2910 Airbnb ROI: -0.18% Traditional ROI: 0.47%
22 Sovereign Drive Hilton Head Island, SC Tucked within the coveted Port Royal Plantation and just a short stroll to the Atlantic, t...	4 beds \| 4 baths \| 3,442 sq.ft.	$1,888,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.73% Airbnb Rental Income: $4103 Traditional Rental Income: $3306 Airbnb ROI: 0.68% Traditional ROI: 0.73%
40 Folly Field Road #A325 Hilton Head Island, SC Stunning top-floor DIRECT oceanfront unit with the best views in the complex! Fully update...	1 beds \| 1 baths \| 560 sq.ft.	$459,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.39% Airbnb Rental Income: $708 Traditional Rental Income: $948 Airbnb ROI: -0.88% Traditional ROI: 0.39%
4 Indigo Run Drive #3920 Hilton Head Island, SC Few Cypress floorplans at 1,813 sq. ft. become available in the highly sought-after commun...	3 beds \| 2 baths \| 1,813 sq.ft.	$599,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 2.27% Airbnb Rental Income: $1105 Traditional Rental Income: $2238 Airbnb ROI: -0.42% Traditional ROI: 2.27%
40 Folly Field Road #C248 Hilton Head Island, SC Beautiful 2nd floor villa in C building with great views & private balcony! **BONUS Owner ...	1 beds \| 1 baths \| 592 sq.ft.	$284,900	Airbnb cash on cash: -0.42% Traditional cash on cash: 2% Airbnb Rental Income: $708 Traditional Rental Income: $1051 Airbnb ROI: -0.42% Traditional ROI: 2%
40 Folly Field Road #B344 Hilton Head Island, SC Hilton Head Beach & Tennis #344B is a third-floor villa with a fantastic ocean view and a ...	1 beds \| 1 baths \| 592 sq.ft.	$275,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.29% Airbnb Rental Income: $708 Traditional Rental Income: $1095 Airbnb ROI: -0.38% Traditional ROI: 2.29%
1 Brown Pelican Road Hilton Head Island, SC This exceptional second-row ocean home in Sea Pines offers a compelling blend of location,...	4 beds \| 4 baths \| 2,918 sq.ft.	$4,200,000	Airbnb cash on cash: -1.21% Traditional cash on cash: -0.81% Airbnb Rental Income: $2018 Traditional Rental Income: $3036 Airbnb ROI: -1.21% Traditional ROI: -0.81%
35 Scarborough Head Road Hilton Head Island, SC Located in Port Royal Plantation, Hilton Head Island's only private, gated oceanfront comm...	3 beds \| 2 baths \| 2,038 sq.ft.	$1,075,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.56% Airbnb Rental Income: $1232 Traditional Rental Income: $2224 Airbnb ROI: -0.82% Traditional ROI: 0.56%
5 Gumtree Road #H15 Hilton Head Island, SC MARSHSIDE VILLAS! Welcome to 5 Gumtree Road, Unit H15-an elegant 2-bedroom, 2.5-bath resid...	2 beds \| 3 baths \| 1,120 sq.ft.	$289,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 4.24% Airbnb Rental Income: $912 Traditional Rental Income: $1673 Airbnb ROI: 0.19% Traditional ROI: 4.24%
663 William Hilton Parkway #2219 Hilton Head Island, SC PRICE Reduction!! This villa is priced to sell today. A great 2 bedroom villa located in t...	2 beds \| 2 baths \| 843 sq.ft.	$269,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.68% Airbnb Rental Income: $958 Traditional Rental Income: $1424 Airbnb ROI: 0.47% Traditional ROI: 3.68%
49 Widewater Road Hilton Head Island, SC Welcome to 49 Widewater in the highly sought-after waterfront community of Spanish Wells. ...	4 beds \| 5 baths \| 3,448 sq.ft.	$1,425,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 1.67% Airbnb Rental Income: $2641 Traditional Rental Income: $4375 Airbnb ROI: -0.12% Traditional ROI: 1.67%
1 High Bluff Road #2017 Hilton Head Island, SC Nestled off the 10th green of the Dolphin Head Golf Course, this 3-bedroom 3-bath villa of...	3 beds \| 3 baths \| 1,586 sq.ft.	$550,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 2.35% Airbnb Rental Income: $948 Traditional Rental Income: $2106 Airbnb ROI: -0.58% Traditional ROI: 2.35%

Real Estate investment in Hilton-head-island, SC

There are 828 properties for sale in the city of Hilton Head Island . The median list price in Hilton Head Island is $679,000 and the average price per square foot is $388. In May 2026, the average monthly cash on cash return in Hilton Head Island is N/A%. The average monthly rental income in Hilton Head Island is $1,403.

Hilton-head-island, SC Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 828 investment properties available for sale in Hilton-head-island.

In 2026, the best neighborhood to buy investment property is Blufton.

The ROI for Short-Term is higher than the Long-Term in Hilton-head-island with average rental income of $1,672.

Your search for investment property begins and ends here

Investment Property for Sale in Hilton Head Island, SC

40 Folly Field Road #B114

Hilton Head Island, SC

1 beds | 1 baths | 540 sq.ft.

$320,900

Airbnb cash on cash: -0.55%

Traditional cash on cash: 1.05%

Airbnb Rental Income: $708

Traditional Rental Income: $883

Airbnb ROI: -0.55%

Traditional ROI: 1.05%

66 Timber Lane

Hilton Head Island, SC

3 beds | 4 baths | 2,898 sq.ft.

$699,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $1933

Traditional Rental Income: $2968

Airbnb ROI: 0.02%

Traditional ROI: 2.39%

245 Fort Howell Drive

Hilton Head Island, SC

3 beds | 3 baths | 2,174 sq.ft.

$879,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.63%

Airbnb Rental Income: $null

Traditional Rental Income: $1891

Airbnb ROI: N/A

Traditional ROI: 0.63%

40 Folly Field Road #130

Hilton Head Island, SC

2 beds | 2 baths | 996 sq.ft.

$409,000

Airbnb cash on cash: -3.71%

Traditional cash on cash: -0.8%

Airbnb Rental Income: $571

Traditional Rental Income: $1403

Airbnb ROI: -3.71%

Traditional ROI: -0.8%

28 Lenora Drive

Hilton Head Island, SC

3 beds | 3 baths | 3,174 sq.ft.

$1,075,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $948

Traditional Rental Income: $2528

Airbnb ROI: -1.06%

Traditional ROI: 0.87%

18 Sandpiper Street

Hilton Head Island, SC

3 beds | 2 baths | 1,666 sq.ft.

$1,375,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 0.34%

Airbnb Rental Income: $2165

Traditional Rental Income: $2146

Airbnb ROI: -0.07%

Traditional ROI: 0.34%

1 Gloucester Road #J-2

Hilton Head Island, SC

3 beds | 3 baths | 2,000 sq.ft.

$749,000

Airbnb cash on cash: 0.84%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $2165

Traditional Rental Income: $2637

Airbnb ROI: 0.84%

Traditional ROI: 2.3%

6 Richfield Way

Hilton Head Island, SC

4 beds | 4 baths | 2,432 sq.ft.

$899,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 1.79%

Airbnb Rental Income: $2573

Traditional Rental Income: $2903

Airbnb ROI: 0.66%