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.	$318,900	Airbnb cash on cash: -0.91% Traditional cash on cash: 1.07% Airbnb Rental Income: $576 Traditional Rental Income: $883 Airbnb ROI: -0.91% Traditional ROI: 1.07%
48 Salt Marsh Drive #48 Hilton Head Island, SC Perfectly positioned at the gateway to Hilton Head Island yet firmly rooted in the heart o...	4 beds \| 3 baths \| 1,250 sq.ft.	$345,000	Airbnb cash on cash: 6.46% Traditional cash on cash: 4.24% Airbnb Rental Income: $3460 Traditional Rental Income: $1976 Airbnb ROI: 6.46% Traditional ROI: 4.24%
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: -0.4% Traditional cash on cash: 0.34% Airbnb Rental Income: $1663 Traditional Rental Income: $2146 Airbnb ROI: -0.4% Traditional ROI: 0.34%
1 Gloucester Road #J-2 Hilton Head Island, SC Beautiful and bright 3BR 3BA. End unit. Spacious & inviting living & dining areas with a v...	3 beds \| 3 baths \| 2,000 sq.ft.	$749,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.3% Airbnb Rental Income: $1663 Traditional Rental Income: $2637 Airbnb ROI: 0.24% Traditional ROI: 2.3%
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: -0.63% Traditional cash on cash: 0.02% Airbnb Rental Income: $2036 Traditional Rental Income: $2486 Airbnb ROI: -0.63% Traditional ROI: 0.02%
6 Audubon Place Hilton Head Island, SC Newly rebuilt down to the studs in the gated oceanfront community of Port Royal on Hilton ...	3 beds \| 2 baths \| 1,635 sq.ft.	$949,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 0.51% Airbnb Rental Income: $2036 Traditional Rental Income: $1629 Airbnb ROI: 0.37% Traditional ROI: 0.51%
21 Crosstree Drive Hilton Head Island, SC This charming Charleston-style home features a spacious side entry porch, a beautiful side...	3 beds \| 3 baths \| 2,340 sq.ft.	$915,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.22% Airbnb Rental Income: $1877 Traditional Rental Income: $2464 Airbnb ROI: -0.06% Traditional ROI: 1.22%
22 Timbercrest Circle Hilton Head Island, SC Welcome to easy Hilton Head Island living in this charming 4 bedroom 2.5 bath home located...	4 beds \| 3 baths \| 2,414 sq.ft.	$699,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 2.12% Airbnb Rental Income: $3481 Traditional Rental Income: $2568 Airbnb ROI: 2.34% Traditional ROI: 2.12%
116 Dune Lane Hilton Head Island, SC Renovated second-row beach home in North Forest Beach on Hilton Head Island just steps fro...	4 beds \| 3 baths \| 2,564 sq.ft.	$2,995,000	Airbnb cash on cash: -1.09% Traditional cash on cash: -1.02% Airbnb Rental Income: $3656 Traditional Rental Income: $3050 Airbnb ROI: -1.09% Traditional ROI: -1.02%
234 Ceasar Place Hilton Head Island, SC This is the only 5-bedroom furnished home on Hilton Head Island under $600k. From the fron...	5 beds \| 3 baths \| 2,461 sq.ft.	$569,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $2594 Airbnb ROI: N/A Traditional ROI: 3.45%
10 Myrtle Lane Hilton Head Island, SC Welcome to 10 Myrtle Lane.	4 beds \| 3 baths \| 1,344 sq.ft.	$1,349,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 0.34% Airbnb Rental Income: $2752 Traditional Rental Income: $2223 Airbnb ROI: 0.25% Traditional ROI: 0.34%
4 Egret Street Hilton Head Island, SC Discover the ultimate coastal escape in the heart of Coligny Plaza just a short stroll to ...	3 beds \| 3 baths \| 2,037 sq.ft.	$1,600,000	Airbnb cash on cash: -0.75% Traditional cash on cash: -0.04% Airbnb Rental Income: $1785 Traditional Rental Income: $2364 Airbnb ROI: -0.75% Traditional ROI: -0.04%
32 Plantation Drive Hilton Head Island, SC Set on an exceptionally rare oversized estate lot-over 1.1 acres tucked privately off the ...	3 beds \| 4 baths \| 2,975 sq.ft.	$1,949,000	Airbnb cash on cash: -0.37% Traditional cash on cash: -0.03% Airbnb Rental Income: $2943 Traditional Rental Income: $2879 Airbnb ROI: -0.37% Traditional ROI: -0.03%
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.	$1,089,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 1.4% Airbnb Rental Income: $2207 Traditional Rental Income: $2879 Airbnb ROI: 0.19% Traditional ROI: 1.4%
150 Lighthouse Road #C-726 Hilton Head Island, SC This updated 4-bedroom, 4.5-bath villa in the heart of Harbour Town is ideally located wit...	4 beds \| 5 baths \| 2,228 sq.ft.	$1,789,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.59% Airbnb Rental Income: $2156 Traditional Rental Income: $3672 Airbnb ROI: -0.65% Traditional ROI: 0.59%
42 S Forest Beach Drive #3076 Hilton Head Island, SC One of the finest 3 BR, 2 BA villas in Seascape, featuring an additional bonus room and of...	3 beds \| 2 baths \| 1,427 sq.ft.	$659,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 1.31% Airbnb Rental Income: $1785 Traditional Rental Income: $1864 Airbnb ROI: 0.39% Traditional ROI: 1.31%
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.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.71% Airbnb Rental Income: $null Traditional Rental Income: $1685 Airbnb ROI: N/A Traditional ROI: 0.71%
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: -0.95% Traditional cash on cash: 0.89% Airbnb Rental Income: $805 Traditional Rental Income: $1648 Airbnb ROI: -0.95% Traditional ROI: 0.89%
1 Gloucester Road #E-2 Hilton Head Island, SC New Price improvement! Nestled in the gated Shipyard community of Golfmaster II, the fully...	3 beds \| 3 baths \| 2,000 sq.ft.	$740,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 2.08% Airbnb Rental Income: $1663 Traditional Rental Income: $2607 Airbnb ROI: 0.03% Traditional ROI: 2.08%
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: -0.9% Traditional cash on cash: 1.66% Airbnb Rental Income: $576 Traditional Rental Income: $1051 Airbnb ROI: -0.9% 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: -0.96% Traditional cash on cash: -0.52% Airbnb Rental Income: $2752 Traditional Rental Income: $3148 Airbnb ROI: -0.96% 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: 0.86% Traditional cash on cash: 3.85% Airbnb Rental Income: $1053 Traditional Rental Income: $1421 Airbnb ROI: 0.86% Traditional ROI: 3.85%
21 Rusty Rail Lane Hilton Head Island, SC Meticulously maintained, stylishly updated residence with impressive curb appeal and sweep...	3 beds \| 3 baths \| 2,538 sq.ft.	$965,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.05% Airbnb Rental Income: $null Traditional Rental Income: $2440 Airbnb ROI: N/A Traditional ROI: 1.05%
16 Spindle Lane #16 Hilton Head Island, SC Very rare 3-bedroom, end unit townhome that lives like a home without the outside maintena...	3 beds \| 4 baths \| 2,010 sq.ft.	$675,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 2.84% Airbnb Rental Income: $1877 Traditional Rental Income: $2867 Airbnb ROI: 0.47% Traditional ROI: 2.84%
118 Ceasar Place Hilton Head Island, SC Welcome to this beautiful 4-bedroom home with a spacious bonus room that can easily serve ...	4 beds \| 4 baths \| N/A	$659,899	Airbnb cash on cash: N/A Traditional cash on cash: 3.57% Airbnb Rental Income: $null Traditional Rental Income: $3257 Airbnb ROI: N/A Traditional ROI: 3.57%
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: 1.56% Traditional cash on cash: 1.84% Airbnb Rental Income: $2436 Traditional Rental Income: $1996 Airbnb ROI: 1.56% 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.	$1,395,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 0.61% Airbnb Rental Income: $3481 Traditional Rental Income: $2910 Airbnb ROI: 0.45% Traditional ROI: 0.61%
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.	$1,699,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 0.92% Airbnb Rental Income: $2425 Traditional Rental Income: $3306 Airbnb ROI: -0.02% Traditional ROI: 0.92%
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: -1.14% Traditional cash on cash: 0.39% Airbnb Rental Income: $576 Traditional Rental Income: $948 Airbnb ROI: -1.14% Traditional ROI: 0.39%
17 Christo Drive Hilton Head Island, SC Pristine, thoughtfully updated residence with sweeping golf, tidal marsh and lagoon views ...	4 beds \| 4 baths \| 2,938 sq.ft.	$1,195,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.57% Airbnb Rental Income: $null Traditional Rental Income: $3071 Airbnb ROI: N/A Traditional ROI: 1.57%
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: -0.83% Traditional cash on cash: 2% Airbnb Rental Income: $576 Traditional Rental Income: $1051 Airbnb ROI: -0.83% 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.	$270,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 2.37% Airbnb Rental Income: $576 Traditional Rental Income: $1095 Airbnb ROI: -0.79% Traditional ROI: 2.37%
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: -1.18% Traditional cash on cash: -0.81% Airbnb Rental Income: $2156 Traditional Rental Income: $3036 Airbnb ROI: -1.18% Traditional ROI: -0.81%
8 Azalea Street Hilton Head Island, SC Nestled just steps from the ocean, this charming beach cottage offers the perfect blend of...	3 beds \| 2 baths \| 1,291 sq.ft.	$955,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 0.26% Airbnb Rental Income: $2036 Traditional Rental Income: $1719 Airbnb ROI: 0.03% Traditional ROI: 0.26%
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.	$999,999	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.72% Airbnb Rental Income: $2036 Traditional Rental Income: $2224 Airbnb ROI: -0.05% Traditional ROI: 0.72%
225 Berwick Drive #225 Hilton Head Island, SC Fantastic Berwick Green villa! This rare end-unit in Indigo Run offers 3 bedrooms plus an ...	4 beds \| 4 baths \| 3,010 sq.ft.	$1,250,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.18% Airbnb Rental Income: $3557 Traditional Rental Income: $3288 Airbnb ROI: 0.74% Traditional ROI: 1.18%
59 Summerfield Court #513 Hilton Head Island, SC Beautifully remodeled first-floor villa located in the gated Summerfield community. Featur...	2 beds \| 2 baths \| 1,000 sq.ft.	$399,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 2.13% Airbnb Rental Income: $1512 Traditional Rental Income: $1478 Airbnb ROI: 1.05% Traditional ROI: 2.13%
20 Lighthouse Lane #1102 Hilton Head Island, SC 2ND ROW SOUND IN WORLD RENOWNED HARBOURTOWN...Just a short stroll to the water's edge for ...	3 beds \| 2 baths \| 1,344 sq.ft.	$1,499,000	Airbnb cash on cash: -0.01% Traditional cash on cash: -0.5% Airbnb Rental Income: $2943 Traditional Rental Income: $1579 Airbnb ROI: -0.01% Traditional ROI: -0.5%
400 Wm Hilton Parkway #54 Hilton Head Island, SC This 3-bedroom, 2.5-bath villa offers over 1,200 square feet and is perfect for first-time...	3 beds \| 3 baths \| 1,269 sq.ft.	$274,990	Airbnb cash on cash: 3.89% Traditional cash on cash: 5.08% Airbnb Rental Income: $2036 Traditional Rental Income: $1817 Airbnb ROI: 3.89% Traditional ROI: 5.08%

Real Estate investment in Hilton-head-island, SC

There are 769 properties for sale in the city of Hilton Head Island . The median list price in Hilton Head Island is $814,513 and the average price per square foot is $467. In July 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 $1,394.

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

There are 769 investment properties available for sale in Hilton-head-island.

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

The ROI for Long-Term is higher than the Short-Term in Hilton-head-island with average rental income of $1,394.

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.

$318,900

Airbnb cash on cash: -0.91%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $576

Traditional Rental Income: $883

Airbnb ROI: -0.91%

Traditional ROI: 1.07%

48 Salt Marsh Drive #48

Hilton Head Island, SC

4 beds | 3 baths | 1,250 sq.ft.

$345,000

Airbnb cash on cash: 6.46%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $3460

Traditional Rental Income: $1976

Airbnb ROI: 6.46%

Traditional ROI: 4.24%

18 Sandpiper Street

Hilton Head Island, SC

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

$1,375,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 0.34%

Airbnb Rental Income: $1663

Traditional Rental Income: $2146

Airbnb ROI: -0.4%

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: 0.24%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $1663

Traditional Rental Income: $2637

Airbnb ROI: 0.24%

Traditional ROI: 2.3%

3 Craven Place

Hilton Head Island, SC

3 beds | 3 baths | 2,438 sq.ft.

$1,625,000

Airbnb cash on cash: -0.63%

Traditional cash on cash: 0.02%

Airbnb Rental Income: $2036

Traditional Rental Income: $2486

Airbnb ROI: -0.63%

Traditional ROI: 0.02%

6 Audubon Place

Hilton Head Island, SC

3 beds | 2 baths | 1,635 sq.ft.

$949,000

Airbnb cash on cash: 0.37%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $2036

Traditional Rental Income: $1629

Airbnb ROI: 0.37%

Traditional ROI: 0.51%

21 Crosstree Drive

Hilton Head Island, SC

3 beds | 3 baths | 2,340 sq.ft.

$915,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 1.22%

Airbnb Rental Income: $1877

Traditional Rental Income: $2464

Airbnb ROI: -0.06%

Traditional ROI: 1.22%

22 Timbercrest Circle

Hilton Head Island, SC

4 beds | 3 baths | 2,414 sq.ft.

$699,000

Airbnb cash on cash: 2.34%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $3481

Traditional Rental Income: $2568

Airbnb ROI: 2.34%