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
58 Spindle Lane #58 Hilton Head Island, SC Nestled in Windmill Harbour, Hilton Head Islandsâ premier boating community, this villa ...	2 beds \| 2 baths \| 1,595 sq.ft.	$485,000	Airbnb cash on cash: -0.8% Traditional cash on cash: 2.47% Airbnb Rental Income: $949 Traditional Rental Income: $2086 Airbnb ROI: -0.8% Traditional ROI: 2.47%
141 Lamotte Drive #E4 Hilton Head Island, SC Discover this updated 2-bedroom, 2-bath villa in Palmetto Commons, a quiet and charming co...	2 beds \| 2 baths \| 985 sq.ft.	$289,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.53% Airbnb Rental Income: $751 Traditional Rental Income: $1480 Airbnb ROI: -0.3% Traditional ROI: 3.53%
155 Dillon Road #2122 Hilton Head Island, SC Turnkey short-term rental in Cotton Hope Villas! This fully furnished 2BR/2.5BA villa feat...	2 beds \| 3 baths \| 1,120 sq.ft.	$225,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 6.15% Airbnb Rental Income: $751 Traditional Rental Income: $1738 Airbnb ROI: 0.05% Traditional ROI: 6.15%
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.	$750,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 2.16% Airbnb Rental Income: $2087 Traditional Rental Income: $2968 Airbnb ROI: 0.13% Traditional ROI: 2.16%
16 Combahee Road Hilton Head Island, SC Welcome to 16 Combahee Road, a fully updated, move-in-ready home in the prestigious, priva...	4 beds \| 5 baths \| 3,712 sq.ft.	$1,595,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 1.53% Airbnb Rental Income: $1269 Traditional Rental Income: $4673 Airbnb ROI: -1.04% Traditional ROI: 1.53%
6 Black Skimmer Road Hilton Head Island, SC Fantastic location just five rows from the ocean and directly on the walkway to the beach!...	4 beds \| 3 baths \| 3,327 sq.ft.	$2,495,000	Airbnb cash on cash: -1.12% Traditional cash on cash: -0.17% Airbnb Rental Income: $1588 Traditional Rental Income: $3312 Airbnb ROI: -1.12% Traditional ROI: -0.17%
2 Red Maple Rd Hilton Head Island, SC Set on a lush Â¾-acre lot overlooking the 17th tee of Heron Point, this 3,285 SqFt Sea Pin...	3 beds \| 4 baths \| 3,285 sq.ft.	$1,875,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.12% Airbnb Rental Income: $1723 Traditional Rental Income: $2801 Airbnb ROI: -1.01% Traditional ROI: -0.12%
3 Claire Drive Hilton Head Island, SC Tucked away on a quiet cul-de-sac in private, oceanfront Port Royal Plantation, this beaut...	4 beds \| 4 baths \| 3,223 sq.ft.	$1,649,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.53% Airbnb Rental Income: $1599 Traditional Rental Income: $3309 Airbnb ROI: -0.88% Traditional ROI: 0.53%
20 China Cockle Lane Hilton Head Island, SC Just a few short steps to the Bluff and Port Royal Sound, this beautifully renovated coast...	4 beds \| 4 baths \| 3,962 sq.ft.	$1,775,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 0.39% Airbnb Rental Income: $969 Traditional Rental Income: $3310 Airbnb ROI: -1.25% Traditional ROI: 0.39%
29 Oleander Street Hilton Head Island, SC Charming and pristine home located in a quiet area of HOLIDAY HOMES and a short 5-minute w...	4 beds \| 3 baths \| 2,320 sq.ft.	$1,049,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.91% Airbnb Rental Income: $1599 Traditional Rental Income: $2510 Airbnb ROI: -0.49% Traditional ROI: 0.91%
16 Timber Marsh Lane Hilton Head Island, SC Welcome to Lowcountry luxury at this 4 bd/4.5-ba builders personal custom model home! This...	4 beds \| 5 baths \| 3,513 sq.ft.	$1,279,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 2.33% Airbnb Rental Income: $969 Traditional Rental Income: $4724 Airbnb ROI: -1.12% Traditional ROI: 2.33%
8 Chickadee Road Hilton Head Island, SC Looking to down size or just need the perfect vacation home? This is turn key! Lots of u...	2 beds \| 2 baths \| 1,547 sq.ft.	$639,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 1.59% Airbnb Rental Income: $751 Traditional Rental Income: $1925 Airbnb ROI: -0.91% Traditional ROI: 1.59%
33 N Port Royal Drive Hilton Head Island, SC Only 300 yards from the sand, this Port Royal home ensures the Beach is part of your every...	4 beds \| 5 baths \| 3,972 sq.ft.	$2,295,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.47% Airbnb Rental Income: $1599 Traditional Rental Income: $4426 Airbnb ROI: -1.07% Traditional ROI: 0.47%
11 Muirfield Road Hilton Head Island, SC Located on the 2nd fairway of the world-famous Harbour Town Golf Links, this beautifully r...	4 beds \| 4 baths \| 2,066 sq.ft.	$1,749,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.06% Airbnb Rental Income: $1588 Traditional Rental Income: $2731 Airbnb ROI: -0.92% Traditional ROI: 0.06%
24 Ridgewood Lane Hilton Head Island, SC One of the finest homes in the Harbour Town area, this beautifully updated property offers...	3 beds \| 4 baths \| 3,565 sq.ft.	$2,750,000	Airbnb cash on cash: -1.11% Traditional cash on cash: -0.48% Airbnb Rental Income: $1723 Traditional Rental Income: $2866 Airbnb ROI: -1.11% Traditional ROI: -0.48%
50 Broad Pointe Drive Hilton Head Island, SC Full of character and charm, 50 Broad Pointe Drive may be one of the most iconic homes in ...	4 beds \| 4 baths \| 3,348 sq.ft.	$1,649,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.57% Airbnb Rental Income: $1168 Traditional Rental Income: $3357 Airbnb ROI: -1.11% Traditional ROI: 0.57%
35 Carnoustie Road #56 Hilton Head Island, SC Welcome to 56 Fazio! This updated 3-bedroom, 3-bath end-unit Fazio Villa is a rare opportu...	3 beds \| 3 baths \| 2,017 sq.ft.	$1,069,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 0.92% Airbnb Rental Income: $1284 Traditional Rental Income: $2659 Airbnb ROI: -0.87% Traditional ROI: 0.92%
40 Folly Field Road #B127 Hilton Head Island, SC DIRECT OCEANFRONT -- 1st floor, 1 bed/1 bath condo. See views of the ocean/pool and hear t...	1 beds \| 1 baths \| 560 sq.ft.	$349,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 1.17% Airbnb Rental Income: $541 Traditional Rental Income: $991 Airbnb ROI: -1.05% Traditional ROI: 1.17%
3 Shelter Cove Lane #7474 Hilton Head Island, SC Top-floor 3-bedroom, 3-bathroom condo in the highly desirable Anchorage Villas at Shelter ...	3 beds \| 3 baths \| 1,555 sq.ft.	$599,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 2.18% Airbnb Rental Income: $2048 Traditional Rental Income: $2188 Airbnb ROI: 0.98% Traditional ROI: 2.18%
20 Queens Folly Road #1661 Hilton Head Island, SC Welcome to your island getaway in the highly desirable St. Andrews community of Palmetto D...	2 beds \| 2 baths \| 1,177 sq.ft.	$595,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 1.1% Airbnb Rental Income: $1025 Traditional Rental Income: $1576 Airbnb ROI: -0.54% Traditional ROI: 1.1%
6 Village North 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.	$689,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.85% Airbnb Rental Income: $751 Traditional Rental Income: $1648 Airbnb ROI: -1.03% Traditional ROI: 0.85%
21 S Forest Beach Drive #231 Hilton Head Island, SC Oceanfront villa with ocean views and refreshing coastal breezes! This beautifully furnish...	2 beds \| 2 baths \| 1,125 sq.ft.	$949,900	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.14% Airbnb Rental Income: $1317 Traditional Rental Income: $1601 Airbnb ROI: -0.64% Traditional ROI: 0.14%
6 Woodward Avenue #B3 Hilton Head Island, SC Renovated Coastal Villa Just Steps from the Beach! Priced to sell, this beautifully update...	2 beds \| 1 baths \| 833 sq.ft.	$399,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.72% Airbnb Rental Income: $1317 Traditional Rental Income: $951 Airbnb ROI: 0.61% Traditional ROI: 0.72%
70 Shipyard Drive #125 Hilton Head Island, SC Immaculate renovation without compromise! This meticulously maintained 2-bedroom, 2-bath t...	2 beds \| 2 baths \| 1,420 sq.ft.	$699,500	Airbnb cash on cash: -0.36% Traditional cash on cash: 1.11% Airbnb Rental Income: $1282 Traditional Rental Income: $1836 Airbnb ROI: -0.36% Traditional ROI: 1.11%
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: -1% Traditional cash on cash: 1.66% Airbnb Rental Income: $541 Traditional Rental Income: $1051 Airbnb ROI: -1% Traditional ROI: 1.66%
36 Deallyon Avenue #114 Hilton Head Island, SC Welcome to this updated 2nd-floor Springwood Villa, ideally located just down the street f...	2 beds \| 3 baths \| 1,250 sq.ft.	$475,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 2.63% Airbnb Rental Income: $1317 Traditional Rental Income: $1779 Airbnb ROI: 0.67% Traditional ROI: 2.63%
85 Folly Field Road #116 Hilton Head Island, SC Beach beauty awaiting a new owner. Rare gem in Island Club, fully renovated with water an...	1 beds \| 2 baths \| 881 sq.ft.	$447,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 1.32% Airbnb Rental Income: $541 Traditional Rental Income: $1301 Airbnb ROI: -1.16% Traditional ROI: 1.32%
27 Arrow Wood Road Hilton Head Island, SC Incredible New Price - Best Deal In HHP! Immaculate 3 BR 2BA home in HHP close to Spring L...	3 beds \| 2 baths \| 1,693 sq.ft.	$629,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 1.75% Airbnb Rental Income: $1968 Traditional Rental Income: $2040 Airbnb ROI: 0.75% Traditional ROI: 1.75%
67 Summerfield Court #623 Hilton Head Island, SC Charm, Comfort and Convenience in the Heart of Hilton Head Island! Don't miss this beautif...	3 beds \| 3 baths \| 1,430 sq.ft.	$399,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.72% Airbnb Rental Income: $1547 Traditional Rental Income: $2447 Airbnb ROI: 1.12% Traditional ROI: 4.72%
663 William Hilton Parkway unit: 4205 #4205 Hilton Head Island, SC Welcome to 4205 Hilton Head Resort! This turnkey 2-bedroom villa in Building 4 at Hilton H...	2 beds \| 2 baths \| 831 sq.ft.	$285,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 2.64% Airbnb Rental Income: $815 Traditional Rental Income: $1365 Airbnb ROI: -0.62% Traditional ROI: 2.64%
663 William Hilton Parkway #3321 Hilton Head Island, SC Investorâs Dream on Hilton Head Island! This fully furnished & renovated 3BR/2BA villa i...	3 beds \| 2 baths \| 1,186 sq.ft.	$415,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 1.22% Airbnb Rental Income: $1547 Traditional Rental Income: $1662 Airbnb ROI: -0.23% Traditional ROI: 1.22%
1 Yacht Club Drive Hilton Head Island, SC Best value in Windmill Harbour! Located just half a block from the exclusive South Carolin...	3 beds \| 4 baths \| 2,759 sq.ft.	$949,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 1.52% Airbnb Rental Income: $2378 Traditional Rental Income: $2815 Airbnb ROI: 0.36% Traditional ROI: 1.52%
22 Sovereign Drive Hilton Head Island, SC Refined Coastal Elegance in Port Royal Plantation Nestled within the prestigious Port Roya...	4 beds \| 4 baths \| 3,442 sq.ft.	$2,150,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 0.52% Airbnb Rental Income: $1599 Traditional Rental Income: $3306 Airbnb ROI: -0.57% Traditional ROI: 0.52%
108 Lighthouse Road #2366 Hilton Head Island, SC Lowest priced Villa with 1+ bedroom in Sea Pines! Discover a remarkable, light-filled one-...	1 beds \| 1 baths \| 761 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.79% Airbnb Rental Income: $null Traditional Rental Income: $1182 Airbnb ROI: N/A Traditional ROI: 0.79%
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: -0.94% Traditional cash on cash: 2% Airbnb Rental Income: $541 Traditional Rental Income: $1051 Airbnb ROI: -0.94% Traditional ROI: 2%
40 Folly Field Road #B344 Hilton Head Island, SC Wake to the morning sun rising out of the Atlantic. 344B Hilton Head Beach and Tennis is ...	1 beds \| 1 baths \| 592 sq.ft.	$285,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 2.16% Airbnb Rental Income: $541 Traditional Rental Income: $1095 Airbnb ROI: -0.94% Traditional ROI: 2.16%
4 N Forest Beach Drive #127 Hilton Head Island, SC Experience coastal living at its best in this oceanfront condo located in the highly desir...	1 beds \| 1 baths \| 518 sq.ft.	$495,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 0.56% Airbnb Rental Income: $1147 Traditional Rental Income: $1077 Airbnb ROI: -0.11% Traditional ROI: 0.56%
147 Lighthouse Road #667 Hilton Head Island, SC Enjoy all that Harbour Town has to offer from this beautiful 2 bed/2 bath Sea Pines Resort...	2 beds \| 2 baths \| 1,002 sq.ft.	$650,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.87% Airbnb Rental Income: $1473 Traditional Rental Income: $1497 Airbnb ROI: 0.12% Traditional ROI: 0.87%
113 Shipyard Drive #198 Hilton Head Island, SC Lowest priced condo in Shipyard for more than one Year. Bring your pets to this furnished ...	1 beds \| 2 baths \| 1,215 sq.ft.	$449,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 2.02% Airbnb Rental Income: $1147 Traditional Rental Income: $1601 Airbnb ROI: 0.04% Traditional ROI: 2.02%

Real Estate investment in Hilton-head-island, SC

There are 696 properties for sale in the city of Hilton Head Island . The median list price in Hilton Head Island is $669,000 and the average price per square foot is $370. In December 2025, the average monthly cash on cash return in Hilton Head Island is 1.00%. The average monthly rental income in Hilton Head Island is $1,751.

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

There are 696 investment properties available for sale in Hilton-head-island.

In 2025, the best neighborhood to buy investment property is Wexford.

The ROI for Short-Term is higher than the Long-Term in Hilton-head-island with average rental income of $1,317.

Your search for investment property begins and ends here

Investment Property for Sale in Hilton Head Island, SC

58 Spindle Lane #58

Hilton Head Island, SC

2 beds | 2 baths | 1,595 sq.ft.

$485,000

Airbnb cash on cash: -0.8%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $949

Traditional Rental Income: $2086

Airbnb ROI: -0.8%

Traditional ROI: 2.47%

141 Lamotte Drive #E4

Hilton Head Island, SC

2 beds | 2 baths | 985 sq.ft.

$289,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $751

Traditional Rental Income: $1480

Airbnb ROI: -0.3%

Traditional ROI: 3.53%

155 Dillon Road #2122

Hilton Head Island, SC

2 beds | 3 baths | 1,120 sq.ft.

$225,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 6.15%

Airbnb Rental Income: $751

Traditional Rental Income: $1738

Airbnb ROI: 0.05%

Traditional ROI: 6.15%

66 Timber Lane

Hilton Head Island, SC

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

$750,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $2087

Traditional Rental Income: $2968

Airbnb ROI: 0.13%

Traditional ROI: 2.16%

16 Combahee Road

Hilton Head Island, SC

4 beds | 5 baths | 3,712 sq.ft.

$1,595,000

Airbnb cash on cash: -1.04%

Traditional cash on cash: 1.53%

Airbnb Rental Income: $1269

Traditional Rental Income: $4673

Airbnb ROI: -1.04%

Traditional ROI: 1.53%

6 Black Skimmer Road

Hilton Head Island, SC

4 beds | 3 baths | 3,327 sq.ft.

$2,495,000

Airbnb cash on cash: -1.12%

Traditional cash on cash: -0.17%

Airbnb Rental Income: $1588

Traditional Rental Income: $3312

Airbnb ROI: -1.12%

Traditional ROI: -0.17%

2 Red Maple Rd

Hilton Head Island, SC

3 beds | 4 baths | 3,285 sq.ft.

$1,875,000

Airbnb cash on cash: -1.01%

Traditional cash on cash: -0.12%

Airbnb Rental Income: $1723

Traditional Rental Income: $2801

Airbnb ROI: -1.01%

Traditional ROI: -0.12%

3 Claire Drive

Hilton Head Island, SC

4 beds | 4 baths | 3,223 sq.ft.

$1,649,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $1599

Traditional Rental Income: $3309

Airbnb ROI: -0.88%