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
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: -0.08% Traditional cash on cash: 2.39% Airbnb Rental Income: $1859 Traditional Rental Income: $2968 Airbnb ROI: -0.08% 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.	$899,500	Airbnb cash on cash: N/A Traditional cash on cash: 0.58% Airbnb Rental Income: $null Traditional Rental Income: $1891 Airbnb ROI: N/A Traditional ROI: 0.58%
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.	$419,000	Airbnb cash on cash: -2.97% Traditional cash on cash: -0.37% Airbnb Rental Income: $685 Traditional Rental Income: $1403 Airbnb ROI: -2.97% Traditional ROI: -0.37%
2 Red Maple Rd Hilton Head Island, SC Set on a lush 3/4-acre lot overlooking the 17th tee of Heron Point, this 3,285 SqFt Sea Pi...	3 beds \| 4 baths \| 3,285 sq.ft.	$1,775,000	Airbnb cash on cash: -0.84% Traditional cash on cash: -0.04% Airbnb Rental Income: $1988 Traditional Rental Income: $2801 Airbnb ROI: -0.84% Traditional ROI: -0.04%
27 Bridgetown Road Hilton Head Island, SC Set on one of Wexford's most desirable corner lots, 27 Bridgetown Road impresses immediate...	4 beds \| 5 baths \| 3,315 sq.ft.	$3,390,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.06% Airbnb Rental Income: $2260 Traditional Rental Income: $3276 Airbnb ROI: -0.55% Traditional ROI: -0.06%
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: 0.14% Traditional cash on cash: 0.53% Airbnb Rental Income: $3481 Traditional Rental Income: $3309 Airbnb ROI: 0.14% Traditional ROI: 0.53%
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: -0.06% Traditional cash on cash: 0.34% Airbnb Rental Income: $2188 Traditional Rental Income: $2146 Airbnb ROI: -0.06% Traditional ROI: 0.34%
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: 0.28% Traditional cash on cash: 2.28% Airbnb Rental Income: $2195 Traditional Rental Income: $3310 Airbnb ROI: 0.28% Traditional ROI: 2.28%
20 China Cockle Lane Hilton Head Island, SC LOCATION, PRIVACY, MOVE-IN READY! Exceptional Value Near the Bluff, Now Offered at $1,560,...	4 beds \| 4 baths \| 3,962 sq.ft.	$1,560,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 0.65% Airbnb Rental Income: $719 Traditional Rental Income: $3310 Airbnb ROI: -1.35% Traditional ROI: 0.65%
61 Tucker Ridge Court Hilton Head Island, SC Welcome to 61 Tucker Ridge and "Palmetto Hall"! This 4 bedroom/3.5 bath home with gorgeou...	4 beds \| 4 baths \| 2,519 sq.ft.	$850,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 1.97% Airbnb Rental Income: $719 Traditional Rental Income: $2892 Airbnb ROI: -1.17% Traditional ROI: 1.97%
2 Cattail Court Hilton Head Island, SC Looking for privacy, luxury finishes, and exceptional outdoor living in one of Hilton Head...	3 beds \| 3 baths \| 2,638 sq.ft.	$1,395,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.64% Airbnb Rental Income: $null Traditional Rental Income: $2644 Airbnb ROI: N/A Traditional ROI: 0.64%
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.	$1,699,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.11% Airbnb Rental Income: $2341 Traditional Rental Income: $2731 Airbnb ROI: -0.51% Traditional ROI: 0.11%
3 Fairway Winds Place Hilton Head Island, SC On the ocean-facing side of Fairway Winds in Port Royal Plantation, this special property ...	4 beds \| 4 baths \| 2,311 sq.ft.	$1,750,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 0.39% Airbnb Rental Income: $3481 Traditional Rental Income: $3276 Airbnb ROI: 0.05% Traditional ROI: 0.39%
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: -1.48% Traditional cash on cash: -0.02% Airbnb Rental Income: $899 Traditional Rental Income: $2447 Airbnb ROI: -1.48% Traditional ROI: -0.02%
11 Tanglewood Drive #34 Hilton Head Island, SC Discover the perfect getaway at this updated villa, ideally situated near Hilton Head Isla...	2 beds \| 2 baths \| 1,036 sq.ft.	$498,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.11% Airbnb Rental Income: $1536 Traditional Rental Income: $2184 Airbnb ROI: 0.76% Traditional ROI: 3.11%
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.	$3,250,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.94% Airbnb Rental Income: $3569 Traditional Rental Income: $3276 Airbnb ROI: -1.1% Traditional ROI: -0.94%
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: -0.67% Traditional cash on cash: 1.59% Airbnb Rental Income: $899 Traditional Rental Income: $2644 Airbnb ROI: -0.67% Traditional ROI: 1.59%
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: 0.02% Traditional cash on cash: 1.06% Airbnb Rental Income: $2068 Traditional Rental Income: $2644 Airbnb ROI: 0.02% Traditional ROI: 1.06%
35 Carnoustie Road #56 Hilton Head Island, SC Welcome to 56 Fazio! This updated 3-bedroom, 3-bath end-unit Fazio Villa offers a rare com...	3 beds \| 3 baths \| 2,017 sq.ft.	$989,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 1.07% Airbnb Rental Income: $1452 Traditional Rental Income: $2659 Airbnb ROI: -0.71% Traditional ROI: 1.07%
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: -0.9% Traditional cash on cash: 1.1% Airbnb Rental Income: $786 Traditional Rental Income: $1576 Airbnb ROI: -0.9% 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.	$679,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.89% Airbnb Rental Income: $598 Traditional Rental Income: $1648 Airbnb ROI: -1.23% Traditional ROI: 0.89%
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: -0.44% Traditional cash on cash: 0.14% Airbnb Rental Income: $1536 Traditional Rental Income: $1601 Airbnb ROI: -0.44% 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.	$398,500	Airbnb cash on cash: 1.11% Traditional cash on cash: 0.73% Airbnb Rental Income: $1536 Traditional Rental Income: $951 Airbnb ROI: 1.11% Traditional ROI: 0.73%
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: -1.06% Traditional cash on cash: 1.11% Airbnb Rental Income: $731 Traditional Rental Income: $1836 Airbnb ROI: -1.06% Traditional ROI: 1.11%
1 Gloucester Road #E-2 Hilton Head Island, SC Fully furnished, beautiful 3BR/3BA villa offers the perfect blend of luxury & comfort. Nes...	3 beds \| 3 baths \| 2,000 sq.ft.	$799,999	Airbnb cash on cash: 0.5% Traditional cash on cash: 1.81% Airbnb Rental Income: $2188 Traditional Rental Income: $2607 Airbnb ROI: 0.5% Traditional ROI: 1.81%
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: -0.41% Traditional cash on cash: 1.66% Airbnb Rental Income: $752 Traditional Rental Income: $1051 Airbnb ROI: -0.41% Traditional ROI: 1.66%
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: -1.01% Traditional cash on cash: 3.85% Airbnb Rental Income: $501 Traditional Rental Income: $1421 Airbnb ROI: -1.01% Traditional ROI: 3.85%
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.	$439,900	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.37% Airbnb Rental Income: $752 Traditional Rental Income: $1301 Airbnb ROI: -0.73% Traditional ROI: 1.37%
24 Lands End Court Hilton Head Island, SC Absolutely fabulous views of the Sound and the iconic Harbour Town Lighthouse from this st...	4 beds \| 3 baths \| 1,844 sq.ft.	$1,895,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 0.24% Airbnb Rental Income: $2341 Traditional Rental Income: $3276 Airbnb ROI: -0.62% Traditional ROI: 0.24%
663 William Hilton Parkway unit: 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.	$275,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 2.77% Airbnb Rental Income: $771 Traditional Rental Income: $1365 Airbnb ROI: -0.75% Traditional ROI: 2.77%
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: -1.38% Traditional cash on cash: 1.22% Airbnb Rental Income: $1009 Traditional Rental Income: $1662 Airbnb ROI: -1.38% Traditional ROI: 1.22%
125 Shipyard Drive #197 Hilton Head Island, SC Beautifully updated coastal villa in a prime Hilton Head Island location, offering effortl...	2 beds \| 2 baths \| 1,272 sq.ft.	$690,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.68% Airbnb Rental Income: $731 Traditional Rental Income: $2184 Airbnb ROI: -1.06% Traditional ROI: 1.68%
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: -0.61% Traditional cash on cash: 0.76% Airbnb Rental Income: $1923 Traditional Rental Income: $3310 Airbnb ROI: -0.61% Traditional ROI: 0.76%
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.	$1,949,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 0.67% Airbnb Rental Income: $3481 Traditional Rental Income: $3306 Airbnb ROI: 0.34% Traditional ROI: 0.67%
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: -0.8% Traditional cash on cash: 0.39% Airbnb Rental Income: $752 Traditional Rental Income: $948 Airbnb ROI: -0.8% 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: -0.57% Traditional cash on cash: 2.99% Airbnb Rental Income: $1009 Traditional Rental Income: $2644 Airbnb ROI: -0.57% Traditional ROI: 2.99%
10 N Forest Beach Drive #2213 Hilton Head Island, SC Enjoy ocean views from your private balconies overlooking the N Forest Beach area in this ...	2 beds \| 2 baths \| 1,391 sq.ft.	$899,900	Airbnb cash on cash: 0.09% Traditional cash on cash: 1.4% Airbnb Rental Income: $1536 Traditional Rental Income: $2184 Airbnb ROI: 0.09% Traditional ROI: 1.4%

Real Estate investment in Hilton-head-island, SC

There are 804 properties for sale in the city of Hilton Head Island . The median list price in Hilton Head Island is $675,000 and the average price per square foot is $380. In April 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 $2,130.

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

There are 804 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 $1,915.

Your search for investment property begins and ends here

Investment Property for Sale in Hilton Head Island, SC

66 Timber Lane

Hilton Head Island, SC

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

$699,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $1859

Traditional Rental Income: $2968

Airbnb ROI: -0.08%

Traditional ROI: 2.39%

245 Fort Howell Drive

Hilton Head Island, SC

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

$899,500

Airbnb cash on cash: N/A

Traditional cash on cash: 0.58%

Airbnb Rental Income: $null

Traditional Rental Income: $1891

Airbnb ROI: N/A

Traditional ROI: 0.58%

40 Folly Field Road #130

Hilton Head Island, SC

2 beds | 2 baths | 996 sq.ft.

$419,000

Airbnb cash on cash: -2.97%

Traditional cash on cash: -0.37%

Airbnb Rental Income: $685

Traditional Rental Income: $1403

Airbnb ROI: -2.97%

Traditional ROI: -0.37%

2 Red Maple Rd

Hilton Head Island, SC

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

$1,775,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: -0.04%

Airbnb Rental Income: $1988

Traditional Rental Income: $2801

Airbnb ROI: -0.84%

Traditional ROI: -0.04%

27 Bridgetown Road

Hilton Head Island, SC

4 beds | 5 baths | 3,315 sq.ft.

$3,390,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $2260

Traditional Rental Income: $3276

Airbnb ROI: -0.55%

Traditional ROI: -0.06%

3 Claire Drive

Hilton Head Island, SC

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

$1,649,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $3481

Traditional Rental Income: $3309

Airbnb ROI: 0.14%

Traditional ROI: 0.53%

18 Sandpiper Street

Hilton Head Island, SC

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

$1,375,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 0.34%

Airbnb Rental Income: $2188

Traditional Rental Income: $2146

Airbnb ROI: -0.06%

Traditional ROI: 0.34%

6 Richfield Way

Hilton Head Island, SC

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

$899,000

Airbnb cash on cash: 0.28%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $2195

Traditional Rental Income: $3310

Airbnb ROI: 0.28%