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
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 Ln Hilton Head Island, SC Value priced, updated/superbly maintained residence with charming curb appeal and lagoon v...	3 beds \| 3 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%
34 Bridgetown Road Hilton Head Island, SC Beautifully light, bright, and open, this gorgeous home features designer touches througho...	4 beds \| 5 baths \| 5,276 sq.ft.	$2,849,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.52% Airbnb Rental Income: $2685 Traditional Rental Income: $4469 Airbnb ROI: -0.4% Traditional ROI: 0.52%
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 \| 3 baths \| 3,285 sq.ft.	$1,799,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.06% Airbnb Rental Income: $1723 Traditional Rental Income: $2801 Airbnb ROI: -0.99% Traditional ROI: -0.06%
3 Claire Dr 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 Ln Hilton Head Island, SC EXCEPTIONAL VALUE NEAR THE BLUFF - NOW OFFERED AT $1,650,000. Perfectly positioned just on...	4 beds \| 4 baths \| 4,054 sq.ft.	$1,635,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 0.53% Airbnb Rental Income: $969 Traditional Rental Income: $3310 Airbnb ROI: -1.22% Traditional ROI: 0.53%
29 Oleander St 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%
61 Tucker Ridge Ct Hilton Head Island, SC Welcome to 61 Tucker Ridge and "Palmetto Hall"! This 4 bedroom/3.5 bath home with gorgeou...	4 beds \| 3 baths \| 2,519 sq.ft.	$850,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.97% Airbnb Rental Income: $969 Traditional Rental Income: $2892 Airbnb ROI: -0.9% Traditional ROI: 1.97%
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 Rd Hilton Head Island, SC Location, location! Right on the 2nd fairway of the world-famous Harbour Town Golf Links, ...	4 beds \| 4 baths \| 2,235 sq.ft.	$1,699,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.11% Airbnb Rental Income: $1588 Traditional Rental Income: $2731 Airbnb ROI: -0.91% Traditional ROI: 0.11%
17 Gunnery Lane Hilton Head Island, SC Must see this truly turnkey Sea Pines home in a beach oriented location. Completely reimag...	4 beds \| 4 baths \| 2,140 sq.ft.	$2,100,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.23% Airbnb Rental Income: $1588 Traditional Rental Income: $2693 Airbnb ROI: -1.03% Traditional ROI: -0.23%
2 Tall Pines Road Hilton Head Island, SC Bright, open, and airy newer-style home built in 2002, offering 3 bedrooms, 3.1 baths, and...	3 beds \| 4 baths \| 2,596 sq.ft.	$1,150,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 0.93% Airbnb Rental Income: $1968 Traditional Rental Income: $2764 Airbnb ROI: -0.3% Traditional ROI: 0.93%
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 Rd #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: -0.86% Traditional cash on cash: 1.07% Airbnb Rental Income: $1284 Traditional Rental Income: $2659 Airbnb ROI: -0.86% Traditional ROI: 1.07%
3 Shelter Cove Ln #7474 Hilton Head Island, SC Top-floor 3-bedroom, 3-bathroom condo in the highly desirable Anchorage Villas at Shelter ...	3 beds \| 3 baths \| 1,551 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 Rd #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 Dr #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 Dr #231 Hilton Head Island, SC Oceanfront villa with ocean views and refreshing coastal breezes! This beautifully furnish...	2 beds \| 2 baths \| 1,200 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 Ave #B3 Hilton Head Island, SC Renovated Coastal Villa Just Steps from the Beach! Priced to sell, this beautifully update...	2 beds \| 1 baths \| 960 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 Dr #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 Rd #A209 Hilton Head Island, SC Welcome to the ultimate beachside getaway on Hilton Head Island! This beautifully renovate...	1 beds \| 1 baths \| 540 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%
85 Folly Field Rd #116 Hilton Head Island, SC Beach beauty awaiting a new owner. Rare gem in Island Club, fully renovated with water an...	1 beds \| 1 baths \| 881 sq.ft.	$439,900	Airbnb cash on cash: -1.16% Traditional cash on cash: 1.37% Airbnb Rental Income: $541 Traditional Rental Income: $1301 Airbnb ROI: -1.16% Traditional ROI: 1.37%
7 Sandpiper St Hilton Head Island, SC This is your opportunity to enjoy true Hilton Head Island living at 7 Sandpiper Street, ju...	5 beds \| 5 baths \| 2,459 sq.ft.	$1,975,000	Airbnb cash on cash: -0.54% Traditional cash on cash: -0.03% Airbnb Rental Income: $2590 Traditional Rental Income: $2912 Airbnb ROI: -0.54% Traditional ROI: -0.03%
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.	$280,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 2.7% Airbnb Rental Income: $815 Traditional Rental Income: $1365 Airbnb ROI: -0.61% Traditional ROI: 2.7%
663 William Hilton Pkwy #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%
22 Sovereign Dr Hilton Head Island, SC Refined Coastal Elegance in Port Royal Plantation Nestled within the prestigious Port Roya...	4 beds \| 3 baths \| 4,000 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%
40 Folly Field Rd #C248 Hilton Head Island, SC Beautiful 2nd floor villa in C building with great views & private balcony! **BONUS Owner ...	1 beds \| 1 baths \| 540 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 Rd #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 \| 540 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 Dr #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.	$490,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 0.58% Airbnb Rental Income: $1147 Traditional Rental Income: $1077 Airbnb ROI: -0.1% Traditional ROI: 0.58%
113 Shipyard Dr #198 Hilton Head Island, SC Lowest priced condo in Shipyard for more than one Year. Bring your pets to this furnished ...	1 beds \| 1 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%
663 William Hilton Pkwy #4422 Hilton Head Island, SC This little gem resides within the Four Seasons Hilton Head Oceanfront Resort. 2 BR, 2 Ba,...	2 beds \| 2 baths \| 831 sq.ft.	$239,999	Airbnb cash on cash: 0.18% Traditional cash on cash: 4.28% Airbnb Rental Income: $815 Traditional Rental Income: $1419 Airbnb ROI: 0.18% Traditional ROI: 4.28%
45 Folly Field Rd #9H Hilton Head Island, SC Coastal charm meets modern comfort. 2-bedroom, 2-bath Fiddlers Cove Beach & Racquet Club v...	2 beds \| 2 baths \| 757 sq.ft.	$340,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 2.18% Airbnb Rental Income: $630 Traditional Rental Income: $1291 Airbnb ROI: -0.81% Traditional ROI: 2.18%
53 Delander Court #18 Hilton Head Island, SC Welcome to this beautifully updated 2 bedroom, 1 bathroom flat on Hilton Head's desirable ...	2 beds \| 1 baths \| 950 sq.ft.	$295,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 2.86% Airbnb Rental Income: $1515 Traditional Rental Income: $1309 Airbnb ROI: 2.01% Traditional ROI: 2.86%
663 William Hilton Pkwy #2219 Hilton Head Island, SC A great 2 bedroom villa located in the coveted building two of Hilton Head Resort! This v...	2 beds \| 2 baths \| 843 sq.ft.	$289,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 3.32% Airbnb Rental Income: $1025 Traditional Rental Income: $1424 Airbnb ROI: 0.54% Traditional ROI: 3.32%
49 Widewater Road Hilton Head Island, SC Welcome to 49 Widewater, located in the highly sought-after waterfront community of Spanis...	4 beds \| 5 baths \| 3,448 sq.ft.	$1,495,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.52% Airbnb Rental Income: $2621 Traditional Rental Income: $4375 Airbnb ROI: -0.2% Traditional ROI: 1.52%
1 High Bluff Rd #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.	$609,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 1.97% Airbnb Rental Income: $1968 Traditional Rental Income: $2106 Airbnb ROI: 0.82% Traditional ROI: 1.97%

Real Estate investment in Hilton-head-island, SC

There are 915 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 $381. In February 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 $2,031.

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

There are 915 investment properties available for sale in Hilton-head-island.

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

The ROI for Long-Term is higher than the Short-Term in Hilton-head-island with average rental income of $2,031.

Your search for investment property begins and ends here

Investment Property for Sale in Hilton Head Island, SC

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 Ln

Hilton Head Island, SC

3 beds | 3 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%

34 Bridgetown Road

Hilton Head Island, SC

4 beds | 5 baths | 5,276 sq.ft.

$2,849,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $2685

Traditional Rental Income: $4469

Airbnb ROI: -0.4%

Traditional ROI: 0.52%

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 | 3 baths | 3,285 sq.ft.

$1,799,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $1723

Traditional Rental Income: $2801

Airbnb ROI: -0.99%

Traditional ROI: -0.06%

3 Claire Dr

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%

Traditional ROI: 0.53%

20 China Cockle Ln

Hilton Head Island, SC

4 beds | 4 baths | 4,054 sq.ft.

$1,635,000

Airbnb cash on cash: -1.22%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $969

Traditional Rental Income: $3310

Airbnb ROI: -1.22%

Traditional ROI: 0.53%

29 Oleander St

Hilton Head Island, SC

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%