Real Estate Investment Properties for Sale in Wailea, HI

Looking for investment property in Wailea, HI with high ROI ?

Explore a variety of short-term homes & houses in Wailea, HI. Invest wisely with VRBO & Wailea, HI 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 Wailea, HI

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3300 Wailea Alanui Drive #45C Wailea, HI A spectacular one of a kind total remodel - completed 2022 - w/ incredible attention to de...	1 beds \| 1 baths \| 792 sq.ft.	$1,469,000	Airbnb cash on cash: -1.06% Traditional cash on cash: -0.78% Airbnb Rental Income: $2302 Traditional Rental Income: $2108 Airbnb ROI: -1.06% Traditional ROI: -0.78%
209 Holokahiki Ln #103 Wailea, HI Welcome to Makalii one of Wailea's newest luxury residences known for its mid-century mode...	3 beds \| N/A baths \| 1,802 sq.ft.	$2,495,000	Airbnb cash on cash: -3% Traditional cash on cash: -1.29% Airbnb Rental Income: $487 Traditional Rental Income: $4180 Airbnb ROI: -3% Traditional ROI: -1.29%
Investment Properties for Sale in Other Cities of Hawaii
68-1050 Mauna Lani Point Dr #H107 Kamuela , HI A rare find at Mauna Lani Point! This unique property has been beautifully renovated and t...	1 beds \| 1 baths \| 984 sq.ft.	$1,595,000	Airbnb cash on cash: -2.29% Traditional cash on cash: -1.5% Airbnb Rental Income: $2210 Traditional Rental Income: $2822 Airbnb ROI: -2.29% Traditional ROI: -1.5%
3063 Diamond Head Rd Honolulu , HI Located in the heart of one of Oahu's most desirable neighborhoods, this exceptional resid...	4 beds \| 4 baths \| 3,631 sq.ft.	$5,560,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 1.08% Airbnb Rental Income: $1777 Traditional Rental Income: $11742 Airbnb ROI: -0.95% Traditional ROI: 1.08%
1088 Bishop St #1126 Honolulu , HI Located in the heart of Downtown Honolulu, 1088 Bishop Street #1126 offers a unique opport...	1 beds \| 1 baths \| 774 sq.ft.	$385,000	Airbnb cash on cash: -3.58% Traditional cash on cash: -3.12% Airbnb Rental Income: $2549 Traditional Rental Income: $2105 Airbnb ROI: -3.58% Traditional ROI: -3.12%
235 Portlock Rd Honolulu , HI Tucked behind a private gate in prestigious Portlock, this extensively rebuilt residence o...	5 beds \| 5 baths \| 4,736 sq.ft.	$6,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.18% Airbnb Rental Income: $null Traditional Rental Income: $10125 Airbnb ROI: N/A Traditional ROI: 0.18%
1423 Emerson Street #111 Honolulu , HI BEST DEAL IN TOWN. Situated in the upper ward area, this secured building features 2 bedro...	2 beds \| 1 baths \| 796 sq.ft.	$430,000	Airbnb cash on cash: 7.6% Traditional cash on cash: 3.84% Airbnb Rental Income: $4737 Traditional Rental Income: $2245 Airbnb ROI: 7.6% Traditional ROI: 3.84%
1226 Alexander St #1102 Honolulu , HI Beautifully renovated move in ready unit. This residence offers modern finishes, one cover...	2 beds \| 1 baths \| 600 sq.ft.	$390,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.55% Airbnb Rental Income: $3228 Traditional Rental Income: $2314 Airbnb ROI: 5.06% Traditional ROI: 4.55%
1740 S Beretania St #9 Honolulu , HI Discover refined island living in this elegant 2-bedroom, 2.5-bathroom residence located i...	2 beds \| 2 baths \| 1,938 sq.ft.	$1,500,000	Airbnb cash on cash: -3.05% Traditional cash on cash: -1.05% Airbnb Rental Income: $3228 Traditional Rental Income: $5290 Airbnb ROI: -3.05% Traditional ROI: -1.05%
4504 Kahala Ave Honolulu , HI This home is an exceptional buy for the Kahala market. Priced below replacement cost for t...	5 beds \| 6 baths \| 8,325 sq.ft.	$6,998,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.28% Airbnb Rental Income: $null Traditional Rental Income: $9988 Airbnb ROI: N/A Traditional ROI: -0.28%
1888 Kalakaua Ave #2103 Honolulu , HI Discover refined island living at Waikiki Landmark Condo Unit 2103 - a standout residence ...	2 beds \| 2 baths \| 1,111 sq.ft.	$460,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 6.98% Airbnb Rental Income: $3228 Traditional Rental Income: $3930 Airbnb ROI: 3.66% Traditional ROI: 6.98%
445 Seaside Avenue #1921 Honolulu , HI Welcome to Island Colony, a well-established destination in the heart of Waikiki, where th...	1 beds \| 1 baths \| 570 sq.ft.	$488,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 3.01% Airbnb Rental Income: $1938 Traditional Rental Income: $2150 Airbnb ROI: 1.43% Traditional ROI: 3.01%
223 Saratoga Rd #3603 Honolulu , HI Experience unparalleled luxury at Ka La'i Waikiki Beach #3603 where five-star living meets...	2 beds \| 3 baths \| 1,673 sq.ft.	$1,850,000	Airbnb cash on cash: -3.69% Traditional cash on cash: -2.59% Airbnb Rental Income: $3585 Traditional Rental Income: $4688 Airbnb ROI: -3.69% Traditional ROI: -2.59%
421 Olohana St #702 Honolulu , HI Lanikea at Waikiki stands as one of Waikiki's most established and sought-after luxury con...	2 beds \| 2 baths \| 1,023 sq.ft.	$810,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.41% Airbnb Rental Income: $3585 Traditional Rental Income: $4181 Airbnb ROI: -0.42% Traditional ROI: 1.41%

Real Estate investment in Wailea, HI

There are 2 properties for sale in the city of Wailea . The median list price in Wailea is $1,474,118 and the average price per square foot is $1,308. In August 2026, the average monthly cash on cash return in Wailea is 1.00%. The average monthly rental income in Wailea is $3,330.

Wailea, HI Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Wailea.

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

The ROI for Short-Term is higher than the Long-Term in Wailea with average rental income of $3,577.

Your search for investment property begins and ends here

Investment Property for Sale in Wailea, HI

3300 Wailea Alanui Drive #45C

Wailea, HI

1 beds | 1 baths | 792 sq.ft.

$1,469,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: -0.78%

Airbnb Rental Income: $2302

Traditional Rental Income: $2108

Airbnb ROI: -1.06%

Traditional ROI: -0.78%

209 Holokahiki Ln #103

Wailea, HI

3 beds | N/A baths | 1,802 sq.ft.

$2,495,000

Airbnb cash on cash: -3%

Traditional cash on cash: -1.29%

Airbnb Rental Income: $487

Traditional Rental Income: $4180

Airbnb ROI: -3%

Traditional ROI: -1.29%

Investment Properties for Sale in Other Cities of Hawaii

Kamuela , HI

1 beds | 1 baths | 984 sq.ft.

$1,595,000

Airbnb cash on cash: -2.29%

Traditional cash on cash: -1.5%

Airbnb Rental Income: $2210

Traditional Rental Income: $2822

Airbnb ROI: -2.29%

Traditional ROI: -1.5%

Honolulu , HI

4 beds | 4 baths | 3,631 sq.ft.

$5,560,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $1777

Traditional Rental Income: $11742

Airbnb ROI: -0.95%

Traditional ROI: 1.08%

Honolulu , HI

1 beds | 1 baths | 774 sq.ft.

$385,000

Airbnb cash on cash: -3.58%

Traditional cash on cash: -3.12%

Airbnb Rental Income: $2549

Traditional Rental Income: $2105

Airbnb ROI: -3.58%

Traditional ROI: -3.12%

Honolulu , HI

5 beds | 5 baths | 4,736 sq.ft.

$6,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.18%

Airbnb Rental Income: $null

Traditional Rental Income: $10125

Airbnb ROI: N/A

Traditional ROI: 0.18%

Honolulu , HI

2 beds | 1 baths | 796 sq.ft.

$430,000

Airbnb cash on cash: 7.6%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $4737

Traditional Rental Income: $2245

Airbnb ROI: 7.6%

Traditional ROI: 3.84%

Honolulu , HI

2 beds | 1 baths | 600 sq.ft.

$390,000

Airbnb cash on cash: 5.06%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $3228

Traditional Rental Income: $2314

Airbnb ROI: 5.06%

Traditional ROI: 4.55%

Honolulu , HI

2 beds | 2 baths | 1,938 sq.ft.

$1,500,000

Airbnb cash on cash: -3.05%