Real Estate Investment Properties for Sale in Kailua, HI

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
851 Aalapapa Drive Kailua, HI This stunning home is ready for you to live the ultimate Hawaii paradise lifestyle in the ...	4 beds \| 4 baths \| 2,919 sq.ft.	$4,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.16% Airbnb Rental Income: $null Traditional Rental Income: $5740 Airbnb ROI: N/A Traditional ROI: 0.16%
1469 Humuula Street Kailua, HI Enchanted Lake Kailua home priced very reasonably to bring speedy interest. In an open are...	3 beds \| 2 baths \| 1,626 sq.ft.	$1,400,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.56% Airbnb Rental Income: $null Traditional Rental Income: $3841 Airbnb ROI: N/A Traditional ROI: 1.56%
1312 Aupapaohe Street Kailua, HI Perched in the highly sought-after Hillcrest enclave of Kailua, this fully reimagined 3-be...	3 beds \| 3 baths \| 2,000 sq.ft.	$1,850,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.17% Airbnb Rental Income: $null Traditional Rental Income: $4240 Airbnb ROI: N/A Traditional ROI: 1.17%
21 Kalaka Place Kailua, HI Completed in 2022, this classic beachfront home was redesigned into a spacious, modern pro...	5 beds \| 5 baths \| 3,519 sq.ft.	$11,980,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.64% Airbnb Rental Income: $null Traditional Rental Income: $8934 Airbnb ROI: N/A Traditional ROI: -0.64%
614 Ululani Street Kailua, HI Now offered at $1,420,000 - significant price improvement for a highly desirable Kailua lo...	3 beds \| 2 baths \| 1,164 sq.ft.	$1,420,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.04% Airbnb Rental Income: $null Traditional Rental Income: $3450 Airbnb ROI: N/A Traditional ROI: 1.04%
1015 Aoloa Place #252 Kailua, HI How often does the BEST PRICED 2 bedroom in Kailua's Poinciana Manor come with a renovated...	2 beds \| 2 baths \| 944 sq.ft.	$685,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 2.83% Airbnb Rental Income: $1049 Traditional Rental Income: $2790 Airbnb ROI: -0.47% Traditional ROI: 2.83%
1110 Ilikala Place Kailua, HI Your dream waterfront Kailua residence. This hidden jewel fronting Kawainui Canal with acc...	3 beds \| 3 baths \| 3,291 sq.ft.	$4,250,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.02% Airbnb Rental Income: $null Traditional Rental Income: $4691 Airbnb ROI: N/A Traditional ROI: -0.02%
119 Kuailima Drive Kailua, HI Prime Lanikai Location and Large, Level Land! This lot is 40% larger than a standard Lanik...	3 beds \| 1 baths \| 1,000 sq.ft.	$3,680,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.69% Airbnb Rental Income: $null Traditional Rental Income: $3380 Airbnb ROI: N/A Traditional ROI: -0.69%
536 Olomana Street Kailua, HI $39k PRICE DROP... COME & GET IT!!! Beautifully renovated in 2022 and tucked into one of K...	3 beds \| 2 baths \| 1,301 sq.ft.	$1,410,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.57% Airbnb Rental Income: $null Traditional Rental Income: $3872 Airbnb ROI: N/A Traditional ROI: 1.57%
846 Mokulua Drive Kailua, HI Fabulous Waterfront Estate in Lanikai!! A tropical serene oasis where you can entertain wi...	5 beds \| 4 baths \| 4,612 sq.ft.	$7,888,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.45% Airbnb Rental Income: $null Traditional Rental Income: $5588 Airbnb ROI: N/A Traditional ROI: -0.45%
599 Keolu Drive #B Kailua, HI Court ordered sale. Under Contract. No longer available for showings at this time to facil...	3 beds \| 3 baths \| 1,380 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $3975 Airbnb ROI: N/A Traditional ROI: 3.14%
631 Punaa Street #A Kailua, HI NEWLY REMODELED !!!! Located in the heart of the quiet Coconut Grove neighborhood, this so...	2 beds \| 1 baths \| 1,050 sq.ft.	$1,199,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.23% Airbnb Rental Income: $1049 Traditional Rental Income: $2934 Airbnb ROI: -0.78% Traditional ROI: 1.23%
1225 Mokapu Boulevard Kailua, HI Experience elevated island living in this fully remodeled, single-level home in the heart ...	3 beds \| 3 baths \| 1,258 sq.ft.	$1,890,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.78% Airbnb Rental Income: $null Traditional Rental Income: $3563 Airbnb ROI: N/A Traditional ROI: 0.78%
223 Lanipo Drive Kailua, HI Experience elevated island living in this fully renovated Lanikai retreat where luxury, pr...	4 beds \| 4 baths \| 2,667 sq.ft.	$4,300,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.21% Airbnb Rental Income: $null Traditional Rental Income: $6363 Airbnb ROI: N/A Traditional ROI: 0.21%
338 Manono Street #B Kailua, HI Kailua Fixer Upper in Coconut Grove with Desirable Large Lot at End of Lane! Massive Oppor...	2 beds \| 1 baths \| 843 sq.ft.	$1,125,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.09% Airbnb Rental Income: $1049 Traditional Rental Income: $2608 Airbnb ROI: -0.75% Traditional ROI: 1.09%
29 Alala Road #0 Kailua, HI Your gateway to turquoise waters, soft white sand, and the quintessential island lifestyle...	2 beds \| 2 baths \| 636 sq.ft.	$1,495,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.67% Airbnb Rental Income: $1049 Traditional Rental Income: $2714 Airbnb ROI: -0.79% Traditional ROI: 0.67%
889 Akumu Street Kailua, HI Tastefully renovated and move-in ready, this spacious 5-bedroom, 4-bath Enchanted Lake hom...	5 beds \| 4 baths \| 3,073 sq.ft.	$2,168,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $7059 Airbnb ROI: N/A Traditional ROI: 2.17%
3182 Kuau Street #702 Kailua, HI Welcome to Aikahi Gardens, a desirable community less than a mile from the beach and close...	2 beds \| 2 baths \| 1,048 sq.ft.	$775,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 1.59% Airbnb Rental Income: $1049 Traditional Rental Income: $3058 Airbnb ROI: -1.7% Traditional ROI: 1.59%
676 Mokapu Road Kailua, HI BEAUTIFUL FLEX HOME! Prestigious Kaimalino Neighborhood! This spacious 5 bedroom, 4 bathro...	5 beds \| 4 baths \| 3,962 sq.ft.	$3,288,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.07% Airbnb Rental Income: $null Traditional Rental Income: $7364 Airbnb ROI: N/A Traditional ROI: 1.07%
409 Wanaao Road Kailua, HI Back on the market with a brand new roof!!Experience the Best of Kailua Living in this bea...	4 beds \| 4 baths \| 2,483 sq.ft.	$2,499,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.31% Airbnb Rental Income: $null Traditional Rental Income: $6201 Airbnb ROI: N/A Traditional ROI: 1.31%
322 Aoloa Street #1512 Kailua, HI PRICE DROP TO $899,000 + BUYER CREDIT OF 40K Experience sophisticated island living in thi...	3 beds \| 2 baths \| 1,244 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.19% Airbnb Rental Income: $null Traditional Rental Income: $3688 Airbnb ROI: N/A Traditional ROI: 1.19%
322 Aoloa Street #709 Kailua, HI On the makai side of the bldg with a coastline view. Unit fire sprinklers & bldg plumbing ...	2 beds \| 2 baths \| 956 sq.ft.	$699,000	Airbnb cash on cash: -2.34% Traditional cash on cash: 1.32% Airbnb Rental Income: $1049 Traditional Rental Income: $3071 Airbnb ROI: -2.34% Traditional ROI: 1.32%
1015 Aoloa Place #247 Kailua, HI Experience the best of Kailua living! This beautifully updated 959 sq ft unit offers a mod...	2 beds \| 2 baths \| 959 sq.ft.	$719,000	Airbnb cash on cash: -2.14% Traditional cash on cash: 0.91% Airbnb Rental Income: $1049 Traditional Rental Income: $2727 Airbnb ROI: -2.14% Traditional ROI: 0.91%
14 Aulike Street #904 Kailua, HI Discover a premier opportunity to own one of the few condos in Kailua Town offering true 1...	2 beds \| 2 baths \| 861 sq.ft.	$675,000	Airbnb cash on cash: -1.8% Traditional cash on cash: 1.77% Airbnb Rental Income: $1049 Traditional Rental Income: $2934 Airbnb ROI: -1.8% Traditional ROI: 1.77%
1386 Nanialii Street Kailua, HI This beautiful home provides the perfect blend of Security, Privacy & TONS of space!! The ...	4 beds \| 3 baths \| 3,459 sq.ft.	$2,199,999	Airbnb cash on cash: N/A Traditional cash on cash: 0.99% Airbnb Rental Income: $null Traditional Rental Income: $4738 Airbnb ROI: N/A Traditional ROI: 0.99%
32 Pilipu Place unit: A Kailua, HI Welcome to your beachside paradise-just one lot from the ocean and directly next to the be...	4 beds \| 2 baths \| 2,970 sq.ft.	$3,600,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.35% Airbnb Rental Income: $null Traditional Rental Income: $5376 Airbnb ROI: N/A Traditional ROI: 0.35%
592 Kaimalino Street Kailua, HI Rarely available OCEANFRONT gem in the prestigious KAIMALINO neighborhood in Kailua offeri...	4 beds \| 3 baths \| 1,517 sq.ft.	$3,495,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.44% Airbnb Rental Income: $null Traditional Rental Income: $3998 Airbnb ROI: N/A Traditional ROI: -0.44%
241 Kihapai Street #A Kailua, HI Opportunity awaits in desirable Kailua! This CPR property is situated on a flag lot offeri...	3 beds \| 2 baths \| 1,364 sq.ft.	$1,070,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $3463 Airbnb ROI: N/A Traditional ROI: 2.1%

Real Estate investment in Kailua, HI

There are 72 properties for sale in the city of Kailua . The median list price in Kailua is $1,437,500 and the average price per square foot is $833. In May 2026, the average monthly cash on cash return in Kailua is 1.00%. The average monthly rental income in Kailua is $3,841.

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

There are 72 investment properties available for sale in Kailua.

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

The ROI for Long-Term is higher than the Short-Term in Kailua with average rental income of $3,841.

Your search for investment property begins and ends here

Investment Property for Sale in Kailua, HI

851 Aalapapa Drive

Kailua, HI

4 beds | 4 baths | 2,919 sq.ft.

$4,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.16%

Airbnb Rental Income: $null

Traditional Rental Income: $5740

Airbnb ROI: N/A

Traditional ROI: 0.16%

1469 Humuula Street

Kailua, HI

3 beds | 2 baths | 1,626 sq.ft.

$1,400,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.56%

Airbnb Rental Income: $null

Traditional Rental Income: $3841

Airbnb ROI: N/A

Traditional ROI: 1.56%

1312 Aupapaohe Street

Kailua, HI

3 beds | 3 baths | 2,000 sq.ft.

$1,850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.17%

Airbnb Rental Income: $null

Traditional Rental Income: $4240

Airbnb ROI: N/A

Traditional ROI: 1.17%

21 Kalaka Place

Kailua, HI

5 beds | 5 baths | 3,519 sq.ft.

$11,980,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.64%

Airbnb Rental Income: $null

Traditional Rental Income: $8934

Airbnb ROI: N/A

Traditional ROI: -0.64%

614 Ululani Street

Kailua, HI

3 beds | 2 baths | 1,164 sq.ft.

$1,420,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.04%

Airbnb Rental Income: $null

Traditional Rental Income: $3450

Airbnb ROI: N/A

Traditional ROI: 1.04%

1015 Aoloa Place #252

Kailua, HI

2 beds | 2 baths | 944 sq.ft.

$685,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $1049

Traditional Rental Income: $2790

Airbnb ROI: -0.47%

Traditional ROI: 2.83%

1110 Ilikala Place

Kailua, HI

3 beds | 3 baths | 3,291 sq.ft.

$4,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.02%

Airbnb Rental Income: $null

Traditional Rental Income: $4691

Airbnb ROI: N/A

Traditional ROI: -0.02%

119 Kuailima Drive

Kailua, HI

3 beds | 1 baths | 1,000 sq.ft.

$3,680,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.69%

Airbnb Rental Income: $null

Traditional Rental Income: $3380

Airbnb ROI: N/A