Kailua-Kona, Hawaii

Vacation Rentals in Kailua-Kona, Hawaii

Discover 1,374 vacation rental properties in Kailua-Kona. From 1 to 13 bedrooms. Average $316/night. 100% have pools.

1,374 verified listings Book securely on VRBO Prices updated March 2026

1,374 properties available

Kona Makai Building #1

Kona Makai Building #1

1 bed 1 bath
PoolA/CWiFiBalcony
$189/night
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“Queen palm” Ocean View Studio, Walk to Magic Sands and Kahaluu -Free Wifi

“Queen palm” Ocean View Studio, Walk to Magic Sands and Kahaluu -Free Wifi

1 bath
PoolA/CWiFiBalcony
$130/night
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Oceanfront with Endless Ocean View, Gorgeous sunsets, WiFi, and King Bed

Oceanfront with Endless Ocean View, Gorgeous sunsets, WiFi, and King Bed

1 bed 2 baths
PoolA/CWiFiBalcony
$156/night
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BEAUTIFULLY REMODELED OCEANFRONT ONE BEDROOM 2 BATH CONDOMINIUM

BEAUTIFULLY REMODELED OCEANFRONT ONE BEDROOM 2 BATH CONDOMINIUM

1 bed
PoolA/CWiFiBalcony
$307/night
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KONA MAKAI#5-205 BEAUTIFUL 2ND FLOOR UNIT IN OCEANFRONT COMPLEX!

KONA MAKAI#5-205 BEAUTIFUL 2ND FLOOR UNIT IN OCEANFRONT COMPLEX!

1 bed 1 bath
PoolA/CWiFiBalcony
$123/night
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Oceanfront Sunsets in heart of Kona

Oceanfront Sunsets in heart of Kona

1 bed 1 bath
PoolA/CWiFiBalcony
$189/night
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Ahh.PARADISE 5/14-5/17Special rt.OCEAN VIEW,BEST Snorkeling,Surfing steps away

Ahh.PARADISE 5/14-5/17Special rt.OCEAN VIEW,BEST Snorkeling,Surfing steps away

2 beds 2 baths
PoolA/CWiFiBalcony
$297/night
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KKSR#176 DIRECT OCEANFRONT CORNER AIR CONDITIONED TOWNHOUSE, CLOSE TO POOL

KKSR#176 DIRECT OCEANFRONT CORNER AIR CONDITIONED TOWNHOUSE, CLOSE TO POOL

2 beds 2 baths
PoolA/CWiFiBalcony
$212/night
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Incredible Condo ✨ Two Amazing Views from One Lanai (Ocean and Pool)! 🐠 Kona Reef C-33

Incredible Condo ✨ Two Amazing Views from One Lanai (Ocean and Pool)! 🐠 Kona Reef C-33

1 bed
PoolA/CWiFiBalcony
$161/night
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Top Floor Cozy Condo Nestled Among Tropical Kailua Kona Treetops

Top Floor Cozy Condo Nestled Among Tropical Kailua Kona Treetops

1 bath
PoolA/CWiFiBalcony
$117/night
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Kona Shores 203: Amazing location&fully equipped condo in Oceanfront complex!

Kona Shores 203: Amazing location&fully equipped condo in Oceanfront complex!

1 bath
PoolA/CWiFiBalcony
$105/night
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True Kona Retreat Condo🏄‍♀️ Bedroom and Living Room Faces The Sea! 🌊 Hale Kona Kai 305

True Kona Retreat Condo🏄‍♀️ Bedroom and Living Room Faces The Sea! 🌊 Hale Kona Kai 305

1 bed 1 bath
PoolA/CWiFiBalcony
$187/night
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Kona Reef D24 - Direct Ocean Front Condo - Private Lanai - next to Honl's Beach!

Kona Reef D24 - Direct Ocean Front Condo - Private Lanai - next to Honl's Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$284/night
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Direct Oceanfront Condo on Private Beach Resort *Central AC *

Direct Oceanfront Condo on Private Beach Resort *Central AC *

2 beds 2 baths
PoolA/CWiFiBalcony
$229/night
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Apartment in town-walking distance to everything

Apartment in town-walking distance to everything

1 bed 1 bath
PoolA/CWiFiBalcony
$149/night
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OCEANFRONT/Elevator/AC/Surfers

OCEANFRONT/Elevator/AC/Surfers

2 beds 2 baths
PoolA/CWiFiBalcony
$288/night
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2 bedrooms, 2 bathrooms - Across street from beach and close to Kailua Village

2 bedrooms, 2 bathrooms - Across street from beach and close to Kailua Village

2 beds 2 baths
PoolA/CWiFiBalcony
$189/night
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Waikoloa Fairways #A310: Top Floor,Breathtaking Lake, Golf Course&Ocean Views

Waikoloa Fairways #A310: Top Floor,Breathtaking Lake, Golf Course&Ocean Views

2 beds 2 baths
PoolA/CWiFiBalcony
$250/night
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Direct Oceanfront Condo! Sea Turtles & Beautiful Sunsets from the Lanai

Direct Oceanfront Condo! Sea Turtles & Beautiful Sunsets from the Lanai

1 bed 1 bath
PoolA/CWiFiBalcony
$206/night
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SEA VILLAGE RESORT LAST MINUTE SPECIAL 2024 SUMMER RATES @100+ NT SEE CALENDAR

SEA VILLAGE RESORT LAST MINUTE SPECIAL 2024 SUMMER RATES @100+ NT SEE CALENDAR

1 bed 1 bath
PoolA/CWiFiBalcony
$157/night
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Kona Makai 6-203 BEAUTIFUL OCEAN VIEWS ON 2ND FLOOR, 1 bedroom/1 bath

Kona Makai 6-203 BEAUTIFUL OCEAN VIEWS ON 2ND FLOOR, 1 bedroom/1 bath

1 bed 1 bath
PoolA/CWiFiBalcony
$145/night
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Enchanting oceanfront condo with pool, views & high-speed WiFi

Enchanting oceanfront condo with pool, views & high-speed WiFi

1 bed 2 baths
PoolA/CWiFiBalcony
$189/night
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Spectacular Ocean View At Kona-Isle. Ocean Front Complex-Close to Town & Dining

Spectacular Ocean View At Kona-Isle. Ocean Front Complex-Close to Town & Dining

1 bed 1 bath
PoolA/CWiFiBalcony
$155/night
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Your Hawaiian Vacation Starts Here! II

Your Hawaiian Vacation Starts Here! II

1 bath
PoolA/CWiFiBalcony
$117/night
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Cozy Kailua-Kona Escape Near Pristine Beaches

Cozy Kailua-Kona Escape Near Pristine Beaches

1 bed 1 bath
PoolA/CWiFiBalcony
$109/night
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Kona Shores 219 Gorgeous Upgraded Top Floor Condo w/AC!

Kona Shores 219 Gorgeous Upgraded Top Floor Condo w/AC!

1 bath
PoolA/CWiFiBalcony
$116/night
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Kona Shores#130 Beautifully Remodeled Ground Floor Condo w/AC!

Kona Shores#130 Beautifully Remodeled Ground Floor Condo w/AC!

1 bed 1 bath
PoolA/CWiFiBalcony
$121/night
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CASA DE EMDEKO, Jewel of the Sea Waterfront Property, AC and Full Washer/Dryer

CASA DE EMDEKO, Jewel of the Sea Waterfront Property, AC and Full Washer/Dryer

1 bed 1 bath
PoolA/CWiFiBalcony
$154/night
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Chic oceanfront condo with full ocean views, pool & hot tub

Chic oceanfront condo with full ocean views, pool & hot tub

1 bed 2 baths
PoolA/CWiFiBalcony
$213/night
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Wonderful 2nd Floor Alii Villa Condo. Remodeled Flooring, Counters, Bath & Lanai

Wonderful 2nd Floor Alii Villa Condo. Remodeled Flooring, Counters, Bath & Lanai

1 bed
PoolA/CWiFiBalcony
$140/night
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A Must See! Beautifully renovated Direct Ocean Front condo. 1 Bedroom, 1 Bath.

A Must See! Beautifully renovated Direct Ocean Front condo. 1 Bedroom, 1 Bath.

1 bed 1 bath
PoolA/CWiFiBalcony
$175/night
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Breezy oceanfront condo with pool & hot tub - near shopping, dining & beaches

Breezy oceanfront condo with pool & hot tub - near shopping, dining & beaches

1 bed 2 baths
PoolA/CWiFiBalcony
$199/night
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🏖️Top Floor | Nice Ocean View | Close to Town | vrKCV🏖️

🏖️Top Floor | Nice Ocean View | Close to Town | vrKCV🏖️

1 bed 1 bath
PoolA/CWiFiBalcony
$135/night
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***NICE OCEAN VIEWS FROM LANAI AND LIVING ROOM* GREAT LOCATION***

***NICE OCEAN VIEWS FROM LANAI AND LIVING ROOM* GREAT LOCATION***

1 bed 1 bath
PoolA/CWiFiBalcony
$131/night
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Remodeled oceanfront escape with ocean-view pool/hot tub - close to restaurants

Remodeled oceanfront escape with ocean-view pool/hot tub - close to restaurants

1 bed 1 bath
PoolA/CWiFiBalcony
$248/night
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🌴Kona Bali Kai #305 is absolute oceanfront. Upgraded and overlooking Banyans surf spot.🌴

🌴Kona Bali Kai #305 is absolute oceanfront. Upgraded and overlooking Banyans surf spot.🌴

2 beds 2 baths
PoolA/CWiFiBalcony
$246/night
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Banyan Tree 200 - oceanfront condo with wraparound lanai

Banyan Tree 200 - oceanfront condo with wraparound lanai

2 beds 2 baths
PoolA/CWiFiBalcony
$339/night
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Fabulous Custom 3rd Floor Oceanfront Condo/Kona Bali Kai #304

Fabulous Custom 3rd Floor Oceanfront Condo/Kona Bali Kai #304

2 beds 2 baths
PoolA/CWiFiBalcony
$316/night
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Your Hawaiian vacation starts here!

Your Hawaiian vacation starts here!

1 bath
PoolA/CWiFiBalcony
$118/night
View Details → Book on VRBO
Kona Isle E-24 Direct Ocean front coner unit 2nd Floor,Sleeps 4, Spectacular

Kona Isle E-24 Direct Ocean front coner unit 2nd Floor,Sleeps 4, Spectacular

1 bed 1 bath
PoolA/CWiFiBalcony
$136/night
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Oceanfront Penthouse, As Close As You Can Stay To Ocean, Stunning Views, A/C!

Oceanfront Penthouse, As Close As You Can Stay To Ocean, Stunning Views, A/C!

2 beds 2 baths
PoolA/CWiFiBalcony
$406/night
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Casa De Emdeko 210- 1/1 DELUXE SIZED UNIT,REMODELED, AC, OCEAN VIEW, ELEVATOR

Casa De Emdeko 210- 1/1 DELUXE SIZED UNIT,REMODELED, AC, OCEAN VIEW, ELEVATOR

1 bed 1 bath
PoolA/CWiFiBalcony
$156/night
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🏖️Fabulous Ocean View | Sunset | Lanai Dining | Beautifully Upgraded | vrKCV

🏖️Fabulous Ocean View | Sunset | Lanai Dining | Beautifully Upgraded | vrKCV

1 bed 1 bath
PoolA/CWiFiBalcony
$131/night
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Second-floor, ocean view condo in oceanfront complex with lanai, AC & 2 pools

Second-floor, ocean view condo in oceanfront complex with lanai, AC & 2 pools

1 bed 1 bath
PoolA/CWiFiBalcony
$191/night
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Easy Big Island Living! Ocean-Front Pool, Tranquil Lanai, Lava Rock Grill.

Easy Big Island Living! Ocean-Front Pool, Tranquil Lanai, Lava Rock Grill.

1 bath
PoolA/CWiFiBalcony
$124/night
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Oceanfront condo with ocean view, hot tub, pool, private lanai, & W/D

Oceanfront condo with ocean view, hot tub, pool, private lanai, & W/D

2 beds 2 baths
PoolA/CWiFiBalcony
$196/night
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Kona Oceanfront complex I Updated I AC I Heated Pool I Best Location

Kona Oceanfront complex I Updated I AC I Heated Pool I Best Location

1 bed 1 bath
PoolA/CWiFiBalcony
$180/night
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Oceanfront condo with lanai, full water view, hot tub & pool

Oceanfront condo with lanai, full water view, hot tub & pool

1 bed 2 baths
PoolA/CWiFiBalcony
$170/night
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Showing 48 of 1,374 properties

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