Vacation Home Rentals By Owner In Kailua Kona, HI

Showing 20 Of 557 Vacation Rentals

Exceptional(56)

$2600.64

/ Nightly

Private Vacation Home

️Gorgeous Ocean Front Estate | Gated Community | Walk to Town

Kailua Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(51)

$2015.95

/ Nightly

Private Vacation Home

Stunning Ocean Front Home

Kailua-Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(3)

$6988.03

/ Nightly

Private Vacation Home

Hualalai Discover Your Sanctuary at Waiulu

Kailua-Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(7)

$6572.06

/ Nightly

Private Vacation Home

Luxurious & Serene Home w/ Private Pool & Spa

Kailua-Kona, Hawaii, United States

Bath

Sleeps

Exceptional(1)

$5767.2

/ Nightly

Private Vacation Home

Hualalai private 4 bedroom home with 2 golf carts & Ocean View

Kailua Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(8)

$5602.46

/ Nightly

Private Vacation Home

Hualalai Golf lovers delight Lau'eki

Kailua Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(3)

$2286.75

/ Nightly

Private Vacation Home

★★Across street from Magic Sand Beach private Pool/SPA/AC 5 minutes to downtown⚡

Kailua-Kona, Hawaii, United States

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Bath

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Exceptional(5)

$2344.71

/ Nightly

Private Vacation Home

Big home across the street from the beach, right at the golf course Pool/Spa/AC

Kailua-Kona, Hawaii, United States

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Bath

Sleeps

$5145.12

/ Nightly

Private Vacation Home

Golf Villa 5102 - Best Ocean Views | Daily Housekeeping

Kailua Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(99)

$2409.09

/ Nightly

Private Vacation Home

Hale Pua: Private Oceanfront Luxury Home w/Pool, Spa, AC & Lanai - Relax & Enjoy

Kailua Kona, Hawaii, United States

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Bath

Sleeps

$4772.43

/ Nightly

Private Vacation Home

Fabulous Kona 11 bedrooms for 34 with pool and hot tub!

Kahaluu-Keauhou, Hawaii, United States

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Bath

Sleeps

Exceptional(2)

$4300.63

/ Nightly

Private Vacation Home

Premier 5BR Hualalai Estate—Infinity Pool, 2 Golf Carts, Ocean Vistas

Kailua Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(116)

$2504

/ Nightly

Private Vacation Home

Dolphin House Oceanfront Estate

Kailua Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(28)

$2507.05

/ Nightly

Private Vacation Home

Ohana Retreat - The Real Hawaiian Experience

Kailua-Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(1)

$2532.96

/ Nightly

Private Vacation Home

Waiulu Villa 119A – Bright & Updated | Includes Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

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Bath

Sleeps

$3341.82

/ Nightly

Private Vacation Home

Waiulu Villa 125B – Spacious Golf View | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

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Bath

Sleeps

$3854.9

/ Nightly

Private Vacation Home

Kaulu Villa 129D – Updated & Modern Island Villa | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

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Bath

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Exceptional(2)

$3835.55

/ Nightly

Private Vacation Home

Exclusive 4BR Hainoa Estate 102 at Hualalai – Infinity Pool & Ocean Views

Kailua Kona, Hawaii, United States

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Bath

Sleeps

Exceptional(36)

$3308.04

/ Nightly

Private Vacation Home

Ali'i Point #9: Lavish Oceanfront Home w/Pool & Spa- Relax & Watch the Waves

Kailua Kona, Hawaii, United States

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Bath

Sleeps

$3355.43

/ Nightly

Private Vacation Home

Ke Alaula Villa 217A – Private Ocean Views | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

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Bath

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Rent a place that suits your needs

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Most popular vacation rentals in Kailua Kona

$1924.18

/ Nightly

Private vacation home

Magic Sands Oceanfront! Sleeps 18, 6-bedroom house in charming Kailua-Kona!

Kailua-Kona, Hawaii, United States

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Bath

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$1980.24

/ Nightly

Private vacation home

Hualalai Palm Villa 126A - Perfect location along the15th Fairway!

Kailua-Kona, Hawaii, United States

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Bath

Sleeps

$1973.10

/ Nightly

Condo

Beautiful Fairway Villa 104A at Hualalai w/Resort Pool, AC & Two Golf Carts

Kailua Kona, Hawaii, United States

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Bath

Sleeps

$1972.45

/ Nightly

Private vacation home

Exclusive area. Private, Ocean view, Putting Green, SW Infinity pool

Kona, Hawaii, United States

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Bath

Sleeps

$1957.89

/ Nightly

Private vacation home

HALE ONA LOA: DIRECT OCEANFRONT, GATED, ICONIC OCEANFRONT LUXURY WITH POOL

Kailua Kona, Hawaii, United States

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Bath

Sleeps

$1953.22

/ Nightly

Villa

Four Seasons Resort Hualalai at 4th Fairway, Ocean View with 2 Golf Carts

Kailua-Kona, Hawaii, United States

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Bath

Sleeps

$1826.57

/ Nightly

Villa

Beautiful 2-BR Villa at Four Seasons Hualalai

Kailua Kona, Hawaii, United States

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Bath

Sleeps

$1789.55

/ Nightly

Private vacation home

Fabulous Waterfront Modern Home on the Keiki Beach, Walking Distance to Town

Kailua-Kona, Hawaii, United States

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Bath

Sleeps

$1824.43

/ Nightly

Villa

Luxury 3BR Palm Villa 130B at Hualalai – Ocean Views & Renovated 2026

Kailua Kona, Hawaii, United States

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Bath

Sleeps

$1982.66

/ Nightly

Private vacation home

?️Kona Home w/ Pool, Ocean Views & A/C | Sleeps 10

Kailua Kona, Hawaii, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Kailua Kona, HI

$2600.64

$2015.95

$6988.03

$6572.06

$5767.2

$5602.46

$2286.75

$2344.71

$5145.12

$2409.09

$4772.43

$4300.63

$2504

$2507.05

$2532.96

$3341.82

$3854.9

$3835.55

$3308.04

$3355.43

Rent a place that suits your needs

Most popular vacation rentals in Kailua Kona

$1924.18

$1980.24

$1973.10

$1972.45

$1957.89

$1953.22

$1826.57

$1789.55

$1824.43

$1982.66

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