Home Vacation Home Rentals By Owner In Kailua Kona, HI

Showing 120 Of 559 Vacation Rentals
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$5145.12

/ Nightly
Private Vacation Home

Golf Villa 5102 - Best Ocean Views | Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$5145.12

/ Nightly
Private Vacation Home

Kahikole 2 – Tranquil & Serene | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$5481.44

/ Nightly
Private Vacation Home

Golf Villa 2102 – Contemporary & Ocean Views | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$5492.1

/ Nightly
Private Vacation Home

Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$5564.51

/ Nightly
Private Vacation Home

Hualalai Puka Pa Private Estate With 2 Golf Carts

Hawaii County, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(8)

$5602.46

/ Nightly
Private Vacation Home

Hualalai Golf lovers delight Lau'eki

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(1)

$5767.2

/ Nightly
Private Vacation Home

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

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 1

Bath

Sleep 8

Sleeps
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$6143.4

/ Nightly
Private Vacation Home

Kulanakauhale 11 – Elegant & Modern | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(5)

$6206.12

/ Nightly
Private Vacation Home

Gorgeous Estate Home at Hualalai Resort -Ocean and Golf Course Views- 3 Golf Carts

Kailua Kona, Hawaii, United States

Bed 5

Bed

Sleep 8

Sleeps
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$6385.8

/ Nightly
Private Vacation Home

Exquisite 4BR Ka 'Ulu Estate 102A at Hualalai – Infinity Pool & Golf Views

Kailua-Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(7)

$6572.06

/ Nightly
Private Vacation Home

Luxurious & Serene Home w/ Private Pool & Spa

Kailua-Kona, Hawaii, United States

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(3)

$6988.03

/ Nightly
Private Vacation Home

Hualalai Discover Your Sanctuary at Waiulu

Kailua-Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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$7531.9

/ Nightly
Private Vacation Home

Hainoa 10 – Commanding Ocean Views | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$7654.39

/ Nightly
Private Vacation Home

Waiulu Estate 152B – Ocean View & Fully Renovated | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(6)

$7696.05

/ Nightly
Private Vacation Home

Experience luxury at Hale Kahikole in Kailua Kona, featuring 5 bedrooms and a private pool.

Kailua Kona, Hawaii, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(3)

$7715.94

/ Nightly
Private Vacation Home

Two Private hosted Oceanfront Homes conveniently located in Kailua Kona, Hawaii

Kailua Kona, Hawaii, United States

Bed 13

Bed

Bath 9

Bath

Sleep 34

Sleeps
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$7967.69

/ Nightly
Private Vacation Home

Pu’ukole 28 – Deluxe Ocean View | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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$8021.09

/ Nightly
Private Vacation Home

Kulanakauhale 7 – Deluxe Ocean View | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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$8035.21

/ Nightly
Private Vacation Home

Spacious 8BR w/Ocean Views, Sleeps 16 with AC in fabulous Kailua-Kona

Kailua-Kona, Hawaii, United States

Bed 8

Bed

Bath 7

Bath

Sleep 16

Sleeps
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Exceptional(3)

$8286.97

/ Nightly
Private Vacation Home

Unmatched location Four Seasons Hualalai 5BR/5BA Ocean Estate 6500sqft 3/4 acre

Kailua-Kona, Hawaii, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Home Most popular vacation rentals in Kailua Kona

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Exceptional(3)

$1924.18

/ Nightly
Private vacation home

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

Kailua-Kona, Hawaii, United States

Bed 6

Bed

Bath 5

Bath

Sleep 18

Sleeps
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Exceptional(3)

$1980.24

/ Nightly
Private vacation home

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

Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$1973.10

/ Nightly
Condo

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

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(3)

$1972.45

/ Nightly
Private vacation home

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

Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$1957.89

/ Nightly
Private vacation home

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

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(3)

$1953.22

/ Nightly
Villa

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

Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$1826.57

/ Nightly
Villa

Beautiful 2-BR Villa at Four Seasons Hualalai

Kailua Kona, Hawaii, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(3)

$1789.55

/ Nightly
Private vacation home

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

Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(3)

$1824.43

/ Nightly
Villa

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

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(3)

$1982.66

/ Nightly
Private vacation home

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

Kailua Kona, Hawaii, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps

Most Popular Cities in Hawaii