Home Vacation Home Rentals By Owner In Kailua Kona, HI

Showing 20 Of 559 Vacation Rentals
Slider Thumb
Exceptional(1)

$3745.16

/ Nightly
Private Vacation Home

Exclusive 4BR Ke Alaula Estate 124 at Hualalai – Infinity Pool & Ocean Views

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb

$4553.23

/ Nightly
Private Vacation Home

Hualalai Pakui Street Estate on the 14th Green.

Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(2)

$4300.63

/ Nightly
Private Vacation Home

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

Kailua Kona, Hawaii, United States

Bed 5

Bed

Bath 5

Bath

Sleep 10

Sleeps
Slider Thumb

$4265.94

/ Nightly
Private Vacation Home

Oceanfront Retreat w/Sunset Views & Paddleboards

Kailua-Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(5)

$4210.09

/ Nightly
Private Vacation Home

Elevated 4BR Kahikole Estate 218 at Hualalai – Indoor-Outdoor Living & Views

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(76)

$4202.83

/ Nightly
Private Vacation Home

Experience luxury near golf courses, 4 mins to Four Seasons Resort

Kailua-Kona, Hawaii, United States

Bed 4

Bed

Bath 1

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(17)

$4155.4

/ Nightly
Private Vacation Home

Hualalai Resort Remodeled Villa w/ Pool, Spa & Views

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(43)

$4141.85

/ Nightly
Private Vacation Home

Private Kona Oceanfront Estate · Infinity Pool & Spa

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(17)

$4117.49

/ Nightly
Private Vacation Home

OCEAN FRONT PRIVATE RESIDENCE AT KEAUHOU BAY WITH POOL & PRIVATE DOCK

Kailua, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
Slider Thumb

$4098.68

/ Nightly
Private Vacation Home

Experience luxury at Hale Alii Honu Kai in Kailua Kona—3BR, pool, and space for 9.

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 9

Sleeps
Slider Thumb

$4024.18

/ Nightly
Private Vacation Home

Hualalai 4 bedroom 5 bathroom privacy, central to all Four Seasons amenities

Kailua-Kona, Hawaii, United States

Bed 4

Bed

Bath 5

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(2)

$3910.8

/ Nightly
Private Vacation Home

Luxury 5BR Kulanakauhale Estate 3558 at Hualalai – Infinity Pool & Ocean Views

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb

$3863.69

/ Nightly
Private Vacation Home

Kaulu Villa 111A – Just Updated! | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb

$3854.9

/ Nightly
Private Vacation Home

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

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(2)

$3835.55

/ Nightly
Private Vacation Home

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

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(7)

$3822.23

/ Nightly
Private Vacation Home

Exquisite 4BR Hainoa Estate 122 at Hualalai – Ocean Views & Infinity-Edge Pool

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(82)

$3778.36

/ Nightly
Private Vacation Home

FOUR SEASONS HUALALAI HALE”, RESORT ACCESS, OCEAN-VIEW, 1.5-ACRES, 7 DAY RATE!

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb

$3296.37

/ Nightly
Private Vacation Home

Ke Alaula Villa 228A – Prime Ocean View | Onsite Staff & Daily Housekeeping

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(7)

$3275.46

/ Nightly
Private Vacation Home

Hualalai 72-139 Pakui~Ocean View~pool~spa

Hualalai Resort, Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(21)

$3239.47

/ Nightly
Private Vacation Home

Luxury Oceanfront Estate

Kailua-Kona, Hawaii, United States

Bed 5

Bed

Bath 6

Bath

Sleep 12

Sleeps
map-loader

Home Rent a place that suits your needs

Hotel resort

Hotel resort

View 62 Hotel resort
Condo

Condo

View 1915 Condo
Private vacation home

Private vacation home

View 557 Private vacation home
Villa

Villa

View 48 Villa

Home Most popular vacation rentals in Kailua Kona

Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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
Slider Thumb
Exceptional(21)

$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