Home Vacation Rentals By Owner In Kailua Kona, HI

Showing 2760 Of 2866 Vacation Rentals
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$1670.45

/ Nightly
Condo

Two Units in Kona Makai- Oceanview, Gated Complex, 5 Bedrooms in total, w/ AC's.

Kailua-Kona, Hawaii, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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$695.82

/ Nightly
Condo

Oceanfront 4BR for 12 in Kailua-Kona!

Kailua-Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(4)

$271.95

/ Nightly
Condo

Serene Ocean View Retreat in Keauhou Palena

Kailua Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(12)

$285.39

/ Nightly
Apartment

Oceanview Balinese Oasis in the Heart of Kona Town

Kailua-Kona, Hawaii, United States

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(14)

$257.66

/ Nightly
Private Vacation Home

the cozy large studio 30+days stays

Kailua-Kona, Hawaii, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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$1001.86

/ Nightly
Condo

Kailua Kona Hawaii 2 Bedroom Sleeps 6

Kailua-Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$253

/ Nightly
Condo

Alii Cove HH21 Beautiful Top Floor Spacious 3 Bedroom with AC

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(18)

$1282.25

/ Nightly
Private Vacation Home

Holua Moana Hale: Spectacular Oceanfront Home with Pool, Spa and Putting Green

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(126)

$389.65

/ Nightly
Condo

Surf and Stay Hale | Absolute Oceanfront Getaway | Upgraded | Overlooking Banyans surf spot

Kailua Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(21)

$548.5

/ Nightly
Condo

WOW! GORGEOUS DIRECT OCEANFRONT Kona Reef Condo! TWO A/C UNITS, STUNNING VIEWS!

Kailua-Kona, Hawaii, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(45)

$588.94

/ Nightly
Condo

Gorgeous Oceanfront 2 Bed/2 Bath Condo with A/C at Kona Bali Kai Resort Unit 306

Kailua-Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(48)

$274.48

/ Nightly
Condo

Kona Condo: Steps to Ocean, Surf, Pool, Hot Tub

Kailua-Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(27)

$747.11

/ Nightly
Private Vacation Home

Hale A Kai: Big Island Home w/partial Ocean view, AC &WiFi

Kailua Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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$1679.37

/ Nightly
Private Vacation Home

Kailua-Kona Hawaii 3 Bedroom House Sleeps 6

Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$457.35

/ Nightly
Condo

Charming 2-bedroom condo with AC in serene Kailua-Kona

Kailua-Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$347.62

/ Nightly
Condo

New Listing, Kanaloa, Golf Course Views, AC

Kailua-Kona, Hawaii, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(5)

$570.54

/ Nightly
Condo

Kksr#3302 Hale Kania Kai, Direct Oceanfront Top Floor with Ac

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(2)

$539.14

/ Nightly
Condo

Amazing, Close to Ironman Start: Kona Islander Inn

Kailua-Kona, Hawaii, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$298.16

/ Nightly
Condo

Beachside Oasis on Ironman 2025 Swim & Run Route

Kailua Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(55)

$491.87

/ Nightly
Condo

Kona Plaza#212: Kona Hawaii Beach Vacation Rental: AC, Pool, Modern, WiFi!

Kailua Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Home Most popular vacation rentals in Kailua Kona

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Exceptional(55)

$1857.83

/ Nightly
Villa

Sky Villa Estate Luxury Gated Retreat with Amazing Ocean View

Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(55)

$1992.35

/ 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(55)

$1958.10

/ 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(55)

$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(55)

$1933.80

/ 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(55)

$1913.71

/ 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(55)

$1826.36

/ 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(55)

$1764.48

/ Nightly
Villa

Hualalai Fairway Villa 116C - NEWLY Renovated, 2 golf carts, BEST LOCATION.

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(55)

$1801.52

/ 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(55)

$1993.64

/ 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

Most Popular Cities in Hawaii