Home Vacation Home Rentals By Owner In Kailua Kona, HI

Showing 440 Of 559 Vacation Rentals
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Exceptional(36)

$897.4

/ Nightly
Private Vacation Home

️Oceanfront Kona Townhome w/ A/C | Walk to Magic Sands

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(98)

$899.5

/ Nightly
Private Vacation Home

Oceanfront Kona Beach House

Kailua-Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(11)

$899.55

/ Nightly
Private Vacation Home

Luxury 3BR Kona Dreams w/ Ocean Views, Private Pool, Central AC & Prime Location

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(6)

$901.83

/ Nightly
Private Vacation Home

My Kona Paradise

Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(26)

$908.11

/ Nightly
Private Vacation Home

️Private Pool + 2 Suites | Walk to Pickleball

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(5)

$914.55

/ Nightly
Private Vacation Home

LUXURY/MOST POPULAR SNORKELING & SURFING BEACH ! Turtles!

Kailua-Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(14)

$918.86

/ Nightly
Private Vacation Home

Ho'okipa Hale in Kona: Wade Pool, Pacific Views & Stunning Sunsets

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(122)

$926.97

/ Nightly
Private Vacation Home

Kailua- Kona, Hi Vacation Rental Home With Pool

Kailua-Kona, Hawaii, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(85)

$927.97

/ Nightly
Private Vacation Home

️Great Ocean Views | Private Pool | WiFi | Expanded Lanai!

Kailua Kona, Hawaii, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(29)

$928.41

/ Nightly
Private Vacation Home

LAST MINUTE DISCOUNT SPECIAL! Central A/C Double Master Suite Home.

Kailua-Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(9)

$930.13

/ Nightly
Private Vacation Home

Blocks to Beach- Kailua Kona Group Villa- AC, Kitchens, WD, WIFI, BBQ, Local Fun

Kailua-Kona, Hawaii, United States

Bed 4

Bed

Bath 2

Bath

Sleep 11

Sleeps
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Exceptional(94)

$931.84

/ Nightly
Private Vacation Home

Ironman Special, Ocean-front sanctuary in Kailua Kona, 2-bedroom retreat with luxury amenities.

Kailua-Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(25)

$938.24

/ Nightly
Private Vacation Home

Kailua View Estates - Private Home Retreat w/ Lanai, Hot Tub, Laundry, BBQ, A/C

Kailua-Kona, Hawaii, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(77)

$939.48

/ Nightly
Private Vacation Home

Stunning Luxury Estate Superb Private Lanai & Breathtaking Sunsets! Keauhou Luxury Estate

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(36)

$940.56

/ Nightly
Private Vacation Home

Piece of heaven ! Enjoy the sounds of ocean and beautiful sunsets. Explore the nearby beach.

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(82)

$940.94

/ Nightly
Private Vacation Home

Private Home with Pool in Secure Gated Community on Kona Country Club Fairway

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(76)

$943.6

/ Nightly
Private Vacation Home

Kona Bay Oceanfront Home close to Town & Shopping

Kailua Kona, Hawaii, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(61)

$944.84

/ Nightly
Private Vacation Home

Unique Oceanfront Home in Enclosed Area

Kailua, Hawaii, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(104)

$945.37

/ Nightly
Private Vacation Home

️Kona Ocean View Home w/ Pool + Lanai | Kahakai Estates

Kailua Kona, Hawaii, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(102)

$954.38

/ Nightly
Private Vacation Home

VERY PRIVATE, expansive ocean VIEWS, close to BEST BEACH

Kailua-Kona, Hawaii, United States

Bed 5

Bed

Bath 4

Bath

Sleep 18

Sleeps
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Home Most popular vacation rentals in Kailua Kona

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Exceptional(102)

$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(102)

$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(102)

$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(102)

$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(102)

$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(102)

$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(102)

$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(102)

$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(102)

$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(102)

$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