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Island of Hawaii Vacation Rentals & Homes with Swimming Pool - 233 Rentals Available.

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233 Vacation rentals

Filters applied: Swimming pool

(1)

1 / 17

Kailua-Kona Condo

  • 1
  • 2
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Air conditioning

$162.00

Excellent (1 reviews)

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from $162.00 / night

(2)

1 / 24

Waikoloa Townhouse

  • 3
  • 6
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
“My wife and our 3 kids loved staying here for 9 days. Everything you needed in the kitchen if you plan on staying in and making meals. Surfboards, boogie boards, coolers, chairs, wagon to transport for your day at the beach. Spacious home, very clean...”
- Review left on 06/16/2017

$251.00

Excellent (2 reviews)

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from $251.00 / night

(1)

1 / 36

Kailua-Kona House

  • 5
  • 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$599.00

Excellent (1 reviews)

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from $599.00 / night

(4)

1 / 18

Kailua-Kona Manor house

  • 2
  • 7
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$200.00

Excellent (4 reviews)

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from $200.00 / night

1 / 33

Hilo Condo

  • 1
  • 2
  • 30 nights min
  • Nearest beach 0.01 mi
  • Swimming pool

$80.00

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from $80.00 / night

1 / 15

Keaau House

  • 4
  • 8
  • 7 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Ask about children

$155.00

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from $155.00 / night

(10)

1 / 13

Kailua-Kona Condo

  • 1
  • 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“This condo is truly on the ocean. The surf drowns out any other sound and sings you to sleep. There is something magical about that! We ate in almost exclusively and the kitchen had everything we needed to prepare lovely meals. I mean, what...”
- Review left on 02/28/2018

$136.00

Excellent (10 reviews)

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from $136.00 / night

(9)

1 / 52

Waikoloa Townhouse

  • 2
  • 4
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

$236.00

Excellent (9 reviews)

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from $236.00 / night

(3)

1 / 22

Kohala Coast Apartment

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$496.00

Excellent (3 reviews)

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from $496.00 / night

(10)

1 / 105

Kailua-Kona House

  • 6
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Swimming pool

$449.00

Very Good (10 reviews)

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from $449.00 / night

(3)

1 / 23

Kailua-Kona House

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“8 of us came to Kona on a family vacation and the home was perfect. Located very conveniently to everything in Kona, but nestled in a quiet neighborhood we couldn't not have enjoyed it more. Beautiful, well-appointed home, comfortable and spacious....”
- Review left on 06/24/2016

$565.00

Excellent (3 reviews)

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from $565.00 / night

(1)

1 / 25

Kailua-Kona Condo

  • 1
  • 4
  • 6 nights min
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$170.00

Excellent (1 reviews)

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from $170.00 / night

(12)

1 / 15

Kailua-Kona House

  • 4
  • 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The Hibiscus Pool Home was an awesome fit for our vacation in Kona. We were close to the beaches, to town, and family was nearby. The kids loved the pool and all the beach gear was much appreciated. The sunsets from the lanai were stunning every...”
- Review left on 02/26/2016

$215.00

Excellent (12 reviews)

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from $215.00 / night

(8)

1 / 30

Kailua-Kona Condo

  • 1
  • 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“Being at the Sea cliff is my first experience at a resort, on The Big Island of Hawaii. I walked back and forth to Kailua, while getting to know the area. Loved the markets, shopping spots and the helpful local Hawaiian people. The entertainment...”
- Review left on 10/14/2016

$119.00

Very Good (8 reviews)

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from $119.00 / night

(2)

1 / 39

Kailua-Kona House

  • 5
  • 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$399.00

Excellent (2 reviews)

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from $399.00 / night

1 / 11

Kailua-Kona House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly

$249.00

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from $249.00 / night

1 / 45

Kailua-Kona House

  • 4
  • 15
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Swimming pool

$599.00

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from $599.00 / night

(1)

1 / 50

Kailua-Kona House

  • 6
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

$599.00

Excellent (1 reviews)

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from $599.00 / night

(5)

1 / 8

Kailua-Kona House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
“You can not find a better location for your stay on the big island. Large private home with a backyard you would never want to leave. We picked fresh bananas from the tree out back! Great home for people of all ages and large families. Fabulous floor...”
- Review left on 02/14/2017

$350.00

Excellent (5 reviews)

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from $350.00 / night

1 / 19

Kailua-Kona House

  • 3
  • 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

$199.00

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from $199.00 / night

1 / 13

Kailua-Kona Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children

$140.00

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from $140.00 / night

1 / 25

Kailua-Kona House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly

$355.00

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from $355.00 / night

(1)

1 / 24

Kailua-Kona House

  • 5
  • 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,185.00

Excellent (1 reviews)

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from $1,185.00 / night

1 / 64

Kailua-Kona House

  • 5
  • 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$499.00

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from $499.00 / night

1 / 25

Keauhou House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly

$465.00

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from $465.00 / night

(1)

1 / 12

Kailua-Kona Condo

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$159.00

Excellent (1 reviews)

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from $159.00 / night

1 / 28

Kailua-Kona House

  • 10
  • 20
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,765.00

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from $1,765.00 / night

(26)

Certificate of Excellence

1 / 19

Kailua-Kona Condo

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

Certificate of Excellence

“Kona Bali Kai #220 was exactly as it was pictured online. We enjoyed our stay here very much. This is the 4th time we've stayed at the Kona Bali Kai (every time in a different unit). We love being able to fall asleep to the sound of the ocean...”
- Review left on 04/01/2018

$190.00

Excellent (26 reviews)

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from $190.00 / night

1 / 35

Hilo Condo

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$122.00

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from $122.00 / night

1 / 23

Kailua-Kona House

  • 3
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$505.00

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from $505.00 / night

1 / 19

Waikoloa House

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$575.00

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from $575.00 / night

1 / 40

Kailua-Kona House

  • 7
  • 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

$966.00

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from $966.00 / night

1 / 19

Pahoa House

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly

$299.00

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from $299.00 / night

(1)

1 / 25

Kailua-Kona House

  • 5
  • 22
  • 7 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Ask about children
“We had 19 family members and we found plenty of space in this house to not feel cramped at all. We were creative in our sleeping arrangements, but we all found places (some more comfortable than others!) Great pool, laundry machines, tons of outdoor...”
- Review left on 12/01/2016

$900.00

Very Good (1 reviews)

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from $900.00 / night

1 / 20

Kailua-Kona House

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Ask about children

$859.00

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from $859.00 / night

1 / 24

Kailua-Kona Villa

  • 4
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$589.00

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from $589.00 / night

1 / 23

Kailua-Kona Manor house

  • 4
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$1,575.00

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from $1,575.00 / night

(1)

1 / 24

Kailua-Kona House

  • 4
  • 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$520.00

Excellent (1 reviews)

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from $520.00 / night

1 / 41

Kailua-Kona House

  • 10
  • 23
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

$1,750.00

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from $1,750.00 / night

1 / 36

Kailua-Kona Apartment

  • 10
  • 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,245.00

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from $1,245.00 / night