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Island of Hawaii Vacation Rentals & Homes with Swimming Pool - 215 Rentals Available.

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215 Vacation rentals

Filters applied: Swimming pool

1 / 27

Kailua-Kona House

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

$199

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from $199 / night

(8)

1 / 105

Kailua-Kona House

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

$395

Excellent (8 reviews)

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from $395 / night

1 / 26

Kailua-Kona House

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

$499

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from $499 / night

(12)

1 / 12

Kailua-Kona Condo

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This was my 4th reservations with Rita at Kona Islander Inn. There was a little rearranging so my boyfriend (his first stay) and I ended up staying in another condo than previously thought which was pleasant but not Rita's room. It all worked out ( I...”
- Review left on 02/09/2017

$79

Very Good (12 reviews)

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from $79 / night

(19)

1 / 19

Kailua-Kona Condo

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“Enjoyed the view of the ocean and wildlife while staying at this condo. The amenities were more than we expected! Boogie boards, snorkeling equipment, cheese slicer, and a bedroom right off the deck so you could leave the doors open and hear the...”
- Review left on 03/12/2017

$183

Excellent (19 reviews)

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from $183 / night

(2)

1 / 16

Kailua-Kona House

  • 5
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The property was beautiful. We had lots of beach/fun in the sun equipment for us to use including towels and boggie boards. We did not have a view of the ocean which was implied in the ad but we had easy beach access across the street in both...”
- Review left on 03/13/2017

$509

Very Good (2 reviews)

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from $509 / night

1 / 25

Kailua-Kona House

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $685 / night

(4)

1 / 14

Pahala Condo

  • 1
  • 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“This was our first visit to Sea Mountain. My parents have been coming for decades every Friday. We stayed in #65. the unit (Studio) was very clean and well stocked with all the linens, dishware etc. we would need for our 5 night stay. The location...”
- Review left on 02/18/2015

$75

Very Good (4 reviews)

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from $75 / night

(7)

1 / 13

Kailua-Kona Condo

  • 1
  • 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“This is a beautiful spot to stay at. We watched the sunset from the lanai and the white sands beach across the street. This is a nice and quiet location. The condo was perfect and had everything we needed. To be able to listen to the waves crash...”
- Review left on 03/13/2017

$130

Excellent (7 reviews)

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from $130 / night

1 / 17

Kailua-Kona House

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children

from $600 / night

(1)

1 / 24

Kailua-Kona House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children

$560

Excellent (1 reviews)

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from $560 / night

(1)

1 / 12

Kailua-Kona Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$159

Excellent (1 reviews)

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from $159 / night

1 / 34

Kailua-Kona House

  • 4
  • 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Swimming pool

$699

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from $699 / night

1 / 11

Kailua-Kona House

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

$249

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from $249 / night

(1)

1 / 23

Kailua-Kona Villa

  • 6
  • 18
  • Min stay varies
  • Swimming pool
  • Child friendly
“Family from Australia, Chicago and Vermont -17 in all- spent 6 days in this truly stunning villa. This very spacious residence is beautifully decorated and very well equipped. The pool was happily occupied by young and old alike most of the day....”
- Review left on 07/10/2016

$746

Excellent (1 reviews)

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from $746 / night

(1)

1 / 24

Kailua-Kona House

  • 5
  • 18
  • 7 nights min
  • Swimming pool
  • Ask about children

$845

Excellent (1 reviews)

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from $845 / night

(1)

1 / 24

Kailua-Kona House

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

$385

Excellent (1 reviews)

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from $385 / night

1 / 13

Kailua-Kona Condo

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

$140

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from $140 / night

1 / 14

Holualoa House

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Ask about children

from $179 / night

(1)

1 / 12

Kailua-Kona Villa

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children

$800

Excellent (1 reviews)

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from $800 / night

(6)

1 / 42

Holualoa House

  • 7
  • 16
  • Min stay varies
  • Swimming pool
  • Child friendly
“We stayed here for our wedding and had the whole wedding party stay in the house. Everything was awesome loved it. Close to the beach and shopping. The contact was more than helpful and very nice. Will be telling everyone we know and visiting the...”
- Review left on 09/10/2015

$650

Excellent (6 reviews)

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from $650 / night

1 / 12

Kailua-Kona House

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly

from $575 / night

1 / 36

Kailua-Kona Apartment

  • 10
  • 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1150

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from $1150 / night

(1)

1 / 15

Waikoloa Condo

  • 2
  • 4
  • 5 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Ask about children
“This is a nice, quiet condo overlooking the golf course and within walking distance to the public beach. Since we eat in a lot, the well stocked kitchen was perfect. We walked across the street to the Hilton to watch the dolphins and walked to the...”
- Review left on 03/03/2016

$149

Excellent (1 reviews)

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from $149 / night

1 / 28

Kailua-Kona House

  • 10
  • 20
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1375

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from $1375 / night

(2)

1 / 39

Kailua-Kona House

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

$299

Excellent (2 reviews)

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from $299 / night

(9)

1 / 97

Kailua-Kona Condo

  • 2
  • 6
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
“We stayed with our two kids as the last stop in a month of travel - this was a wonderful, luxurious way to finish our trip! The kids loved snorkeling across the street at Kahaluu beach and playing in the pool, and the boogie boards and beach chairs...”
- Review left on 07/31/2016

$186

Excellent (9 reviews)

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from $186 / night

(3)

1 / 23

Kailua-Kona House

  • 4
  • 10
  • 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

$595

Excellent (3 reviews)

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from $595 / night

(1)

1 / 21

Kailua-Kona House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1500

Excellent (1 reviews)

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from $1500 / night

1 / 23

Kailua-Kona House

  • 3
  • 8
  • 5 nights min
  • Swimming pool
  • Ask about children

from $411 / night

(5)

1 / 51

Kailua-Kona House

  • 5
  • 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My family and I really enjoyed the stay at this property. The setting and the facilities are perfect for an active family. The location and weather was perfect. We would not hesitate to recommend this property to our friends and family. We would also...”
- Review left on 10/17/2016

$395

Very Good (5 reviews)

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from $395 / night

(1)

1 / 52

Kailua-Kona House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“the neighbourhood is quiet and very peaceful especially at night . watching the sun set in the evening while sitting on the pool deck is a pleasant way to end the day . the view is unobstructed and you can tell what day of the week it is by observing...”
- Review left on 05/17/2016

$990

Excellent (1 reviews)

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from $990 / night

(1)

1 / 25

Kailua-Kona House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children

$1100

Excellent (1 reviews)

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from $1100 / night

1 / 15

Hilo Condo

  • 1
  • 2
  • 1 night min
  • Nearest beach 0.01 mi
  • Swimming pool

$80

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from $80 / night

1 / 19

Waikoloa Condo

  • 2
  • 4
  • Min stay varies
  • Nearest beach 0.5 mi
  • Swimming pool
  • Ask about children

from $155 / night

1 / 46

Kailua-Kona House

  • 5
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$299

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from $299 / night

(9)

1 / 41

Waikoloa Townhouse

  • 2
  • 4
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly

$229

Excellent (9 reviews)

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from $229 / night

1 / 20

Kailua-Kona House

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

from $815 / night

1 / 29

Kailua-Kona Villa

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children

from $800 / night

(2)

1 / 15

Waikoloa Condo

  • 1
  • 2
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Ask about children

$149

Excellent (2 reviews)

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from $149 / night