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Island of Hawaii Vacation Rentals & Homes with Swimming Pool - 249 Rentals Available.

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249 Vacation rentals

Filters applied: Swimming pool

1 / 17

Kailua-Kona Condo

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

$162.00

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from $162.00 / night

(1)

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

$250.00

Excellent (1 reviews)

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from $250.00 / 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

(9)

1 / 52

Waikoloa Townhouse

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

$235.00

Excellent (9 reviews)

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from $235.00 / 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

(5)

1 / 51

Kailua-Kona House

  • 5
  • 13
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“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

$395.00

Very Good (5 reviews)

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from $395.00 / 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

(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

(3)

1 / 22

Kohala Coast Apartment

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

$495.00

Excellent (3 reviews)

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from $495.00 / night

(6)

1 / 42

Holualoa House

  • 7
  • 16
  • Min stay varies
  • Nearest beach 13 mi
  • 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

$595.00

Excellent (6 reviews)

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from $595.00 / night

(9)

1 / 12

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 (9 reviews)

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from $136.00 / night

(25)

1 / 19

Kailua-Kona Condo

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

$205.00

Excellent (25 reviews)

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from $205.00 / 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

(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

(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)

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 / 23

Kailua-Kona Manor house

  • 4
  • 12
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$1,575.00

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from $1,575.00 / night

1 / 23

Kailua-Kona House

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

$505.00

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from $505.00 / night

(1)

1 / 21

Kailua-Kona House

  • 4
  • 8
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$2,200.00

Excellent (1 reviews)

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from $2,200.00 / 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

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 / 25

Kailua-Kona House

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

$355.00

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from $355.00 / 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 / 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 / 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 / 31

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 / 25

Kailua-Kona House

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

$889.00

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from $889.00 / night

(15)

1 / 12

Kailua-Kona Condo

  • 1
  • 4
  • 1 night min
  • 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

$99.00

Very Good (15 reviews)

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from $99.00 / 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

(11)

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

$205.00

Excellent (11 reviews)

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from $205.00 / 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

$625.00

Excellent (3 reviews)

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from $625.00 / night

1 / 41

Kailua-Kona House

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

$1,685.00

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from $1,685.00 / night

(1)

1 / 49

Kailua-Kona House

  • 3
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
“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

$1,000.00

Excellent (1 reviews)

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from $1,000.00 / night

(1)

1 / 24

Kailua-Kona House

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

$405.00

Excellent (1 reviews)

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from $405.00 / 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

1 / 25

Kailua-Kona House

  • 4
  • 10
  • 3 nights min
  • Swimming pool
  • Child friendly

$465.00

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from $465.00 / 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 / 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 / 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 / 12

Kailua-Kona House

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

$620.00

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from $620.00 / night