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Island of Hawaii Vacation Rentals & Homes with Swimming Pool - 247 Rentals Available.

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247 Vacation rentals

Filters applied: Swimming pool

(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

(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

(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 / 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

(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)

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

(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

(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

(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

(5)

1 / 20

Kailua-Kona House

  • 4
  • 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The pictures do not do this rental justice. We walked in and were in awe. Speechless. It is beautiful inside. Extremely spacious. The landscaping is luscious and gorgeous. Very private. An added plus is the private pool which we used at least two to...”
- Review left on 10/10/2015

$295.00

Excellent (5 reviews)

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from $295.00 / 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

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

(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

(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

(1)

1 / 25

Kailua-Kona Condo

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

$170.00

Excellent (1 reviews)

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from $170.00 / night

(1)

1 / 24

Kailua-Kona House

  • 5
  • 18
  • 7 nights min
  • Swimming pool
  • Child friendly

$887.00

Excellent (1 reviews)

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from $887.00 / 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

(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 / 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 / 24

Kailua-Kona House

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$986.00

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from $986.00 / night

(20)

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

$205.00

Excellent (20 reviews)

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from $205.00 / 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 / 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

$875.00

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from $875.00 / 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 / 40

Kailua-Kona House

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

$1,065.00

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from $1,065.00 / 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)

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

(8)

1 / 12

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

$136.00

Excellent (8 reviews)

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from $136.00 / 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

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)

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 / 12

Kailua-Kona House

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

$620.00

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from $620.00 / 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 / 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

Kailua-Kona House

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

$465.00

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from $465.00 / night

1 / 11

Kailua-Kona Apartment

  • 1
  • 4
  • 7 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Ask about children

$200.00

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from $200.00 / 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 / 20

Kailua-Kona House

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

$858.00

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from $858.00 / 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