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Island of Hawaii Waterfront Vacation Rentals, Homes & More - 474 Rentals Available.

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474 Vacation rentals

Filters applied: Waterfront

1 / 26

Kailua-Kona House

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

$499

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from $499 / night

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

(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

(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)

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 / 30

Kealakekua Cottage

  • 1
  • 4
  • Min stay varies
  • Child friendly
  • Private garden

$90

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from $90 / night

(3)

1 / 22

Kohala Coast Apartment

  • 3
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$466

Excellent (3 reviews)

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from $466 / 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

(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

(74)

1 / 10

Volcano House

  • 4
  • 8
  • 2 nights min
  • Child friendly
“Ohana House is in a great location for visiting the volcano and the Hilo area, 30 minutes north. The home is well positioned in the rainforest. If you arrive at night, it can be an adventure to locate even with the big sign on the street. The view...”
- Review left on 11/21/2016

$225

Very Good (74 reviews)

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from $225 / 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

$89

Very Good (12 reviews)

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from $89 / night

1 / 16

Kailua-Kona Townhouse

  • 3
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning

$185

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from $185 / night

1 / 29

Kailua-Kona Villa

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

from $800 / night

1 / 20

Kealakekua House

  • 3
  • 6
  • 3 nights min

$499

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from $499 / night

1 / 24

Kailua-Kona Apartment

  • 3
  • 8
  • 5 nights min
  • Ask about children
  • Air conditioning

$189

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from $189 / night

1 / 25

Kailua-Kona House

  • 4
  • 17
  • Min stay varies
  • Ask about children

from $520 / 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

(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

$550

Excellent (6 reviews)

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from $550 / 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 / 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

(11)

1 / 14

Kailua-Kona House

  • 3
  • 8
  • 6 nights min
  • Ask about children
“What a great place to live while in paradise. Very cute place maybe 50 yards to the beach and the waves. Tom and Gidget have the home really stocked up. Upgraded kitchen with a dishwasher and lots of counter space. Plenty of pillows blankets and...”
- Review left on 01/18/2017

$130

Very Good (11 reviews)

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from $130 / night

1 / 25

Kailua-Kona House

  • 3
  • 6
  • Min stay varies
  • Ask about children

from $310 / night

1 / 26

Kailua-Kona House

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

from $685 / 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 / 25

Kailua-Kona House

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

from $685 / night

(23)

1 / 27

Kailua-Kona House

  • 3
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about children
“Warm and inviting family home. I could have spent the whole vacation on the balcony watching the ocean and spotting whales. Great location for exploring the rest of Hawai'i too! Owner was delightful in arranging our stay, very accommodating...”
- Review left on 03/02/2017

$288

Excellent (23 reviews)

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from $288 / night

(6)

1 / 21

Kailua-Kona House

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
“Our family of five enjoyed three nights at this wonderful ocean-view site. Cathleen was great to work with, and we even had a gorgeous bouquet of fresh flowers there to greet us! For us, the house was more of a base of operations than a place to hang...”
- Review left on 07/23/2016

$300

Excellent (6 reviews)

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from $300 / 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 / 12

Kailua-Kona House

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

from $575 / night

1 / 12

Kailua-Kona House

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children

from $500 / night

(1)

1 / 14

Kailua-Kona House

  • 4
  • 22
  • Min stay varies
  • Swimming pool
  • Ask about children
“This house could not have been better for our group. It is such a great space, open yet with private rooms and floors to accommodate our group of sixteen teenagers(eight boys and eight girls) with three adults.The view from the deck is amazing, and...”
- Review left on 06/19/2015

$300

Excellent (1 reviews)

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from $300 / night

(24)

1 / 14

Kailua-Kona House

  • 8
  • 18
  • Min stay varies
  • Ask about children
“The Ohana Retreat on the Big Island is an excellent property. With 8 bedrooms and nine bathrooms and two separate kitchens, one on upper floor and one on lower floor, it is wonderful for families and extended family/friends. We enjoyed all of the...”
- Review left on 01/10/2017

$1000

Excellent (24 reviews)

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from $1000 / night

1 / 11

Kailua-Kona House

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

$249

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from $249 / night

(7)

1 / 30

Kailua-Kona Condo

  • 1
  • 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Air conditioning
“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

$99

Very Good (7 reviews)

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from $99 / night

(1)

1 / 24

Kailua-Kona House

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

$750

Excellent (1 reviews)

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from $750 / night

(9)

1 / 41

Waikoloa Townhouse

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

$239

Excellent (9 reviews)

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from $239 / night

(5)

1 / 15

Milolii House

  • 3
  • 8
  • 1 night min
  • Beach/lakeside relaxation
  • Ask about children
“If you want a place a little out of the ordinary on the Big Island, Hale Kai is it. A spectacular location at the edge of the lave flow in the Milolii beach community,right above the ocean. Almost feels like you are in the ocean if you are in the...”
- Review left on 11/20/2016

$275

Excellent (5 reviews)

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from $275 / night

1 / 24

Kailua-Kona House

  • 5
  • 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$800

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from $800 / night

1 / 20

Kailua-Kona House

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

from $815 / night