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Kailua-Kona Waterfront Vacation Rentals, Apartments & More - 266 Rentals Available.

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266 Vacation rentals

Filters applied: Waterfront

(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

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

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)

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

(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 / 24

Kailua-Kona Apartment

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

$189

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from $189 / 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

(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

(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

(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 / 25

Kailua-Kona House

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

from $310 / 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)

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 / 34

Kailua-Kona House

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

$700

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from $700 / 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

1 / 25

Kailua-Kona House

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

from $685 / night

1 / 26

Kailua-Kona House

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

from $685 / 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

(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 / 11

Kailua-Kona House

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

$249

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from $249 / night

1 / 25

Kailua-Kona House

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

from $520 / night

(11)

1 / 24

Kailua-Kona House

  • 5
  • 12
  • 6 nights min
  • Swimming pool
  • Ask about children
“We enjoyed a family reunion at this comfortable, well equipped home. The family with the baby slept downstairs where he could nap quietly. It was a very safe set-up for little ones with a convenient high-chair, crib, and appropriate pool toys. We...”
- Review left on 05/28/2016

$290

Very Good (11 reviews)

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from $290 / night

1 / 29

Kailua-Kona Villa

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

from $800 / 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

(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

1 / 17

Kailua-Kona House

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

from $600 / night

(1)

1 / 16

Kailua-Kona House

  • 5
  • 12
  • Min stay varies
  • Ask about children
“very good rental house with a good pool, nice yard, full kitchen, beer coolers and boogie boards to use at the beach. I would stay again...”
- Review left on 01/09/2014

$600

Excellent (1 reviews)

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from $600 / night

1 / 20

Kailua-Kona House

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

from $815 / 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

(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 / 18

Kailua-Kona Condo

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

from $160 / night

1 / 12

Kailua-Kona House

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

from $500 / night

1 / 12

Kailua-Kona House

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

from $575 / night

(1)

1 / 24

Kailua-Kona House

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

$749

Excellent (1 reviews)

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from $749 / 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

(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 / 24

Kailua-Kona House

  • 3
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$525

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from $525 / 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

1 / 23

Kailua-Kona Villa

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

from $650 / night