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Island of Hawaii Holidays & City Breaks - Holiday Lettings

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28 properties suitable for city breaks and holidays

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Captain Cook holiday cottage rental

Captain Cook cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“spectacular!!!” What a total dream this place is.. the owners are so wonderful and have thought of everything. the outdoor kitchen and living room and shower make the experience everything you hope for in a vacation rental! a little slice of paradise. mahalo iva and jerry peele

from £137 / night

£959 / week

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Kailua-Kona holiday home accommodation

Kailua-Kona house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“"I must be dreaming!"” We were so lucky to come across this Gem! It was our first time on Kona and not sure where we should stay. I was searching online and came across Kona-Leilani. The interior & exterior is beautiful. I was impressed how efficient and helpful they were answering all my questions. The landscape is gorgeous the views are amazing and the location is perfect! It's within walking distance to a beautiful black pebble beach and lots of hiking trails. Let me add that as you scroll through the photos of this property online I'm sure you're thinking what a lovely home but wait until you drive up to the horseshoe driveway, it's stunning! I believe they put all their heart & soul into making sure your stay is one you will cherish forever! We enjoyed every minute of our stay at Kona-Leilani. Thank you! =) Mahalo!

from £215 / night

£1,503 / week

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Holiday home in Kalapana

Kalapana house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £91 / night

£503 - £982 / week

1 / 35

Holiday apartment in Kailua-Kona

Kailua-Kona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £183 / night

£1,279 / week

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Home rental in Kailua-Kona

Kailua-Kona house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Amazing beachfront home to relax in” Beachfront home that is comfortable and well furnished with what you need to make yourself at home for your stay. Between Kona and Keauhou, provides a place for a peaceful retreat; close enough to town, shopping, swimming and snorkeling beaches. Perfect for our family of 4 adults.

from £1,044 / night

£7,307 / week

1 / 27

Holiday home in Honalo

Honalo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £365 / night

£2,551 / week

1 / 45

Holiday tented camp in Naalehu

Naalehu tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £256 / night

£1,791 / week

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Cottage rental in Volcano

Volcano cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £411 / night

£2,877 / week

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Kailua-Kona holiday home rental

Kailua-Kona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“An exceptional place” Kona Beach House is in the middle of the rather busyand touristy Kailua Kona area an unexpectedly tranquil place. The house has its own spirit and breathes history. A lot of loving attention is paid to detail. Anywhere you go or sit in the house seems to be a special place in itself and invites you to stay. The view onto the sea is wonderful, breathtaking and it seems all yours. An exceptional place!

from £731 / night

£5,480 / week

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Holiday home in Milolii

Milolii house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £124 / night

£864 / week

1 / 20

Hilo holiday apartment rental

Hilo apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £164 / night

£868 - £1,124 / week

1 / 33

Home rental in Naalehu

Naalehu house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £146 / night

£1,017 / week

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Apartment rental in Kailua-Kona with shared pool

Kailua-Kona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £182 / night

£1,273 / week

1 / 42

Home rental in Keaau with swimming pool

Keaau house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £781 / night

£5,467 / week

1 / 27

Papaikou holiday home rental

Papaikou house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £438 / night

£3,063 / week

1 / 39

Home rental in Keaau

Keaau house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £164 / night

£1,145 / week

1 / 54

Holiday condo with shared pool in Kailua-Kona

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“wonderful vacation” I recently stayed for a week in condo # 216 , which is a privately owned condo and I loved it. I found their place to be clean and comfortable with nice furnishings, well equipped kitchenette, very comfy bed, and a fantastic pool view lit up with tiki torches at night. Their condo is in the perfect location in Kailua Kona with lots to do and within walking distance to shopping, restaurants, and beaches. The pool was clean and inviting and I would return to #216 in the Kona Islander without hesitation and recommend it to family and friends...

from £155 / night

£1,081 / week

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Hilo holiday home rental

Hilo house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £155 / night

£927 / week

1 / 36

Captain Cook holiday home rental

Captain Cook house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £182 / night

£1,247 - £1,886 / week

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Home accommodation in Milolii

Milolii house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Lovely, bright and well provisioned home” The house was very accommodating for myself and my 2 kids (10 and 17). The large deck offers great views and is a wonderful place to enjoy the comfortable deck furniture. The snorkeling at the end of the road was some of the best we had. Although we did not make use of the lower level it was a great place for teens or an adult reprieve. It had a huge bedroom that was recently tastefully redecorated. My only word of caution would be to try ensure you arrive during the daylight as it can be difficult to find in the dark.

from £242 / night

£1,918 - £3,325 / week

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Holiday condo in Kailua-Kona

Kailua-Kona condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £456 / night

£3,191 / week

1 / 26

Waikoloa holiday apartment rental

Waikoloa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“A perfect place to relax and enjoy island life” A very well appointed and comfortable Condo with great facilities and very easy access to the sandy beach. Our boys had to be dragged from the pool at the end of each day. We loved our staff and would readily return should we find ourselves on The Big Island again.

from £292 / night

£2,312 - £2,639 / week

1 / 106

Apartment rental in Kailua-Kona

Kailua-Kona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £229 / night

£1,599 / week

1 / 33

Holiday condo in Kailua-Kona

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £200 / night

£1,096 - £1,735 / week

1 / 11

Holiday home in Mountain View

Mountain View house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £83 / night

£544 / week

1 / 25

Holiday cottage in Volcano

Volcano cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £118 / night

£825 / week

1 / 21

Holiday home in Hilo

Hilo house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

“Quiet accessible neighborhood” Kawahi is a very gracious, knowledgeable, and friendly host. She provided us with much information about local shopping, culture, geography, and activities. Her home is in a quiet residential area with room to park your vehicle off the street. We didn't spend much daytime there as there is so much to do and experience in the Hilo area. The inside of the unit is as pictured with lots of dishes and a good gas range. Kewahi introduced us to lau lau, which is a specially cooked pork dish that I would kill for. She also explained lots of little tidbits about local cultural traits of the people and historical accounts of the area which was very helpful as we traveled around the island. Yes, we would stay with her again.

from £151 / night

£1,055 / week

1 / 36

Holiday condo with golf nearby in Waikoloa

Waikoloa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £218 / night

£1,439 / week

1 / 55

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