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Family Friendly Holidays in Island of Hawaii - Holiday Lettings

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4,227 family friendly properties

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Holiday condo rental

Kailua-Kona condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £222 / night

£1,653 / week

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Holiday home in Kailua-Kona

Kailua-Kona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £86 / night

£591 - £902 / week

1 / 22

Holiday apartment with shared pool in Kailua-Kona

Kailua-Kona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £107 / night

£747 / week

1 / 10

Holiday condo in Kailua-Kona

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £122 / night

£853 / week

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Apartment rental in Kailua-Kona

Kailua-Kona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Wonderful Location!” We have stayed several times in this unit and enjoyed just being able to walk across the street to the best beach on the island. Walk back and jump in the pool. Enjoyed the outdoor BBQ facilities. Well stocked apartment, clean and very comfortable. Love sitting on the lanai early morning and in the evening and taking in the ocean views. Easy to get to town as off the main street. Have fun!

from £144 / night

£893 - £1,010 / week

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Apartment rental in Kailua-Kona with shared pool

Kailua-Kona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £177 / night

£1,239 / week

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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 £134 / night

£934 / week

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Holiday apartment with shared pool in Kailua-Kona

Kailua-Kona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £222 / night

£1,550 / week

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Holiday condo in Kailua-Kona

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £125 / night

£872 / week

1 / 27

Holiday home in Kailua-Kona

Kailua-Kona house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £544 / night

£3,805 / week

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Holiday cottage in Pahoa

Pahoa cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £124 / night

£712 / week

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Kailua-Kona holiday apartment rental

Kailua-Kona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £195 / night

£1,359 / week

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Holiday apartment in Kailua-Kona

Kailua-Kona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Dan and Adelle C.'s review of Casa De Emdeko 330 - 1/1 DELUXE i” Time to replace couch pads, clean carpets and replace deck loungers that are torn and falling apart!

from £195 / night

£1,359 / week

1 / 27

Holiday home in Kalapana

Kalapana house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £88 / night

£489 - £956 / week

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Holiday cottage rental

Pahoa cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £133 / night

£756 / week

1 / 24

Holiday studio in Kailua-Kona

Kailua-Kona studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £105 / night

£734 / 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 £209 / night

£1,463 / week

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Yurt rental in Ocean View

Ocean View yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Peaceful” Really enjoyed my stay! Living in a yurt was an interesting experience that was on my bucket list. I would have given it a 5 rating except there was no working wireless and I needed it to deal with some items from work while I was away.

from £76 / night

£529 / week

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Holiday home in Hilo

Hilo house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Fabulous!” As retired school teachers, we give Lopaka's, Bev and Samson an a+++. Cleanliness, friendliness, centrally located for our interests which varied from hiking to events at the University. Excellent views. Loved the fresh fruit. Well-equipped kitchen and laundry. Bev went above and beyond our needs. Can't wait to return.

from £120 / night

£752 / week

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Holiday apartment rental

Kailua-Kona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £136 / night

£952 - £1,332 / week

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Holiday home in Hilo

Hilo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £129 / night

£756 / week

1 / 15

Holiday home in Kailua-Kona

Kailua-Kona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“A comfortable welcoming place to stay.” Our stay at Bears' Place Guest House was very nice. Nanette and anne were very attentive to our needs, checking in daily to be sure everything was going well for our stay. Anne and Nanette were both happy to share the local places to go and things to do. The house itself was kept very clean. Everything you needed of a beach vacation was available for use. Boogie Boards, beach chairs, ice chests, anything we needed was provided. The house is located directly above the airport, but there was no plane noise as we are up the hill at an elevation of about 1500 ft. The ocean view from the Lanai was spectacular, nice sunsets each night.

from £200 / night

£1,331 - £1,766 / week

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B&b rental in Kealakekua

Kealakekua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £137 / night

£959 / week

1 / 15

Holiday cottage in Volcano

Volcano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £129 / night

£721 - £938 / week

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Holiday home in Hilo

Hilo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £160 / night

£1,121 / week

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Holiday apartment with shared pool in Kailua-Kona

Kailua-Kona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £174 / night

£1,214 / week

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Holiday b&b in Kealakekua

Kealakekua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £160 / night

£1,114 / week

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Holiday home in Kailua-Kona

Kailua-Kona house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £306 / night

£2,142 / week

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Pahoa holiday home rental

Pahoa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £138 / night

£885 / week

1 / 30

Holiday home in Kailua-Kona

Kailua-Kona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £352 / night

£2,459 / 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 £236 / night

£1,868 - £3,237 / week

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Holiday condo with shared pool in Kailua-Kona

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £156 / night

£1,767 / week

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Condo rental in Kailua-Kona

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £134 / night

£934 / week

1 / 35

Holiday condo in Kailua-Kona

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £195 / night

£1,067 - £1,689 / week

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Cottage rental in Pahoa

Pahoa cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £129 / night

£823 - £885 / week

1 / 28

Holiday home rental

Kailua-Kona house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

from £200 / night

£1,712 / week

1 / 21

Condo rental in Kailua-Kona with shared pool

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £156 / night

£1,088 / week

1 / 27

Holiday condo with golf nearby in Waikoloa

Waikoloa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £176 / night

£1,401 / week

1 / 55

Holiday condo with shared pool in Pahala

Pahala condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £107 / night

£747 / week

1 / 6

Holiday villa in Holualoa

Holualoa villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“"I am in heaven!!!"” "I am in heaven," my wife said the first morning we were at the Kona View Estate. "Look how good my hair looks. Even it's happy to be here." We have been very fortunate to have visited all 50 of our States and have seen many foreign countries through cruises we have taken. But Kona View Estate is the best place we have ever stayed...It begins with co-owners Randy and atsumi, who live adjacent to the rental so they are there if you have any problems..The unit has a large bedroom with a master bath. There is a large living room that leads to a fully-equipped kitchen. Off the kitchen, there is a washer-drier...There is also a deck off the bedroom and living room and you sit there and look out at Kona bay. There is also a gas grill should you choose to cook out...Also, there is an infinity pool and hot tub right there on the property and we made use of both...Randy is also a great resource for information on places to see and eat on the Big Island...The unit is situated on a coffee plantation that Randy and atsumi own. On the first morning, there was a pound of their coffee waiting for us. And, there is nothing better than Kona coffee...This is a perfect place if you are looking for a restful, peaceful place to say. But, if you are looking to be close to a bigger town with places to shop and excellent restaurants, then you are a short drive to Kailua-Kona...Should we ever return to the Big Island (It's a long way from our home in Boston.), or should we have friends planning to visit this beautiful island, we will be sure to recommend Kona View Estate.

from £401 / night

£2,801 / week

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