15 Best Hawaii Kai Apartments on Holiday Lettings - Vacation rentals

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1,085 Vacation rentals

33

Vacation villa in Hawaii Kai

Oahu / Hawaii Kai

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Come stay at the waterfront in the residential area of ​​Hawaii Kai, in the beautiful Villa Kenneth, for up to 12 people. Direct pontoon boat available kayaks, Wifi Internet and air conditioning, 4 bedrooms with bathrooms, large living room with fully equipped kitchen, …see more

from $677 / night

$4,736 / week

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from $677 / night

(1) Excellent 

24

Hawaii Kai Vacation home rental

Oahu / Hawaii Kai

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Very quite & private fully furnished Island living home with 3 bedroom + 1 Sofa coach and 1 bathroom. Licensed B&B with the State of Hawaii. Indoor yoga room with infrared sauna outdoor by the relaxing pool area. BBQ area with outdoor living room to relax and overlook t …see more

from $221 / night

$1,392 - $2,261 / week

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avg. 2 hours 13 minutes

from $221 / night

10

Vacation home rental

Oahu / Hawaii Kai

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
Lower level Master Suite of home with private entrance and lanai overlooking ocean. Sleeps up to 4 (oversize California King Size Bed & Queen size air mattress) living/breakfast area, his & hers sinks, large walk in closet, jacuzzi tub. A few nearby attractions include …see more

from $118 / night

$826 / week

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from $118 / night

64

Vacation condo in Hawaii Kai

Oahu / Hawaii Kai

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Aloha! Welcome to Modern Hawaiian Living! New from top to bottom!!! Newly built and beautifully decorated with custom teak furniture from Bali and the most comfortable sofas, beds, linens and more! This home is equipped with everything you need, truly a home away fr …see more

from $550 / night

$3,850 / week

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Responds fast!
avg. 1 hour 33 minutes

from $550 / night

(1) Excellent 

89

Home rental in Hawaii Kai

Oahu / Hawaii Kai

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
LOCATION! Here on Oahu's most exciting and active coastline, "Hale Kahakai" (Beach House) offers extraordinary access to your own beachfront without a hotel in sight. This vintage 1940's cottage sits among the large beach estates on East Honolulu's beautiful and tranqui …see more

from $235 / night

$1,645 / week

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from $235 / night

25

Vacation studio in Hawaii Kai

Oahu / Hawaii Kai

Studio 2 4 nights min

  • Studio
  • Sleeps 2
  • 4 nights min
  • Air conditioning
This is a newly renovated and spacious studio with a Hawaiian Tiki Bar! This studio has a separate entrance and has all the conveniences of home with its own washer and dryer, walk- in closet, A/C, hardwood floors, 2 burner cooktop, sink, refrigerator, microwave oven, …see more

from $90 / night

$630 / week

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from $90 / night

5

Vacation home in Hawaii Kai

Oahu / Hawaii Kai

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This 2 bedroom is just a block from the beach in Hawaii Kai. It offers the best balance between being close to everything Waikiki has to offer (just 10 min away) but is away from the hustle and bustle of the city. Here you can relax on the beach which is safe for childr …see more

from $260 / night

$1,820 / week

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from $260 / night

16

Home rental in Hawaii Kai with shared pool

Oahu / Hawaii Kai

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
"Wow!" is the usual reaction of folks seeing the view from this traditional Hawaiian home. Furnished comfortably, with attention to detail for a wonderful, relaxing vacation. Spectacular sunsets. In winter, humpback whales cavort in the ocean just below the house. At ni …see more

from $650 / night

$4,550 - $5,075 / week

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from $650 / night

48

Vacation home with swimming pool in Hawaii Kai

Oahu / Hawaii Kai

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
20% OFF RATES - Summer Special! NOW until July 1st!  Oahu's Newest Luxury Estate Ocean House is the newest residence in the collection of ultra-luxury homes designed by renowned Hawaii Architect Jim McPeak and built by San Diego based developer Mark Gosselin. This est …see more

from $6,000 / night

$42,000 / week

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from $6,000 / night

25

Home rental in Hawaii Kai

Oahu / Hawaii Kai

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Child friendly
Aloha! Welcome to Modern Hawaiian Living! Luxuriously appointed open style living for 18 guests. 3 Living Rooms, 3 BBQs, 3 Outdoor BBQ areas and lots of on property parking and more! Recently built and beautifully decorated with custom teak furniture from Bali and t …see more

from $1,095 / night

$7,665 / week

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Responds fast!
avg. 1 hour 33 minutes

from $1,095 / night

16

Vacation villa in Hawaii Kai

Oahu / Hawaii Kai

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Find serenity, island style, at Hale Laulea. This Oahu vacation rental, whose Hawaiian name translates to “house of peace and happiness,” is a beautifully designed contemporary retreat close to some of the island’s best beaches. Invite up to eight friends or family memb …see more

from $685 / night

$4,795 / week

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avg. 2 minutes

from $685 / night

21

Vacation apartment in Hawaii Kai

Oahu / Hawaii Kai

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Nearest beach 0.5 mi
  • Child friendly
Enjoy this East Oahu private guest suite, ideal for 2 adults + 2 children. Conveniently located close to Waimanalo & Haunama Bay, with lots of shopping and dining in Hawaii Kai & Aina Haina. Easy drive to Waikiki or Honolulu. Family- and kid-friendly. 1 queen bed, 2 twi …see more

from $89 / night

$559 - $769 / week

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from $89 / night

24

Vacation home rental

Oahu / Hawaii Kai

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
This gorgeous property overlooks the Ala Moana marina with sweeping views of mountain ranges Hawaii is known for. Escape to this home away from home located in the heart of Waikiki. This is a fully-equipped unit that will allow you and your family to entertain friends w …see more

from $425 / night

$2,975 / week

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Responds fast!
avg. 17 minutes

from $425 / night

24

Vacation home in Hawaii Kai

Oahu / Hawaii Kai

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Suitable for children age 5+
** Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay ** Come experience pure paradise in Honolulu, Hawaii! If you’re dreaming of a tropical escape in the sand, surf, and sun, then this tranquil Honolulu va …see more

from $115 / night

$805 / week

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avg. 13 minutes

from $115 / night

20

Vacation home with swimming pool in Hawaii Kai

Oahu / Hawaii Kai

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
Set on the west slope o Koko Head crater, adjacent to Hanauma Bay this casual, island-style home offers panoramic ocean views over Maunalua Bay toward Diamond Head and the mountains beyond. The lower level consists of the pol and pool deck which is solar heated to help …see more

from $550 / night

$3,850 / week

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from $550 / night

42

Vacation apartment in Hawaii Kai

Oahu / Hawaii Kai

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Car not necessary
Please note that due to Honolulu City and County regulations, the minimum rental period for this unit is 30 days. This is a newly renovated 800 sql 1 bedroom apartment attached to a main house with separate private entrance. Perfect for those requiring longer than usual …see more

from $95 / night

$665 / week

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from $95 / night

26

Hawaii Kai Vacation apartment rental

Oahu / Hawaii Kai

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
* Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay * Your Hawaiian holiday begins at the 'Lanai House,' a newly renovated 2-bedroom,1-bathroom home in Honolulu. This vacation rental boast …see more

from $210 / night

$1,470 / week

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Responds fast!
avg. 35 minutes

from $210 / night

26

Vacation studio rental

Oahu / Hawaii Kai

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
* Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay * Experience the best of paradise at this charming studio vacation rental that sleeps 2 in Honolulu. This home is nestled between the K …see more

from $110 / night

$770 / week

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Responds fast!
avg. 35 minutes

from $110 / night

55

Vacation villa in Hawaii Kai

Oahu / Hawaii Kai

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Ask about children
  • Ask about pets
Located just outside of Honolulu’s downtown area, surrounded by some of Hawaii’s most famous beaches and golf courses, Hanohano Villa is hillside luxury home with a spectacular view of Kalama Valley and Koko Head. With four well-appointed en-suite bedrooms and plenty of …see more

from $980 / night

$6,860 / week

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avg. 2 minutes

from $980 / night