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Hawaii Kai Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
58 rentals in Hawaii Kai.
Open and relaxing vacation home with breathtaking panoramic ocean view, holiday rental in Hawaii Kai
Open and relaxing vacation home with breathtaking panoramic ocean view, holiday rental in Hawaii Kai
Open and relaxing vacation home with breathtaking panoramic ocean view, holiday rental in Hawaii Kai

Open and relaxing vacation home with breathtaking panoramic ocean view

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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EXCLUSIVE EXECUTIVE HOME WITH FABULOUS 180o OCEAN VIEW., holiday rental in Hawaii Kai
EXCLUSIVE EXECUTIVE HOME WITH FABULOUS 180o OCEAN VIEW., holiday rental in Hawaii Kai
EXCLUSIVE EXECUTIVE HOME WITH FABULOUS 180o OCEAN VIEW., holiday rental in Hawaii Kai

EXCLUSIVE EXECUTIVE HOME WITH FABULOUS 180o OCEAN VIEW.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Please contact me for specific dates that you may be interested in., holiday rental in Hawaii Kai
Please contact me for specific dates that you may be interested in., holiday rental in Hawaii Kai
Please contact me for specific dates that you may be interested in., holiday rental in Hawaii Kai

Please contact me for specific dates that you may be interested in.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Simple studio with lanai, standing desk, WiFi & great location near beaches, holiday rental in Hawaii Kai
Simple studio with lanai, standing desk, WiFi & great location near beaches, holiday rental in Hawaii Kai
Simple studio with lanai, standing desk, WiFi & great location near beaches, holiday rental in Hawaii Kai

Simple studio with lanai, standing desk, WiFi & great location near beaches

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury Condominium in Peninsula at Hawaii Kai, holiday rental in Hawaii Kai
Luxury Condominium in Peninsula at Hawaii Kai, holiday rental in Hawaii Kai
Luxury Condominium in Peninsula at Hawaii Kai, holiday rental in Hawaii Kai

Luxury Condominium in Peninsula at Hawaii Kai

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lagoon Waterfront Retreat, holiday rental in Hawaii Kai
Lagoon Waterfront Retreat, holiday rental in Hawaii Kai
Lagoon Waterfront Retreat, holiday rental in Hawaii Kai

Lagoon Waterfront Retreat

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tranquil and Chic 1 Bd and Bth with Car and Sauna, holiday rental in Hawaii Kai
Tranquil and Chic 1 Bd and Bth with Car and Sauna, holiday rental in Hawaii Kai
Tranquil and Chic 1 Bd and Bth with Car and Sauna, holiday rental in Hawaii Kai

Tranquil and Chic 1 Bd and Bth with Car and Sauna

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Honolulu Retreat w/ Pool Access, Near Beaches, holiday rental in Hawaii Kai
Cozy Honolulu Retreat w/ Pool Access, Near Beaches, holiday rental in Hawaii Kai
Cozy Honolulu Retreat w/ Pool Access, Near Beaches, holiday rental in Hawaii Kai

Cozy Honolulu Retreat w/ Pool Access, Near Beaches

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious Cottage with A/C and Patio, holiday rental in Hawaii Kai
Spacious Cottage with A/C and Patio, holiday rental in Hawaii Kai
Spacious Cottage with A/C and Patio, holiday rental in Hawaii Kai

Spacious Cottage with A/C and Patio

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Private, Peaceful & Prestigious Home w/ Ocean, other Islands, and Mountain, holiday rental in Hawaii Kai
Private, Peaceful & Prestigious Home w/ Ocean, other Islands, and Mountain, holiday rental in Hawaii Kai
Private, Peaceful & Prestigious Home w/ Ocean, other Islands, and Mountain, holiday rental in Hawaii Kai

Private, Peaceful & Prestigious Home w/ Ocean, other Islands, and Mountain

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Seabreeze Vacation Home - Quiet/Pool/Free Wi-Fi/Parking, holiday rental in Hawaii Kai
Seabreeze Vacation Home - Quiet/Pool/Free Wi-Fi/Parking, holiday rental in Hawaii Kai
Seabreeze Vacation Home - Quiet/Pool/Free Wi-Fi/Parking, holiday rental in Hawaii Kai

Seabreeze Vacation Home - Quiet/Pool/Free Wi-Fi/Parking

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tropical Escape with Lanai & Private Yard | Walk to Maunalua Bay Beach, holiday rental in Hawaii Kai
Tropical Escape with Lanai & Private Yard | Walk to Maunalua Bay Beach, holiday rental in Hawaii Kai
Tropical Escape with Lanai & Private Yard | Walk to Maunalua Bay Beach, holiday rental in Hawaii Kai

Tropical Escape with Lanai & Private Yard | Walk to Maunalua Bay Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Lagoon House, holiday rental in Hawaii Kai
The Lagoon House, holiday rental in Hawaii Kai
The Lagoon House, holiday rental in Hawaii Kai

The Lagoon House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Home with ocean views, studio, large lanai, koi pond, washer/dryer, holiday rental in Hawaii Kai
Home with ocean views, studio, large lanai, koi pond, washer/dryer, holiday rental in Hawaii Kai
Home with ocean views, studio, large lanai, koi pond, washer/dryer, holiday rental in Hawaii Kai

Home with ocean views, studio, large lanai, koi pond, washer/dryer

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Maile Hale, holiday rental in Hawaii Kai
Maile Hale, holiday rental in Hawaii Kai
Maile Hale, holiday rental in Hawaii Kai

Maile Hale

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Niuiki~ Private Oceanfront, near Honolulu, holiday rental in Hawaii Kai
Niuiki~ Private Oceanfront, near Honolulu, holiday rental in Hawaii Kai
Niuiki~ Private Oceanfront, near Honolulu, holiday rental in Hawaii Kai

Niuiki~ Private Oceanfront, near Honolulu

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Executive Balinese Vacation Home in Hawaii Kai, holiday rental in Hawaii Kai
Executive Balinese Vacation Home in Hawaii Kai, holiday rental in Hawaii Kai
Executive Balinese Vacation Home in Hawaii Kai, holiday rental in Hawaii Kai

Executive Balinese Vacation Home in Hawaii Kai

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Aloha Nalu: Luxury family friendly Home w/Pool,AC,soaking tub,Diamond Head, holiday rental in Hawaii Kai
Aloha Nalu: Luxury family friendly Home w/Pool,AC,soaking tub,Diamond Head, holiday rental in Hawaii Kai
Aloha Nalu: Luxury family friendly Home w/Pool,AC,soaking tub,Diamond Head, holiday rental in Hawaii Kai

Aloha Nalu: Luxury family friendly Home w/Pool,AC,soaking tub,Diamond Head

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Hale Maunalua hillside hideaway with ocean views & pool - walk to Hanauma Bay, holiday rental in Hawaii Kai
Hale Maunalua hillside hideaway with ocean views & pool - walk to Hanauma Bay, holiday rental in Hawaii Kai
Hale Maunalua hillside hideaway with ocean views & pool - walk to Hanauma Bay, holiday rental in Hawaii Kai

Hale Maunalua hillside hideaway with ocean views & pool - walk to Hanauma Bay

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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15% Off Summer Special! Luxury Oceanfront Estate: Ocean House 4BD, holiday rental in Hawaii Kai
15% Off Summer Special! Luxury Oceanfront Estate: Ocean House 4BD, holiday rental in Hawaii Kai
15% Off Summer Special! Luxury Oceanfront Estate: Ocean House 4BD, holiday rental in Hawaii Kai

15% Off Summer Special! Luxury Oceanfront Estate: Ocean House 4BD

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Moana Lani: Oceanfront Home w/ Private Pool & Jacuzzi, Walk to the Beach, holiday rental in Hawaii Kai
Luxury Moana Lani: Oceanfront Home w/ Private Pool & Jacuzzi, Walk to the Beach, holiday rental in Hawaii Kai
Luxury Moana Lani: Oceanfront Home w/ Private Pool & Jacuzzi, Walk to the Beach, holiday rental in Hawaii Kai

Luxury Moana Lani: Oceanfront Home w/ Private Pool & Jacuzzi, Walk to the Beach

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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NEWLY REMODELED Mansion with Central A/C, Pool & Jacuzzi overlooking the Ocean, holiday rental in Hawaii Kai
NEWLY REMODELED Mansion with Central A/C, Pool & Jacuzzi overlooking the Ocean, holiday rental in Hawaii Kai
NEWLY REMODELED Mansion with Central A/C, Pool & Jacuzzi overlooking the Ocean, holiday rental in Hawaii Kai

NEWLY REMODELED Mansion with Central A/C, Pool & Jacuzzi overlooking the Ocean

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Thanksgiving Special! Hale Ola w/ Ocean & Diamond Head Views,Private Heated, holiday rental in Hawaii Kai
Thanksgiving Special! Hale Ola w/ Ocean & Diamond Head Views,Private Heated, holiday rental in Hawaii Kai
Thanksgiving Special! Hale Ola w/ Ocean & Diamond Head Views,Private Heated, holiday rental in Hawaii Kai

Thanksgiving Special! Hale Ola w/ Ocean & Diamond Head Views,Private Heated

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Hale Makana: Luxury, Pool, AC & Stunning Ocean Views, holiday rental in Hawaii Kai
Hale Makana: Luxury, Pool, AC & Stunning Ocean Views, holiday rental in Hawaii Kai
Hale Makana: Luxury, Pool, AC & Stunning Ocean Views, holiday rental in Hawaii Kai

Hale Makana: Luxury, Pool, AC & Stunning Ocean Views

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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10% Off Summer Special!  Luxury Oceanfront Estate: Ocean House, holiday rental in Hawaii Kai
10% Off Summer Special!  Luxury Oceanfront Estate: Ocean House, holiday rental in Hawaii Kai
10% Off Summer Special!  Luxury Oceanfront Estate: Ocean House, holiday rental in Hawaii Kai

10% Off Summer Special! Luxury Oceanfront Estate: Ocean House

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Home near Beach. Peaceful Community w/ Swimming Pool and Boat Dock, holiday rental in Hawaii Kai
Waterfront Home near Beach. Peaceful Community w/ Swimming Pool and Boat Dock, holiday rental in Hawaii Kai
Waterfront Home near Beach. Peaceful Community w/ Swimming Pool and Boat Dock, holiday rental in Hawaii Kai

Waterfront Home near Beach. Peaceful Community w/ Swimming Pool and Boat Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Long term rental Marina Front rental in Hawaii Kai with pool, holiday rental in Hawaii Kai
Long term rental Marina Front rental in Hawaii Kai with pool, holiday rental in Hawaii Kai
Long term rental Marina Front rental in Hawaii Kai with pool, holiday rental in Hawaii Kai

Long term rental Marina Front rental in Hawaii Kai with pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Home w/Ocean-Mountain Views in East Oahu Serene Family Vacation, holiday rental in Hawaii Kai
Stunning Home w/Ocean-Mountain Views in East Oahu Serene Family Vacation, holiday rental in Hawaii Kai
Stunning Home w/Ocean-Mountain Views in East Oahu Serene Family Vacation, holiday rental in Hawaii Kai

Stunning Home w/Ocean-Mountain Views in East Oahu Serene Family Vacation

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 3 Bedroom / 2 Bath / Sleeps 8, holiday rental in Hawaii Kai
Spacious 3 Bedroom / 2 Bath / Sleeps 8, holiday rental in Hawaii Kai
Spacious 3 Bedroom / 2 Bath / Sleeps 8, holiday rental in Hawaii Kai

Spacious 3 Bedroom / 2 Bath / Sleeps 8

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Hawaii home right on the water, holiday rental in Hawaii Kai
Gorgeous Hawaii home right on the water, holiday rental in Hawaii Kai
Gorgeous Hawaii home right on the water, holiday rental in Hawaii Kai

Gorgeous Hawaii home right on the water

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Kuliouou Cottage - Pet Friendly - 5 min from the beach!, holiday rental in Hawaii Kai
Kuliouou Cottage - Pet Friendly - 5 min from the beach!, holiday rental in Hawaii Kai
Kuliouou Cottage - Pet Friendly - 5 min from the beach!, holiday rental in Hawaii Kai

Kuliouou Cottage - Pet Friendly - 5 min from the beach!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning Marina Townhome with Ocean and Mountain Views, holiday rental in Hawaii Kai
Stunning Marina Townhome with Ocean and Mountain Views, holiday rental in Hawaii Kai
Stunning Marina Townhome with Ocean and Mountain Views, holiday rental in Hawaii Kai

Stunning Marina Townhome with Ocean and Mountain Views

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW Modern Marina Front on Hawaii Quay, holiday rental in Hawaii Kai
NEW Modern Marina Front on Hawaii Quay, holiday rental in Hawaii Kai
NEW Modern Marina Front on Hawaii Quay, holiday rental in Hawaii Kai

NEW Modern Marina Front on Hawaii Quay

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront home of peaceful joy: Villa Laule'a, holiday rental in Hawaii Kai
Waterfront home of peaceful joy: Villa Laule'a, holiday rental in Hawaii Kai
Waterfront home of peaceful joy: Villa Laule'a, holiday rental in Hawaii Kai

Waterfront home of peaceful joy: Villa Laule'a

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Waterfront Living, holiday rental in Hawaii Kai
Amazing Waterfront Living, holiday rental in Hawaii Kai
Amazing Waterfront Living, holiday rental in Hawaii Kai

Amazing Waterfront Living

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Breathtaking Ocean Views! Peaceful Retreat/No Resort Fees., holiday rental in Hawaii Kai
Breathtaking Ocean Views! Peaceful Retreat/No Resort Fees., holiday rental in Hawaii Kai
Breathtaking Ocean Views! Peaceful Retreat/No Resort Fees., holiday rental in Hawaii Kai

Breathtaking Ocean Views! Peaceful Retreat/No Resort Fees.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean View Cottage with Separate Suite, holiday rental in Hawaii Kai
Ocean View Cottage with Separate Suite, holiday rental in Hawaii Kai
Ocean View Cottage with Separate Suite, holiday rental in Hawaii Kai

Ocean View Cottage with Separate Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Island Style Elegance on a Beach Access, holiday rental in Hawaii Kai
Island Style Elegance on a Beach Access, holiday rental in Hawaii Kai
Island Style Elegance on a Beach Access, holiday rental in Hawaii Kai

Island Style Elegance on a Beach Access

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Marina front home with Koko Crater views & sparkling blue Makapu'u Pool!, holiday rental in Hawaii Kai
Marina front home with Koko Crater views & sparkling blue Makapu'u Pool!, holiday rental in Hawaii Kai
Marina front home with Koko Crater views & sparkling blue Makapu'u Pool!, holiday rental in Hawaii Kai

Marina front home with Koko Crater views & sparkling blue Makapu'u Pool!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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…………………….., holiday rental in Hawaii Kai
…………………….., holiday rental in Hawaii Kai
…………………….., holiday rental in Hawaii Kai

……………………..

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ultimate Oceanfront Luxury Living with Pool and Hot Tub, holiday rental in Hawaii Kai
Ultimate Oceanfront Luxury Living with Pool and Hot Tub, holiday rental in Hawaii Kai
Ultimate Oceanfront Luxury Living with Pool and Hot Tub, holiday rental in Hawaii Kai

Ultimate Oceanfront Luxury Living with Pool and Hot Tub

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Kuapa Isle gem with Koko Crater views & pool - by the beach, holiday rental in Hawaii Kai
Waterfront Kuapa Isle gem with Koko Crater views & pool - by the beach, holiday rental in Hawaii Kai
Waterfront Kuapa Isle gem with Koko Crater views & pool - by the beach, holiday rental in Hawaii Kai

Waterfront Kuapa Isle gem with Koko Crater views & pool - by the beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Upscale Mariana Front House - waterfront jacuzzi. - $12,000/mt, holiday rental in Hawaii Kai
Upscale Mariana Front House - waterfront jacuzzi. - $12,000/mt, holiday rental in Hawaii Kai
Upscale Mariana Front House - waterfront jacuzzi. - $12,000/mt, holiday rental in Hawaii Kai

Upscale Mariana Front House - waterfront jacuzzi. - $12,000/mt

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Marina-Water Front Luxury Home, holiday rental in Hawaii Kai
Newly Renovated Marina-Water Front Luxury Home, holiday rental in Hawaii Kai
Newly Renovated Marina-Water Front Luxury Home, holiday rental in Hawaii Kai

Newly Renovated Marina-Water Front Luxury Home

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hawaiian Waterfront Home with Private Swimming Pool and Mountain Views, holiday rental in Hawaii Kai
Hawaiian Waterfront Home with Private Swimming Pool and Mountain Views, holiday rental in Hawaii Kai
Hawaiian Waterfront Home with Private Swimming Pool and Mountain Views, holiday rental in Hawaii Kai

Hawaiian Waterfront Home with Private Swimming Pool and Mountain Views

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset, holiday rental in Hawaii Kai
Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset, holiday rental in Hawaii Kai
Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset, holiday rental in Hawaii Kai

Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Newly Renovated and Listed 3 Bedroom 2 bathroom Home, holiday rental in Hawaii Kai
Newly Renovated and Listed 3 Bedroom 2 bathroom Home, holiday rental in Hawaii Kai
Newly Renovated and Listed 3 Bedroom 2 bathroom Home, holiday rental in Hawaii Kai

Newly Renovated and Listed 3 Bedroom 2 bathroom Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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HUGE discount or Maui fire victims, holiday rental in Hawaii Kai
HUGE discount or Maui fire victims, holiday rental in Hawaii Kai
HUGE discount or Maui fire victims, holiday rental in Hawaii Kai

HUGE discount or Maui fire victims

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool, holiday rental in Hawaii Kai
Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool, holiday rental in Hawaii Kai
Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool, holiday rental in Hawaii Kai

Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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7-BEDROOM HOME SPECTACULAR POOL WALK EVERYWHERE AROUND HAWAII KAI!, holiday rental in Hawaii Kai
7-BEDROOM HOME SPECTACULAR POOL WALK EVERYWHERE AROUND HAWAII KAI!, holiday rental in Hawaii Kai
7-BEDROOM HOME SPECTACULAR POOL WALK EVERYWHERE AROUND HAWAII KAI!, holiday rental in Hawaii Kai

7-BEDROOM HOME SPECTACULAR POOL WALK EVERYWHERE AROUND HAWAII KAI!

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Showing results 1-50 of 58
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