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572 houses

Ono Hale: Gorgeous Home with pool. Breathtaking ocean views.

Kailua-Kona house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$700

Pahukoa Hale - Direct Ocean Front Hawaiian Style home in Kona Bay Estates.

Kailua-Kona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Some patina but well maintained and great location” The property is old (as we knew from the description) but in very good condition. We would suggest to add a water boiler since the antique stove is slow and inconvenient. But this is a minor issue, altogether the property is very nice, spacious, in good condition, we would definitely use it again and recommend it to others. Particularly the pool is just great - large and deep, made for diving.

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$700

The Pineapple Palace

Milolii house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 28 minutes

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$545

REMODELED BEACHFRONT ESTATE, MAGNIFICENT MANGO SURF

Kihei house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Kihei Private Home” Wanted to try "villa" living on Maui and this was spectacular! Private, modern, fully equipped and right on the beach. Easy to get to anyplace on Maui. Able to but local seafood and vegetables and cook great meals rather than dine out every night. There was nothing we wanted for and will likely return again!

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,595

Mika Kai - Blue Hawaii Oceanfront

Keaau house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$981

Launiupoko, Private Luxury Home "Kalapana"

Lahaina house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Beautiful Home” The setting and view is spectacular. All the rooms were very nice. We enjoyed the pool table upstairs, although be careful as there is a flaw in the slate and the cue ball can go flying! The Sonos music system is also great. The backyard is perfect. Lots of pool toys. We enjoyed the evenings watching the stars. We did have a few minor issues. We had 3 adult couples and it wasn't clear that two of the bedrooms had a shared bath. The other bath was across the hall. We had expected private baths for each bedroom. The showers are beautiful but water pressure is minimal. Lastly, it seems that pool and hot tub controls are managed by the owner down below. The pool light would turn off and if you wanted to swim late, we couldn't find a pool light switch. Lastly, we didn't have heat in the hot tub the first day/night and requested help from the owner. No response. The pool maintenance person fixed it for us the next day. Even with these minor issues, I would recommend the home again. It is beautiful and has stunning views. We enjoyed the fruit trees, too.

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,595

Turtle Rock - Ocean Front Cottage with pool

Keauhou house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Just what we were looking for!” Turtle Rock was perfect for our family of four, you couldn't ask for a better location! It's close to town if your looking to partake in some of the shopping, restaurants and excursions that Kailua has to offer, but far enough to relax and enjoy the beauty of the Big Island. The pool was clean and refreshing, the kitchen was fully stocked with pots and pans, plates, utensils, and the BBQ came in quite handy. Outdoor furniture was comfortable for watching the sunset, surfers and sea life that flourished right under you! Geckos were out and about but not overwhelming. We did run into a few bugs and insects, but nothing that would keep us from coming back. The place could use a little maintenance but overall seemed well taken care of for being so close to the ocean. It was also a little warm because there is no air conditioning but opening all of the doors cooled off the place quickly. The snorkeling down the road and even right out from the house was amazing, better than our excursion snorkeling by far!! We saw turtles and tons of fish, it can get a little sketchy near the rocks so be careful. Basically we would go back in a heartbeat! A big mahalo to the owners for sharing their piece of heaven with the rest of us :)

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,600

Hawaii kona home 2 miles from the beach,

Kailua-Kona house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$258

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$1,603

Kona Palm House 3 Bed/2.5 Bath with Pool

Kailua-Kona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$454

Loke Lani luxury home/AC+guest house+pool

Poipu house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$796

Diamond Head Seaside Hideaway

Honolulu house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$2,008

ROMANTIC MAUI BEACH HOME, 3-BR/3 BATH, 3 MINUTES TO BABY BEACH

Paia house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,715

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Price per night from

$592

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$406

Relaxed Home in Oahu's best neighborhood

Honolulu house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 45 minutes

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$2,237

Hale Ohana, Pool, Ocean View Home/Hawaii Kai, Oahu 3+BD/3Bath

Hawaii Kai house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$912

SOUTH MAUI'S SPECTACULAR OCEANFRONT WAILEA SUNSET ESTATE WELCOMES YOU!

Wailea house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

“Truly Spectacular” This house is nothing short of spectacular. We chose this home for a family get-together and it worked perfectly. The Master Suite gave my husband and me the privacy we wanted, while our children and grandchildren had their own privacy. Each bedroom has its own bath. Everything was provided and ready for us upon arrival. We had T-times for golf, paddle boards, sea kayaks, snorkeling gear, as well as high chairs and cribs. Nothing was overlooked. We even took the opportunity to have a private chef (highly recommend just for the experience) cook dinner four different evenings, as well as adding on some additional cleaning. The sunsets were beautiful, the whales were breeching and the turtles surfed up to the rocky beach every night. Because of a tropical storm, we were able to watch professional surfers from our chairs on the grass. The larger hotels are within walking distance, but other than using the Spa facility at the Four Seasons, we felt no reason to leave this beautiful property. The management of Tropical Villa Vacations were extremely professional and easy to work with. For a group I would highly recommend this home. Everyone in our family had such a relaxing get-away that we plan to make this a bi-annual vacation and can't wait for 2016. There is nothing better than spending quality time with family, and this is the house to spend it in...truly spectacular!

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$2,895

Loke Lani luxury home with Pool and AC

Poipu house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$630

“The unit far exceeded out epectations!!” Th villa was as beautiful as presented on line. Very spacious and , well appointed. The kitchen featured high end appliances not normally seen in rental units. Beautiful decor. The owner has clearly put a lot of thought and resources into the comfort of his guests, right down to a fully stocked executive bar to every kitchen gadget you could possibly think of!!! The location was perfect. The unit was strategically located between the adults only and family pools... just s two minute walk to the beach. The concierge and rental agents were a pleasure to deal with and usually responded to any request within a hour. Great unit! Great experience!

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,295

Hale Nalani - Private luxury with a pool and A/C

Princeville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$425

NEW Luxury Rental! Kahala Oceanside-6bed/6bath - Sleeps 14

Honolulu house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$4,016

NEWLY RENOVATED, PRIVATE BEACHFRONT HIDEAWAY ^MOANA^ SLEEPS 8!!

Kihei house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Paradise vacation” Moana Hideaway met all of our families needs. We didn’t even have to rent snorkel equipment because the property provided enough sets for all eight of us. The house is spacious and a single story so the older relatives didn’t have to climb stairs. The sunsets and sunrises were spectacular. Watching the green sea turtles while in the pool made our trip the ultimate Hawaiian experience. The property mgmt group was available for our questions and made sure everything was to our liking. Hoping to return to this amazing property some time in the future.

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$2,995

"WOW IT'S LIKE OUR OWN PRIVATE RESORT!"... recent guest.

Kihei house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,824

LUXURY BEACHFRONT KA'ANAPALI BEACH! FABULOUS SEA SHELLS BEACH HOUSE – Slee

Ka'anapali house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“A Fantastic Home Right on the Beach Where You Wouldn't Expect it” We were looking for a beachfront house on Maui for a family of 7 (one an infant). In the end, we liked the options in Kihei but most were in an area where the beach wasn't great, so we looked at West Maui. This house caught our eye. The house is located on the property where the old Ka'anapali airport used to be until the mid-1980s. While this area is mostly full of resorts, this house is wedged in with a few other properties between the big hotels. The house itself is all about the big family room/sitting area/kitchen which is huge and great. There is a big master bedroom and two other standard bedrooms with one open office corner. The layout of the house is a bit strange - it's not how I would allocate space in my own place, but it was great for a rental. There is a ton of natural light and a great view straight out to the water. The yard area is great with a hammock between two palm trees, a full bbq area, an above ground spa, and a shallow pool. Even though the walkway along the beach is nearby, the landscaping is done so well that you rarely see it. You feel isolated. It's a short walk through that landscaping and you're on a great beach. It's a bit narrower than some other parts of Ka'anapali but it's also much less crowded since it's not in front of a resort. The sand is great, and a reef begins in the ocean just to the north of the property for snorkeling. (We had a nice swim with a turtle.) Our concierge that met us there was very helpful and stayed with us initially to get us oriented, as did the property manager.

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,850

Keoniana Kai - Pool and hot tub with ocean views

Princeville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$800

Kona Bubbles: Pristine Luxury 4 bedroom Home with Amazing Pool & Oceanviews!

Kailua-Kona house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$750

Hualalai 72-105 Pakui~private residence~pool~spa~walking distance to resort

Kailua-Kona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 7 minutes

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$5,888

Kona House of Palms

Kailua-Kona house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$831

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,205

Private home at Hualalai Resort, near Four Seasons. Pool, Spa, Exclusive!

Kailua-Kona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 7 minutes

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$5,888

Honu Kai Hale - Oceanfront home on Kahalu'u Bay

Kailua-Kona house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,033

ULTRA LUXURY SOLARA LUXE POOL VILLA D101, NEWLY RENOVATED, SLEEPS 8!

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“Even more beautiful than the pictures.” We highly recommend Tropical Villa Vacations. Irene helped us find the perfect spot for our vaction. D101 is a beautiful addition to their inventory. The unit is spectacular. The Wailea Beach Villas property is a perfect spot for anyone looking for a luxurious condo in the heart of Wailea. Beautiful property, great ocean views and top notch service from a team that truly cares about your vacation experience!

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,450

Luxurious and Private Maui Home with Swimming Pool

Haiku house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Serenity in Maui” My husband and I spent eight days at this lovely property, and quite simply, was the best house rental, and the best vacation we have ever taken. There are not enough words to tell you how beautiful the home is with all the stunning landscaping, yummy fruit trees,and great, private saltwater pool. The home is immaculate, and luxurious. Extremely clean, and absolutely stunning. Very comfortably furniture and great beds. Claudia, the owner is charming, and will be there when you need her for anything. Please, do yourself a favor and stay in this home. It is paradise!

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,033

Hale Hokuu T00 - Poipu-/Ocean Front/AC/Spouting Ho

Koloa house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$1,549

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!

Kailua house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$653

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$803

Bungalow-Beach House

Kailua-Kona house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$379

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