Vacation Rentals & Condos in Princeville

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Amazing House w/ Pool, Cabana & More Kihei Wailea

Kihei house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

“Best family holiday we have had in ages” This is a really lovely place. The pool area and cabana are private and very user friendly. Beach in the morning and sheltered pool area in the afternoon, ideal with 3 teenagers. Bedrooms are spacious and everything works. We didn't bother with a/c just opened the house up and used the ceiling fans. Plenty of living space and room for people to do their own thing if they wanted to. Close to most things but far enough away from noise and crowds. It helps that Maui is absolutely brilliant. Andrew leaves you alone but is readily available to help with any minor issues. The kids said it was the best family holiday they have been on in ages. We agree.

Responds fast! avg. 3 hours 44 minutes

Match: Jacuzzi or hot tub Private outdoor pool (heated) Secure parking

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Price per night from

$1,430

Ko Olina Beach Villa BT1003 - Ocean Views 10th Floor Sunset and Ocean Views

Kapolei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“First rate all the way” This location goes beyond all expectations. Everyone visiting Hawaii has preconceived ideas and expectations, this condo goes well beyond what you are expecting. I highly suggest this triple a location and enjoy the area! Fabulous

Match: Jacuzzi or hot tub Private outdoor pool (heated) Secure parking

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Price per night from

$681

LUXURY BEACH HOME POOL EXCELLENT LOCATION

Kihei house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Wonderful stay in the perfect home. Great golf and beach locatio” My friends and I stayed in this high-end well-appointed home while we were on Maui. Our main purpose was to fit in as many games of golf as possible as our wives shopped and relaxed by the pools and enjoyed the beaches. This plan worked out perfectly since we were located right on golf course and a short walk from the beach. Everyone was more than happy with our accommodations and being able to rent a spacious home in the center of a luxury resort was ideal. This home was an exceptional value when you consider that most of the hotel rooms in the Wailea/Kihei area go for the same price for just one room. Everyone in our group felt as though this was our own home in Maui and we expect we will return again as soon as we can. We highly recommend this place and would like to thank the owners for extending us their every kindness. Sincerely, Don M

Match: Jacuzzi or hot tub Private outdoor pool (heated) Secure parking

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Price per night from

$5,558

ELEGANT BEACH HOME POOL & VIEW PERFECT LOCATION

Kihei house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Jacuzzi or hot tub Private outdoor pool (heated) Secure parking

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Price per night from

$4,411

“This Place Has Everything You're Looking for on Maui” We really enjoyed staying at Maui Kai 806. The setting suns and moons as well as the layout of the unit, and the extremely helpful staff (especially Rowena) made our stay wonderful. We would recommend this place to our closest friends and relatives. It is ideally situated with access to all that Maui has to offer. Close to terrific beaches (snorkeling, sunning, etc.), close enough to beautiful sightseeing around Maui, and access to wonderful Lahaina, this place is simply amazing. It was my first trip to Hawaii and definitely a 5 star stay. This place rocks!

Match: Jacuzzi or hot tub Private outdoor pool (heated) Secure parking

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Price per night from

$424

Match: Jacuzzi or hot tub Private outdoor pool (heated) Secure parking

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Price per night from

$458

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MAKENA SURF RESORT, #C-102

Wailea apartment

  • 2 bedrooms
  • sleeps 6

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$497

BEST KEPT SECRET ON MAUI. OCEANFRONT 2B, 2B LUXURY CONDO AT AFFORDABLE PRICE

Lahaina apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Peaceful and relaxing” We had a relaxing stay at this condo. The pool and common areas were well kept and our neighbors were polite and friendly. We did not use the beach access here but did drive to nearby beaches. The condo had some upgrades such as the large kitchen island. In fact, the openness of the kitchen to the living room was very nice. We also enjoyed the lanai for eating meals and for whale watching. Watching the sunset from the property was a favorite way to end the day. The amenities were improving with the addition of new washers and driers in the community laundry room. Some may find this condo to be more rustic than luxurious but it met our expectations within the price point as cozy and a nice place to stay after adventure filled days. A big plus is that this condo community seems to attract a very considerate group of people. It was peaceful and relaxing to stay here and our overall impression was favorable.

2 of 3 match: Jacuzzi or hot tub, Private outdoor pool (heated), Secure parking

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Price per night from

$373

2 of 3 match: Jacuzzi or hot tub, Private outdoor pool (heated), Secure parking

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Price per night from

$592

SUGAR BEACH RESORT, #535^

Kihei apartment

  • 2 bedrooms
  • sleeps 6

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$326

WAIKIKI 1BD CRN,FREE PKG,WIFI,NETFLIX,YOU TUBE, BEACH ITEMS,CALLS,

Honolulu apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

“Great” We arrived late after 3 weeks in usa mainland, where we did not stop. Getting our keys and into theunit was so easy. It was so close to get to everything from the unit. We had a family of five and with the sofa bed out it was quite tight. Maybe not so many little tables and trinkets. But that would be our only complaint. Everything was just as the photos showed and a great place for a family. We went and did food shopping at safeway, but then found Wallmart cheaper. Thanks heaps for having us

2 of 3 match: Jacuzzi or hot tub, Private outdoor pool (heated), Secure parking

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Price per night from

$194

OCEANFRONT 1 BEDROOM CONDO SPECTACULAR VIEWS!

Lahaina apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“You Should Be Here!!!” Within the pat 2 years, we have experienced an amazing time in Lahaina. Julie is an amazing person to deal with. Her hospitality has always been sincere and genuine. The condo location is ideal good people. Everything is within walk-in distance. Very clean, comfortable, relaxing with an amazing view of the sunset, sunrise, fresh crosswinds,turtles, whales, and that amazing sound of the ocean that serenade you 24/7. As I said before "You Should Be Here." I plan to every year!!!

2 of 3 match: Jacuzzi or hot tub, Private outdoor pool (heated), Secure parking

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Price per night from

$395

Private, Romantic Cottage, Panoramic Ocean View, King-Bed, Hot Tub

Haiku cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Even better than expected” I stayed at this cottage for 11 nights. I felt so much at home that I did not want to leave, not even to go to the beach. The views are stunning. It is very private and quiet. I really liked the sound of the water fall in the gulch below. The cottage offers anything one can dream of... fully equipped kitchen, washer, dryer, towels, beach chairs, sun umbrellas, deck chairs, BBQ, outside showers, TV, DVD and a very fast and stable internet. Haiku town is only a few minutes by car (3 minutes to be precise) where you can find groceries, restaurants and a fitness centre (which offers weekly and daily passes for tourists). Paia town and beaches can easily be reached within 15 minutes, Makawao town is also around the corner. Barbara and Hank, the owners of this beautiful property, are very nice people and extremely helpful.

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$410

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$689

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$519

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$374

Kihei Garden Estates #C-208 Fully Renovated Loft-Style unit, Shared Hot Tub

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$475

OCEANFRONT ELEGANCE AT OCEAN DREAMS GRAND RESIDENCE 2203 MONTAGE KAPALUA

Kapalua villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“Heavenly” Lovely amenities in this condo...perfect location for our family's activities. Relaxing and the staff is amazing!!! We had a couple issues with the appliances and the staff was there immediately. The entire experience was perfect. The Swimming pool and the private grottos, plantings not to mention the size of it, was awesome.

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$1,750

“Great location at an affordable price!” This little condo was perfect for our needs. The location served as the perfect place for me to experience Waikiki for the first time. Just a short walk to Waikiki beach, Dukes, Island Vintage coffee, and shopping. We really only used the room for showers and sleeping (3 days 2 nights) so the size was just fine. If the stay was longer I would have preferred a more conventional kitchen with a range but we ended up eating out for the most part. Mark was great, very accessible by phone and took care of a little hiccup with the cleaner timely and professionally. I would absolutely stay here again for short trips to Waikiki!

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$144

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

Kihei house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 30 minutes

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$1,824

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$619

NEW Clean Condo; Tropical Gardens; Pool - Hot Tub!

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Clean condominium with all amenities on beautiful grounds” This condominium was absolutely wonderful and provided all the comforts of home while maintaining the feel of a resort. The photos provided were accurate. The kitchen was clean with new silverware and appliances. The carved cupboards added subtle beauty. The rooms were also clean, beds comfortable, and bathrooms clean and stocked. Views from the lanai were so relaxing. As an added bonus, plentiful beach gear was also provided, which made for fun days at the beach each day. Aside from the condo itself, the location was prime and accessible to each part of the island, which we were able to visit. I definitely recommend renting this condo for your trip to Maui.

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$250

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$419

“Incredibly relaxing!” It's a home away from home with everything you might need - with quality stuff too. Bright, beachy, quite and so relaxing.

Responds fast! avg. 59 minutes

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$354

“Wonderful time!” My husband and I had the opportunity to spend 10 days at Tracy's place and loved everyday! She has stocked everything needed to make it a worry free vacation. It was wonderful to watch the sunset each night from our place. Also, there are a bunch of delicious places to eat at nearby. It was nice to be able to bring home leftovers, to enjoy the next day. Highly recommend Tracy's place.

Responds fast! avg. 59 minutes

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$331

OCEAN View Studio w/FREE Parking

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$95

Kaanapali Royal F101 - Updated and Family Friendly.

Lahaina condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$516

Whaler on Kaanapali Studio Ground Floor Condo

Ka'anapali apartment

  • 1 bathroom
  • sleeps 4

“Home away from home.” My third time staying at the condo. Love the location right next to the Whaler's Shops, great value and the beautiful beach just a few steps away from your balcony. Every time I call Larry to make my reservations he is very courteous and helpful. Always a great vacation!!!

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$270

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$351

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

2 of 3 filters match

Price per night from

$351

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

Honolulu house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

2 of 3 filters match

Price per night from

$4,015

Kahana Nui Tropical Estate - Private Oceanside Villa

Napili-Honokowai house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$3,901

One Bedroom, Renovated, Closest to Beach

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$338

“Perfect Stay in Paradise!” Tracy's condo was perfect for our 30th wedding anniversary stay! We would not stay anywhere else on Maui except in one of Tracy's amazing rentals! The condo has a great location (across from the beach) and close to restaurants and shops. It is brightly decorated with happy cheerful colors and special touches! It was like a ray of sunshine! Both my husband and I loved the fact that the condo was well supplied --- everything from shampoo to an ice cooler and more. Tracy has thought of everything you need for a terrific stay --- even electric candles! The bed was so comfortable and relaxing! Tracy's binder on the coffee table was full of tips for a great vacation as well as menus from area restaurants. We loved seeing the large sea turtles swimming in the lagoon section at the beach across the street. The property is extremely clean and well maintained and we enjoyed the pool and jacuzzi at the condo as well. We were sorry to leave and return home. We can't wait to return to stay again at one of Tracy's Tropical Treasures condos! We enjoyed it so much that I have recommended it to a recently engaged friend for her honeymoon. Thank you Tracy for providing such wonderful accommodations and making our 30th wedding anniversary so memorable! We will definitely be back!

Responds fast! avg. 59 minutes

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

2 of 3 filters match

Price per night from

$331

Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach-3 min walk, Remodeled

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

“Relaxing and Beautiful Getaway” My husband and I stayed at 33a in Ekahi for a week long vacation. The condo and surroundings exceeded all of our expectations. It is very tastefully decorated, extremely clean with all the amenities needed for a relaxing getaway. The grounds, pool area and beach are wonderful. The lanai is a serene retreat. We ate all of our breakfasts and lunches out there and then dined on fantastic food for dinner from the many choices of restaurants. The keyless entry and parking were very convenient. We will return next summer with our children.

2 of 3 match: Private outdoor pool (heated), Jacuzzi or hot tub, Secure parking

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Price per night from

$430

Luxury Maalaea Banyans- Perfect Honeymoon Spot! FABULOUS OCEAN VIEWS.

Maalaea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“What a wonderfully relaxing get-a-way!” From the moment we arrived, we received such a warm welcome! Every detail thought of: a welcome basket of fruit, beautiful flowers in the room & all amenities you need in the condo. We loved this unit & thought it was really cozy. The balcony view was fantastic & we could not get enough of whale & turtle watching along with all the daily boat activities.

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$339

Upscale Furnishings, Gorgeous Lawns For Kids

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$218

“A wonderful week on Maui” Maui Kamaole #A-202 in Kihei was a perfect place for my wife and I and two teenage daughters to stay. Plenty of space and a well stocked accomodation made us feel very comfortable for our week long stay.

2 of 3 match: Secure parking, Jacuzzi or hot tub, Private outdoor pool (heated)

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Price per night from

$410

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