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Hawaii Rentals with Pools

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2,849 house rentals in Hawaii with pools

Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!

Honolulu condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$199

Ocean Front Kona Makai Perfect Sunset Views Furnished 1 bedroom Condo

Kailua-Kona condo

1 bedroom / 1 bathroom / sleeps 4

“Execellent and affordable place to stay in Kona.” We have stayed here five times in past seven years. It is definitely our favorite place to stay in Kona. We have visited every Hawaiian island except Lanai. The Big Island is our favorite and the Kona Makai is a wonderful, beautiful, quite and relaxing place to stay. Grills are located on the ocean front. Excellent sunsets with the occasional "green flash." Walk to town, restaurants, church, numerous beaches and stores. We highly recommend it to family and friends.

Responds fast! avg. 38 minutes

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Price per night from

$151

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

Kailua-Kona house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$550

Plantation Hale A1

Kapaa apartment

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 47 minutes

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Price per night from

$125

G405 - Top Floor Incredible Mountain Views **AC** Resort Pool & Restaurant

Kapaa apartment

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$320

VISTAS WAIKOLOA E105 - SPECIAL LOW RATE 2 bedroom, 2 bath Villa! Saline Pool!

Waikoloa apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Vista Wikolia” Great pool for lap swimming. Condo was renovated which made a big difference

Responds fast! avg. 3 minutes

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Price per night from

$209

Direct Oceanfront 1 BR - Valley Isle Resort #1009

Lahaina apartment

1 bedroom / 1 bathroom / sleeps 4

“Fabulous Sunsets and Whale Watching - Room 1009!” I had the great fortune to come to Maui during whale season and was able to see all of the action from my lanai in Room 1009. This room at the Valley Isle is just spectacular! It is private, beautifully decorated and stocked with everything we needed. There were beach chairs, a cooler, and boogie boards which saved us rental money. The view was unbelievable! Watched whales jumping and turtles swimming by. Watched the sunset every night and had magnificent views of Molokai. We will definitely book this room when we come back. Highly recommend it!

Responds fast! avg. 2 hours 0 minutes

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Price per night from

$201

Kahana Reef 212

Lahaina condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$153

One-of-a-Kind Maui Getaway!

Wailea house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 14 minutes

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Price per night from

$1,650

Pili Mai 1-G

Koloa house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 47 minutes

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Price per night from

$286

Oceanfront Condo - Spectacular Views - Low Rates!!

Princeville apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Wow! What a view!” It is with humble apologies to John that I write this review. It's been over a year since we stayed at John's condo in Princeville and, in writing a review for a recent trip to another city, I realized that somehow I never left a review for the time we spent there. We arrived at night, found our way to Princeville and fell asleep listening to the ocean waves. Upon waking, I realized that hearing the ocean was nothing compared to the breathtaking view that greeted me. The beautiful Pacific as far as the eye could see! The view is truly spectacular. There's nothing like being able to whale watch from your Lanai! The condo was large and well-equipped. Perfect for our family of three generations. Our toddler child-tested every nook and cranny of the place and came away unscathed. The complex is located close to several shopping and dining options in Princeville. We also made our way over to the St. Regis for Cocktail hour and sunset views over Hanalei Bay. Princeville is a great place to use as a home base from which to explore Kauai. It is much less touristy than the Southern Beach cities, and close enough to drive to everything. The Northern Coast can be a bit rough in the winter months, but there's still plenty to do. John was a great host. From the first e-mail he was friendly and helpful and worked with us to ensure that our vacation time went smoothly. John helped us coordinate delivery of baby gear (portable crib, high chair, etc.) for our stay and even referred us to a local sitter that he knew. He also generously accommodated our request for a later check out time. A belated, but genuinely heartfelt, Mahalo to you for everything! We can't wait to go back!

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$254

Oceanfront Luxury, Private Pool and Hot Tub

Keaau house

3 bedrooms / 2 bathrooms / sleeps 7

“Beautiful House located in a quiet setting” We loved the house. The sights and sounds of the ocean were spectacular. The rooms were spacious and the kitchen was well stocked. My daughter loved the lap pool and jacuzzi. We were also surprised to come home and find our deposit waiting for us. That was a nice surprise. We would highly recommend this property.

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Price per night from

$515

Amazing House w/ Pool, Cabana & More Kihei Wailea

Kihei house

4 bedrooms / 5 bathrooms / sleeps 12

“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.

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Price per night from

$1,112

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Price per night from

$115

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.

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Price per night from

$600

Beautiful Oceanview Condo-Steps to the Beach

Kapaa condo

1 bedroom / 1 bathroom / sleeps 4

“Cozy & Perfect just like home!” We couldn't have been any happier with this condo!! It had everything we needed or wanted during our vacation to Kauai. The condo was very nice and clean and felt very cozy from the moment we walked in the door. Our favorite place to hang out was the lanai!! The view was 5 stars, there was always a cool breeze blowing, the sound of the waves & taking it all in was absolutely wonderful! I contacted the owners a few times with questions prior to our travels and they were very nice & helpful in answering my questions. I was very impressed with how they sent us a very detailed email right before our stay with specific instructions as to how to get to the condo, phone numbers of who to contact if needed and condo info. I would highly recommend this condo!! Mr & Mrs Merchant, thank you for allowing us to stay in your wonderful condo during our stay in Kauai!! We can't wait to come stay again!! Mahalo!!

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Price per night from

$206

Kamaole Sands -inner court -views-Summer special$$ fill In rate

Kihei apartment

1 bedroom / 2 bathrooms / sleeps 4

“Great place to stay!” We had a wonderful time in Maui and we owe a great part of that to our stay in this condo. It was the perfect retreat and place to come home to after the day's outings. The grounds are beautiful and the condo complex is well located with beaches just across the street and others just a few minutes' drive south. I loved sitting on the lanai and looking out onto a small section of the ocean which was visible through the trees. Judy graciously called us shortly after we arrived to see how we were doing and if she could help us in any way. We would definitely recommend this place to a friend.

Responds fast! avg. 2 hours 43 minutes

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Price per night from

$200

KKSR#5104 DIRECT OCEANFRONT, BEST GROUND FLOOR CORNER! REMODELED!, AC!!!

Kailua-Kona apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Great location” We loved the location, clean , beds comfortable, views were wonderful! We were worried there was no air conditioner but we didn't need it.

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$525

“Kihei Stay” I would consider coming back. Very affordable pricing. The unit has been upgraded (except for the TV). We did spot one cockroach, but those are native to the island. Location isn't uber busy, which I recommend for a mellow/relaxing vacation. I would definitely consider coming back.

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$115

KKSR3202 DIRECT OCEANFRONT, Spacious, 2nd Flr

Kailua-Kona apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great Location” We very much enjoyed our 6 nights in this condo, from morning breakfast on the balcony to watching the sunset. Location is superb - there are 2 beaches within walking distance and you can walk up a short hill to a great espresso and creperie shop. We will stay here again.

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$325

BEACHFRONT three bedroom oceanfront penthouse on the east side

Kapaa apartment

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$600

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

Kapolei apartment

2 bedrooms / 2 bathrooms / sleeps 6

“This place offers the best of all worlds” My boyfriend and I spent a week at this spectacular villa and can't wait to come back next year. We were greeted by Louie upon arrival and he escorted us to our underground parking space and walked us up to the villa. The first thing we noticed when we walked into the villa was the breathaking views; you have the ocean to the left and the mountains to the right. It was the perfect combination of water and nature. Louie explained the resort's amenities, including a fully equiped fitness facilty and lagoon. The villa is tastefully furnished and equipped with all the amenities you would expect from a high end home. We visit Hawaii once a year and have stayed at several high end hotels, including the Royal Hawaiian in Waikiki, Fairmont in Wailea, etc., and this villa is up there with the best accommodations the islands have to offer. The best part of the stay was that we always looked forward to coming back to the relaxing atmosphere of the villa. We often drove to Waikiki for shopping or to visit friends during the day, and enjoyed coming back to the Ko Olina area at night as it was peaceful and quiet compared to the hustle and bustle of Waikiki. The drive is only about 35 minutes so we truly had the best of both worlds in staying at this resort. We also enjoyed walking from the villa to Roy's for their happy hour specials as well as the shopping center nearby. There is a small market and a good variety of food and restaurants at the shopping center. We feel like we've uncovered a hidden treasure by finding this place. We are excited to return soon!

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$532

“Fantastic Kam Sands Condo!!!” We have stayed at Kamaole Sands a number of times now, and this is the best unit that we have found. The condo if very nicely upgraded, it has been very well maintained, and Joe and Gee have taken great care to make sure that it is fully stocked with all that you might need. Don't hesitate to book this one - you will be very impressed!!! Allen

Responds fast! avg. 20 minutes

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$175

Milowai #204--Tropical Maui Oceanfront Condo

Maalaea apartment

1 bedroom / 1 bathroom / sleeps 4

“Breathtakingly beautiful” From the morning sunrises with coffee on the lanai to the afternoon/evenings watching the turtles this place is simply amazing. It is very quiet away from the hustle and bustle of being near all the hotels yet very centrally located and easy to get anywhere on the island. We didn't want to leave and can't wait to come back. This will be our Maui home unless we do something crazy and invest in our own piece of paradise

Responds fast! avg. 48 minutes

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Price per night from

$195

Wailea Ekolu #201 2Bd/2Ba Ocean View Condo Near Beach, A/C, Wifi, Sleeps 6

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$250

Papakea Resort, Unit G-407

Ka'anapali apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great condo, Great Location!” Great condo, great location! ★ ★ ★ ★ ★ We recently returned home from a 10 day stay at Papakea G-407! I wish I could have stayed forever! The condo is in a great location convenient to several gorgeous beaches and a short drive to Lahaina town. We had all the conveniences needed to prepare meals in and enjoyed dinner on the lanai several evenings with a beautiful sunset! Anne provided a great deal of information on the area as well as helpful hints for shopping, sightseeing, etc. The grounds at Papakea are absolutely beautiful! There are two great pools as well as two large jacuzzis. We will definitely return to this condo on our next visit to beautiful Maui! Thank you, Anne and Wes for sharing your home with us! Tina and Bob

Responds fast! avg. 37 minutes

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Price per night from

$340

Waiohuli Beach Hale #B-206 Ocean View Oceanfront 1Bd/1Ba Great Rates Sleeps 4

Kihei apartment

1 bedroom / 1 bathroom / sleeps 4

“Maui journey july 2013” 5 nights journey in Kihei to explore major key spots of the island.

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$179

Kihei Bay Vista #C-106 Best Location, Garden View, Sleeps 4, Great Rates!

Kihei apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$125

Wailea Ekolu #406 2BD/2BA Panoramic Ocean View Near Beach, Full A/C, Sleeps 4

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$330

Kona Plaza#402 TOP FLOOR OCEAN VIEW IN HEART OF KONA TOWN! AC & Elevators!

Kailua-Kona condo

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$200

306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai.

Kailua-Kona apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Trip to Paradise” The condo was amazing, no expense was spared. Great beds, furniture, cookware, everything. We watched surfers from the lanai nearly every day, and the sunsets were the most spectacular we've ever seen. A car is needed for this location - honestly like all locations on the island, a car is absolutely needed to be able to fully experience and appreciate the big island. We absolutely would love to stay again. Kyle was an amazing host, and the big island was like no place we've ever seen in our lives. Truly a paradise on earth!

Responds fast! avg. 1 hour 10 minutes

Match: Swimming pool

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Price per night from

$275

Kihei Bay Vista #A-102 1Bd/1Ba Across From The Beach Great Rates! Sleeps 4

Kihei apartment

1 bedroom / 1 bathroom / sleeps 4

“Great Stay in Kihei” The property was excellent and well furnished. The provided accessories really made it worthwhile and could not have been better. The only thing we would have liked to see would have been a curtain or light blocking covering in the bedroom window to stop the early morning sunlight...not a negative for early risers, but for us sleep inners, a nice to have. Otherwise this is the best furnished and set up property we have rented...especially for the excellent price. We would definitely recommend this place to others and will use it again the next time we return to Maui..Mahalo and Aloha

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Price per night from

$125

Special! Maui Sunset 502B, 1 BR, 2 BA with Partial Ocean View

Kihei apartment

1 bedroom / 2 bathrooms / sleeps 4

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$165

The most Gorgeous 2bd2ba OV Villa in Kapalua!

Kapalua hotel apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Every morning on the patio, with a cup of coffee, made us realiz” We had a wonderful time in Maui and your home was so comfortable and up to date. It had everything we needed, and the coffee table book you put together (with all the suggestions of things to do & where to eat) was so helpful. Before arriving, we were skeptical of being on the first floor but it was absolutely the best place to be. And the view... down the fairway right down to the waves crashing on the coast!!! Breathtaking!!! I will pass along your condo information to our friends who are looking to visit Maui.

Responds fast! avg. 3 hours 58 minutes

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Price per night from

$487

OCEAN VIEW Poipu Bliss** FAST WIFI** Ground Floor**

Koloa condo

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$209

Kapaa Shore 117

Kapaa apartment

1 bedroom / 1 bathroom / sleeps 4

“Great Condo, Beautiful grounds.” This condo is kept in great conditions from the room itself to the grounds & pool. It was very easy to feel comfortable here. The kitchen was equipped with everything needed and then some. We utilized the pool area a lot, and the lawn chairs on the beach. I was concerned about not having a laundry right in the room but the shared laundry is very close to the room it wasn't a problem at all. If it was just my husband and I this would have been a 5 star in our books. My only "complaint" (if you can even call it that) was that we rented a pack n play for our daughter for the week and when we arrived to the condo at 10pm we tried setting it up but it kept collapsing. It was extremely old/warn out so we had to go to Kmart the next day and purchase a new one which was a bit of a blow. Also the floors of the condo are very creaky so it was hard to keep quiet walking around while the baby was sleeping. aside from the creaky floors and pack n play (which isn't worth getting bent out of shape about) this place was worth every penny spent and we were very impressed, we highly recommend, especially for a couple! PS to the owner: We ended up staying at one of your rental homes in Aliomanu Bay for our second half of our vacation and left the new pack n play there. Maybe it can be put in this condo for future guests!?

Responds fast! avg. 3 hours 47 minutes

Match: Swimming pool

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Price per night from

$125

Keauhou Gardens 11-303 1 BR, 1.5 BA Oceanview

Kailua-Kona condo

1 bedroom / 2 bathrooms / sleeps 2

Responds fast! avg. 3 hours 4 minutes

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Price per night from

$131

Luxury at the Beach

Makaha apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 0 minutes

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Price per night from

$150

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