Vacation Rentals & Apartments in Kailua

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Luxury Home, Awesome Views, Heated Pool, in town

Kailua-Kona house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Games room Private outdoor pool (heated)

All filters match

Price per night from

$916

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MAKENA SURF RESORT, #C-102

Wailea apartment

  • 2 bedrooms
  • sleeps 6

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$496

Honolulu's Luxurious Cliff House (Min 30-days)

Hawaii Kai house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 12

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$3,432

SUGAR BEACH RESORT, #535^

Kihei apartment

  • 2 bedrooms
  • sleeps 6

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$325

Quintessential of luxury

Keauhou house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 47 minutes

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,316

Ocean View Deluxe Condo Minutes from Lahaina w/ Beach Access & Resort Pool

Napili-Honokowai house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Private outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$525

Partial Ocean View Condo Near Lahaina w/ WiFi, Beach Access & Resort Pool

Napili-Honokowai house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Private outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$433

Conveniently Located Waikiki Studio with Parking

Honolulu studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Private outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$177

Kolea 16A

Waikoloa villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$591

NEW, BEACHFRONT KONA REEF ALOHA CONDO WITH A/C

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$300

Exclusive Home at Hualalai | Heated Pool | Hot Tub | Ocean Views | Cottage

Kailua-Kona house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$6,975

KONA REEF D-17: DIRECT OCEANFRONT, REMODELED, AIR CONDITIONING, ELEVATORS!

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$425

Cozy Condo Minutes from Lahaina w/ WiFi, Beach Access & Resort Pool

Napili-Honokowai house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Private outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$362

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Private outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$327

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Private outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$193

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

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$475

“Great 2 bdrm condo in central location” Very nice home away from home.Great location, convenient to lots of activities. Will recommend to friends and family.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$620

Mahina Surf Unit 227

Lahaina apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$280

“Wiohuli Beach” Love it here and will come back. People are friendly and nice. Clean and relaxing.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$442

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$519

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$374

“A sweet sunset view, right on the ocean” The unit was fine; very clean and quiet, on the second floor with a terrace with an ocean view. We were glad to find plenty of towels, sheets, kitchen equipment, and even beach chairs and umbrellas. The grounds are beautiful and well maintained. We did notice a few unsavory characters hanging out and drinking nearby, but we never felt in danger from them. The beach, though pretty, isn't great for swimming, but happily, we spotted sea turtles feeding along the shore at sunset several times. And terrific swimming/snorkeling beaches are a quick drive away.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$440

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$770

“Good stay” Good stay

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$422

“Wonderful in every way” We loved the size, cleanliness, and amenities of this condo. The price was well worth it. Its location is perfect for exploring all of Maui, but especially the southern area. We will be back.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$464

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$413

“This was a great place to stay in Kehei.” The pool was great. The unit was very nice and was just what we needed. The beach was nice for sunsets and sunrises and walks on the beach but the one draw back was there was a large amount of seaweed on the beach and in the water which made swimming there not very desirable. There are other great Beaches for swimming and snorkeling not very far away.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$440

“Zowie in Maui” The rental had the most equipped kitchen I've ever stayed in. The place was spacious and I love the art work throughout. The beds were comfortable. I liked the view and the proximity to the grocery store. The pool was lovely. It wasn't a place I would want to hang out in though, and the beach isn't that great; but we loved it for its cleanliness and proximity to various "day trip destinations" like the road to Hana, Haleakana, Big Beach, a coral reserve, a farmer's market, the Iao Needle, etc. in Maui. We enjoyed our stay. The only problem I had is that I wish we could have paid the entire fee by credit card and I would have glad paid an extra fee to do so for the convenience.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$389

“Great place to stay!” Great location, clean, affordable, comfortable, helpful owners/management.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$569

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$608

“The view... sigh, the view” We stayed on Maui for a week and really enjoyed the central location and ocean view from this property. It's big and comfortable enough for two people and the updates to the unit did not go unnoticed. Would definitely stay again if we were lucky enough to come back!

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$392

“127” This is a wonderful place to stay. It's almost heaven...watching the ocean, swimming in the great pool, really nice other tenants and great location.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$569

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$442

“First Maui Visit” This was a great spot for the kids and to relax. Beach was just a walk across the grounds which made it convenient for all of us and reduced the stress of traveling. We had three condos all close together which made it a great trip for all of us.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$464

“Our Maui Holiday” Although I didn't personally stay in #214 ..... I rented that unit for my daughter and her children, I know they had a wonderful time but did leave a short list of items that were of concern. It is a beautiful location and a wonderful place to holiday.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$405

“Maui” WE loved the location, and the extra snorkel gear in the patio box was perfect. The property was well cared for but could have been cleaner. The bathroom needed a good wipe when we arrived. But I would absolutely recommend this property.

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$422

Kamahana 3

Princeville condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$142

1 of 2 match: Games room, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,108

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