Vacation Rentals & Apartments in Kailua

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1,238 apartments

Beautiful, luxury Resort Condo with LOW rates!

Kihei apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Vaca” We loved it! We loved the location, easy access to multiple beach parks, eating and shopping. Can't wait to go back!

Match: Jacuzzi or hot tub Smoking allowed

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Price per night from

$194

Maui Chalet - tropical North Shore private retreat

Haiku chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Jacuzzi or hot tub Smoking allowed

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Price per night from

$418

Unique Artist Condo's Home refreshed Spring 2019

Kihei apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great island feel, clean, all the amenities you’d ever want, and close to it all.” We used this as the perfect spot to start and end our days. Stopped at Costco on way from the airport to get our basics. Had a homemade breakfast and dinner most nights and packed a few picnics. Great information supplied on which restaurants and attractions to see supplied by the owner. The decore was so adorable in the unit it was great to come home to. The unit was clean and had everything we needed. The pool and hot tub were immaculate as well. After exploring the island it was soothing to relax here. We even got a chance to see our beloved Toronto Maple leafs play thanks to the Great cable coverage. Walked across to the beach several times and saw turtles and whales. Can’t wait to come back.

Match: Jacuzzi or hot tub Smoking allowed

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Price per night from

$292

Hawaii kona home 2 miles from the beach,

Kailua-Kona house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Jacuzzi or hot tub Smoking allowed

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Price per night from

$258

Kahana Nui Tropical Estate - Private Oceanside Villa

Napili-Honokowai house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Jacuzzi or hot tub Smoking allowed

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Price per night from

$3,893

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Dolphin House

Kahaluu-Keauhou house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,106

A Tortoise and Bird Refuge #2

Lahaina private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$194

Quiet Hanauma Bay Hideaway

Hawaii Kai studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$138

Spacious 3-Bedroom, 2-Bath Apartment with Kitchen and AC

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$242

Stylish 1-Bedroom Apartment with AC* Just Moments from Kailua Beach

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

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Price per night from

$149

THIS is Peace & Quiet... *Kohala Lodge* Exceeded our Expectations!

Kohala Coast house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Absolument Magnifique!” Visited from the South of France in January 2013 and just loved it! These buccolic and splendid homestead, far enough from the heat and crowds of Kona, is set in the middle of rolling pastures, with a splendid view of the ocean! The cabin is rustic, yet refined and extremely comfortable! Chris and Carol have a wonderful eye for details and a great sense of aesthetics. The house is located near the charming and laid back town of Hawi which, by the way, has a gorgeous banyan tree, and a lovely farmers market under it, where Chris and his band play bluegrass music! It doesn't get any better...This is truly paradise!!!

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$572

*Beautiful and Cheerful Hale Mokolea in Lanikai*

Kailua cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$245

WAILEA ELUA, #0702

Wailea apartment

  • 2 bedrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$409

Kona Islander Inn 336

Kailua-Kona studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$155

Kamaole Beach Royale 1 Bedroom Seaviews

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 6 minutes

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$258

A Tortise and Bird Refuge

Lahaina private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$160

Elegant Queen's Royal Suite in the Boutique Vegan BnB

Hawi b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$480

Large 2BD/2BA Kahala Beach Front Condo Furnished

Kahala apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Smoking allowed

1 of 2 filters match

Price per night from

$384

2 Bedroom, 2 Bath Oceanview Penthouse Condo! Walk to the Beach!

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 20 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$286

MAKENA SURF RESORT, #C-102

Wailea apartment

  • 2 bedrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$496

Sunset Shores - Waialua Oceanfront Retreat

Waialua condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$196

Waikoloa Villas G 201 w Ocean views

Waikoloa condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$196

Waikoloa Villas B 202 Golf and Ocean Views

Waikoloa condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$161

Ground floor 2 bedroom 2 bath Condo in Waikoloa

Waikoloa condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$149

16TH FLOOR CONDO -1.5 BLOCK FROM WAIKIKI BEACH

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$212

Kaanapali Shores panoramic ocean - view sleeps 4

Ka'anapali apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$344

SUGAR BEACH RESORT, #535^

Kihei apartment

  • 2 bedrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$325

Vista Waikoloa G306

Waikoloa condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$283

Kihei Bay Surf B113

Kihei studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$190

Waikoloa Villa The House of Heavenly Aloha

Waikoloa condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$173

Vista Waikoloa F104 with views

Puako condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$235

Spacious Downtown Executive Retreat - Free Parking

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

30 Day Rental in Waikiki with Parking!

Honolulu studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$110

Idyllic Waikoloa Retreat w Ocean View Easy Golf

Waikoloa condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$203

Stunning skyview, pool, fabulous location!

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$319

Shores Banyan Tower 322

Puako condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$245

Kihei Bay Surf D142 A Safe Place to Stay

Kihei studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$172

Surf & Racquet Club Lovely open and airy 2bd/2bth 2nd floor unit.

Kailua-Kona condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Smoking allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$249

Viewing 38 of 1,238
rentals in Kailua

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