Vacation Rentals & Apartments in Kailua

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67 apartments

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 58 minutes

Match: Cot available Table tennis

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Price per night from

$1,429

Luxury Princeville Retreat - Sleeps 16 Views, Golf

Princeville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 16

Responds fast! avg. 47 minutes

Match: Cot available Table tennis

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Price per night from

$665

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North Shore of Maui - 2bd-2bath

Paia apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$516

A Tortise and Bird Refuge

Lahaina private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$159

Amazing Ohana Retreat on the Big Island 8 bedrooms

Kailua-Kona house

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 18

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$1,598

Beautiful Hanalei Home One Block to Beach at Hanalei Bay

Hanalei house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 55 minutes

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$801

Newly listed luxury home - great location, views and AC

Princeville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$630

Waikiki Banyan: Pool, Jacuzzi, Sauna, Free Parking, AC, Wi-Fi, Mountain View

Honolulu apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$223

Ocean view #201

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 22 minutes

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$331

North Shore 3BR Ohana - A/C, WiFi, Comfort

Kahuku house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 47 minutes

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$289

Beautiful Property, on Ka'anapali Beach, Maui!!

Lahaina condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$343

Large Family Friendly, Re-modeled Princeville Home

Princeville house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$1,028

Westin Maui - 1 bedroom

Ka'anapali villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$817

Actual Owner! 2 bedroom Villa / Oceanfront - Sleeps 8 - All dates

Lahaina villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 8 minutes

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$637

Wailea Ekahi 11f: Ocean View/Remodel 2 BR Condo

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful condo in Paradise!” Our stay at Ekahi Villiage 11F was nothing short of wonderful. The beautiful, well appointed condo is just a short walk to the pool pavilion and beach. We enjoyed many mornings sipping coffee on the well decorated Lani over looking the manicured grounds and ocean. We will be sure to book 11F again the next time we plan a trip to Maui!

Responds fast! avg. 1 hour 32 minutes

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$972

Beach Front Hawaiian Princess Corner Unit Condo

Waianae condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$303

Private, Gated Residence, Panoramic Ocean Sunset Views

Kailua-Kona house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Cot available, Table tennis

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Price per night from

$1,250

Responds fast! avg. 1 hour 35 minutes

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$343

Maui oceanfront with Lanai and Molokai island view and spectacular sunsets

Napili-Honokowai studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Cot available, Table tennis

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Price per night from

$228

Stunning 1 Bedroom with Ocean and Island Views ~ Sleeps 4 ~ Royal Kahana 514

Napili-Honokowai condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Table tennis

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Price per night from

$197

Rent your own 6500 sf Bed and Breakfast

Kalaoa b&b

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Cot available, Table tennis

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Price per night from

$951

PENTHOUSE WOW! OCEANFRONT, Hear The Waves, Balcony ,AC. Pool

Napili-Honokowai penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$258

Kaanapali Royal F101 - Updated and Family Friendly.

Lahaina condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$516

Relax and Enjoy Spectacular Oceanfront Views!

Napili-Honokowai condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Table tennis

1 of 2 filters match

Price per night from

$297

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

Kailua-Kona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Amazing place!” We loved our stay at the Banyan Tree Condos. The highlight is, without a doubt, having breakfast on the deck watching the waves and the surfers. This condo has everything you'd possibly need for your stay and I highly recommend it. Next time we're on the Big Island, this is definitely where we'll be staying!

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$286

Honua Kai! HUGE 1 BED (248)

Ka'anapali apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Our First Maui Vacation” My girlfriend and I have used Vrbo before, for properties in Europe and have never had an issue. Jill and Terry did not disappoint! The Honua Kai property and more specifically the unit we stayed in owned by Jill and Terry was absolutely incredible! I think it's rated as 4 stars, but clearly it was closer to 5 stars in our opinion. The description and photos on the unit were quite accurate. Jill was amazing with customer service and always helped us when needed. The amount of local information made available to us in the form of a very big binder or two in their condo was awesome. The condo unit was very clean and tidy when we arrived. We highly recommend a visit to Honolua Bay to go snorkling. It's only about a 15 minutes drive from the property, and worth the visit! It's a rocky beach, so leave the beach chairs at home and just take towels and snorkel equipment with you. Also, if you're a foodie, check out Roy's, about 5 miles south of Honua Kai. As well, Duke's is on the Honua Kai resort property and it's an awesome restaurant for drinks, lunch and dinner-highly recommend both Dukes and Roy's. We also went to the Old Lahaina Luau one night, and boy it was just amazing! Great entertainment and food. We would recommend this property to anyone, and have already done so with our friends.

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$457

Garden view 1BR/1BA (sleeps 4) Kihei Condo by Kamaole 2 Beach (#125)

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$201

RENOVATED & SPACIOUS 798 SQ FT Ocean View Suite + Den, FREE PARKING

Honolulu hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$158

Stunning Corner Unit 3BD OCEAN VILLA w/Ocean Views From All Rooms!

Kawela Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 26 minutes

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$1,271

Adorable new Ohana house in a gated community

Makaha cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$258

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$372

Ocean View #200

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 22 minutes

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$342

Oceanfront Family Retreat - Views, A/C & Wi-Fi

Kaaawa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 47 minutes

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$494

Oceanfront Family Retreat - Views, Wi-fi & A/C

Kaaawa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 47 minutes

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$510

Oceanfront Family Retreat - Large Groups Sleeps 20+

Kaaawa house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 24

Responds fast! avg. 47 minutes

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$1,240

1 BR/1BA (Sleeps 4) Kihei Condo by Kamaole II Beach (#252)

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great stay” Spent 2 weeks here and was not disappointed at all, it met all of our needs. The condo was very clean, kitchen we'll stocked, and most important was the bed was very comfortable. There was never any noise problems day or night. It's in a great location, short walk to lots of restaurants, gift shops, and. Of course the ice cream shop. Condo us also furnished with snorkel gear, beach chairs, and mats. If you stay here you will not be disappointed.

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$206

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!

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$1,030

Waikiki Banyan Corner Unit - Beautiful Ocean View

Kahala condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Cot available

1 of 2 filters match

Price per night from

$171

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