Maui Vacation Rentals

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477 condos

Waikiki Beach Resort

Honolulu house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 1 hour 7 minutes

Match: Private outdoor pool (unheated) Staffed property Horse riding

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Price per night from

$3,441

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Celebrate Christmas and New Year’s in Maui!

Ka'anapali villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$803

Kona Palm House 3 Bed/2.5 Bath with Pool

Kailua-Kona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Staffed property, Horse riding, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$454

Renovated Kona Mansion infinity pool & ocean views

Kailua-Kona villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 13

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$3,434

Hilo Private Luxury Suite

Hilo studio

  • Studio
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$207

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$244

Club Wyndham Mauna Loa Village

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$299

Responds fast! avg. 3 hours 10 minutes

2 of 3 match: Horse riding, Private outdoor pool (unheated), Staffed property

2 of 3 filters match

Price per night from

$287

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$493

Maui oceanfront with Lanai and Molokai island view and spectacular sunsets

Napili-Honokowai studio

  • Studio
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$229

Hale Ohana, Pool, Ocean View Home/Hawaii Kai, Oahu 3+BD/3Bath

Hawaii Kai house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 3 match: Staffed property, Horse riding, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$912

Beach Front Hawaiian Princess Corner Unit Condo

Waianae condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$304

Sunshine & Rainbows 402 Valley Isle Resort

Napili-Honokowai apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$270

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

Napili-Honokowai penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$258

Luxury Beachfront with Breathtaking views & AC

Hauula condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$377

Condo at Magic Sands: Brand New Rental, Top Floor, Ocean Views and Quiet

Kailua-Kona condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$274

2 of 3 match: Horse riding, Private outdoor pool (unheated), Staffed property

2 of 3 filters match

Price per night from

$263

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 38 minutes

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$1,275

PEGGY'S PLACE AT KONA REEF HAWAII

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$172

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 (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$270

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 (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$431

Maui ocean front paradise with miles of beach at Menehune Shores

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$276

Christmas 3Bdrm Beachfront Nanea Westin Kaanapali

Ka'anapali villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$4,590

Maui Budget Luxury: 3bd/2ba Modern Beachfront w/Central Air

Kapalua condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$1,033

THE WHALER ON KAANAPALI BEACH LUXURIOUS OCEAN VIEW CORNER UNIT

Ka'anapali condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$798

OCEAN VIEW STUDIO AT BEACH FRONT RESORT

Ka'anapali hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$1,030

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$523

BEACH FRONT RESORT TOP FLOOR STUDIO

Ka'anapali hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), Horse riding, Staffed property

2 of 3 filters match

Price per night from

$1,030

1 of 3 match: Horse riding, Private outdoor pool (unheated), Staffed property

1 of 3 filters match

Price per night from

$75

Leilani Magikal Gardens Bed & Breakfast

Pahoa house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Horse riding, Private outdoor pool (unheated), Staffed property

1 of 3 filters match

Price per night from

$155

1 of 3 match: Horse riding, Staffed property, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$803

Stunning 4-BR Villa Kailua Beach

Kaneohe house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Horse riding, Staffed property, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$630

1 of 3 match: Horse riding, Private outdoor pool (unheated), Staffed property

1 of 3 filters match

Price per night from

$689

Relaxed Home in Oahu's best neighborhood

Honolulu house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 45 minutes

1 of 3 match: Horse riding, Staffed property, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$2,238

Diamond Head Seaside Hideaway

Honolulu house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Horse riding, Staffed property, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$2,008

Spacious Waterfront with Gorgeous Views & Private Pool

Kaneohe villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 3 match: Horse riding, Staffed property, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$2,008

Luxury Bed Oceanfront Villa with Beach Access and Pool in Kailua-Kona

Kailua-Kona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 3 match: Horse riding, Staffed property, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$2,174

Sun, Beach, Golf Romantic Getaway! A Safe Place

Lahaina condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 3 match: Horse riding, Staffed property, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$527

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