50 Best Maui Vacation rentals on Holiday Lettings - Condos

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Vacation rentals Lahaina
1,062 properties
Condos Kihei
744 properties
Condos Wailea
264 properties
Ka'anapali
180 properties
Condos Napili-Honokowai
109 properties
Villas Kapalua
85 properties
Apartments Wailuku
79 properties
Condos Maalaea
57 properties
Vacation rentals Paia
27 properties
Haiku
25 properties
Vacation rentals Hana
13 properties
Makawao
10 properties
Kula
7 properties

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2,676 Vacation rentals

23

Vacation studio with shared pool in Ka'anapali

Maui / Ka'anapali

Studio 3 4 nights min

  • Studio
  • sleeps 3
  • 4 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Experience breathtaking views of the ocean, tropical gardens and newly renovated garden pool from one of the best vantage points in the entire complex. If the daytime views of the ocean and the island of Lanai aren't enough, wait until sunset when you see the tiki torc …see more

from $175 / night

$1,225 / week

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from $175 / night

12

Vacation home in Huelo

Maui / Huelo

2 5 5 nights min

  • 2 bedrooms
  • sleeps 5
  • 5 nights min
  • Child friendly
  • Pet friendly
A Magical Location with WATERFALL hike, Wonderful Panoramic Ocean Views from the cottage & a large very private back yard with out a neighbor in sight! Surround with nature preserve this is a taste of old Hawaii! Nature Activities & beaches 15 mins away! A Fun Nature P …see more

from $128 / night

$896 / week

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from $128 / night

(1)  

21

Vacation condo with shared pool in Kihei

Maui / Kihei

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Kamaole Sands is an award-winning condo complex situated just across from one of the best beaches on Maui. Kamaole Sands III beach, is recognized as one of the best beaches in Maui. Boogie board, surf, snorkel straight off the beach. We have seen turtles, Manta rays and …see more

from $219 / night

$1,533 / week

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from $219 / night

68

Condo rental in Wailuku

Maui / Wailuku

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
~~~Your own private window to the whales. Conveniently situated in quaint Maalaea Village. We invite you to come aboard, and set sail into a radiant Maui sunset. You'll see whimsical turtles playing peekaboo in the gentle surf (year round) and magnificent humpback wh …see more

from $300 / night

$2,100 / week

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Responds fast!
avg. 1 hour 17 minutes

from $300 / night

16

Vacation studio in Lahaina

Maui / Lahaina

Studio 4 7 nights min

  • Studio
  • sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Our "Studio Premium" is the most affordable unit you can book at the luxurious Westin Kaanapali Ocean Resort and has all Westin amenities including king-size "heavenly" bed and queen-size sofa, whirlpool bath, lanai and all the facilities available at the resort. A wint …see more

from $400 / night

$1,990 / week

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from $400 / night

10

Kihei Vacation condo rental

Maui / Kihei

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Child friendly
Welcome to this home away from home. This is a lovely, well-maintained 1 bedroom condo in the family friendly complex of Hale Kamaole. Walking distance to Kamaole II and III, shopping, restaurants, and parks. Complex has 2 pools, gas and coal BBQs, and a tennis court, a …see more

from $152 / night

$1,064 / week

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from $152 / night

(1) Good 

6

Vacation studio rental

Maui / Lahaina

Studio 4 7 nights min

  • Studio
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
*** this is for a Studio Premium unit*** This property is 3 minutes walk from the beach. Set between North Ka’anapali Beach and the mountains of West Maui, this Lahaina, Hawaii resort features 6 outdoor pools. It has spacious villas with views of the ocean or island. …see more

from $399 / night

$2,793 / week

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from $399 / night

20

Vacation home in Lahaina

Maui / Lahaina

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
272-3 Upscale Oceanfront Townhome 272-3 is an upcale 3 bedroom 3.5 bath oceanfront unit with bikes, steps to the beach ccess, a lot of ocean stuff and a very well equipped kitchen . The unit has a Mr. Coffee pot and a Keurig coffee machine a we …see more

from $610 / night

$4,270 / week

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from $610 / night

20

Vacation condo in Kihei

Maui / Kihei

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
1 bedroom corner unit. Close to beachfront, bbq's and pool. Located on a 5 mile sandy beach, ideal for taking long walks. Surf is calm, activities include kayaking, paddle boarding and snorkelling. Condo has recently been updated with new bathroom, flooring and furnishi …see more

from $160 / night

$1,120 / week

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from $160 / night

12

Vacation apartment with shared pool in Ka'anapali

Maui / Ka'anapali

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
New Westin Nanea Premium resort with full access to adjacent Westin property. 4 pools including kids pool, water slides, hot tubs, several semi private pools, etc. On the beach with private beach lounge chairs included. Snorkelling off the beach. Full service hotel with …see more

from $400 / night

$2,800 - $4,550 / week

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from $400 / night

(28) Very Good 

21

Vacation home in Ka'anapali

Maui / Ka'anapali

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Ask about children
  • Ask about pets
Maui Eldorado A203, enjoy spectacular views of the ocean and golf course, 15 minute walk to Whaler's Village shops and restaurants. The updated kitchen is made for the gourmet chef with granite countertops and new stainless appliances, offering a configuration that is p …see more

from $170 / night

$1,190 / week

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Responds fast!
avg. 2 hours 46 minutes

from $170 / night

27

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our remodeled villa has all of the modern amenities of home! It is situated half way between Kaanapali and Kapalua Bay with plenty of shopping and restaurants near by. This beautifully furnished 2 bedroom 1 bath condo sleeps up to 6 people and has a large lanai that ove …see more

from $160 / night

$1,051 - $1,597 / week

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Responds fast!
avg. 3 hours 12 minutes

from $160 / night

24

Vacation home in Kapalua

Maui / Kapalua

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
Welcome to Hale O Kapalua which translates to 'Home where arms embrace the sea'. Hale O Kapalua is one of the newest additions to the Platinum Maui Vacations Ohana. We are excited to add this unique top row, 1 bedroom, 2 bath Kapalua Golf Villa with Amazing Ocean Views …see more

from $199 / night

$1,393 - $2,093 / week

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Responds fast!
avg. 1 hour 55 minutes

from $199 / night

(3) Excellent 

24

Lahaina Vacation apartment rental

Maui / Lahaina

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
Introducing Maui Resort Rentals – Luxury Vacation Rentals By Maui Resort Realty... — Licensed Maui real estate brokerage & property manager specializing in resort real estate…we are the only company with 8000+ sq. ft. of office and warehouse space just steps from Honua …see more

from $210 / night

$1,470 - $4,970 / week

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avg. 1 hour 16 minutes

from $210 / night

33

Vacation home in Hana

Maui / Hana

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
The Hana Ocean Palms Bungalow is located across from one of Hana’s most beautiful oceanfront pools; Waioka Pond (Venus Pool). The property is nestled in a coconut palm grove and surrounded by almost an acre of lush tropical flowers, fruit trees and bamboo. Pick avocados …see more

from $335 / night

$2,345 / week

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from $335 / night

(8) Excellent 

29

Vacation apartment in Lahaina

Maui / Lahaina

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Ask about children
This is the best location on Maui! From your private lanai, enjoy an ever-changing ocean show of beautiful sunsets, sunrises and rainbows over the islands of Lanai and Molokai. Enjoy seasonal whale watching. In addition, sea turtles swim and feed at the water edge daily …see more

from $139 / night

$973 - $1,750 / week

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Responds fast!
avg. 3 hours 28 minutes

from $139 / night

(2) Excellent 

14

Vacation condo with shared pool in Maalaea

Maui / Maalaea

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Newly renovated unit on the ground floor with direct access to Sugar Beach, Maui's longest white sand beach. Literally take 10 steps off your lanai and you're on the beach. Located in the Hono Kai condominium complex this corner unit offers views of Haleakala, Kihei, …see more

from $165 / night

$1,155 / week

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Responds fast!
avg. 1 hour 7 minutes

from $165 / night

(25) Excellent 

14

Vacation hotel apartment rental

Maui / Lahaina

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Serious inquiries only. We are charged for each one. Ask about discounts for Military, law enforcement, seniors, disabled, local stays. .Welcome to Valley Isle Resort, an ocean front property where you can feel the sand beneath your feet and the sea on your face. Come …see more

from $121 / night

$847 / week

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from $121 / night

(5) Excellent 

29

Kihei Vacation apartment rental

Maui / Kihei

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Aloha and welcome!! This unit is a large, tastefully furnished, one bedroom, one bath condo with a huge lanai overlooking the lush tropical gardens of Kihei Resort Kihei Resort is a perfect private little getaway, it is lushly landscaped, with a pool, spa and BBQ area. …see more

from $142 / night

$994 / week

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Responds fast!
avg. 2 hours 39 minutes

from $142 / night

(26) Very Good 

23

Vacation tented camp in Hana

Maui / Hana

1 8 1 night min

  • 1 bedroom
  • sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
Hana Camping under the Stars! Gorgeous campground at picturesque setting by volcanic Black Sand Beach & freshwater pool caves. Both are great for swimming! Campground features free parking, restrooms, running water & picnic tables. We provide complete camping equipm …see more

from $60 / night

$420 / week

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from $60 / night

(1) Excellent 

41

Vacation condo with shared pool in Kihei

Maui / Kihei

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Gorgeously updated 1 bedroom with AC- right on the beach! This unit has 2 full bathrooms, a great kitchen, a lanai with ocean view. With one Queen in the bedroom, two twin pullout sleeper ottomans, a leather folding sleeper futon, and additional queen and twin air matt …see more

from $149 / night

$1,043 - $1,603 / week

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Responds fast!
avg. 3 hours 28 minutes

from $149 / night

(24) Excellent 

Certificate of Excellence

37

Cottage rental in Paia

Maui / Paia

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
MAUI NORTH SHORE OCEAN VIEW Maui by the Sea is a beautiful vacation rental - an ideal ocean-view cottage located between Paia and Hookipa, on Maui's scenic and exciting North Shore. Our two-story plantation-style cottage has gorgeous views of a sapphire ocean with danc …see more

Certificate of Excellence

from $295 / night

$2,065 / week

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Responds fast!
avg. 46 minutes

from $295 / night

(7) Excellent 

44

Vacation condo rental

Maui / Wailea

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
5 Star Property located across from Kihei's favorite beach. 2 roomy bedrooms and 2 bath unit with many high quality, unique upgrades rarely found in a vacation rental: sea turtles inlaid in the porcelain tile flooring, beautiful mulberry flooring leading to and in the u …see more

from $150 / night

$995 - $1,200 / week

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from $150 / night

(4) Excellent 

24

Apartment rental in Lahaina

Maui / Lahaina

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Royal Kahana Resorts boast one of the best locations in West Maui / Kahana area. The Royal Kahana is situated on a quiet, sandy 1/2 mile of beachfront. We share our beachfront with visiting Turtles and passing whales. We are located between Kaanapali Beach Resort a …see more

from $165 / night

$1,155 / week

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Responds fast!
avg. 56 minutes

from $165 / night

(36) Excellent 

33

Vacation apartment rental

Maui / Ka'anapali

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Suite 802. The Whaler Maui. Luxurious 2 bedroom / 2 bathroom privately owned oceanfront corner condominium located on Kaanapali Beach, Maui, Hawaii. Unobstructed views of the Pacific Ocean, Molokai Channel, Kaanapali Beach, famous Black Rock, and neighboring islands …see more

from $750 / night

$5,250 - $5,775 / week

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Responds fast!
avg. 20 minutes

from $750 / night

(20) Excellent 

38

Vacation hotel apartment with golf nearby in Ka'anapali

Maui / Ka'anapali

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
GoVisitMaui presents unit Konea 106 at Honua Kai. Before booking, please read the Known Construction / Maintenance Disclaimer at the bottom of this description. The unit is a 945 square foot (plus 325 sq ft Lanai/Garden), 2 bedroom / 1 bath luxury condo, and it inclu …see more

from $405 / night

$1,675 - $4,025 / week

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Responds fast!
avg. 2 hours 41 minutes

from $405 / night

(1) Excellent 

15

Vacation apartment in Wailea

Maui / Wailea

2 8 4 nights min

  • 2 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 1 mi
  • Child friendly
Our spacious Wailea Ekolu Condominium is fully appointed and includes phone, radio, CD/DVD player, cable TV, and WiFi Internet connection. Three flat screen TVs have been installed. Personal touches for your enjoyment and convenience. This unit is a 2,000-square-foot to …see more

from $190 / night

$1,300 - $1,580 / week

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Responds fast!
avg. 3 hours 4 minutes

from $190 / night

(2) Excellent 

26

Apartment rental in Ka'anapali

Maui / Ka'anapali

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
Introducing Maui Resort Rentals – Luxury Vacation Rentals By Maui Resort Realty... — Licensed Maui real estate brokerage & property manager specializing in resort real estate…we are the only company with 8000+ sq. ft. of office and warehouse space just steps from Honua …see more

from $190 / night

$1,680 - $4,970 / week

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Responds fast!
avg. 1 hour 16 minutes

from $190 / night

(22) Excellent 

Certificate of Excellence

30

Vacation apartment with golf nearby in Ka'anapali

Maui / Ka'anapali

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
[Latest upgrades: We replaced the single box AC unit on the lanai with 3 Fujitsu, tri-zone AC units with wireless remotes to provide AC throughout the condo, not just in the LR; we replaced the original lanai doors and jalousies with new a six-panel, Thermopane wall of …see more

Certificate of Excellence

from $235 / night

$1,645 / week

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Responds fast!
avg. 3 hours 41 minutes

from $235 / night

(1) Excellent 

34

Lahaina Vacation apartment rental

Maui / Lahaina

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children
Whales and dolphins frolic in our clear, warm water and you can watch surfers, windsurfers, and kite surfers playing in our waves. The occasional sea turtle (Honu) pops his head up for a quick peek at our visitors. Snorkeling and kayaking are also a favorite right out i …see more

from $135 / night

$945 - $1,750 / week

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Responds fast!
avg. 3 hours 28 minutes

from $135 / night

(3) Excellent 

12

Kula Vacation home rental

Maui / Kula

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child friendly
Experience a stay in upcountry maui. Our Ohana home has beautiful views of the ocean and mountains. We are located in a terrific walking neighborhood. Our home is kept nice and clean, with a comfortable bed and has a full kitchen. If you are keeping Kosher, we are wa …see more

from $185 / night

$1,295 / week

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Responds fast!
avg. 2 hours 12 minutes

from $185 / night

(1) Very Good 

24

Apartment rental in Wailea with shared pool

Maui / Wailea

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Imagine yourself sitting on the lanai with a drink in hand, watching the gorgeous colors of the Hawaiian sunset! This is a perfect budget getaway. Come explore the island! See gorgeous beaches, taste the island cuisine, shop the local businesses and unwind to the magic …see more

from $135 / night

$945 - $1,393 / week

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Responds fast!
avg. 3 hours 28 minutes

from $135 / night

(3) Very Good 

31

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child friendly
Incredible ocean views and sunset views from this west facing 2-story condo. Wrap around windows and lanai with one of the most expansive view on West Maui. Watch dolphins, sea turtles, and whales from the private lanai. Extra wide and spacious totally remodeled unit. J …see more

from $159 / night

$1,113 - $2,793 / week

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Responds fast!
avg. 3 hours 28 minutes

from $159 / night

(16) Very Good 

Certificate of Excellence

27

Kihei Vacation apartment rental

Maui / Kihei

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
ALOHA! Imagine enjoying your morning coffee as whales play in the warm Pacific Ocean that lies just yards away. Enjoy long strolls on the beach - a refreshing dip in the pool and a relaxing Jacuzzi hot tub under the Maui stars and moon with the ambiance of Hawaiian tiki …see more

Certificate of Excellence

from $155 / night

$900 / week

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from $155 / night

13

Home rental in Ka'anapali

Maui / Ka'anapali

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
Newly Remodeled Ocean Front 1 Bedroom Ground Floor Condo Within A Paradise. An ocean front 1 bedroom ground floor condo within a paradise. This Maui Vacation Rental is the perfect escape destination. Walk just steps to a white sand beach almost all to yourself. Come un …see more

from $149 / night

$1,043 / week

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from $149 / night

(2) Excellent 

13

Condo rental in Lahaina

Maui / Lahaina

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Child friendly
The resort is located right on the beach. Humpback whale watching season is from November to April, with March being the best, so be sure and bring your binoculars during that time. First sightings can occur as early as September. The whales are in the channel between …see more

from $175 / night

$1,225 / week

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from $175 / night

(1) Excellent 

33

Villa rental in Wailea with shared pool

Maui / Wailea

3 8 6 nights min

  • 3 bedrooms
  • sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Come relax and enjoy the good life at our spectacular ocean-view luxury villa, located directly across from the Grand Wailea Hotel & Spa on the beautiful island of Maui. Situated on the third row at Ho'olei, this beautiful two-story villa boasts dramatic Pacific Ocean …see more

from $695 / night

$4,865 / week

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from $695 / night

(35) Excellent 

Certificate of Excellence

6

Vacation cottage in Hana

Maui / Hana

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
Our CABANA is secluded and private in a garden setting with an ocean view. The studio cottage with its open beam ceiling and ceiling fan offers a bright and airy tropical hideaway from which to explore the many natural wonders of Hana. Tastefully decorated in island sty …see more

Certificate of Excellence

from $175 / night

$1,225 / week

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from $175 / night

(2) Excellent 

33

Vacation home in Makawao

Maui / Makawao

4 6 min stay varies

  • 4 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden
Step back in time... to the early Nineteen-hundreds and explore Maui from the homestead of the first manager of Haleakala Ranch! This is a very unique vacation rental in Upcountry Maui. Kilohana was designed and built in Nineteen-sixteen/seventeen by the Haleakala Ca …see more

from $325 / night

$2,275 / week

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Responds fast!
avg. 2 hours 19 minutes

from $325 / night

24

Vacation apartment in Lahaina

Maui / Lahaina

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
Introducing Maui Resort Rentals – Luxury Vacation Rentals By Maui Resort Realty... — Licensed Maui real estate brokerage & property manager specializing in resort real estate…we are the only company with 8000+ sq. ft. of office and warehouse space just steps from Honua …see more

from $510 / night

$3,955 - $16,236 / week

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Responds fast!
avg. 1 hour 16 minutes

from $510 / night