50 Best Maui Vacation rentals on Holiday Lettings - Condos

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Vacation rentals Lahaina
995 properties
Condos Kihei
640 properties
Condos Wailea
160 properties
Ka'anapali
147 properties
Villas Kapalua
115 properties
Condos Napili-Honokowai
85 properties
Haiku
36 properties
Vacation rentals Paia
26 properties
Condos Maalaea
23 properties
Apartments Wailuku
19 properties
Vacation rentals Hana
12 properties
Makawao
11 properties
Kula
7 properties

Maui

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2,284 Vacation rentals

(6) Excellent 

124

Vacation home in Haiku

Maui / Haiku

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Aloha! The perfect location, perfect amount of privacy, perfect aloha spirit, perfectly natural....perfectly luxurious! Please make sure to see if your questions are asked already here before emailing. Mahalo! If you want to have a relaxing, fun, vacation, and are kin …see more

from $95 / night

$665 / week

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avg. 3 hours 42 minutes

from $95 / night

(11) Very Good 

142

Vacation home in Haiku

Maui / Haiku

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Aloha! The perfect location, perfect amount of privacy, perfect aloha spirit, perfectly natural....perfectly luxurious vegetarian home! Please make sure to see if your questions are asked already here before emailing. Mahalo! If you want to have a relaxing, fun, vacati …see more

from $95 / night

$665 / week

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avg. 3 hours 42 minutes

from $95 / 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

(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

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

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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avg. 1 hour 55 minutes

from $300 / 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

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

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 $500 / night

$3,500 - $5,250 / week

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from $500 / night

7

Private room rental in Paia

Maui / Paia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 0.5 mi
  • Car not necessary
SUMMARY: No car? Don't feel like driving on vacation? Want to save on car rental? This is THE PERFECT place for you. My place is 5min walking distance to the Beach, restaurants and dining, town center, art and culture, great views, family-friendly activities. You’ll lo …see more

from $127 / night

$801 / week

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from $127 / night

6

Vacation private room in Paia

Maui / Paia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 0.5 mi
  • Car not necessary
SUMMARY: No car? Don't feel like driving on vacation? Want to save on car rental? This is THE PERFECT place for you. My place is 5min walking distance to the Beach, restaurants and dining, town center, art and culture, great views, family-friendly activities. You’ll lo …see more

from $129 / night

$801 / week

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from $129 / night

(42) Very Good 

Certificate of Excellence

19

Vacation apartment in Hana

Maui / Hana

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
Minimum stay is 1 night, except 2 nights minimum during certain holidays and special events. The maximum stay is 3 nights. Escape to a private studio guest suite in beautiful remote Hana, Maui. The air conditioned guest suite offers a comfortable king size bed and ful …see more

Certificate of Excellence

from $189 / night

$1,323 / week

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avg. 1 hour 38 minutes

from $189 / night

(1) Excellent 

24

Vacation apartment with shared pool in Kihei

Maui / Kihei

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Swimming pool
This charming, 1 bedroom, newly renovated (Dec 2013), Maui Vista Condo (Building 1 #1219) is conveniently located in central Kihei - directly across from Charley Young Beach. Sleeps 4 - 1 Queen bed, 1 Queen Sofa Bed. We have a local manager that can help with any pro …see more

from $139 / night

$973 / week

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from $139 / night

(5) Excellent 

22

Apartment rental in Kihei with shared pool

Maui / Kihei

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located across the street from Kamaole 1 & Charley Young Beach. Its a 5 minute walk to the beach! Beautiful swimming and snorkeling beach. Ideal for taking a nice stroll and perfect for watching the sunset at night. Conveniently located within walking distance to many …see more

from $179 / night

$1,253 / week

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avg. 2 hours 58 minutes

from $179 / night

(24) 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 

24

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This beautiful 1 bedroom, 1 bathroom, oceanfront condominium provides everything you need for your vacation in paradise. With spectacular panoramic views over Maui’s neighbor islands, Lanai and Molokai, you can’t beat watching the whales and turtles from the comfort of …see more

from $129 / night

$903 - $1,785 / week

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from $129 / 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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avg. 1 hour 7 minutes

from $165 / night

(3) Excellent 

19

Kapalua Vacation condo rental

Maui / Kapalua

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
Ground level, NO STAIRS. NO RESORT FEES. Ocean and Island views. Covered designated parking steps from the unit. Beautiful Kapalua. Quiet Resort and yet so close to the hustle and bustle of Lahaina Town, Kaanapali, & Kahana. Walking distance to the Ritz Carlton and T …see more

from $218 / night

$1,526 / week

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avg. 2 hours 38 minutes

from $218 / night

(40) Excellent 

24

Apartment rental in Maalaea with shared pool

Maui / Maalaea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
We searched for a second home with an unobstructed ocean view on Maui for many years. We found our piece of paradise and would like to share it with you as a vacation rental. The condo we purchased has been completely remodeled. Email us and we will send you a link to …see more

from $185 / night

$1,295 - $1,890 / week

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avg. 1 hour 13 minutes

from $185 / night

(2) Excellent 

35

Vacation condo in Kihei

Maui / Kihei

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
Aloha! Welcome to our little piece of paradise. We are new owners of this great location at KBR! We are situated in S Kihei, directly across from Kamaole 1 Beach which is one of the three most beautiful Kamaole Beaches in the area! It is approximately 3/4 mile of soft s …see more

from $115 / night

$805 / week

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avg. 31 minutes

from $115 / night

(27) Very Good 

15

Vacation apartment in Kihei

Maui / Kihei

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
We have a welcoming second floor, 723 sq. ft. one bedroom condiminium at the Kihei Kai Nani complex across the street from a beautiful beach, Kamaole II, in Kihei (300 paces to sand). Kamaole II is a beautiful golden sand beach (rated as one of the 15 best beaches on Ma …see more

from $95 / night

$665 / week

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avg. 3 hours 17 minutes

from $95 / night

56

Vacation apartment in Maalaea

Maui / Maalaea

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
We consider our Condo in Maalaea as our 'Hale' in Paradise. It sits directly in front of the blue Ocean with a small private beach and tide pools to explore. Often you will find yourself sunbathing with a 'Honu' (Turtle) right next to you. From the Lanai you can watc …see more

from $150 / night

$875 / week

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from $150 / night

(1) Good 

24

Vacation apartment in Lahaina

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
Imagine yourself sitting on the lanai, sipping on a Mai Tai and watching the sun fall into the Pacific Ocean right in between Lanai & Molokai. This resort sits right on the ocean in Honokowai in between Kapalua and Kaanapali. This 1-bedroom condo can be your home away f …see more

from $99 / night

$693 - $1,743 / week

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from $99 / night

(5) Very Good 

20

Paia Vacation private room rental

Maui / Paia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
Suite w/full private bathroom in shared 2 bed 2 bath condo. Features queen-size bed, TV & free Wi-Fi. Parking may be assigned or unassigned. Shared kitchen, living room & lanai. Laundromat on site. 2 guests max. Close to Ho'okipa & Baldwin Beach, Paia Bay, Twin Falls. …see more

from $100 / night

$700 / week

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from $100 / night

(1) Excellent 

10

Kihei Vacation condo rental

Maui / Kihei

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Across the street from a great beach, family friendly and calm. Resort rooms were renovated in 2015. Must be 21 or older to check in, no smoking, no pets. Resort will ask you for a credit or debit card damage deposit, fully refundable. Unit Amenities · Air conditionin …see more

from $220 / night

$1,540 / week

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avg. 2 hours 40 minutes

from $220 / night

(21) Very Good 

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 $275 / night

$2,065 / week

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avg. 57 minutes

from $275 / night

24

Vacation villa with shared pool in Kapalua

Maui / Kapalua

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
2016 Gold Renovation Complete! This unique oceanfront location is situated on one of the most beautiful parts of the West Maui coast, Fresh out of renovation and rich with every imaginable upgrade. Every surface has been covered in natural stone, glass tile and rich …see more

from $355 / night

$2,485 - $4,025 / week

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avg. 3 hours 11 minutes

from $355 / night

(3) 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 in Kihei premier complex. 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 upstairs ma …see more

from $195 / night

$1,365 / week

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from $195 / night

(2) Very Good 

37

Apartment rental in Kihei

Maui / Kihei

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
OUR CONDO IN PACIFIC SHORES IS LOCATED BETWEEN THE MAUI VISTA AND THE MAUI COAST HOTEL IN SOUTH KIHEI AND IS APPROX. A 3 MINUTE WALK TO THE POPULAR CHARLEY YOUNG BEACH. OUR THREE BEDROOM, THREE BATH FLOOR PLAN ALLOWS US TO ACCOMMODATE 2 TO 8 PEOPLE SO WHETHER YOU ARE …see more

from $275 / night

$1,925 / week

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avg. 51 minutes

from $275 / night

(14) Excellent 

11

Vacation cottage in Hana

Maui / Hana

2 1 night min

  • Sleeps 2
  • 1 night min
  • Child friendly
  • Private garden
Entabeni Cottage vacation rental sits above the world famous "Road to Hana" overlooking the Pacific Ocean in the tropical rainforests of East Maui, Hawaii. Our gentle climate massages body and soul of visitors who come to enjoy our tropical paradise. Entabeni Cot …see more

from $170 / night

$1,190 / week

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from $170 / night

(3) Excellent 

9

Vacation villa with shared pool in Kapalua

Maui / Kapalua

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This ocean view Kapalua Golf Villa has great ocean/fairway/mountain views. There is a huge covered lanai that is partially open for sunning. High definition LCD TV, free high speed wireless internet and free unlimited long distance calling to U.S. & Canada. Central air …see more

from $179 / night

$1,253 - $1,743 / week

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from $179 / night

26

Vacation home in Haleakala National Park

Maui / Haleakala National Park

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 10 mi
  • Child friendly
  • Air conditioning
Each home has a private gated entrance, private parking area and a private garden. Each has a private hot-tub (NOT shared). The two dwellings sit close to each other, but look in opposite directions, so that they do not interfere with the other dwelling. The deck look …see more

from $275 / night

$1,925 / week

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avg. 3 hours 3 minutes

from $275 / night

18

Vacation b&b in Haiku

Maui / Haiku

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 5 mi
  • Ask about children
Beautiful 1800s colonial plantation home, once the location of the original plantation doctor, sits among 2 acres of lush historical gardens with 100 ft pine trees and tropical fruits. Open spaces in true plantation style, large lanais for peaceful days and comfortab …see more

from $725 / night

$4,375 / week

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from $725 / night

(33) Excellent 

8

Home rental in Haiku

Maui / Haiku

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Car not necessary
Maui County Bed and Breakfast permit number : 20090014 Welcome to the Bamboo Valley Inn: Nestled in a hidden tropical valley on Maui's North Shore where all you will hear are the sounds of nature and warm tropical breezes. Located on a very private, quiet, gated, mul …see more

from $169 / night

$1,183 / week

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avg. 1 hour 15 minutes

from $169 / night

(2) Excellent 

37

Kihei Vacation condo rental

Maui / Kihei

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly
The traveler that is seeking comfort but with MODERN UPGRADES will appreciate this newly RENOVATED (Summer 2017) QUIET garden view above the TREELINE condo accented with an ALOHA spirit. This second floor condo is located far away from the busy street noise of South Kih …see more

from $110 / night

$700 - $1,225 / week

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avg. 2 hours 33 minutes

from $110 / night

(1) Excellent 

27

Vacation apartment with shared pool in Ka'anapali

Maui / Ka'anapali

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Kaanapali Plantation #35 - Fully renovated with air conditioning in both bedrooms - free parking right outside your front door - single level - no steps! Walk 10 minutes to North Ka'anapali Beach. Recent upgrades include: new window coverings, crown molding, baseboard …see more

from $195 / night

$1,365 - $2,548 / week

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avg. 44 minutes

from $195 / night

(1) Excellent 

13

Condo rental in Lahaina

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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

(35) Excellent 

9

Vacation villa with shared pool in Haiku

Maui / Haiku

3 5 nights min

  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
An ideal location between the jungles of Hana and the crowded towns of Lahaina and Kihei. Swin in the salt water pool, listen to chirping birds and pounding waves, sunrise and sunset walks on Holokai road, play with our two nanny goats and chickens , BBQ under the stars …see more

from $165 / night

$1,155 - $1,330 / week

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from $165 / night

(3) Excellent 

84

Vacation apartment in Ka'anapali

Maui / Ka'anapali

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
I am Trevor Alt and this is KONEA 142, the KING of the GROUND FLOOR 2 bedroom 2 bath condo-tel homes at the Honua Kai Resort & Spa. This private oasis is uniquely located in the quiet North corner of this luxury resort. Enjoy 1,230 square feet of interior living sp …see more

from $395 / night

$2,625 - $7,133 / week

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avg. 26 minutes

from $395 / night

27

Apartment rental in Kihei

Maui / Kihei

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Voted "Best Island in the World" for 20+ years, Maui captures your heart with its signature island breeze the minute you step off the plane. Breathtaking views and brilliant sunsets await you at this 2-bedroom, 2-bath vacation rental condo in Kihei. Set on lush tropical …see more

from $197 / night

$1,379 / week

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avg. 7 minutes

from $197 / night