50 Best Maui Vacation rentals on Holiday Lettings - Condos

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Vacation rentals Lahaina
1,082 properties
Condos Kihei
853 properties
Condos Wailea
262 properties
Ka'anapali
179 properties
Condos Napili-Honokowai
127 properties
Villas Kapalua
86 properties
Apartments Wailuku
83 properties
Condos Maalaea
49 properties
Haiku
32 properties
Vacation rentals Paia
28 properties
Vacation rentals Hana
14 properties
Makawao
10 properties
Kula
7 properties

Maui

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2,816 Vacation rentals

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 33 minutes

from $300 / 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

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

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

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

(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

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 $450 / night

$3,150 - $4,550 / week

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from $450 / 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

(25) 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

24

Maalaea Vacation apartment rental

Maui / Maalaea

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Maalaea Kai #315 You can't beat the views from this air conditioned direct oceanfront one bedroom / one bath condominium located in the quaint harbor village of Maalaea. Just steps to the ocean, you'll enjoy the sounds of the surf and the palm leaves swaying in our coo …see more

from $157 / night

$1,435 - $1,596 / week

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avg. 1 hour 36 minutes

from $157 / 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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Responds fast!
avg. 2 hours 12 minutes

from $275 / night

(22) 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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Responds fast!
avg. 46 minutes

from $275 / night

(35) 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

(6) Very Good 

14

Vacation tented camp in Hana

Maui / Hana

1 8 1 night min

  • 1 bedroom
  • sleeps 8
  • 1 night min
  • 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

(43) 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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Responds fast!
avg. 1 hour 38 minutes

from $189 / night

(10) Very Good 

16

Vacation apartment in Kihei

Maui / Kihei

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering sweeping views of the Pacific. There are two six story buildings with elevators and the beach fronting the property is exceptional for sunsets, swimming, windsurfing, long rel …see more

from $169 / night

$1,183 - $2,415 / week

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from $169 / night

24

Vacation home in Lahaina

Maui / Lahaina

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

$1,323 - $2,093 / week

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Responds fast!
avg. 54 minutes

from $199 / 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

(10) Very Good 

21

Vacation studio in Ka'anapali

Maui / Ka'anapali

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
Located in the heart of Kaanapali, 15 minute walk to Whaler's Village shops and restaurants, enjoy this bright corner unit studio at the Maui Eldorado Resort G101. Enjoy Maui's Kaanapali beach voted #1 by Conde Naste and exclusive access to the ONLY beachfront clubhouse …see more

from $129 / night

$903 / week

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Responds fast!
avg. 1 hour 12 minutes

from $129 / night

(2) 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

(2) Very Good 

37

Vacation home in Kula

Maui / Kula

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Unit: Kula Jewel | Maui Guidebook Summary For those seeking a family friendly home with private heated pool away from the crowds, while conveniently located near Haleakala National Park, look no further. This stand alone two bedroom two bathroom house is situated on an …see more

from $239 / night

$1,673 / week

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from $239 / night

21

Condo rental in Wailea with shared pool, golf nearby

Maui / Wailea

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
QUIET PRIVACY IN PARADISE This is a luxurious one-bedroom two-bath ground floor villa tucked away in a private and quiet corner in one of the nicest locations in the property. Often the only sound you will hear is the waves crashing on the nearby beaches. The Palms at …see more

from $189 / night

$1,323 / week

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from $189 / 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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Responds fast!
avg. 1 hour 5 minutes

from $185 / night

(7) Excellent 

17

Tented camp rental in Hana

Maui / Hana

1 8 1 night min

  • 1 bedroom
  • sleeps 8
  • 1 night min
  • 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 

4

Vacation b&b in Haiku

Maui / Haiku

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
Private Vacation Rental/ Bed and Breakfast on North Shore, for your Maui vacation - located on a quiet street on the ocean side of Hana Hwy in Haiku. About 15 miles from the airport and half mile towards the ocean off the Road to Hana, along the north shore in Upcountr …see more

from $120 / night

$840 - $1,050 / week

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from $120 / night

25

Vacation home with shared pool in Wailuku

Maui / Wailuku

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
If you are looking for the closest proximity to a perfect white sandy beach then look no further! Hono Kai is the only resort located directly on a sandy beach. Enjoy ten miles of pristine beach with views of Haleakala and Kaho'olawe in the background just steps from yo …see more

from $109 / night

$763 / week

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from $109 / night

16

Vacation apartment in Kihei

Maui / Kihei

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Unit #535 is a jewel at Sugar Beach Resort. A beautiful remodel was completed in June of 2013, complete with granite counter-tops, new appliances and fun, fabulous decor. Every detail has been selected with your perfect beach vacation in mind. Very possibly the best vie …see more

from $325 / night

$2,275 - $3,913 / week

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from $325 / night

(21) Excellent 

Certificate of Excellence

45

Vacation apartment in Kihei

Maui / Kihei

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
The budget conscious person will appreciate this COZY and QUIET, garden view condo accented with an ALOHA spirit. This freshly painted and redecorated GROUND FLOOR, one bedroom, vacation rental condo, containing 741 SF (69 SM), is located within the HEART of the KIHEI R …see more

Certificate of Excellence

from $110 / night

$700 - $1,085 / week

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Responds fast!
avg. 2 hours 15 minutes

from $110 / night

(22) Excellent 

Certificate of Excellence

35

Kihei Vacation apartment rental

Maui / Kihei

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
Experience our luxurious new bathrooms that were both totally remodelled and now feature premium granite vanities, all ceramic tile showers & baths, floors & walls with granite, travertine and onyx accents, tropical etched glass, new fixtures and more!We are pleased to …see more

Certificate of Excellence

from $219 / night

$1,533 / week

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Responds fast!
avg. 1 hour 21 minutes

from $219 / night

(4) Very Good 

26

Vacation home with shared pool in Lahaina

Maui / Lahaina

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This unit is a two story town home which enjoys all the beauty and adventures Puamana has to offer at a great value. Although located on the back highway side it has been sound proofed with double pane glass windows and air conditioning in bedrooms and living room. The …see more

from $225 / night

$1,575 / week

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from $225 / night

(16) Excellent 

24

Ka'anapali Vacation apartment rental

Maui / Ka'anapali

4 min stay varies

  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Upgraded with gorgeous new kitchen including granite counters, custom cabinets, new appliances, plush carpet and more! This studio ground floor condo has a great location. Just open the lanai doors and stroll out onto the grass to the beach, the pool, & the oceanfront b …see more

from $215 / night

$1,450 - $2,150 / week

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Responds fast!
avg. 2 hours 55 minutes

from $215 / night

24

Vacation apartment rental

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 $265 / night

$2,170 - $5,670 / week

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Responds fast!
avg. 1 hour 21 minutes

from $265 / night

(2) Excellent 

10

Lahaina Vacation villa rental

Maui / Lahaina

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Ask about pets
Puunoa Beach Estates lies on 5 tropical acres, just steps from the white sands of Lahaina’s Baby Beach. Enclosed on this gated oceanfront property, this second floor, three-bedroom residence sits among ten other townhomes that offer comforts you’d expect from the most l …see more

from $1,300 / night

$9,100 / week

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Responds fast!
avg. 1 hour 6 minutes

from $1,300 / 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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from $160 / night

(70) Excellent 

Certificate of Excellence

35

Cottage rental in Haiku

Maui / Haiku

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Private garden
Aloha Hookipa Bayview Cottage...Maui's ultimate private, romantic cottage is a unique, architectural Polynesian Pole Home. Secluded, romantic, award winning, with beautiful island inspired decor. There are spectacular panoramic ocean/sunset, coastline views. A honeymo …see more

Certificate of Excellence

from $269 / night

$1,883 / week

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Responds fast!
avg. 1 hour 51 minutes

from $269 / night

(1) Excellent 

28

Vacation apartment rental

Maui / Kapalua

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Some of the best views from this location await you. Open the doors and feel the trade winds blowing, keeping you comfortable while you enjoy the expansive walk-out lanai. A beautiful, remodeled condo with luxury throughout. This condo is nicely equipped with most eve …see more

from $199 / night

$1,393 - $2,975 / week

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Responds fast!
avg. 1 hour 59 minutes

from $199 / night

(1) Excellent 

14

Kihei Vacation condo rental

Maui / Kihei

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Centrally located in Kihei near restaurants and shopping, only 50 yards from Kamaole II beach. Play in the sand, snorkel, go boogie boarding, or just take in the beautiful blue pacific! Our condo has everything you need for a great day on the beach! When your done it wo …see more

from $109 / night

$763 / week

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from $109 / 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 12 minutes

from $325 / night