50 Best Maui Vacation rentals on Holiday Lettings - Condos

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Vacation rentals Lahaina
842 properties
Condos Kihei
723 properties
Condos Wailea
166 properties
Ka'anapali
146 properties
Villas Kapalua
110 properties
Condos Napili-Honokowai
53 properties
Haiku
36 properties
Vacation rentals Paia
30 properties
Vacation rentals Hana
26 properties
Condos Maalaea
25 properties
Apartments Wailuku
15 properties
Makawao
14 properties
Kula
6 properties

Maui

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2,009 Vacation rentals

(1) Excellent 

8

Vacation apartment in Paia

Maui / Paia

2 4 90 nights min

  • 2 bedrooms
  • Sleeps 4
  • 90 nights min
  • Child friendly
Located only 3m to Paia, where you can find yoga studios, restaurants, shopping boutiques and art galleries. 3m to Ho'okipa beach and Baldwin beach where are perfect for surfing, wind surfing and kite surfing. 15m to Kahului airport. The upstairs of the house has two ro …see more

from $130 / night

$780 - $1950 / week

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from $130 / night

6

Vacation apartment rental

Maui / Lahaina

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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. Westin Ka’anapali Ocean Resort Villas offe …see more

from $299 / night

$2093 / week

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from $299 / night

(3) Excellent 

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 $96 / night

$666 / week

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from $96 / night

(1) 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 kind …see more

from $96 / night

$666 / week

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from $96 / night

(1)  

21

Vacation condo with shared pool in Kihei

Maui / Kihei

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • 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

$1533 / week

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from $219 / night

49

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

$2100 / week

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Responds fast!
avg. 1 hour 40 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 $320 / night

$1700 / week

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from $320 / night

20

Vacation condo rental

Maui / Kihei

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
Bright, clean and comfortable, contemporary and uncluttered with a great view of the ocean and the lush tropical gardens below. This is a very well renovated one bed/one bath unit in KA building C unit 509, nicely furnished and well outfitted. Being up higher on the f …see more

from $99 / night

$693 / week

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from $99 / 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

$802 / 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

$802 / week

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from $129 / night

10

Kihei Vacation condo rental

Maui / Kihei

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $100 / night

$700 / week

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from $100 / night

8

Vacation apartment with shared pool in Ka'anapali

Maui / Ka'anapali

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Escape to an exotic island surrounded by glistening, white sandy shores, flourishing tropical scenery and intriguing wild life. The symphony of gently lapping waves beckons visitors to explore Maui’s many hidden wonders. Dive down to the depths of the ocean and discover …see more

from $358 / night

$2500 / week

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from $358 / night

(3) Excellent 

18

Vacation apartment in Lahaina

Maui / Lahaina

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Honua Kai is one of Maui's newest and most luxurious five star resort. Situated on North Kaanapali Beach, this oceanfront property is located just north of Black Rock. If you are looking for modern, luxurious accommodations on a beautiful sandy beach, then this is for y …see more

from $350 / night

$2300 - $5000 / week

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from $350 / night

(4) Very Good 

18

Vacation apartment in Kihei

Maui / Kihei

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Maui Sunset Resort a fabulous oceanfront property in Kihei with its immaculate grounds and tropical landscaping. The 2 elevators in the building accommodate anyone who might not be comfortable with the stairs. The condo you will be staying in is a remodeled, two bedroom …see more

from $185 / night

$1190 - $1855 / week

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Responds fast!
avg. 49 minutes

from $185 / night

24

Vacation apartment in Lahaina

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
You can't get closer to the ocean than this unless you're on a boat. Watch the whales December through April from your lanai and enjoy breath-taking sunsets all year long. This property is beautiful and well kept. This unit has a beautiful remodeled, fully stocked kitc …see more

from $135 / night

$945 - $1785 / week

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from $135 / night

37

Vacation home in Lahaina

Maui / Lahaina

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Enjoy spectacular 180-degree views of the beach, the Pacific Ocean, and the islands of Lanai and Molokai at this elegant three-bedroom condo. It doesn't get any better than this luxurious North Kaanapali Beach escape with an expansive ocean-facing lanai, a gourmet kitch …see more

from $895 / night

$6265 / week

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from $895 / night

25

Vacation apartment in Kihei

Maui / Kihei

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This completely remodeled 3 bedroom and 2 bath second-floor condo is the perfect place for your next family vacation. Your private oasis awaits you in the Master suite. It has a plush Queen sized bed and flat screen TV. Start your day the perfect way with a cup of cof …see more

from $199 / night

$1393 - $3150 / week

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from $199 / night

(3) Excellent 

23

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 $139 / night

$973 / week

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from $139 / night

(33) Very Good 

26

Home rental in Kihei with shared pool

Maui / Kihei

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
The sunsets are stunning from D-612, a top-floor, 1-bedroom, 1-bath oceanview condo at Kihei Akahi. With near perfect weather almost year-round you will enjoy the view from your private lanai not just in the evenings, but in the early mornings and throughout the day. Th …see more

from $99 / night

$665 - $1330 / week

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from $99 / night

21

Vacation condo with shared pool, golf nearby in Ka'anapali

Maui / Ka'anapali

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Low March rates! Peak season! Come see the whales! Remodeled 2bd/2bth Condo on 16th fairway of Kaanapali golf course with partial ocean view. Over 1500sq ft. + huge lanai. Central AC, free WI-FI. 5 min. walk to Whaler's shops, restaurants, and Black Rock beach. Pool, …see more

from $250 / night

$2380 / week

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Responds fast!
avg. 2 hours 17 minutes

from $250 / night

7

Hana Vacation apartment rental

Maui / Hana

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
“Kama” – Unit 107 – is a 1-bedroom, partial ocean view condo located in Hana Kai’s Mauka (upper) building. This is a ground floor, corner unit with a King-size bed in the bedroom a Full size futon and a Single futon chair with ottoman (converts to a junior-sized bed sui …see more

from $230 / night

$1449 - $2090 / week

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from $230 / night

18

Vacation apartment with shared pool in Wailea

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Wailea Ekahi #27B offers Ocean views from the upstairs master bedroom Living area and Lanai. The master bedroom has a King bed, ocean view and en-suite bath. The guest bedroom has a new Queen b …see more

from $415 / night

$2906 - $3745 / week

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from $415 / night

24

Lahaina Vacation apartment rental

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Oceanfront Honua Kai, Maui’s newest full service resort in over 25 years, can be your next vacation choice! Located on world famous Kaanapali Beach, Honua Kai offers a true luxurious Hawaiian vacation. Its’ multiple amenities (3 distinct pool and hot tub areas, dining o …see more

from $195 / night

$1365 - $2450 / week

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from $195 / night

30

Apartment rental in Lahaina with shared pool

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Welcome to paradise! This direct oceanfront condo is just 50 feet from the ocean, with unobstructed ocean views from the living room, lanai, kitchen and the mater bed room. Access gates lead you to the very private sandy/rock beach where you can enjoy snorkeling with tu …see more

from $169 / night

$1183 - $2093 / week

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from $169 / night

(15) Excellent 

Certificate of Excellence

45

Vacation apartment in Kihei

Maui / Kihei

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • 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 $99 / night

$623 - $1085 / week

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Responds fast!
avg. 1 hour 31 minutes

from $99 / night

(1) Excellent 

24

Home rental in Spreckelsville with golf nearby

Maui / Spreckelsville

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Private garden
Just around the corner from Baby Beach and Baldwin Beach. Fully remodeled in 2011!! Gorgeous updated interior. Kahale Makani is located off the ocean in Spreckelsville. By car, we’re just one minute to Sprecks, and one minute to Paia. Kahale Makani has a two story …see more

from $500 / night

$3500 / week

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from $500 / night

35

Home rental in Lahaina

Maui / Lahaina

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Ready for a getaway to paradise? This luxury three-bedroom condo at North Kaanapali Beach has a wraparound lanai, spacious interior, and access to all sorts of resort amenities. Located on the second floor of a building in the upscale, oceanfront Honua Kai Resort (addit …see more

from $675 / night

$4725 / week

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from $675 / night

(6) Excellent 

16

Haiku Vacation villa rental

Maui / Haiku

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
Lilikoi Lani, Maui's luxury plantation home, is the epitomy of Hawaiian Aloha and old style plantation elegance. It is a permitted, (BBPH 2013/0001, SUP2 2012/0008) five bedroom, three bathroom Maui vacation rental home that is your Hawaii dream come true! From the mome …see more

from $499 / night

$3493 - $5593 / week

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from $499 / night

(15) Excellent 

31

Vacation apartment in Kihei

Maui / Kihei

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This gorgeous home is in the Royal Mauian, a beach-side condominium. It has been completely renovated. It is a 2 bedroom / 2 bath Ground Floor home with a partial ocean view. During the renovation, we added a ductless air conditioning system that keeps the home cool an …see more

from $200 / night

$1750 - $2275 / week

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Responds fast!
avg. 54 minutes

from $200 / night

(2) Excellent 

18

Vacation apartment in Maui

Hawaii / Maui

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Royal Mauian 614 has stunning views from both the master bedroom and living area and is perfect for 4 guests! Stylish tropical furniture, cool clean Travertine tile flooring throughout this newly remodeled condominium greet you as you walk in the front door. The living …see more

from $325 / night

$2275 - $3255 / week

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from $325 / night

(5) Excellent 

21

Vacation condo in Napili-Honokowai

Maui / Napili-Honokowai

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Napili Shores Condo #D130 Kick back and relax at beautiful Napili Shores! You can do as much or as little as you want! Lounge poolside, kick back in the jacuzzi, or lay out on the golden sandy beach at Napili Bay and let the stress of daily life just melt away. Or ma …see more

from $120 / night

$840 / week

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from $120 / night

27

Apartment rental in Lahaina with swimming pool

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful 1-bedroom, 1-bathroom oceanfront condominium provides everything you need for your vacation in paradise. With spectacular views of the ocean from the 8th floor and a spanning view of the beautiful resort, you can’t beat the view from the comfort of your l …see more

from $135 / night

$945 - $1855 / week

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from $135 / night

23

Vacation apartment accommodation

Maui / Lahaina

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 $165 / night

$1505 - $3570 / week

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Responds fast!
avg. 2 hours 30 minutes

from $165 / night

(1) Excellent 

28

Home accommodation in Lahaina with shared pool

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
We invite you to come and stay in our upgraded condo just two blocks from famous Front Street! Relax and enjoy Coconut Condos Premier Platinum 2bd/2ba Aina Nalu condo in Lahaina, Maui. 846 sq. ft. for spacious living for up to 6 adults (king bed in master bedroom, queen …see more

from $169 / night

$1183 / week

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Responds fast!
avg. 30 minutes

from $169 / night

(122) Excellent 

26

Vacation apartment with tennis court in Kihei

Maui / Kihei

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Aloha and welcome to our beautiful, fully renovated Condo ideally located in sunny South Maui at Kamaole III Beach Park, one of Maui's great swimming, snorkeling and sunset beaches! We are located between the "local style" shops and restaurants of Kihei town, and the …see more

from $100 / night

$945 / week

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Responds fast!
avg. 2 hours 13 minutes

from $100 / night

24

Vacation apartment with swimming pool in Kihei

Maui / Kihei

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This top floor condo is a gem in South Kihei! Enjoy panoramic views of the ocean while sipping your morning coffee on the spacious lanai. This beautiful 2 bedroom, 2 bathroom condo has a king size bed in the master bedroom, a queen and a twin in the 2nd bedroom and …see more

from $104 / night

$728 - $1925 / week

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from $104 / night

(2) 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 $88 / night

$616 / week

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Responds fast!
avg. 2 hours 19 minutes

from $88 / night

24

Vacation condo with golf nearby in Lahaina

Maui / Lahaina

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
This 2 bedroom & 2 bathroom unit is located on the 3rd floor (K302), and has a wonderful OCEAN VIEW! You are just steps away from sinking your feet in the sand and the ocean waves. The living area has plenty of seating with a flat screen TV, DVD player, and stereo. For …see more

from $220 / night

$1540 / week

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Responds fast!
avg. 2 hours 44 minutes

from $220 / night

(1) Excellent 

14

Vacation apartment with shared pool in Maui

Hawaii / Maui

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Enjoy beautiful sunsets or whale watching during whale season from the ocean front lanai. The condo recently went through a complete remodel with tile flooring throughout, air conditioning, gra …see more

from $280 / night

$1960 - $2765 / week

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from $280 / night

(1) Excellent 

28

Studio rental in Napili-Honokowai with shared pool

Maui / Napili-Honokowai

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
Located in the D building of Pakapkea Resort -Papakea Resort Oceanview Studio D-206 - Lahaina - a tropical oceanfront 13 acre resort - this spacious studio has everything you are looking for in your Maui Vacation. Fully equipped kitchen with full sized appliances and pl …see more

from $116 / night

$1449 - $1540 / week

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Responds fast!
avg. 1 hour 23 minutes

from $116 / night