50 Best Lahaina Vacation rentals on Holiday Lettings - Condos

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2,004 Vacation rentals

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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avg. 3 hours 48 minutes

from $400 / night

(1) Good 

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 $399 / night

$2,793 / week

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from $399 / night

(17) Very Good 

Certificate of Excellence

12

Vacation condo rental

Maui / Lahaina

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
Our corner condo is set up as a second home. So we think you will find amenities that most vacation rentals don't offer. We have a 40" flat screen with blu ray player and surround sound with over 100 new blu ray movies and well over 300 dvd's, concerts, and VHS tapes to …see more

Certificate of Excellence

from $180 / night

$1,260 / week

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from $180 / 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 $165 / night

$1,155 - $1,225 / week

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from $165 / night

(2) Very Good 

34

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Relax and enjoy your time with us at this Maui vacation in this beautiful condo with golf course views on the Ka'anapali Golf course. There are stairs only to this entrance-no elevators. 3 stairs lead down to living room and to master bedroom. The guest bathroom has a w …see more

from $225 / night

$1,575 / week

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from $225 / 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 $139 / night

$973 - $1,785 / week

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from $139 / night

23

Lahaina Vacation home rental

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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

$1,183 / week

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Responds fast!
avg. 28 minutes

from $169 / night

24

Vacation home with shared pool in Lahaina

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
We invite you to come and stay in our upgraded condo just two blocks from famous Front Street! Relax and enjoy Coconut Condos Premier 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 bed in g …see more

from $159 / night

$1,113 / week

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Responds fast!
avg. 28 minutes

from $159 / 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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Responds fast!
avg. 3 hours 57 minutes

from $121 / night

28

Lahaina Vacation home rental

Maui / Lahaina

2 6 Min stay varies

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

from $169 / night

$1,183 / week

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Responds fast!
avg. 28 minutes

from $169 / night

27

Vacation studio with shared pool in Lahaina

Maui / Lahaina

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Welcome to paradise! If you are looking for the ultimate vacation spot to unwind and enjoy the serenity, then the Royal Kahana is the place for you. Our beautifully decorated and fully appointed 4th floor studio unit has an incredible ocean view and features all the a …see more

from $119 / night

$833 - $1,834 / week

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from $119 / night

26

Apartment rental in Lahaina with shared pool

Maui / Lahaina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Deluxe remodeled condo, ocean front on Kahana Bay. Granite kitchen counters and stainless appliances. Updated Hawaiian Style furnishings complete this location. Sit on the ocean front lanai and enjoy your favorite CD's with the player provided. With free wireless intern …see more

from $165 / night

$910 - $1,883 / week

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from $165 / night

37

Lahaina Vacation apartment rental

Maui / Lahaina

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Within walking distance of the world famous Whalers Village, located on the Kaanapali Golf Course, Kaanapali Royal Q-301 is an ideal vacation home. This beautiful Maui home features a townhouse style floor plan with the master bedroom and bath located upstairs for maxim …see more

from $270 / night

$1,890 / week

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from $270 / night

(3) Excellent 

23

Vacation condo in Lahaina

Maui / Lahaina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
You will love the spectacular views from this beautiful, one bedroom, level entry, oceanfront condominium located within the Aston Mahana at Kaanapali and adjacent to Maui's beautiful Kaanapali Beach. The quiet surroundings and manicured tropical gardens at the Mahana …see more

from $305 / night

$2,135 - $3,045 / week

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from $305 / night

24

Home rental in Lahaina with shared pool

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
We invite you to come and stay in our upgraded condo just two blocks from famous Front Street! Relax and enjoy Coconut Condos Premier 2bd/2ba Aina Nalu condo in Lahaina, Maui. Corner-end condo with views of the Makai pool area! 846 sq. ft. for spacious living for up to …see more

from $154 / night

$1,078 / week

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Responds fast!
avg. 28 minutes

from $154 / night

(1) Excellent 

23

Lahaina Vacation home rental

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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

$1,183 / week

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Responds fast!
avg. 28 minutes

from $169 / night

23

Lahaina Vacation home rental

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
We invite you to come and stay in our upgraded condo just two blocks from famous Front Street! Relax and enjoy Coconut Condos Premier 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 bed in g …see more

from $159 / night

$1,113 / week

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Responds fast!
avg. 28 minutes

from $159 / night

26

Vacation home in Lahaina

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
We invite you to come and stay in our upgraded condo just two blocks from famous Front Street! Relax and enjoy Coconut Condos Premier 1bd/1ba Aina Nalu condo in Lahaina, Maui. 515 sq. ft. for spacious living for up to 4 adults (king bed in master bedroom, and queen slee …see more

from $119 / night

$833 / week

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Responds fast!
avg. 28 minutes

from $119 / night

(3) Very Good 

25

Apartment rental 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
11th Floor Ocean Views from this remodeled 2 bedroom, 2 bath Maui vacation rental. Perfect for a family of 6. Private bedrooms with ensuite bathrooms. Master suite features a king size bed (new as of March '17), a 50 in. Vizio TV, amazing ocean views and lanai access. T …see more

from $200 / night

$1,400 / week

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from $200 / night

18

Vacation home with shared pool in Lahaina

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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, king …see more

from $154 / night

$1,078 / week

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Responds fast!
avg. 28 minutes

from $154 / night

22

Lahaina Vacation home rental

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
We invite you to come and stay in our upgraded condo just two blocks from famous Front Street! Relax and enjoy Coconut Condos Premier 2bd/1ba Aina Nalu condo in Lahaina, Maui. 772 sq. ft. for spacious living for up to 6 adults (queen bed in master bedroom, queen bed in …see more

from $140 / night

$980 / week

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Responds fast!
avg. 28 minutes

from $140 / night

22

Lahaina Vacation home rental

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
We invite you to come and stay in our upgraded condo just two blocks from famous Front Street! Relax and enjoy Coconut Condos Premier 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 bed in g …see more

from $154 / night

$1,078 / week

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Responds fast!
avg. 28 minutes

from $154 / night

20

Lahaina Vacation home rental

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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/1ba Aina Nalu condo in Lahaina, Maui. 846 sq. ft. for spacious living for up to 6 adults (queen bed in master bedroom, quee …see more

from $149 / night

$1,043 / week

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Responds fast!
avg. 28 minutes

from $149 / night

(5) Very Good 

23

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

2 7 5 nights min

  • 2 bedrooms
  • Sleeps 7
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Elegant Villa - Complete New Remodel - Luxurious - Kaanapali Royal L-301 Elegant $******* remodel for the discerning traveler. -Tropically Decorated by Tiffany Harris (decorator to the stars) & founder of Layla Grayce: with beautiful decor and local artists. -I …see more

from $305 / night

$2,135 / week

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from $305 / night

38

Vacation studio in Lahaina

Maui / Lahaina

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Enjoy the luxuries of home with this upgraded, impeccably cared for studio unit. You will enjoy spectacular ocean views from within the unit as well as from the lanai! On clear days you will feel like you can touch the island of Molokai and also view the gorgeous West …see more

from $125 / night

$875 - $2,041 / week

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from $125 / night

26

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Imagine Maui. Relax and/or play in this vacation rental resort with a residential feel. This boutique complex is one of the best-kept secrets on Front Street in Lahaina Town. With the ocean at your doorstep, you have front row seats for the turtle watching, seasonal wha …see more

from $160 / night

$1,176 - $2,842 / week

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from $160 / 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
  • Air conditioning
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

$1,183 / week

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Responds fast!
avg. 28 minutes

from $169 / night

21

Home rental in Lahaina with shared pool

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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. Corner-end condo with partial views of the West Maui Mountains! 846 sq. ft. for spaci …see more

from $169 / night

$1,183 / week

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Responds fast!
avg. 28 minutes

from $169 / night

46

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Panoramic ocean views and breathtaking sunsets await you from this spacious 3 bedroom 2 bathroom oceanfront 3rd floor condominium located at the Sands of Kahana. This beautiful oceanfront condominium is all about ocean, beach, vacation, rest and relaxation. The Sands …see more

from $495 / night

$3,465 / week

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from $495 / night

(6) Very Good 

18

Vacation studio with shared pool in Lahaina

Maui / Lahaina

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Spacious ocean front studio in Kahana. Enjoy the convenience of a fully equipped kitchen as well as all the comforts and conveniences of home. Wake up to the sound of the ocean waves & enjoy your morning beverage while taking in the breathtaking 8th floor views of our n …see more

from $120 / night

$770 - $2,450 / week

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from $120 / night

10

Home rental in Lahaina

Maui / Lahaina

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
Enjoy breakfast on your lanai with views of lush tropical landscaping. Explore Lahaina’s Front Street, and then refresh in the resort’s pool before grilling at the picnic area. These 610sf retreats offer a full kitchen, WiFi and flat screen TV. Sleeps 4 in a Queen and S …see more

from $146 / night

$1,022 / week

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from $146 / night

27

Vacation apartment 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
It is all about the views (oh and the location)! This remodeled 2nd floor two bedroom, one bath Maui vacation rentals has Direct Ocean Front Views. Located at Lahaina Roads on Front Street is one of the best kept secrets in Old Lahaina Town! Lahaina Roads is a direct …see more

from $250 / night

$1,750 / week

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from $250 / night

28

Studio rental in Lahaina with shared pool

Maui / Lahaina

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Garden views from the ground floor in North Ka'anapali. The condo has a cool tropical theme with tile throughout. A fully equipped galley kitchen. Bring your laptop and surf free wireless internet access from anywhere in the condo. Listen to your favorite your CD's whil …see more

from $165 / night

$1,155 / week

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from $165 / night

38

Apartment rental in Lahaina with shared pool

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
2nd Floor One bedroom condo in the Aloha Tower at the beautiful beach front resort at The Maui Kaanapali Villas with garden & resort views. Our condo is nicely updated and furnished and feature an XL lanai. Sleeps up to 4 guests maximum with 2 queen beds. No tub/walk in …see more

from $230 / night

$1,610 / week

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from $230 / night

(3) Very Good 

51

Vacation apartment rental

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
It doesn't get much better than this! Come enjoy your amazing Maui Vacation here at the breathtaking Polynesian Shores!! The perfect place for a last minute summer vacation, an upcoming trip this fall or a great spot to watch the Humpback Whales this winter (right out …see more

from $129 / night

$903 - $1,673 / week

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from $129 / night

24

Vacation apartment in Lahaina

Maui / Lahaina

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Our managing agent Maui Beachfront Rentals located on island knows our unit intimately, has the ability to negotiate and is happy to arrange for any special needs you may have. Google "Maui Beachfront Rentals" for personalized service. All bookings are subject to a on …see more

from $149 / night

$1,043 / week

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from $149 / night

(2) Very Good 

25

Apartment rental in Lahaina with shared pool

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Ocean views on Kaanapali Beach from the South tower facing Black Rock. In addition to the TV in the living room there is also a TV in the bedroom. Bring your CD's from home and listen on the player provided. Bring your laptop and enjoy free high speed DSL internet acces …see more

from $215 / night

$1,400 - $1,932 / week

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from $215 / night

30

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
If you are seeking a piece of OLD HAWAII -- away from crowded hotels and resorts, Pohailani Maui 152 is the place for you! There is a sense of peace and privacy here that is not present at large resorts. Our elegantly remodeled 2 bedroom, 1 bathroom condo has all of th …see more

from $140 / night

$980 - $1,540 / week

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from $140 / night

(25) Very Good 

28

Vacation apartment in Lahaina

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
This ocean front corner condo is so light and airy and so close to the water. It is a great 2 bedroom located on the ground floor in Honokowai. The kitchen was updated with new appliances, renovated with granite counters, bamboo cabinets and a glass/stone back splash wi …see more

from $225 / night

$1,575 / week

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from $225 / night

(16) Very Good 

19

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
This oceanfront condo has been fully remodeled with marble counters in kitchen and bathroom. Bamboo cabinets bring an air of the tropics. Fresh furnishings with tile floors. Located on the ground floor in Honokowai area, the center of West Maui. We offer free Wi-Fi inte …see more

from $140 / night

$875 - $1,666 / week

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from $140 / night