50 Best Maui Vacation rentals on Holiday Lettings - Condos

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Vacation rentals Lahaina
947 properties
Condos Kihei
613 properties
Ka'anapali
166 properties
Condos Wailea
131 properties
Villas Kapalua
115 properties
Condos Napili-Honokowai
80 properties
Haiku
36 properties
Vacation rentals Paia
28 properties
Condos Maalaea
20 properties
Apartments Wailuku
16 properties
Makawao
12 properties
Vacation rentals Hana
12 properties
Kula
6 properties

Maui

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2,186 Vacation rentals

(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

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 49 minutes

from $400 / 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

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

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 $350 / night

$2,450 / week

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Responds fast!
avg. 1 hour 51 minutes

from $350 / 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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Responds fast!
avg. 2 hours 41 minutes

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 $550 / night

$3,850 - $5,600 / week

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from $550 / 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) 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

(4) Excellent 

13

Wailuku Vacation apartment rental

Maui / Wailuku

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Maalaea Kai 220 | Maui Guidebook Summary Great oceanfront value; gorgeous ocean and neighbor island views from the lanai and living room. Watch sea turtles and whales (in season) from the lanai. Two master suite makes it perfect for two couples. This is a well mainta …see more

from $182 / night

$1,275 / week

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from $182 / 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

10

Villa rental in Kapalua with shared pool

Maui / Kapalua

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This beautiful ocean front Kapalua Bay Villa is new to our inventory. Unit is very tastefully updated and decorated with Hawaiian Fusion influence. Custom cabinetry and granite counters throughout. New stainless steel appliances in kitchen and new washer/dryer. Tiled fl …see more

from $425 / night

$2,975 - $3,150 / week

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from $425 / 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

(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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Responds fast!
avg. 3 hours 37 minutes

from $179 / night

(15) Very Good 

27

Kihei Vacation apartment rental

Maui / Kihei

1 4 1 night min

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

from $155 / night

$900 / week

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from $155 / 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 20 minutes

from $185 / night

24

Apartment rental in Ka'anapali with shared pool

Maui / Ka'anapali

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
NO RESORT / PARKING FEES The spacious interior of this 3 bed 3 bath tranquil retreat is the perfect blend of premium comfort and contemporary modern design. Stately and well-appointed, it is uniquely positioned for panoramic views of the calm crystal blue ocean, nearb …see more

from $750 / night

$5,250 - $11,200 / week

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from $750 / night

(27) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $95 / night

$665 / week

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Responds fast!
avg. 2 hours 29 minutes

from $95 / night

19

Studio rental in Ka'anapali with shared pool

Maui / Ka'anapali

Studio 3 5 nights min

  • Studio
  • Sleeps 3
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Junior Suite is spacious and well-appointed with a Queen Bed and seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The kitchen comes fully equipped with all the modern conveniences. Bring your favo …see more

from $269 / night

$1,883 / week

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from $269 / night

27

Apartment rental in Kihei with shared pool

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 - $2,723 / week

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Responds fast!
avg. 17 minutes

from $197 / night

(2) Excellent 

36

Vacation apartment rental

Maui / Lahaina

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This Hawaiian themed condo has ocean views from the lanai and both bedrooms in Ka'anapali. Remodeled and updated. The guest bathroom has a glass block walk-in shower only-no tub. Bring your DVD's from home and watch them on the flat screen TV in the living room or in th …see more

from $360 / night

$2,520 / week

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from $360 / 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

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
A Note from the Owner: We enjoy spending time out on the lanai, which has a large grassy area behind it that is great for our grandchildren to play ball on. Ulua beach is just a short walk and it's great for paddle boarding, boogie boarding and snorkeling. The Shops at …see more

from $399 / night

$2,793 - $5,593 / week

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from $399 / night

45

Vacation apartment with shared pool in Lahaina

Maui / Lahaina

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Our Hawaiian “cottage”on Maui Nestled under a canopy of shade trees on the highest point of the property, backing onto the Kaanapali Golf Course, this is one of the most well situated cottages at the International Colony Club for privacy and optimal views. The ICC feat …see more

from $195 / night

$1,365 / week

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from $195 / night

25

Vacation cottage in Haiku

Maui / Haiku

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Swimming pool
Our Ocean Honeymoon Lookout is the top floor of our Lookout House which sports 200 degree views of the north shore coastline all the way to Hana as well as summit views of the 10,000 foot Mt. Haleakala dormant volcano to the south. It comes equipped with a full kitchen …see more

from $395 / night

$2,625 / week

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Responds fast!
avg. 3 hours 4 minutes

from $395 / night

(7) Excellent 

20

Vacation condo in Hana

Maui / Hana

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
In Hawaiian "Kailani" means "Heavenly Sea " The Kailani Suite's panoramic ocean view will connect you to the heavenly ocean in a breathtaking and some say "mystical experience " only Hana can provide. The owners of Bamboo Valley Inn in Haiku, Maui are now offering a …see more

from $230 / night

$1,610 / week

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Responds fast!
avg. 1 hour 14 minutes

from $230 / night

19

Vacation condo in Maalaea

Maui / Maalaea

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This condo offers breathtaking ocean views and is located on the beach, where you can swim and snorkel right out front, or walk for miles. The two-bedroom, two-bathroom unit has a newly remodeled kitchen, includes a washer/dryer and everything you need for a vac …see more

from $175 / night

$1,225 - $1,470 / week

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Responds fast!
avg. 3 hours 44 minutes

from $175 / night

(5) Very Good 

24

Vacation apartment in Paia

Maui / Paia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 0.5 mi
  • Child friendly
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 $105 / night

$735 / week

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from $105 / night

(3) Excellent 

24

Vacation villa with golf nearby in Wailea

Maui / Wailea

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. SPECIAL CANCELLATION RATE IS FOR MINIMUM 7 NIGHT BOOKING DURING 5/7-17/2016. Check availability and BOOK before its gone! Newly built state-of-the-art luxury townhome. Beautiful three bedroom, three and one-half baths, 3363 …see more

from $1,100 / night

$7,700 / week

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from $1,100 / night

(3) Excellent 

12

Ka'anapali Vacation villa rental

Maui / Ka'anapali

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
SPECIFIC WEEKS with guaranteed availability include One-Bedroom and Two-Bedroom Luxury Villas for April 14 - 21 // July 1 - 8 // July 7 - 14 // July 14 - 21 // July 21 - 28 // August 4 -11 // August 11 - 18 // and August 28 - September 1, plus other select weeks through …see more

from $750 / night

$5,250 / week

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from $750 / night

(1) Excellent 

33

Vacation apartment rental

Maui / Lahaina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Outstanding ocean front views on North Ka'anapali beach. Enjoy heavenly sunsets from your living room AND bedroom. This condo has been totally remodeled and is tastefully decorated with an island style theme. The kitchen has granite counter tops and new appliances. Flat …see more

from $280 / night

$1,960 / week

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from $280 / 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

(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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Responds fast!
avg. 2 hours 40 minutes

from $220 / night

(4) Excellent 

15

Apartment rental in Kihei with shared pool

Maui / Kihei

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Best location in South Kihei, across the street from Cove Park Beach for paddle boarding, surfing, kayaking and Kalama Park for morning or sunset strolls. Tennis courts, skateboarding, kids playground at Kalama Park. Remodeled and fully equipped kitchen with granite co …see more

from $195 / night

$1,512 - $2,261 / week

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Responds fast!
avg. 3 hours 8 minutes

from $195 / night

(1) Excellent 

29

Vacation home 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
A highly desirable and rare end-unit facing the ocean, this one bedroom, two bath, single-level, one story townhome rental features an enlarged and expanded living room and bedroom resulting in additional square footage in both the living areas and the bedroom. Wit …see more

from $219 / night

$1,533 / week

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from $219 / night

26

Napili-Honokowai Vacation condo rental

Maui / Napili-Honokowai

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Enjoy stunning ocean views with Molokai and Lanai in the background from this remodeled condo at Hololani Resort! This corner unit layout offers extra lanai areas, with an ocean view lanai from the living room and master bedroom and a lanai with views of the west Maui M …see more

from $159 / night

$1,113 / week

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from $159 / 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 

28

Studio rental in Lahaina with shared pool

Maui / Lahaina

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Fantastic penthouse ocean views from this condo on the ocean at Kahana Bay. Decorated in a tropical theme, it makes a relaxing vacation for a couple or family of three. Both the kitchen and bathroom (no tub) have been remodeled with new appliances and fixtures including …see more

from $165 / night

$840 - $1,771 / week

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from $165 / 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