50 Best Hawaii Vacation rentals on Holiday Lettings - Apartments

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7,743 Vacation rentals

(3) Excellent 

40

Home rental in Hawaii with swimming pool

Hilo / Hawaii Paradise Park

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Hale Mar provides the best value in absolute ocean front homes in Hawaii, with private swimming pool, outdoor hot tub, resort quality furnishings, gourmet kitchen, full laundry, wireless internet, satellite TV channels, and more. Close to the active Volcano for unique d …see more

from $349 / night

$3,213 / week

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avg. 44 minutes

from $349 / night

(1) Excellent 

29

Vacation home rental

Oahu / Waianae

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Spectacular, One Bedroom Ocean View , Pool, Internet, Cable TV. Like all tourists, we came here to experience the Aloha Spirit in the west side of Oahu, and we found the paradise. As we fall in love with everything here, we decided to make this home and now we would lik …see more

from $98 / night

$686 / week

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from $98 / night

21

Vacation cottage in Hawaii

Oahu / Makaha

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Private garden
Be a part of Hawaii's history by staying at E Komo Mai Hale and have a true Hawaiian experience. It offers the utmost Hawaiian relaxation & tranquility in a real plantation setting. Feel the tropical Hawaiian sun, dive into the crystal aqua waters & enjoy your private y …see more

from $87 / night

$609 / week

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avg. 2 hours 14 minutes

from $87 / night

(26) Excellent 

31

Hawaii Vacation home rental

Kauai / Hanalei

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Stay in our private home in Princeville Kauai at a fraction of what a hotel costs! Three bedrooms, 2 baths, open living room with dining room and full kitchen. The kitchen is fully equipped for eating in, plus we have 2 large lanais for outdoor dining overlooking the m …see more

from $230 / night

$1,610 / week

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avg. 3 hours 29 minutes

from $230 / night

(5) Excellent 

28

Vacation guest house with swimming pool in Hilo

Island of Hawaii / Hilo

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
Enter the magnificent Royal Palm lined drive and experience Big Island history. Enjoy the unique ambiance of this one of a kind grounds of the former Ola’a Sugar Plantation residence and its directors cottage, now the guest house. It has been completely and tastefully …see more

from $150 / night

$980 - $1,400 / week

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avg. 3 hours 9 minutes

from $150 / night

23

Vacation condo rental

Oahu / Kahuku

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This homey one bedroom / two bathroom Turtle Bay condo offers the perfect true Hawai'i get-away for up to four lucky humans! The closest condo to the beach and sitting on the 18th hole of PGA Fazio Course, we welcome you to the coveted North Shore! **The Condo** New …see more

from $184 / night

$1,288 / week

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from $184 / night

17

Vacation condo in Hawaii

Kauai / Kapaa

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This condo is part of an exclusive gated Condominium complex that is on a quiet beach cove with natural ocean ponds. This luxurious Penthouse feels much more like a private home with spacious rooms and a full wall of pocket sliding doors that open up completely to exten …see more

from $545 / night

$3,815 / week

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from $545 / night

12

Private room rental in Hilo

Island of Hawaii / Hilo

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
Aloha and welcome to Hale Sunrise! Our home is on 4 lush and serene acres 15 minutes from downtown Hilo and airport. This is where you can stay to soak in the feeling of real and local Hawaii away from the rush of town. You have a continental breakfast, a comfy bed, a p …see more

from $100 / night

$650 / week

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from $100 / night

(3) Very Good 

28

Vacation apartment rental

Kauai / Poipu

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Paradise Found! Secluded End Unit,#331, Partial Ocean View. Quiet, perfect retreat,pristine beaches,stunning garden paradise. Tastefully decorated condo home with lofted ceilings,louvered windows,gleaming new wood floors,large tile entry hall and kitchen update …see more

from $198 / night

$1,351 / week

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from $198 / night

12

Vacation home in Hawaii

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

(13) Very Good 

35

Hawaii Vacation home rental

Island of Hawaii / Volcano

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Private garden
Park reopens on September, 22! Kama'aina discount. Tons of hikes and activities available. We give you a list! Welcome to this Hawaiian paradise in the middle of a magical rainforest near Volcano Village, one mile away from the Hawaii Volcanoes National Park ! This is t …see more

from $160 / night

$1,125 - $1,440 / week

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Responds fast!
avg. 2 hours 39 minutes

from $160 / night

39

Vacation condo rental

Oahu / Makaha

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Cozy, nestled beneath the majestic mountains of the Makaha. A local living in a resort facility. It comes with everything you'll need to feel comfortable. Gated community. It offers a true Hawaiian relaxation and tranquility. Enjoy the tropical Hawaiian sun, dive into …see more

from $87 / night

$609 / week

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avg. 2 hours 14 minutes

from $87 / night

36

Vacation home in Kahala

Oahu / Kahala

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Spectacular panorama views of the Pacific Ocean! We have two to four bedrooms. Please be accurate on total number of guest and how many bedrooms you’d like. Living room and dining area wet bar with a mini kitchenette. Phenomial views from brother master bedrooms. Have c …see more

from $775 / night

$5,425 / week

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avg. 1 hour 55 minutes

from $775 / night

11

Vacation home in Mililani

Oahu / Mililani

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 10 mi
  • Air conditioning
My place is a house and is close to all major Freeway, highways ( H2 , 99 ), Restaurants, shopping, entertainment. One bedroom Suite: * AirCondition Room * Free Wifi and Parking * Internet 42" TV * North Shore ........ 20 minutes ( Best Surf in Hawaii ) "Amazing place i …see more

from $85 / night

$595 / week

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avg. 3 hours 58 minutes

from $85 / night

16

Condo rental in Poipu

Kauai / Poipu

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
A little slice of paradise - Our unit is #227 in building #35. It is a top floor, one bedroom condo, with a lofted ceiling. The bedroom has a comfortable king size bed and the living room couch converts to a comfortable queen size bed. The condo is perfect for 2 guests. …see more

from $199 / night

$1,393 / week

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from $199 / night

7

Vacation studio in Kailua

Oahu / Kailua

Studio 3 3 nights min

  • Studio
  • sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Kailua beach is about 1 mile from Kailua town. Kailua Guesthouse is located half-way between. It's about a 10-minute walk to the beach, a 10-minute walk to town. TheBus stop is about 300 feet from our front gate. My father acquired the property in 1947 and b …see more

from $149 / night

$980 - $1,050 / week

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from $149 / night

10

Vacation condo with golf nearby in Hawaii

Oahu / Honolulu

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Car not necessary
This is a Studio unit not 1 bedroom. Step out of the elevator and on to the warm sands of Waikiki Beach. You can not find a better location! Walk to restaurants, shopping, and all that Waikiki has to offer. You don't walk to the beach, you are on the beach! This Suite …see more

from $145 / night

$1,015 / week

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avg. 1 hour 8 minutes

from $145 / night

14

Vacation condo in Hawaii

Oahu / Honolulu

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located only 1 block from Waikiki Beach, this ocean facing, large corner unit with lanai and extra windows on the 36th floor, has panoramic views of the ocean, beach, pool, and Diamond Head, not to mention the sunrise and sunset views. Breathtaking! Our condo has been …see more

from $150 / night

$1,050 / week

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from $150 / night

(1) Excellent 

23

Vacation home in Hawaii

Island of Hawaii / Keauhou

6 16 min stay varies

  • 6 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Quintessential blend of Luxury, Privacy, and Open Air Living. This 5 bedroom, 6 bath estate is nestled on 5 extremely private acres, but just moments away from Alii Drive, minutes to White Sand Beaches, and local golf courses. This unique offering of ultra-luxury living …see more

from $999 / night

$6,783 - $8,883 / week

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avg. 1 hour 22 minutes

from $999 / night

(1) Very Good 

25

Hawaii Vacation cottage accommodation

Island of Hawaii / Keaau

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Nearest beach 16 mi
  • Swimming pool
  • Private garden
Enter the magnificent Royal Palm lined drive and experience Big Island history. Enjoy the unique ambiance of this one of a kind grounds of the former Ola’a Sugar Plantation residence and its directors cottage, now the guest house. It has been completely and tasteful …see more

from $150 / night

$1,050 / week

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Responds fast!
avg. 3 hours 9 minutes

from $150 / night

13

Vacation cottage rental

Island of Hawaii / Pahoa

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly
Our Rental cabins are for travelers with a taste for an Eco-Zen Luxury experience. Fitted with a Queen bed and surrounded by the Hawaiian jungle in a serene atmosphere accompanied by songs of birds, chirping frogs & ocean waves. We have three cabins available for rent. …see more

from $88 / night

$399 - $506 / week

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from $88 / night

16

Vacation studio in Hawaii

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

(2) Excellent 

34

Vacation studio in Hawaii

Oahu / Honolulu

Studio 4 1 night min

  • Studio
  • sleeps 4
  • 1 night min
  • Nearest beach 7 mi
  • Child friendly
Come to real paradise, 10 minutes walk to paradise park & manoa falls hike, very private and breezy, quiet, cul de sac, hear the birds singing on day time. My place is close to public transport, airport, near city center & shopping few minutes away by car. You’ll love t …see more

from $99 / night

$625 - $975 / week

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avg. 2 hours 15 minutes

from $99 / night

(5) Excellent 

27

Condo rental in Honolulu

Oahu / Honolulu

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
WE WILL REQUEST COPY OF GUESTS ID'S FOR EVERYONE'S SAFETY. ************************************************************************************** THIS UNIT IS IDEAL FOR 2 COUPLES OR 3 GENERATIONAL FAMILIES *************************************************************** …see more

from $495 / night

$3,465 / week

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avg. 3 hours 14 minutes

from $495 / night

(19) Excellent 

20

Hawaii Vacation cottage rental

Island of Hawaii / Volcano

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
In the Hawaiian language, a "kipuka" is a kind of oasis. It can be an island of forest surrounded by lava fields, or an opening within a forest, or even a dwelling, a home within the forest. This is our Kipuka -- a custom-designed cottage, a vacation home for you here o …see more

from $165 / night

$1,015 - $1,715 / week

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from $165 / 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

(1) Excellent 

25

Vacation home accommodation

Oahu / Honolulu

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
A Beautiful high ceiling air conditioned home located on East Oahu. This eloquent home in Hawaii Kai is perched up in a nice quiet neighborhood in Kalama Valley. This 3 bedroom, 2 bathroom house features, three lanais - one outside the master bedroom with table and chai …see more

from $348 / night

$2,436 / week

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avg. 2 hours 8 minutes

from $348 / night

68

Condo rental in Hawaii

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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avg. 1 hour 29 minutes

from $350 / night

(1)  

21

Vacation condo with shared pool in Hawaii

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

14

Hawaii Vacation home rental

Oahu / Makaha

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 2 mi
  • Child friendly
E komo mai (Welcome) to our tropical House of Paradise! We are 1.5 miles from the iconic Makaha Surf beach. Our home is a spacious 4 bedroom, 3 1/2 bath with stunning Makaha Valley views that reach all the way to the ocean! We are located in a gated community overlookin …see more

from $515 / night

$3,605 / week

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from $515 / night

20

Vacation condo in Hawaii

Maui / Kihei

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
1 bedroom corner unit. Close to beachfront, bbq's and pool. Located on a 5 mile sandy beach, ideal for taking long walks. Surf is calm, activities include kayaking, paddle boarding and snorkelling. Condo has recently been updated with new bathroom, flooring and furnishi …see more

from $160 / night

$1,120 / week

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from $160 / 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) Excellent 

13

Vacation condo in Hawaii

Island of Hawaii / Kailua-Kona

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
This is the best deal in Kona! Completely updated 1 bedroom, 1 bathroom condo with a fully equipped kitchen and a reserved parking stall just steps from the condo. This unit is on the 3rd floor with a beautiful view of the garden, a partial ocean view, and takes full ad …see more

from $119 / night

$833 / week

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from $119 / 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

19

Vacation condo with shared pool, golf nearby in Hawaii

Kauai / Princeville

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Fully remodeled quality top floor luxury laid back tropical condo. All furnishings & decor coordinated professionally. Full kitchen & quality cooking appliances & supplies. Relax & enjoy quiet & views from 2 lanais. Everything in condo needed for your special Hawaii …see more

from $165 / night

$1,155 / week

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avg. 43 minutes

from $165 / night

24

Vacation apartment with shared pool in Kailua-Kona

Island of Hawaii / Kailua-Kona

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Come and enjoy your stay in this beautifully upgraded 1 bedroom condo at Kona Reef. Located on a desirable single level overlooking the pool and the ocean, you will find all the comforts you would expect in this tropical paradise. Let the sound of the crashing waves be …see more

from $175 / night

$1,225 / week

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from $175 / night

10

Vacation cottage rental

Island of Hawaii / Pahoa

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
"Kualoli" the Hawaiian translation for Metamorphosis There grows an impressive crown-flower bush, home to hundreds of monarch butterflies. Transforming through their cycle, these beauties symbolize the changes in our own human development. A literal interpretation symbo …see more

from $83 / night

$506 - $745 / week

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from $83 / night

20

Vacation home in Hawaii

Maui / Lahaina

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
272-3 Upscale Oceanfront Townhome 272-3 is an upcale 3 bedroom 3.5 bath oceanfront unit with bikes, steps to the beach ccess, a lot of ocean stuff and a very well equipped kitchen . The unit has a Mr. Coffee pot and a Keurig coffee machine a we …see more

from $610 / night

$4,270 / week

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from $610 / night

12

Vacation hotel apartment in Honolulu

Oahu / Honolulu

2 8 90 nights min

  • 2 bedrooms
  • sleeps 8
  • 90 nights min
  • Swimming pool
  • Air conditioning
PLEASE NOTE: ⚫️This is NOT a Private Rental ⚫️This is NOT a Private Room. ⚫️Private Beds available in a Female Shared Room, Sorry no vacancy in our CO-Ed area at this time. プリンセスパレス ::::: ELS / INTERN STUDENT CONDO HOME STAY - STUDENT SHARE CONDO - ELS - KCC - HPU ♚ …see more

from $37 / night

$250 / week

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from $37 / night

12

Vacation apartment with shared pool in Hawaii

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 $400 / night

$2,800 - $4,550 / week

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from $400 / night

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