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Smoking Allowed Holiday Rentals in Maui

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    Travellers to Maui are booking December dates now. Secure your holiday home today, and have the perfect trip.
    27 Matching Rentals in MauiView all 3,071 rentals
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    Beautiful, luxury Resort Condo with LOW rates!1 / 52
    (132)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    .Hana Camping Under the Stars1 / 14
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 40 Quick View
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    The Whaler 1062 - Studio Ocean View Condominium1 / 29
    (6)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    WBH D115 - Aloha Kai2, Beachfront, 1B/1Bath,Wifi,AC,Pool, Waiohuli Beach Hale1 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2018
    We were skeptical at first as we’ve never stayed in a condo before. But we loved everything about it. The condo was super cute and Hawaiian and had everything we needed and more...
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    About this property
    We want to share a piece of Paradise, what we call the 'Aloha Kai Suite' with you. This is part of our Aloha Aku Rentals family where the South Maui weather is dependably sunny and warm year long. Tradewinds caress you as you relax on the shore of a forever ocean. In the SUMMER these same...
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    Kihei, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Hot Tub
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We want to share a piece of Paradise, what we call the 'Aloha Wai2 Suite' with you. This is part of our Aloha Aku Rentals family where the South Maui weather is dependably sunny and warm year long. Tradewinds caress you as you relax on the shore of a forever ocean. In the SUMMER these same...
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    Kihei, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    $199/NIGHT SPECIAL  1Bd/1Bath Condo, Whaler 2591 / 21
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Sauna
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2014
    This is the 2nd year I have stayed in this large 1 bedroom, 1 bath condo. The best part about it is the location. It is on the 2nd floor of the Whaler condo complex in Tower 2...
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    About this property
    $199 + tax Price Drop! Take advantage of our DEEP DISCOUNTED RATES now thru the end of September! Price reflects our studio rate for this super cute vacation home. The Whaler on Kaanapali Beach #259, is a one bedroom, one bath partial ocean view condominium located on the 2nd floor on the south...
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    Lahaina, Maui 96761
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Maui Chalet - tropical North Shore private retreat1 / 10
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Washer
    • Hot Tub
    • Porch
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2016
    Our stay at Maui Chalet was a nice change from the hustle and bustle in our everyday lives. Spent the first 5 days in Kihei and wanted a different environment. The property was...
    Reviewed 11 April 2015
    We couldn't have been more thrilled with our stay at the Maui Chalet. It was spacious, beautiful, clean and well stocked with all one needs. The views and decks were fantastic...
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    About this property
    Note to Maui County Inspectors: ( Our Permit: STARTS PH 2013/0011 - our Tax ID looks like a phone #, and is not allowed by Trip Advisor, but it is on Maui and ends in1328-01) We are a husband/wife team, providing a unique island experience on North Shore Maui, Hawaii. This is one of the few lush...
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    Haiku, Maui 96708
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    The Whaler 813 - Studio Ocean View Condominium1 / 29
    (5)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Washer
    • Hot Tub
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Whaler on Kaanapali Beach #813, is an ocean view studio suite condominium located on the popular courtyard side of Tower I on the 8th floor. Sitting on your lanai, enjoy views of the West Maui Mountains to your left and Kaanapali Beach and the neighbor island of Lanai to your right. King bed,...
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    Lahaina, Maui 96761
    Condo/Apartment - 1 Bathroom, Sleeps 2
    OCEAN FRONT SALE!  The Whaler 1102 Deluxe 2-Bedroom/2-Bath Condo1 / 28
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Sauna
    • Grill
    • Hot Tub
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2013
    This was a repeat visit for our family. We were not disappointed. This unit has all that you want for a vacation. Great views, easy access to beach, restaurants & shopping and...
    Reviewed 13 April 2012
    Fabulous comes to mind with this rental. Lots of space, beachfront, beautifully appointed unit in Whalers village condos. Plenty to do right in the heart of Kaanapali beach.
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    About this property
    DEEP DISCOUNTED RATES thru October 2019! The Whaler on Kaanapali Beach #1102, is a 2-bedroom, 2-bath direct ocean front condominium located on the north side of Tower I. Its 11th floor corner location offers breathtaking, unobstructed views from the West Maui Mountains, down to Kaanapali Beach and...
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    Lahaina, Maui 96761
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    *Maui Vista*  Great condo at Affordable Prices1 / 31
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2015
    This was a great condo! Comfy bed, kitchen and bathroom totally remodeled and stocked with everything needed, tile floors...it was great. The best part was the proximity to the...
    Reviewed 9 January 2015
    We absolutely loved this condo! It was wonderful to have a fully functional kitchen to cook meals all week. The BBQ pit area was also very handy, and we made use of it several...
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    About this property
    Our ground floor Maui Vista condo overlooking the gardens has been recently remodeled to create a resort style vacation spot at an affordable price. A sunny lanai provides a perfect spot for morning coffee. Located at 2191 S. Kihei Road, Kihei, HI 96753 It has a full sized kitchen with new...
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    Kihei, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    The Whaler 965 - Studio Ocean View Condominium1 / 22
    (7)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Hot Tub
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Sauna
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2014
    Stayed there for 5 days, the room was always clean, quiet and the staff very accomidating.The view was great and we were able to walk to shops, the beach and restuarants. The...
    Reviewed 4 November 2013
    Updated, immaculately clean, luxurious, and extremely economical during off season.Incredible ocean view, modern with full kitchen, beautiful furnishings, quiet, flat screen TV...
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    About this property
    The Whaler on Kaanapali Beach #965, is an ocean view studio condominium located on the south side of Tower II. High above Whalers Village on the 9th floor, this unit offers expansive views stretching from the West Maui Mountains, south to Lahaina and out to the neighbor island of Lanai. Enjoy...
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    Lahaina, Maui 96761
    Condo/Apartment - 1 Bathroom, Sleeps 2
    SUPER SALE!  Direct Ocean Front 1-Bedroom/2-Bath Whaler #4011 / 35
    (4)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    • Washer
    • Sauna
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DEEP DISCOUNTED RATES thru October 2019! The Whaler on Kaanapali Beach #401, is a Direct Ocean Front one-bedroom, two-bath condominium located in Tower 1 on the 4th floor. This suite offers sweeping views spanning from Black Rock to the north, across Kaanapali Beach and beyond to the neighbor...
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    Lahaina, Maui 96761
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    SALE!  The Whaler 963 - Studio Ocean View Condominium1 / 28
    (3)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Sauna
    • Washer
    • Parking
    • Grill
    • Hot Tub
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2013
    Very good location, right on beach. Building modern, everything works, staff friendly. Difficult to find something better for this price.One drawback: on Whaler's Village side...
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    About this property
    DEEP DISCOUNTED RATES thru September 2019! The Whaler on Kaanapali Beach #963, is a studio ocean view condominium located on the south side of Tower II. High above Whalers Village on the 9th floor, this unit offers expansive views stretching from the West Maui Mountains, south to Lahaina and out...
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    Lahaina, Maui 96761
    Condo/Apartment - 1 Bathroom, Sleeps 2
    MAUI SPECIAL!  Whaler 1174 - One Bedroom, Two Bath Ocean View1 / 31
    (4)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Sauna
    • Washer
    • Hot Tub
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 December 2014
    Typical quality you expect from the Whaler. This is my 6th time staying at the Whaler and this particular condo was great. Big, clean and being on the end was a bonus.
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    About this property
    DEEP DISCOUNTED RATES thru October 2019! The Whaler on Kaanapali Beach #1174, is a one bedroom, two bath ocean view unit located on the courtyard corner of Tower II. It's 11th floor location provides expansive views that stretch from the lush West Maui mountains across the courtyard and out to...
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    Lahaina, Maui 96761
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Kamaole Beach Royale 1 Bedroom Seaviews1 / 23
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Balcony
    • Parking
    • Washer
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    We had a fabulous time at our Kamaole Beach Royale condo. The location is terrific, a stones throw from the beach. The amenities of the Condo were great, everything a mature age...
    Reviewed 2 February 2015
    Have stayed at this well decorated, updated condo a couple times. In a super convenient location with several great beaches just a short walk away. Enjoyed fantastic sunsets...
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    About this property
    Spacious 1 bedroom 750 sf apartment in a great location next to Dolphin Plaza. A short walk to Kamaole I Beach! Remodeled in 2012 tastefully decorated, comfortable and quiet space for your vacation. Kitchen renovated in September 2016. Safe neighborhood, inviting pool in a lovely garden...
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    Kihei, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Parking
    • Sauna
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Whaler on Kaanapali Beach #1074, is a one-bedroom, two-bath ocean view unit located on the courtyard corner of Tower II. With it's 10th floor location and wrap around lanai, this gorgeous home provides expansive views that stretch from the lush West Maui mountains across the courtyard and out...
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    Ka'anapali, Maui 96761
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Sauna
    • Washer
    • Grill
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Whaler on Kaanapali Beach #564, is a recently remodeled studio condominium with a fabulous ocean view, located on the popular courtyard side of Tower II on the 5th floor. Enjoy afternoon shade on your lanai with views of the West Maui Mountains to your right and Kaanapali Beach and the neighbor...
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    Ka'anapali, Maui 96761
    Condo/Apartment - 1 Bathroom, Sleeps 4
    The Whaler 715 - Studio Ocean View Condominium1 / 28
    (5)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Sauna
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Whaler on Kaanapali Beach #715, is an ocean view studio condominium located on the popular courtyard side of Tower I. Sitting on your lanai, enjoy views of the West Maui Mountains to your left and Kaanapali Beach and the neighbor island of Lanai to your right. King bed, Queen sofa sleeper,...
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    Lahaina, Maui 96761
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Sauna
    • Grill
    • Wi-Fi
    • Hot Tub
    • Washer
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Whaler on Kaanapali Beach #1118, has one of the most popular views of Black Rock and Kaanapali Beach. Being located on the north side of Tower One, this unit offers a shady retreat after enjoying a beautiful day in the Maui sun. This unit has a King size bed and sleeps 2 people comfortably....
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    Ka'anapali, Maui 96761
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Kahana Nui Tropical Estate - Private Oceanside Villa1 / 9
    (3)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Hot Tub
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2018
    This vacation rental is absolutely spectacular and there’s nothing else like it on the West side of Maui. Sweeping ocean views, private pool, semi-private beach, and stunning...
    Reviewed 8 February 2018
    We had a great time. The house is beautiful! It was very clean. The location was awesome. Spent many of our meals on deck, watching the whales go by. Love the privacy. Thank...
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    About this property
    Aloha, For many visitors to Maui the idea of staying in a private tropical beachfront estate appears impossible or just an idyllic scene of yesteryear. But a stay at the Kahana Nui Villa will make this dream come true. As you enter through your own automatic wood gate, you'll find yourself...
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    Napili-Honokowai, Maui 96761
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Parking
    • Wi-Fi
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    $299/Night Price Drop! Take advantage of our DEEP DISCOUNTED RATES now thru the end of October! The Whaler on Kaanapali Beach #370 is a super cute 1-bedroom/2-bath condo with lovely ocean and garden views, that over looks the beautifully manicured courtyard and waterfall. The spacious lanai even...
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    Ka'anapali, Maui 96761
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Wi-Fi
    • Sauna
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DEEP DISCOUNTED RATES thru October 2019! The Whaler on Kaanapali Beach #956, is a Premium ocean view one-bedroom, one-bath condo located in Tower 2 on the 9th Floor, and is beautifully remodeled throughout. Enjoy a gourmet kitchen that is fully appointed with elegant granite counters, spacious and...
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    Ka'anapali, Maui 96761
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Sauna
    • Hot Tub
    • Wi-Fi
    • Washer
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Whaler on Kaanapali Beach #557, is a deluxe ocean yiew one-bedroom, two-bath condo located in Tower 2 on the 5th floor, and is beautifully remodeled throughout. Enjoy a gourmet kitchen with beautiful granite counters, spacious and comfortable living area with dining area for a family of four,...
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    Ka'anapali, Maui 96761
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    $399/NIGHT SPECIAL 2Bd/2Bath Condo, Whaler 9231 / 32
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    $399/Night Price Drop! Take advantage of our DEEP DISCOUNTED RATES now thru the end of September! Whaler 923 is a beautiful spacious 2 bedroom, 2 bath ocean view condominium located on the popular courtyard side of Tower I. It's 9th floor location offers expansive view stretching from the West...
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    Ka'anapali, Maui 96761
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    MAUI VACATION SALE!  The Whaler 411- Deluxe 1-Bedroom/2-Bathroom1 / 30
    (1)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DEEP DISCOUNTED RATES thru October 2019! The Whaler on Kaanapali Beach #411, is a Premium 1-Bedroom, 2-Bath ocean view condo located in Tower 1 on the 4th floor, and is beautifully remodeled throughout. Enjoy a gourmet kitchen with elegant granite counters and top rated appliances. A comfortable...
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    Lahaina, Maui 96761
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Children's Pool
    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kahana Sunset is a beachfront resort on the world famous west coast of Maui between Kaanapali and Kapalua. You will be swimming and snorkeling with turtles and tropical fish off of the white sandy beach of protected Keoni Nui Bay. There is also a heated swimming pool that has an adjoining...
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    Napili-Honokowai, Maui 96761
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    you won't miss one of the most amazing thing in this world, the sunrise at Haleakala. No permit needed, only pay the entrance fee and take our camping equipment to enjoy this wonderful and magical sunrise! you will fell comfortable, sleeping in our tent.. the camping ground its only 35min away to...
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    Haleakala National Park, Maui 96790
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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