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Watersports Holidays in Maui - Holiday Lettings

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426 properties with watersports onsite or nearby

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Holiday condo with shared pool in Kihei

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £183 / night

£1,278 / week

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Haiku holiday home rental

Haiku house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £365 / night

£2,556 / week

1 / 35

Condo rental in Kihei with shared pool

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £274 / night

£1,917 / week

1 / 18

Condo rental in Ka'anapali

Ka'anapali condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £402 / night

£2,811 / week

1 / 39

Holiday apartment with shared pool in Maalaea

Maalaea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £302 / night

£2,108 / week

1 / 23

Holiday cottage in Makawao

Makawao cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £206 / night

£1,438 / week

1 / 25

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

Ka'anapali condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £542 / night

£3,795 / week

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Holiday home with swimming pool in Haiku

Haiku house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“We found Paradise!” Hale Mauka Makai was everything my family and I hoped it would be and more. My husband, two daughters (ages 9 and 12) and I are from Rhode Island and have never been off the East Coast. We were very excited to be spending 10 days in Maui! It has always been our dream vacation and Hale Mauka Makai lived up to every expectation we had (and then some!). Claudia and Kevin were the perfect hosts. They gave us a detailed tour of the house and the grounds so that we were completely comfortable with everything that the property had to offer us. After the tour we did not see them for the rest of our time there...they understood that we would want our privacy during our stay in this amazing home. The house was pristine and beautifully decorated. The pool was amazing!!! We made time to swim and lounge by the pool every single day that we were there (sometimes during the day to soak up the sun and other times at night swimming under the stars). 5 stars doesn't seem like enough when rating Hale Mauka Makai... It is perfection and I can't think of one thing I would have changed about it.

from £822 / night

£5,749 / week

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Holiday apartment in Kihei

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Near the action yet quiet.” It was a short walk to a beautiful beach and quite a lot of traffic before there but the condo was quiet with the sounds of birds and a cool breeze passing through so AC wasn't needed even in the heat of summer.

from £165 / night

£1,118 - £1,182 / week

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Kihei holiday condo rental

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £165 / night

£1,118 - £1,182 / week

1 / 39

Holiday home in Kihei

Kihei house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £2,008 / night

£14,054 / week

1 / 14

Kihei holiday condo rental

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £273 / night

£1,910 / week

1 / 27

Ka'anapali holiday apartment rental

Ka'anapali apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £288 / night

£2,013 / week

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Holiday apartment rental

Ka'anapali apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £209 / night

£1,463 / week

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Holiday apartment in Kihei

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £133 / night

£831 / week

1 / 20

Holiday apartment with golf nearby in Ka'anapali

Ka'anapali apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful well kept unit with a gorgeous view!” We stayed at Papakea Resort, Unit G-407 in October. My husband and I along with my older son had a great time in Maui. This unit is very close to the ocean front with a full view. We had drinks and many suppers on the Lani, watching the sunsets. G-407 is on the top floor. It has a very nice loft with two single beds or one king bed, along with an additional bathroom which was handy. Nobody was fighting for the showers. The kitchen is fully supplied, with wonderful cutlery, pots, pans, dishes, wine glasses, coffee maker and many other things that most vacation rentals don't have. They also had body surf boards, umbrellas and beach towels. This unit was recommended to us by a friend. I would highly recommend it to anybody. We were in Maui for a wedding and everybody that came to our unit loved it. Upon arrival it was very clean. Parking is also convenient with an easy check in procedure. This is where I am hopefully staying every time we come to Maui.

from £343 / night

£2,396 / week

1 / 30

Cottage rental in Paia

Paia cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful host and so relaxing!” Valerie was a wonderful and welcoming host and we greatly enjoyed our time at the cottage. Sitting out in front of the ocean view with a book was our favorite part!

from £292 / night

£2,044 / week

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Holiday condo with shared pool, golf nearby in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £354 / night

£2,479 / week

1 / 8

Holiday home with golf nearby in Napili-Honokowai

Napili-Honokowai house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £3,103 / night

£21,719 / week

1 / 9

Holiday home with golf nearby in Kihei

Kihei house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

from £867 / night

£5,766 / week

1 / 21

Holiday apartment in Kihei

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fabulous!” What can I say... from start to finish this was a fabulous experience. Lisa the owner is a great person to deal with and gave excellent sevice and lots of useful tips. The condo, facilities and grounds were kept in very good condition and was in a an ideal location to take in the sights and sounds of Kihei and Maui. Even a good location if you don't have a car. Would recommend to all if you are looking for a laid back chilled vacation in a cool location.

from £218 / night

£1,527 / week

1 / 12

Villa rental in Lahaina with shared pool

Lahaina villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £906 / night

£6,343 / week

1 / 23

Kihei holiday apartment rental

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £215 / night

£1,501 / week

1 / 49

Condo rental in Kihei

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £265 / night

£1,853 / week

1 / 21

Cottage rental in Paia

Paia cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £434 / night

£2,556 / week

1 / 7

Cottage rental in Haiku

Haiku cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Perfect in every way for our first trip to Hawaii !!!” We stayed at "The Cottage" March 31-April 8th to celebrate 35 years of marriage, 2 retirements, and a birthday and it was perfect in every way! We knew as we drove down the citrus and flower-lined drive to the sign pointing our way to the cottage that we had found Paradise! But only for 8 nights!! When planning a vacation and where we will stay, we look at location, cleanliness, views, amenities, and price. The cottage was near grocery stores, beaches, towns, and the best restaurant on Maui, "Mama's Fish House". The cottage was spotless and we could have eaten off of the floors inside and also outside on the lanai (deck). It was amazingly clean! The views of the water, mountains, pastures, flowers, fruits, sunrises and sunsets were unbelievable. We loved sitting on the lanai and also inside we could enjoy the views. The personal touches from our perfect hosts were something that did not go unnoticed or unappreciated. After booking, Barbara sent us a highlighted map and typed directions to help us get from the airport to the cottage. There was a magazine rack full of guidebooks to help us plan our days. Barbara had typed directions to grocery stores with comments about what they sold. The Welcome Basket was beautiful and delicious and I loved the fresh flowers on the soap and candy dishes! Hank had also left tools under the the sink, if needed, and they had laundry detergent for us to use on the front-load washer and dryer. There is so much more I could say about how wonderful our visit to the cottage was...Paradise is just the best way. My husband said we would go back next year for 2 weeks! I can't wait! Aloha Ya'll!

from £327 / night

£2,287 / week

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Holiday apartment in Wailea

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £182 / night

£1,272 / week

1 / 21

Holiday apartment rental

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £167 / night

£1,166 / week

1 / 31

Holiday condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,591 / week

1 / 18

Holiday condo rental

Ka'anapali condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £365 / night

£2,549 / week

1 / 37

Holiday condo rental

Ka'anapali condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £500 / night

£3,501 / week

1 / 37

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

Ka'anapali condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £469 / night

£3,284 / week

1 / 37

Holiday condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £303 / night

£2,120 / week

1 / 16

Holiday villa with golf nearby in Ka'anapali

Ka'anapali villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £848 / night

£5,932 / week

1 / 11

Holiday condo with shared pool, golf nearby in Kihei

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £151 / night

£1,054 - £1,182 / week

1 / 34

Apartment accommodation in Kihei with golf nearby

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Friendly, caring staff” Kamaole Nalu is a comfortable home away from home with an outstanding location. It is convenient to most amenities that I needed and next time I will try to get a smaller car as the parking spots are pretty small. The on-site chick - Patty Law - was awesome; helpful, hardworking and fun. Hope to be back next year.

from £271 / night

£1,892 / week

1 / 36

Holiday condo rental

Ka'anapali condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £236 / night

£1,649 / week

1 / 10

Holiday cottage in Haiku

Haiku cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £178 / night

£1,246 / week

1 / 28

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £279 / night

£1,947 / week

1 / 24

Holiday apartment with shared pool in Ka'anapali

Ka'anapali apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Convenient and affordable” This condo was ideally arranged for feeding a family a meal or two each day to keep down costs. The condo had all the basic necessities plus other helpful items like kick boards, chairs, beach towels, and snorkels-masks. Being able to park right out front meant we were in the van on on the beach without wasting much time. It was also great to be able to do laundry, so that we could pack light. The condo was clean and well-maintained. The park across the street was a great place for watching the sunset. Great coffee and a farmers markets steps away also was a real treat.

from £168 / night

£1,094 - £1,221 / week

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