Wailea Rentals with Pools

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726 condos in Wailea with pools

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One-of-a-Kind Maui Getaway!

Wailea house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$2,000

Wailea Ekolu #201 2Bd/2Ba Ocean View Condo Near Beach, A/C, Wifi, Sleeps 6

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$400

Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Great Getaway!!” I loved unit 1105 at The Palms. It was totally updated and very clean. The beach chairs and boogie boards were nice to have. Loved the quiet nature of the Palms and the proximity to all of the beautiful beaches!!

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$383

Palms at Wailea #205: Look no further! Fully Air-conditioned & Renovated!

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$396

Wailea Ekolu #805 Deluxe 2Bd/2Ba, Ocean View Townhouse! Full A/C, Sleeps 4

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ekolu Unit 805” Wailea Ekolu Unit 805 is a comfortable, clean, spacious, beautifully updated two bedroom/two bath condo. This first floor unit with a nice lanai has a partial view of the ocean and is located in a quiet area of the complex. I would not hesitate to rent this unit again.

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$341

Palms at Wailea #1102 Probably the best ocean view at the Palms at Wailea!

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place to stay for the price” We loved the location and views from our units. The pool was warm and quite nice despite having many restrictions. The units were clean and nice looking however many of the amenities promised (ie. beach equipment) were not in good enough shape to even be useful. If you are advertising these amenities, they should be in decent shape (both beach umbrellas were broken and the cooler bag was so beat up it leaked water all over the place). The property managers skimped on some of the simple things like providing more than a couple of garbage bags and rolls of toilet paper or making sure the light bulbs were new (3 went out during our 10day stay). The garbage disposal in one unit was broken altogether and the screen door in the other had no handle from the outside (a big problem if you go outside and close the door behind you). The rental agency was difficult to reach but did eventually come and replace the light bulbs. All in all we had a good stay but these little things would make a big difference.

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$395

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Price per night from

$802

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$400

“Best experience ever in USA. Loved every minute of our stay.” #51 @ #48 condos were by far even better than the reviews and pictures described. My family from Canada and myself were truly impressed by the attention to detail and how well the units were presented. From the moment we walked in til the moment we left, we felt right at home with absolutely everything we could have needed or wanted to make our vacation complete.

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$389

Wailea Ekahi 46F- Spacious 2 bedroom 2 Bath Condo in Wailea!

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great trip to Maui” My family and I enjoyed our time at Ekahi. Loved the view from the balconies, and chairs and other beach equipment was there for our use. The property management was very accomodating and when we had one thing missing from the condo, it was there the next day. I think this is a great condo for a family of 2 adults 2 the layout offers privacy in the master suite and a pool, is just outside the condo. Just be advised, it is a bit of a walk to the beach, however, you can drive down and park. The grounds are beautifully maintained. Quiet and pleasant. Lovely pool and rec area at the beach. I would stay here again, just a little closer to the beach.

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Price per night from

$400

Wailea Ekolu #503 Panoramic Ocean View, Great Location, 2Bd/2Ba, Sleeps 4

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$372

Wailea Ekahi Ocean View 50A

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$395

Palms at Wailea #1902 Garden View 2Bd/2Ba, Fully Air Conditioned, Sleeps 6

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“A breath of fresh air” I have stayed at many different rentals never knowing if the pictures show what the condo really looks like. This rental was exactly what was shown and more! We were impressed with the updated features and location. The balcony was our favorite and the condo was very clean and accommodating for all our needs. Thank you for having a beautiful place that added to a wonderful vacation!

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$371

Castaway Cove C201 at Wailea Beach Villas

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$1,495

Wailea Grand Champions #50 is a 2Bd/2Ba, Great Location Near Pool, Sleeps 6

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Loved it” Loved the area the condo was located. Very clean, and spacious. Kids loved the pool =)

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$303

Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 47 minutes

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Price per night from

$1,143

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$252

Remodeled Mountain View 2 BDRM Condo - Royal Mauian #601

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$209

Gorgeous Remodeled Ocean Front Condo - Makena Surf Resort G-206

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$949

Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$389

STOP! LOOK NO FURTHER! Palms at Wailea #1503 2Bd Ocean View Best Location!

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$476

Beautifully Renovated 2 BDRM WAILEA ELUA, #2201

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$549

“Here is a Gem of a Condo!” The owner of this condo, Lawrence Daluz was easily available and great to work with! The condo is clean, beautiful and comfortable in most every way. This condo is placed in a hotel setting (as it turns out our friends were renting a hotel-owned condo just across the driveway) so we got to see the inside of one of the hotel-owned-and run units. This one was far superior to theirs, though the layout for the unit is exactly the same. The sunny kitchen in this condo was extremely well-supplied (the best we have run across, ever, which we really appreciated) and all the appliances we used worked great. This unit has a stove, a microwave, a 'fridge with freezer and a decent-sized oven. We like to cook our own food (the main reason for getting a condo in the first place), so all of this came in VERY handy. Even the dishes were up-to-date and pretty! The bedroom is really nice and the bed, perfect and super-comfortable (especially for this girl with back issues), the living room is lovely (and beautiful) to relax in and the inside dining area furniture, classy and generous-sized. The lanai is mostly quiet (there is a street nearby but the noise there was minimal in our opinion). The lanai was also surprisingly private and quite well-supplied including a huge gas barbecue (which we didn't try out), and a nice dining table which we used often. There are also two comfortable loungers with pillows on the lanai as well. Though we brought our own snorkeling equipment, Lawrence has included a generous supply of usable snorkeling gear and children's sand toys (though we didn't use any of it.) The only "con" for this unit: The best a/c unit is in the bedroom (it works great) but the living room a/c unit, is added on and has to be closely looked after as it is a bit temperamental - and doesn't really give the living room that fully air conditioned feel (something kind of important to this middle-aged couple). But it was sufficient enough and after being in Maui for about five days, we both finally got used to the warmer larger room (we live in the cooler mountains at some altitude so the heat was a bit of a shock to us the first few days). The internet in this unit can be spotty, too, but it worked well enough for the most part (something we have experienced in other condos and on other islands as well.) All in all I give this condo an A+. It's clean, modern feeling, beautiful, convenient to everything in this area, well-supplied and quite nice to "live in" during a vacation in Maui. I highly recommend it and I also thank Lawrence for keeping it up so well.

Match: Swimming pool

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Price per night from

$337

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$384

Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach-3 min walk, Remodeled

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

“Relaxing and Beautiful Getaway” My husband and I stayed at 33a in Ekahi for a week long vacation. The condo and surroundings exceeded all of our expectations. It is very tastefully decorated, extremely clean with all the amenities needed for a relaxing getaway. The grounds, pool area and beach are wonderful. The lanai is a serene retreat. We ate all of our breakfasts and lunches out there and then dined on fantastic food for dinner from the many choices of restaurants. The keyless entry and parking were very convenient. We will return next summer with our children.

Match: Swimming pool

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Price per night from

$400

Upgraded Unit w/ Beautiful Ocean Views Makena Surf Resort # C-103

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful week in paradise!” The staff at ali'i Resorts is fantastic and helped us to plan fun adventures for our family throughout our stay. The housekeeping staff was attentitive and worked hard each day to help make our stay great. The property and condo were both very well maintained and beautiful- with spectacular views throughout. One of our favorite features was the patio and the amazing view that we enjoyed while dining outdoors. The beach access was convenient, just a short walk down a paved path to the beach that offered kid friendly boogie boarding waves and rock outcropings for snorkeling. We have stayed in a few of the luxury hotels in Wailea and prefer the relaxed environment of Makena Surf.

Match: Swimming pool

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Price per night from

$649

SPECIAL SPRING RATE FOR AN "ALOHA" OCEAN VIEW AT MAUI KAMAOLE G-212

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$314

Ground Floor 2 BDRM Condo Wailea Elua Village # 1503

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$537

Second Floor 2 BDRM w/ Sweeping Views WAILEA ELUA, #2010

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$399

Palms at Wailea #1501 Ocean View Inner Court Ground Floor 1Bd 1Ba Sleeps 4

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Enjoyable Stay!” Our overall experience was good. The property was quite comfortable. We loved the beautiful landscaping BUT the view of the ocean could be enhanced with a bit of selective trimming of the shrubs surrounding the patio area. The property managers were very quick to respond to questions before we arrived. We were somewhat surprised, however, after we arrived that we never saw or heard from "anyone." We let ourselves in and let ourselves out. It worked fine but made us wonder! We would definitely call Rentals Maui when we are planning a return trip.

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$380

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$583

Stunning, Remodeled, 2 Bedroom WAILEA EKOLU, #914

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Swimming pool

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Price per night from

$289

Palms at Wailea #603 2Bd/2Ba Fully Air Conditioned, Great Rates! Sleeps 6

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Love Maui and the Palms” The Palms is our favourite place to stay in Maui. Room 603 was in very good shape but we had an incident the second to last day with water from the room above but the property management and rental management groups got on it right away. The 2 bedroom room size is perfect for our group and the lanai's can't be beat for comfort and use. We make great use of the kitchen and can't beat having your own barbeque on the patio. We love Keawakapu beach - 10 minute walk or 1 minute drive and there is very good parking, lots of space and a great beach.

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$370

Palms at Wailea #2303 Spacious Ground Floor 2Bd/2Ba Unit, Split A/C Sleeps 6

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Family Trip” Enjoyed every minute of it!

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$388

Upgraded Unit w/ Beautiful Ocean Views -MAKENA SURF RESORT, #F-107

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$1,259

Grand Champions #143 is a 3Bd/2Ba 1st floor golf course view condo, sleeps 6

Wailea apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 43 minutes

Match: Swimming pool

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Price per night from

$450

Luxurious Oceanfront Corner Unit SURF RESORT, #F-212

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Amazing and Beautiful” Loved staying at this condo. Great accommodations, great services and support staff. The only odd thing was the power kept going out in the master bedroom/bathroom. Other than that, it was a 10!

Match: Swimming pool

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Price per night from

$759

Stunning 1 Bedroom Wailea Condo Wailea Elua # 206

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Swimming pool

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Price per night from

$519

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