Vacation Rentals & Condos in Wailea

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86 condos

Wailea Ekahi Ocean View 50A

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$396

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$1,061

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$252

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.

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$430

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

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$316

Wailea Ekolu 2/2 - Elegant, Spacious, Modern, Ocean View!

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$445

Wailea Ekahi Village Relaxing Ocean and Mountain Views

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$327

2 Bedroom, 2 Bath Oceanview Penthouse Condo! Walk to the Beach!

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 20 minutes

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$286

Renovated Studio Steps from the Beach & Pool - A/C

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$228

Unrivaled S Kihei Maui location! Walk to it all!

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$224

Great rentals within 20 miles that match your search

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$304

Super Luxury, Direct Oceanfront

Maalaea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$379

Palm Cottage

Paia cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$545

Luxurious and Private Maui Home with Swimming Pool

Haiku house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Serenity in Maui” My husband and I spent eight days at this lovely property, and quite simply, was the best house rental, and the best vacation we have ever taken. There are not enough words to tell you how beautiful the home is with all the stunning landscaping, yummy fruit trees,and great, private saltwater pool. The home is immaculate, and luxurious. Extremely clean, and absolutely stunning. Very comfortably furniture and great beds. Claudia, the owner is charming, and will be there when you need her for anything. Please, do yourself a favor and stay in this home. It is paradise!

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Price per night from

$1,032

Terrific Ocean View Penthouse Suite!

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$230

Exceptional,Ocean View,Beautiful New Kitchen& Bath

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$343

Upscale Furnishings, Gorgeous Lawns For Kids

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$218

606 Hale Pau Hana Beachfront, Phenomenal Views

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$516

Great Special!! 2bdrm/2BA Ocean View

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$424

Kihei Kai Nani #105 steps from the beach

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$171

“Luxurious, well maintained, quiet "Paradise Beach Condo".” Firstly, the location was within walking distance to three great beaches, local shopping and great restaurants. This newly renovated condo was a "Home away from Home" with a "Wow" factor. The grounds were well maniquered with a lovely pool, hot tub and BBQ. Every detail in beach accessory from boogie boards, to snorkling gear to beach chairs etc. was at your disposal for a great day at the beach. We will come back again!!!

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$229

Oceanview Fabulous 2 Bedroom Condo,Great Location

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“A wonderful, relaxing place to stay in Maui” Just what we wanted! The place is very convenient, and has the amenities needed for a relaxing beach vacation, including beach chairs & mats, towels, boogie boards etc. Parking is a breeze, and it's close to the bus line as well. The well equipped kitchen inspired us to eat in most evenings. I would recommend to my friends as family.

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$274

“Paradise!” Our stay in 427 Sugar Beach Resort was awesome! Beautiful, comfortable condo that was very clean and well stocked. Having free long distance to Canada was a real bonus for us, we were able to call home everyday!

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$297

South Maui 4 bdrm close to beaches, restaurants

Kihei house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Exceptional home away from home!” Just as described, the kihei oasis is an excellent vacation rental. The layout of the home, furnitionings and it's convenient surroundings, I would definitely recommend staying here. The jacuzzi was a hit, but the real bonus was the little amenities that you don't really think of until you need it. I opened the kitchen cabinets and found foil, oil, shoyu sauce and lots of helpful seasonings. The bathroom cabinets also had additional body wash, shampoo, lotion and for kids too. Although we brought our own amenities, I'm glad you have them available especially for large families. Also a garage wall dedicated to fun in the sun activities, boardgames and so much more. Mahalo to the Morts ohana for providing such a lovely home away from home, We definitely enjoyed ourselves!

Responds fast! avg. 40 minutes

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Price per night from

$1,032

Hale Kamaole #309 -Spacious 2+ bdrm Kihei Condo

Kihei apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Hale Kameole #309 - A great find!!” We ust returned from a glorious holiday to Maui (10 days) and the Molokai (4 days). This is our 7th trip to the Islands, and I fall more in love every time! Maui had last been a destination in 1995 and although we found a lot of changes - much has stayed the same. We stayed, for the first time, in #309 (Hale Kamaole) - a 3rd story condo with an ocean view - renting the unit through Vrbo. This was a very clean and well appointed condo and allowed the four of us (2 couples) ample room and comfotable surroundings. The owner (Brenda) was easy to deal with and always helpful and honest. We loved so much about this location - it's proximitiy to Kamaole 3 Beach (right across the road, and a really great beach in it's own), shopping, dining and, of course, the beaches in Wailea (Ulua and Big Beach). The condo was extremely clean and...well, comfortable - the kind of place that you're anxious to return to after a long and tough day of beaching or shopping. Do not think we missed having cocktails on the lanai one day, watching the sun go down to the tunes of other residents performing their "conch" ceremony (not to be missed). We all loved this place, and would not hesitate to stay here again.

Responds fast! avg. 3 hours 34 minutes

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Price per night from

$453

Oceanfront Paradise! Awesome Views! Ground floor! A/C Throughout!

Kihei apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$343

One Bedroom, Renovated, Closest to Beach

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$339

Maui by the Sea cottage

Paia cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Loved Maui by the Sea!” Valerie, We loved our stay at the cottage. Couldn't have been better! Tavares beach was our favorite, just watching turtles and hanging out. Paia is a great town. It really felt like home and we hope to be back soon. Thank you to you and Craig for the hospitality. Mahalo, Tom and Michelle

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$367

“Incredibly relaxing!” It's a home away from home with everything you might need - with quality stuff too. Bright, beachy, quite and so relaxing.

Responds fast! avg. 1 hour 2 minutes

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$355

Kamaole Sands Condo Renovated in South Kihei

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Exactly as promised” Very nice accommodation very central. Less than mile from downtown business. Some much closer. Shaved ice and other restaurants are closer.

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$224

“Breath Taking Views” This penthouse is as advertised! Views are incredible. We saw spouting whales daily ( in season) The humpback whale foundation is right next door and you can hear the conch shells at sunset nightly. There is an Indian restaurant downstairs that serves nightly... So convenient. Makenna beach just down the road was our favorite beach... We would love to return someday!

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$320

Maui Island HIdeaway

Maalaea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Hideaway for Best Getaway” Location: We travelled all over the island, seeing every little nook and cranny. What we realized was that our home base, the "Hideaway" is ideally located on the island. You're centrally located between Kihei (our favourite town), the airport, Lahaina, et al. You're also near some of the best beaches around, including Sugar Beach, the one on which the Hideaway sits, which has one of the best views on all of the island. One suggestion is to stop to get supplies from one of the major grocers near the airport, when you first arrive, to get a firm base of what you need: beer, snacks, meat, veggies, etc. Then you can shop at the nearby general stores for convenience or 10 minute drive to Foodland for following shopping needs. Amenities: The "\Hideaway has everything you need to operate comfortably: dishes, utensils, bedding, beach supplies, cleaning supplies, washer/dryer, brand new oven/stove, brand new TV/sound system, etc. The balcony has the best view. The unit being on the second floor is great in that you get an elevated view but you're still quick to access parking or the pool by elevator or stairs. Facilities: The pool area is superior in its craftsmanship and comfort. It has the only Jacuzzi in the area. You wouldn't think something like this would be necessary in a hot area but it's amazing, especially in the hot, bright sun. One of, if not the biggest highlight about this building is its proximity to the ocean. Not only is there no road between your balcony and the ocean but you're so near to it that you can see the sea turtles floating by. Apparently this luxury of being so close to the ocean is not something you'll see anymore on Maui as they have changed their regulations so that buildings need to be built much further from the ocean. Owners: Accommodating to the max. Wendall and Sally only want you to have the best possible experience on Maui and in the Hideaway. I can't even go to the lengths at which Wendall went to make sure our stay was excellent, suffice to say that it couldn't have been as good without having them to help us out. Conclusion: If you can get in to the Hideaway, go with the opportunity and you will be happy you did.

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$241

Cozy Quiet Garden View Condo, Kihei Kai Nani, Maui

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.

Responds fast! avg. 3 hours 23 minutes

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Price per night from

$207

Newly remodeled Beautiful Beach Front condo at Kanai A Nalu Maalaea Maui

Maalaea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Completely Enjoyed it. Cant wait to return.” We surprised our children with a trip to Maui over their winter break while home from college. When we found this condo open at the last minute, we were a bit leery since it was during the peak season. The surprise was all ours. What a beautiful place!! We could tell the condo had recently been renovated with all new furnishings and amenities. The owner did a wonderful job redecorating and tying the theme together throughout. I'm very particular when it comes to sleeping away from home as you never know how mattresses are going to feel in rentals. I was delighted at how comfortable the beds were and energized each morning when I woke. We truly were in paradise inside and out. The owner was most helpful with booking our trip, especially since it was last minute, providing us with many fun activities to do during our stay. Looking forward to booking our next visit and staying in this beautiful condo.

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Price per night from

$321

Private, Romantic Cottage, Panoramic Ocean View, King-Bed, Hot Tub

Haiku cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Even better than expected” I stayed at this cottage for 11 nights. I felt so much at home that I did not want to leave, not even to go to the beach. The views are stunning. It is very private and quiet. I really liked the sound of the water fall in the gulch below. The cottage offers anything one can dream of... fully equipped kitchen, washer, dryer, towels, beach chairs, sun umbrellas, deck chairs, BBQ, outside showers, TV, DVD and a very fast and stable internet. Haiku town is only a few minutes by car (3 minutes to be precise) where you can find groceries, restaurants and a fitness centre (which offers weekly and daily passes for tourists). Paia town and beaches can easily be reached within 15 minutes, Makawao town is also around the corner. Barbara and Hank, the owners of this beautiful property, are very nice people and extremely helpful.

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$411

Renovated; Clean Ground Floor Unit; Walk to Top Rated Kihei Beach!

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$401

Maui Vacation Condo - 2BR\2BA Corner Unit, Steps from the Beach!

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$223

“Great place” It had everything you needed and a great location. I will try to get her place again. We have been coming to Maui for over 10 years and this is my favorite place.

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$407

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