Vacation Rentals & Condos in Wailea

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Match: Walking trips

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Price per night from

$1,060

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: Walking trips

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Price per night from

$430

Unrivaled S Kihei Maui location! Walk to it all!

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$224

Great rentals within 20 miles that match your search

Upscale Furnishings, Gorgeous Lawns For Kids

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$218

“Perfect Stay in Paradise!” Tracy's condo was perfect for our 30th wedding anniversary stay! We would not stay anywhere else on Maui except in one of Tracy's amazing rentals! The condo has a great location (across from the beach) and close to restaurants and shops. It is brightly decorated with happy cheerful colors and special touches! It was like a ray of sunshine! Both my husband and I loved the fact that the condo was well supplied --- everything from shampoo to an ice cooler and more. Tracy has thought of everything you need for a terrific stay --- even electric candles! The bed was so comfortable and relaxing! Tracy's binder on the coffee table was full of tips for a great vacation as well as menus from area restaurants. We loved seeing the large sea turtles swimming in the lagoon section at the beach across the street. The property is extremely clean and well maintained and we enjoyed the pool and jacuzzi at the condo as well. We were sorry to leave and return home. We can't wait to return to stay again at one of Tracy's Tropical Treasures condos! We enjoyed it so much that I have recommended it to a recently engaged friend for her honeymoon. Thank you Tracy for providing such wonderful accommodations and making our 30th wedding anniversary so memorable! We will definitely be back!

Responds fast! avg. 1 hour 2 minutes

Match: Walking trips

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Price per night from

$331

SPECIAL! Closest to beach! King Bed

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Walking trips

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Price per night from

$281

"Kihei Akahi D-211: Ocean View, Opposite Kamaole Beach, Remodeled"

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Walking trips

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Price per night from

$258

Remodeled condo across from beautiful Kam 1 beach!

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$344

KAMAOLE SANDS BLDG 4 - OCEAN CLOSE - LARGE LANAI

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$201

Palm Cottage

Paia cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$544

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!

Match: Walking trips

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Price per night from

$1,031

Terrific Ocean View Penthouse Suite!

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$229

Exceptional,Ocean View,Beautiful New Kitchen& Bath

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

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Price per night from

$343

1 BR/1BA (Sleeps 4) Kihei Condo by Kamaole II Beach (#252)

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great stay” Spent 2 weeks here and was not disappointed at all, it met all of our needs. The condo was very clean, kitchen we'll stocked, and most important was the bed was very comfortable. There was never any noise problems day or night. It's in a great location, short walk to lots of restaurants, gift shops, and. Of course the ice cream shop. Condo us also furnished with snorkel gear, beach chairs, and mats. If you stay here you will not be disappointed.

Match: Walking trips

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Price per night from

$207

Garden view 1BR/1BA (sleeps 4) Kihei Condo by Kamaole 2 Beach (#125)

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Walking trips

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Price per night from

$201

One Bedroom, Renovated, Closest to Beach

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Walking trips

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Price per night from

$338

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.

Match: Walking trips

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Price per night from

$224

Keawakapu Ocean View, renovated green 2BR 2B

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Maui's Best!” Honu place is absolutely amazing! Better than described! My wife and I spent our two week honeymoon here and we couldn't have been happier! Susie and Rick have provided every amenity imaginable to make your stay comfortable and memorable. It is beautifully remodeled and tastefully decorated. The location is perfect, set slightly back from South Kihei Rd and a five minute walk to Maui's best - Keawakapu Beach, Honu Place is the perfect place to relax and rejuvenate. Just minutes away from shops and dinning in both Kihei and Wailea! Honu Place is a true hidden gem and one of Maui's best kept secrets. We can't wait to stay again!

Responds fast! avg. 1 hour 13 minutes

Match: Walking trips

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Price per night from

$401

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.

Match: Walking trips

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Price per night from

$240

Milowai #204--Tropical Maui Oceanfront Condo

Maalaea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Breathtakingly beautiful” From the morning sunrises with coffee on the lanai to the afternoon/evenings watching the turtles this place is simply amazing. It is very quiet away from the hustle and bustle of being near all the hotels yet very centrally located and easy to get anywhere on the island. We didn't want to leave and can't wait to come back. This will be our Maui home unless we do something crazy and invest in our own piece of paradise

Responds fast! avg. 27 minutes

Match: Walking trips

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Price per night from

$229

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.

Match: Walking trips

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Price per night from

$411

Match: Walking trips

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Price per night from

$453

Maui ocean front paradise with miles of beach at Menehune Shores

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Walking trips

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Price per night from

$275

Match: Walking trips

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Price per night from

$287

Quiet, secluded 1-bd cottage retreat plus sleeping loft & work space

Makawao cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 27 minutes

Match: Walking trips

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Price per night from

$258

“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!

Match: Walking trips

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Price per night from

$297

Enjoy Your Oceanside Dream at Kihei

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Walking trips

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Price per night from

$441

“Wonderful time!” My husband and I had the opportunity to spend 10 days at Tracy's place and loved everyday! She has stocked everything needed to make it a worry free vacation. It was wonderful to watch the sunset each night from our place. Also, there are a bunch of delicious places to eat at nearby. It was nice to be able to bring home leftovers, to enjoy the next day. Highly recommend Tracy's place.

Responds fast! avg. 1 hour 2 minutes

Match: Walking trips

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Price per night from

$331

Hale Kiana: Quiet mountain-side retreat. Great Views

Kula house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Match: Walking trips

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Price per night from

$315

Match: Walking trips

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Price per night from

$523

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Price per night from

$252

“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

Match: Walking trips

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Price per night from

$354

Spacious 1 Bedrm Unit. Stunning Ocean View

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Walking trips

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Price per night from

$258

Match: Walking trips

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Price per night from

$244

South Maui 3 bedroom at Kamaole One Beach Park

Kihei apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great Location and host” Plenty of space for 5 adults and being so close to the beach and shops meant that we could get away from each other whenever we wanted to. We all thoroughly enjoyed our first trip to Maui!

Match: Walking trips

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Price per night from

$516

1 Block from Beach, Great Price in Kihei, Maui HI.

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$344

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

Match: Walking trips

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Price per night from

$1,031

VIES VIEWS VIEWS

Maalaea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Walking trips

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Price per night from

$287

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