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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Price per night from

$396

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Price per night from

$1,061

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Price per night from

$253

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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Price per night from

$430

Sweeping Ocean Views; Private High End Condo!

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

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Price per night from

$260

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Price per night from

$665

Wailea Ekahi 11f: Ocean View/Remodel 2 BR Condo

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful condo in Paradise!” Our stay at Ekahi Villiage 11F was nothing short of wonderful. The beautiful, well appointed condo is just a short walk to the pool pavilion and beach. We enjoyed many mornings sipping coffee on the well decorated Lani over looking the manicured grounds and ocean. We will be sure to book 11F again the next time we plan a trip to Maui!

Responds fast! avg. 1 hour 32 minutes

Match: Sea view

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Price per night from

$975

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

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$445

Wailea Ekahi Village Relaxing Ocean and Mountain Views

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$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 16 minutes

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Price per night from

$286

KBM Resorts Kamaole Sands KSD-10-312 1 Bdm Views

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$407

1 BD Condo: Top Floor, Ocean Views, Walk to Beach

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$688

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Price per night from

$688

Top Floor 1BD Condo: Pool, Self Check-In, Walk to Beach

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$688

K B M Resorts: Maui Banyan MBY-Q106, 1 Bedroom, Large Floorplan, Steps to

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$470

K B M Resorts: Maui Banyan MBY-H413, 1Bdm with A/C

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$415

KBR-208 New AC Steps to Maui Beaches

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$360

Great rentals within 20 miles that match your search

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

Super Luxury, Direct Oceanfront

Maalaea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$379

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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Price per night from

$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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Price per night from

$297

Eco-Friendly Condo Located in the Heart of Kihei

Kihei house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Well equipped and maintained, comfortable and easy access to beach, food and shopping.” This was my second stay at this lovely 1 BR condo in Kihei and I enjoyed it even more. The location is great, just across S Kihei Rd from the beach at the north end of Kamaole Beach #1. You can walk on the beach all the way to Ulua Beach if you want. The place is amazingly well equipped. All you need to cook and toys for the beach. This time, I even discovered two yoga mats in covers and two yoga blocks to go with them. Perfect for home yoga or taking them to the beach yoga classes that sometime happen. It is also possible to walk to good food and even the grocery store. The building has a great pool for afternoon cooling and laundry facilities are available on site. There is a bit of a view of the ocean from the lanai, but the general vista of palm trees and tropical vegetation in the neighboring buildings was quite nice. Never used the AC, screens and fans kept things comfortable. Finally the electronics were great, big screen and lots of music and video service choices.

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Price per night from

$509

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

“Wonderful accommodations” We stayed at Jean's condo for 2 weeks in Feb/March 2014. The condo was outstanding on the quiet end of Kihei Rd. This is a very nice condo with an island color scheme. The furnishings were comfortable both inside and on the lanai. There is air conditioning but you can get a nice breeze moving if you use the ceiling fans and keep the windows open. Everything was there for our use. The only thing you need to bring is a change of clothes, perishable groceries and a toothbrush. The cupboards were well stocked with almost everything imaginable including aloe vera for my husbands nasty sunburn. Having a washer and dryer in the unit is a great advantage. The laundry detergent & fabric softener were provided. The kitchen has all kinds of stuff you might need including a mix master, food processor etc. We have made several trips to Maui and have never stayed somewhere that was so well stocked. The condo was very well cleaned without a speck of dust anywhere. The floors shined. The gardeners are meticulous. Not a single blade of grass was out of place. The area around the pool has several bbq's and an outdoor kitchen. The pool and hot tub were nice and didn't have excessive chemicals used. Jean was very attentive to our needs. She answered phone calls and replied to all emails within minutes. She provided a lovely gift basket for us filled with coffee, potato chips, chocolates plus other goodies. She has a book of information in the condo with recommendations for restaurants, activities, etc. I would highly recommend this condo for anybody that needs a two bedroom. I wish there was a way to leave more than 5 stars because this place is a 10. Thank you again Jean for sharing your lovely condo with us. I cannot wait to go back. We will most certainly rent from you again on our next trip.

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Price per night from

$430

ELEGANT BEACH HOME POOL & VIEW PERFECT LOCATION

Kihei house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$4,409

LUXURY BEACH HOME POOL EXCELLENT LOCATION

Kihei house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Wonderful stay in the perfect home. Great golf and beach locatio” My friends and I stayed in this high-end well-appointed home while we were on Maui. Our main purpose was to fit in as many games of golf as possible as our wives shopped and relaxed by the pools and enjoyed the beaches. This plan worked out perfectly since we were located right on golf course and a short walk from the beach. Everyone was more than happy with our accommodations and being able to rent a spacious home in the center of a luxury resort was ideal. This home was an exceptional value when you consider that most of the hotel rooms in the Wailea/Kihei area go for the same price for just one room. Everyone in our group felt as though this was our own home in Maui and we expect we will return again as soon as we can. We highly recommend this place and would like to thank the owners for extending us their every kindness. Sincerely, Don M

Match: Sea view

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Price per night from

$5,555

“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

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Price per night from

$332

Aloha! 2 Bed Room, 2 bath Sleeps Six MAUI

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$250

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: Sea view

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Price per night from

$402

2BR**Sleeps 6**Direct Beach Access**Overlooking the Pool and Ocean

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Kihei stay” The condo was wonderful. Plenty of room for our family of six. Clean and well stocked with necessities. Great having the beach chairs, umbrella, beach towels and more, ready to use. So nice to have the washer and dryer to keep up with everything! Cable and wifi, really all the comforts of home.

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Price per night from

$802

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: Sea view

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Price per night from

$230

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!

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Price per night from

$516

“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: Sea view

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Price per night from

$332

Kamaole Villa Maui County Conditional Permit 2003/0009

Kihei house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$2,523

Milo Cottage

Paia house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$975

"WOW IT'S LIKE OUR OWN PRIVATE RESORT!"... recent guest.

Kihei house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 30 minutes

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Price per night from

$1,823

SPECIAL! Closest to beach! King Bed

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$281

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