Vacation Rentals & Condos in Wailea

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29 condos

Wailea Ekahi Ocean View 50A

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$396

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Price per night from

$1,061

Match: Wheelchair accessible

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Price per night from

$253

Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Wailea Ekahi 48C” This condo is a bit dated. The bed was very comfortable. The showers weren't working well. Wailea Ekahi is a gorgeous setting. This unit is up the hill, a little walk from the beach and main pool. Wifi worked well which was key for me since this was a working vacation.

Match: Wheelchair accessible

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Price per night from

$375

Great rentals within 20 miles that match your search

“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: Wheelchair accessible

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Price per night from

$297

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

Match: Wheelchair accessible

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Price per night from

$453

More Aloha For Your Money!

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Second stay in this lovely condo...” We stayed in this condo two years ago and was impressed with the price and comforts of home that we decided to stay a second time. This condo is still the best value in Kihei. We enjoyed the ocean view from the lanai every morning and went boogie boarding and snorkeling at Kam II everyday. Snorkeling was amazing. We saw beautiful fish and turtles each time. The complex is well maintained and clean. We even used the outdoor grill by the pool and it looked brand new. We will definitely be back.

Match: Wheelchair accessible

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Price per night from

$183

ELEGANT BEACH HOME POOL & VIEW PERFECT LOCATION

Kihei house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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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: Wheelchair accessible

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Price per night from

$5,555

Aloha! 2 Bed Room, 2 bath Sleeps Six MAUI

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$250

Kamaole Beach Royale 1 Bedroom Seaviews

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 6 minutes

Match: Wheelchair accessible

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Price per night from

$258

Surfrider Unobstructed Seaviews 1Bedroom

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 6 minutes

Match: Wheelchair accessible

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Price per night from

$258

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.

Match: Wheelchair accessible

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Price per night from

$802

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 3 minutes

Match: Wheelchair accessible

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Price per night from

$207

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: Wheelchair accessible

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Price per night from

$516

Kamaole Villa Maui County Conditional Permit 2003/0009

Kihei house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$2,523

Upscale Furnishings, Gorgeous Lawns For Kids

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$218

“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.

Match: Wheelchair accessible

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Price per night from

$407

Beachfront Property 1 day free after 7

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$253

Kihei Kai Nani #123 Beautiful ground floor condo

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Wheelchair accessible

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Price per night from

$149

Romantic Beachfront Getaway

Maalaea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$213

Ohana Hale

Kihei house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 30 minutes

Match: Wheelchair accessible

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Price per night from

$228

South Maui Partial ocean views Maui Sunset 112A 1 BR, 2BA

Kihei apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$350

Maui Sunset 113A ~ 1 BR, 2 BA, Ground Floor, Ideal for Families!

Kihei apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

“We'll be back (said in my best Schwarzenegger voice)” Our 10 days at the Maui Sunset were amazing. Beautiful grounds, great for the kids, just open the door and go. We will definitely stay at the Maui Sunset again. That being said, this particular unit could use just a little tlc. A few updates on fixtures (faucets in particular). Also, we travelled with 3 other families and the other 3 units offered beach accesorries, ie; chairs, boogie boards, large cooler, etc. Our unit did not offer any of these items. We found out that it is up to the individual owners what the guests have access to. By no means am I complaining, those items just would have been nice. In closing, I highly reccommend the Maui Sunset and this particular unit. The Robinson's

Match: Wheelchair accessible

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Price per night from

$325

“A Maui trip to remember” What a great birthday getaway!!! The condominium, its location and proximity to the beach, and its overall amenities exceeded all of my and my mate’s expectations. I would positively jump at the chance to stay there again. A great place for both relaxation and celebration. So a mahalo nui loa to the renters and to Flip Key for making this holiday one for the ages.

Match: Wheelchair accessible

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Price per night from

$327

Unique Artist Condo's Home refreshed Spring 2019

Kihei apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great island feel, clean, all the amenities you’d ever want, and close to it all.” We used this as the perfect spot to start and end our days. Stopped at Costco on way from the airport to get our basics. Had a homemade breakfast and dinner most nights and packed a few picnics. Great information supplied on which restaurants and attractions to see supplied by the owner. The decore was so adorable in the unit it was great to come home to. The unit was clean and had everything we needed. The pool and hot tub were immaculate as well. After exploring the island it was soothing to relax here. We even got a chance to see our beloved Toronto Maple leafs play thanks to the Great cable coverage. Walked across to the beach several times and saw turtles and whales. Can’t wait to come back.

Match: Wheelchair accessible

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Price per night from

$292

Ocean/Mountain View Cottage. Private Island Retreat. Great Rates.

Haiku cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Wheelchair accessible

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Price per night from

$224

ROMANTIC MAUI BEACH HOME, 3-BR/3 BATH, 3 MINUTES TO BABY BEACH

Paia house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Wheelchair accessible

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Price per night from

$1,712

Match: Wheelchair accessible

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Price per night from

$523

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