Vacation Rentals & Condos in Wailea

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One-of-a-Kind Maui Getaway!

Wailea house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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

Price per night from

$400

“Exceeded expectations by a mile!” From the moment we arrived we were amazed at the way the condos we rented (we had #48 as well) were decorated, furnished and stocked with anything we could possibly have wanted for our holiday. Even items for the beach were there. I can't think of a bad thing to say. Would love to go back.

Responds fast! avg. 3 hours 43 minutes

Price per night from

$332

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

Price per night from

$388

Maui Wailea Townhouse, 2BR, 2.5 Ba, air conditioned, sleeps 8, ocean view

Wailea apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$241

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

Price per night from

$400

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

Price per night from

$346

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

Price per night from

$395

Price per night from

$802

Responds fast! avg. 3 hours 43 minutes

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

Price per night from

$395

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.

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

Price per night from

$380

Wailea Ekahi Ocean View 50A

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$396

Responds fast! avg. 47 minutes

Price per night from

$1,117

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

Price per night from

$375

Castaway Cove C201 at Wailea Beach Villas

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$1,125

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

Price per night from

$304

Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 47 minutes

Price per night from

$1,146

Price per night from

$252

Remodeled Mountain View 2 BDRM Condo - Royal Mauian #601

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$209

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

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$950

WAILEA ELUA, #0702

Wailea apartment

  • 2 bedrooms
  • sleeps 6

Price per night from

$410

Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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

Price per night from

$488

Beautifully Renovated 2 BDRM WAILEA ELUA, #2201

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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.

Price per night from

$338

Responds fast! avg. 3 hours 43 minutes

Price per night from

$391

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.

Price per night from

$401

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.

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

Price per night from

$315

Ground Floor 2 BDRM Condo Wailea Elua Village # 1503

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$539

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

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

Price per night from

$385

Responds fast! avg. 3 hours 43 minutes

Price per night from

$590

Stunning, Remodeled, 2 Bedroom WAILEA EKOLU, #914

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

Price per night from

$378

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

Price per night from

$393

Viewing 38 of 859
rentals in Wailea

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About Wailea

Famous for its five half-moon shaped beaches and world-class golf courses, Wailea is five times the size of Honolulu’s Waikiki with unmatched Pacific Ocean views. For a luxurious Hawaiian vacation in a very sought-after location, visit FlipKey where you will find a Wailea vacation rental to suit all your needs.

About Wailea

Wailea is located on the south-western part of Hawaiian Island of Maui, just 14 miles from Kahului Airport.

Meticulously laid out over 1,500 acres of lush tropical vegetation, the beach at Wailea is one of the most visited on Maui. The popularity of the beach is partly due to the area’s luxurious oceanfront resorts and spas, as well as its legendary year-round average temperature of 82 degrees!

Even the shopping at Wailea has an upmarket feel with Gucci, Louis Vuitton, Prada and Tiffany & Co all represented next to surfing boutiques such as Quicksilver, Rip Curl and the Honolulu Surfing Company.

When it comes to fine dining, you will be spoilt for choice with American, international and Hawaiian specialties all available.

Top Wailea events include the February Whale Week and the Maui Film Festival. See if you can catch one during your stay!

What to do

Avid golfers flock to Wailea just to play the Gold Course (one of the top golfing destinations in the country!). Robert Trent Jones II designed championship course that takes advantage of the natural surroundings, while incorporating stunning ocean views from every tee. A true thinking man’s course, and considered one of the best designed courses in the world.

Hawaii is, of course, all about surfing and Maui has its fair share of top spots where the pros come to catch big winter waves. But on the south of the island, the waves are around three feet in height, making them perfect for beginners.

Go hiking in the Haleakala National Park and climb to the top of the world’s largest dormant volcano, Haleakala, where you will be rewarded with fantastic views of the island.

Top Wailea travel tips

With almost perfect weather all year round, there is no bad time to visit Wailea.

For beach attire, avoid the fancy stores and ask the locals where they go shopping, instead. Consider buying a snorkel, mask, and fins as it can actually work out cheaper than renting.

Hawaii is a no-brainer for a tropical beach vacation, but with so many great amenities, Wailea truly is a world-class destination. To find your slice of paradise, FlipKey has dozens of Wailea vacation rentals to suit all budgets.

Top Destination reviews

Beautiful, Renovated, Hale Kamaole 159 now available! Walk to Kamaole III Beach!
Family friendly

The location is perfect. This is a family-friendly condo. The beach is a short walk. The lanai is nice for breakfast lunch or dinner...with a view of the ocean. We were comfortably accommodated. Thank you Yoshiko. Janeille uostairs was quick to get television rebuted. Our family enjoyed some very needed quality time together. Will like to stay here again if possible. Mahalo! … see more
Aqua Lani J305 Wailea Beach Villas
Beautiful condo in Wailea!

A wonderful condo with 3 bedrooms & 3 bathrooms for six adults that was decorated with a modern touch & clean facilities. The beach is walking distance & the private pool very relaxing (separate kids pool area); didn't take advantage of the wonderful Grand Wailea facilities next door which was accessible with the rental. Would come back in a heart beat & we thoroughly enjoyed my birthday! It was a little pricey but so worth it if you anticipate the cost if three hotel rooms at a five star hotel for 5 nights! … see more
Upgraded Unit w/ Beautiful Ocean Views Makena Surf Resort # C-103
Paradise in South Maui

Beautiful condo on a wonderful beach. Large rooms, well appointed, great view, terrific lanai. Beach is only steps away and not crowded. Pool area is also very nice. Great snorkeling right from beach - head toward the point in front of Makena Surf Resort and look for turtles (this spot seems to be one of the "turtle towns" which snorkel boats head to - but you don't need a boat to see it!). We saw five weddings on the beach in one week - the location is that spectacular. … see more
Bella Luna D302 Wailea Beach Villas
Simply Divine in Wailea

Our family of 6, 2 teen boys and 2 teen girls, had the pleasure of staying at Bella Luna in March. It was even better than the pictures. Sure it was a splurge, but there is simply no better accommodations to be had in the Wailea area. The unit was so complete and so well stocked that there was not one single thing we could think of that wasn't already there. The furnishings were spectacular, the view from the lanai was breathtaking, and the sliding glass walls allowed us to enjoy the open air all the time. The appliances, electronics, were all top notch, as were the cookware and dishes. I was impressed too with the management company, Tropical Villa Vacations. They were really on top of everything to make sure our trip was special. We will definitely go back to Wailea and stay in this unit again. I wouldn't want to stay anywhere else! … see more
Lovely Ground Floor Unit MAKENA SURF RESORT, #C-102
Perfect Location, Amazing Views, Fantastic Condo!

We spent five nights during our spring break at the Makena Surf condo and loved every minute of it. The pictures are a great representation, but don't really do justice to this place. I enjoyed having my Kona coffee out on the patio each morning to the sound of the surf and the stunning view across the bay. The condo is well appointed and missing almost nothing (boogie boards might be nice; we purchased a few ourselves at the store). The office lends tennis racquets out to those who want to play but didn't bring them along, which was fun for our family. Beds are very comfortable and we slept soundly. The absolute highlight of this location for us is the amazing snorkeling. We paid for an excursion that went out to Molokini, but honestly it wasn't really necessary. There were many turtles every time we snorkeled right at the south end of our beach, and even more around the point, along with countless colorful fish. You could also hear the whales underwater. It was really a treat! Being away from the heavily trafficked and touristy parts of the island was a big plus for us. It was fun to visit Lahaina or go for ice cream at Lappert's in Wailea, but we liked being away from the hustle and bustle of those areas yet still easily accessible to them. Beautiful hiking is nearby just past Makena along the lava fields and oceanfront, where the road ends. Communication from the team at Alii Resorts was timely and complete and we didn't have a single issue. Would happily recommend this place! … see more
NEW REMODEL 2020-65”SONY 4K UHD LED LCD TV & BOSE SURROUND SOUND- GORGEOUS GEM
Happy with our stay

We enjoyed our stay. The location was very close to the beach and a pool, and there were chairs and gear we could use which was great. The room itself was quite nice and comfortable, including an excellent entertainment system and patio for us to hang out at. Lawrence was prompt to respond to any questions we had which was appreciated. If you are looking to stay in Wailea or Maui in general, this come recommended. … see more

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