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Vacation Rentals & Condos in Wailea

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1,429 condos

One-of-a-Kind Maui Getaway!

Wailea house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 21 minutes

Price per night from

$1,650

Updated Spacious 3 Bdrm. Wailea Ocean View Condo

Wailea apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Great condo!” We absolutely loved the condo.  It was well appointed and spacious.  We hosted a gathering of about 20 people and the kitchen, dining, living spaces combined with the lanai comfortably held that many people. The location was perfect, right on the golf course and a few minute drive to shops and the beach. Unfortunately one of our party got sick and we needed to do laundry. Having the full size washer and dryer in the condo was a godsend. We would stay here again if we return to Maui and would certainly recommend it to our friends.

Responds fast! avg. 2 hours 53 minutes

Price per night from

$350

Wailea Ekolu #201 2Bd/2Ba Ocean View Condo Near Beach, A/C, Wifi, Sleeps 6

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$250

Wailea Ekolu #406 2BD/2BA Panoramic Ocean View Near Beach, Full A/C, Sleeps 4

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$255

OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA

Wailea cottage

1 bedroom / 2 bathrooms / sleeps 3

“Wonderful view and property” This was the perfect place for our annual stay on Maui. Dennis is the best host and takes care of any request you may have. The cottage is newly updated with all the conveniences and space needed. It is a very quiet area in the upper residential part of Kihei and Wailea border with a killer view. All the spacious rooms and layout is perfect. The kitchen was well appointed with everything you would need to cook. Very nice to have a washer and dryer in the space and not outside, as most places in Hawaii. Dennis also provided us with fresh fruit some mornings from the surrounding trees. The air conditioning is an added plus as Hawaii can get quite warm during the day. But at night the cool breezes were perfect to cool off. The deck is also nice for a sunset view. The king bed is quite comfortable, providing for the needed rest we were seeking. We will be back for future stays in this perfect cottage.

Responds fast! avg. 59 minutes

Price per night from

$285

Grand Champions #51 is a 2Bd 2Ba is a large condo that sleeps 6. Great Rates!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“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.

Price per night from

$223

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!!

Price per night from

$299

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

Wailea apartment

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 47 minutes

Price per night from

$237

Palms at Wailea #205, 2Bd/2Ba, Luxurious, Spacious, Fantastic Location!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$278

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.

Price per night from

$292

Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Golf Course. Sleeps 4.

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“Exceeded Expectations” I love this property. We had looked at alot of places and time was running out. When this property popped up, I never thought it looked liked the way it did in person. It looked better in person. We are definitely returning. Mahalo.

Price per night from

$193

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.

Price per night from

$411

Wailea Orchid Villa - Panoramic Views! 3 Bd/3 Ba

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 8

“Wonderful stay in the Penthouse Villa...” Service: 5 Stars - The owner was very prompt in replying to email with questions, concerns. Concierge and front desk staff were courteous and very helpful. The bellman/staff even brought all of our luggage (6+ pieces) to our Villa and even parked both of our rental cars. Home: 5 Stars -Villa was immaculate! Master bedroom was gorgeous and the other guest rooms were beautiful and spacious as well. Open floor plan is great for entertaining and views from living room and lanai were breathtaking. Location: 5 Stars - just a short leisurely walk to the beach, adult-only pool and you can access the kiddie pool directly from the garage. Amenities were great - housekeeping promptly replaced shampoo and toilet paper. The Penthouse Villa offers guests a private elevator with key card access. Liked the views and proximity to beach, pools, shops the best.

Responds fast! avg. 58 minutes

Price per night from

$1,398

Responds fast! avg. 3 hours 30 minutes

Price per night from

$630

Wailea Ekolu #205 2Bd/2Ba Ocean View, Ground Floor, Near Beach, Wifi Sleeps 6

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$265

Grand Champions #48: Stunning 180 Degree Ocean Views. Top Floor Paradise Home

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“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.

Price per night from

$249

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

$295

Oceanview Condo just Moments from the Beach

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$385

Wailea Ekahi Ocean View 50A

Wailea condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 48 minutes

Price per night from

$284

5 Star Luxury Condo - Walk to the Beach

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

Price per night from

$224

The Perfect Location for a Relaxing Hawaiian Getaway - Grand Champions #103

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“This is a beautiful condo, wonderfully maintained, in a great lo” We have stayed at many condos on Maui for years, and this is absolutely our favorite. We were lucky enough to be the first guests, and everything was even better than expected. The photos don't do it justice. Spacious, beautifully decorated and furnished, everything new and very high quality from the furniture to the linens (no cheapo rattan here), a kitchen with every conceivable appliance and utensil, tour books, high end electronics, games, everything you could need. Even has a printer and paper! Lanai is quiet with a beautiful view and nice seating. Even saw a huge herd of deer running across the golf course. Perfectly managed and maintained by Paradise Comforts with every possible needed supply for kitchen, bath, beach, laundry, etc. Absolutely clean and neat. If anything isn't right or is needed, they take care of you immediately. They handle the reservations and check-in aspects very efficiently. (we did have to call them to figure out how to open the tricky door upon arrival, but that was the only problem we had - trivial) The complex is lovely and the location is perfect - 5 minute drive to the best south Maui beaches, 5-10 to Wailea or Kehei restaurants, shops, Safeway, etc. We are a senior couple and stayed for 3 weeks, so we tested it thoroughly. We can't wait to return.

Responds fast! avg. 3 hours 11 minutes

Price per night from

$194

New Listing! Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 33 minutes

Price per night from

$822

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!

Price per night from

$266

Castaway Cove C201 at Wailea Beach Villas

Wailea house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$1,295

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 =)

Price per night from

$222

Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 33 minutes

Price per night from

$881

Fantastic Location - Beautiful Oceanfront Condo -Makena Surf Resort # E-205

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful location, great service” The condo was clean, wonderfully furnished, and offered adequate space for our family of six. We enjoyed the complex for its beautiful landscaping, grills, and easy access to the beach. We went in early December, and there were usually only a handful of other families out on the beach with us! The sand was soft and the water was perfect for body boarding and snorkeling-- we saw several giant sea turtles! We liked being in this quieter part of the island that was still close to interesting activities and dining. The staff at ali'i resorts was always cheerful and helpful. They helped me book snorkel and horseback riding trips. Housekeeping came in every day and replenished laundry detergent, towels, etc. I thought it was nice that a representative from ali'i met us at the condo for check in. He could show us around the unit and answer our questions (like where to get dinner!).

Price per night from

$648

Price per night from

$385

Price per night from

$261

Palms at Wailea #702 Upstairs Garden View 1Bd/2Ba, Great Rates! Sleeps 4

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“Great Stay in #702” The unit was very spacious, very clean(the carpet had just been steam cleaned before we arrived) and is in great location in Wailea which is in the quieter part of Kihei. The lanai was large and perfect to spend the evening sipping wine and looking up at the stars. The dedicated internet connection was very good and all of the appliances also worked well including the barbecue on the lanai which we used 3 times during our stay. Although there is no A/C in the living room, the floor/ceiling fans made the room comfortable. The Property Management(Rentals Maui) employees were very friendly and helpful. Will definitley return to this unit the next time we visit Maui.

Price per night from

$251

Remodeled Mountain View 2 BDRM Condo - Royal Mauian #601

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$179

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$638

WAILEA ELUA, #0702

Wailea apartment

2 bedrooms / / sleeps 6

Price per night from

$423

Remodeled Elegance & Luxury - Daily Housekeeping Elua Village # 2107

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Maui Wailea Elua 2107” Very nice, comfortable 2 BR condo. In the upper tier of buildings in the development, so short walk down the hill to the beachwalk. Though nearer to the road, no noise in unit. Has a front lanai facing the ocean, landscaped back patio with your own grill. Condo has a great newer kitchen, and cooking utensils and kitchenware are high quality. I love to cook, so between the grill in the back and the kitchen, you can put out some fancy meals (also lime trees in front with fresh limes !). Master with King bed, two twins in 2nd BR. Development is undergoing some renovations, so some construction currently, but not noisy or problematic. Nice pool and deck with access to Ulua Beach, which is one of the nicest family beaches (calmer, and new facilities), and has excellent snorkeling. About a hundred yards up from the Shops at Wailea, convenient to the whole West Maui scene. Was pleasantly surprised that there was a maid service for fresh towels and linens when needed. The Ali'i Resorts people were very helpful and courteous.

Price per night from

$382

Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$309

STOP! LOOK NO FURTHER! Palms at Wailea #1503 2Bd Ocean View Best Location!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$360

Great Ocean View Family Friendly GC#42

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$259

Remodeled Second Floor 2 BDRM Condo Wailea Elua Village # 202

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$505

Viewing 38 of 1,429
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

Updated Spacious 3 Bdrm. Wailea Ocean View Condo
Amazing Views

We love going to Maui, love the island and love to explore and also golf. The condo was in great shape, the golf course was awesome and the views off of the 2nd green in the evening was so amazing to see the sunsets! Can't wait to go back. … see more
Family Beach Headquarters: Maui Banyan 2 BR Condo at Beach, Sleeps 4-8
Convenient Condo

The Condo was very nice. Easy access to the beach, restaurants, and pool. The unit was perfectly sized for my family. The patio was great. … see more
Outstanding Luxury Condo for Couples in Paradise - Ocean and Beacfront
Review

We had a fantastic time! The condo was clean, well equipped and was conveniently located. The property was beautiful and the owners were very pleasant to deal with. … see more
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
OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA
Great View, Great Place

Kihei/Wailea is hands down the best area to stay in. Woke up, had breakfast, enjoyed beers on the beach, great food everywhere, and our vacation rental was perfect. Dennis was very nice and easy to talk to, any questions I had he answer quickly and with alot of information. I am not a very social person and Dennis made the check in process quick which I appreciated, especially after a long flight. Over a thousand channels on the TV which was great since nightlife dies around 9PM every day. Extremely clean rental with a washer and dryer, this place was the best place I have stayed at to date. I would definitely recommend staying here, it made our vacation.see more
Wailea Ekahi 7G Luxury Ocean Front S Maui Condo
Absolutely Perfect!

This condo is gorgeous, and set up with everything you could ask for during your stay. We were so pleased with the location, cleanliness, and the setup of the home for us. There was not a single thing that we came across that we needed that we did not find there for us. Beach towels, toiletries, kitchen items, BBQ, etc, and the location could not be better. We highly recommend this to anyone, and will definitely be going back again!see more

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