Vacation Rentals & Condos in Wailea

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1,782 condos

(5) Excellent 

28

One-of-a-Kind Maui Getaway!

Maui / Wailea

Wailea house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$1,340

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$1,340

(35) Excellent 

30

OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA

Maui / Wailea

Wailea cottage

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Air conditioning
“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 are
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Price per night from

$299

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$299

(1) Very Good 

38

Palms at Wailea #1102 Probably the best ocean view at the Palms at Wailea!

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
“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) we
…see more

Price per night from

$295

Responds fast!
avg. 5 minutes

Price per night from

$295

(12) Excellent 

22

Updated Spacious 3 Bdrm. Wailea Ocean View Condo

Maui / Wailea

Wailea apartment

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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, ri
…see more

Price per night from

$285

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$285

(1) Excellent 

47

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

Maui / Wailea

Wailea apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$255

Responds fast!
avg. 5 minutes

Price per night from

$255

(2) Excellent 

23

Brand new 2 bedroom beach front at the Mana Kai Maui Resort! On Keawakapu beach!

Maui / Wailea

Wailea condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$630

Price per night from

$630

(19) Excellent 

32

Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4

Maui / Wailea

Wailea apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
“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!!
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Price per night from

$299

Responds fast!
avg. 5 minutes

Price per night from

$299

(6) Excellent 

21

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

Maui / Wailea

Wailea villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“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
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Price per night from

$1,050

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$1,050

(15) Very Good 

49

Palms at Wailea Unit #2305 1Bd/2Ba Quiet, Very Private! Near Beach, Sleeps 2

Maui / Wailea

Wailea apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
“Great for Couples” For those of us who hate living in hotels, or paying for services we don't use, this 1 bedroom/2 bathroom condo is perfect. It feels and looks even larger than the photos and is equipped with a full kitchen, that is very well stocke
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Price per night from

$189

Responds fast!
avg. 5 minutes

Price per night from

$189

(3) Excellent 

47

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

Maui / Wailea

Wailea apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“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. Mah
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Price per night from

$159

Responds fast!
avg. 5 minutes

Price per night from

$159

46

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

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$265

Responds fast!
avg. 5 minutes

Price per night from

$265

34

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

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$250

Responds fast!
avg. 5 minutes

Price per night from

$250

(14) Very Good 

30

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

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“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 beac
…see more

Price per night from

$210

Responds fast!
avg. 5 minutes

Price per night from

$210

(1) Excellent 

15

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

Maui / Wailea

Wailea apartment

2 8 4 nights min

  • 2 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$218

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$218

(1) Very Good 

21

Wailea Ekahi 46F- Spacious 2 bedroom 2 Bath Condo in Wailea!

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
“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 cond
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Price per night from

$295

Price per night from

$295

(7) Very Good 

46

Wailea Ekolu 805 Deluxe 2Bd/2Ba, Ocean View Townhouse! Full A/C, Sleeps 4

Maui / Wailea

Wailea apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“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
…see more

Price per night from

$215

Responds fast!
avg. 5 minutes

Price per night from

$215

33

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

Maui / Wailea

Wailea villa

3 8 6 nights min

  • 3 bedrooms
  • sleeps 8
  • 6 nights min
  • Child Friendly

Price per night from

$695

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$695

26

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

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$289

Responds fast!
avg. 5 minutes

Price per night from

$289

(31) Very Good 

34

Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“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 wer
…see more

Price per night from

$220

Responds fast!
avg. 5 minutes

Price per night from

$220

(20) Very Good 

27

Palms at Wailea #1902 Garden View 2Bd/2Ba, Fully Air Conditioned, Sleeps 6

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“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
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Price per night from

$235

Responds fast!
avg. 5 minutes

Price per night from

$235

(16) Excellent 

17

Wailea Ekahi Ocean View 50A

Maui / Wailea

Wailea condo

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$252

Responds fast!
avg. 3 hours 46 minutes

Price per night from

$252

(4) Excellent 

16

Fantastic Beach Front 2 Bedroom Condo MAKENA SURF RESORT, #B-205

Maui / Wailea

Wailea apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Great Spot” Great beach snorkeling was so convenient lots of turtles. Quiet area but you can access whatever excitement you want in a short drive. The pool is right next to the condo so you can relax there as well. Very well kept grounds. Highly re
…see more

Price per night from

$762

Price per night from

$762

26

Just Renovated 3bd 3ba in South Kihei, Hawaii

Maui / Wailea

Wailea condo

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$495

Price per night from

$495

26

PSA303 Affordable Paradise! 2 Bd, 2 ba Across from Beach & Mountain /Ocean views

Maui / Wailea

Wailea condo

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$150

Price per night from

$150

(8) Excellent 

31

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

Maui / Wailea

Wailea apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 pho
…see more

Price per night from

$169

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$169

31

Oceanview Condo just Moments from the Beach

Maui / Wailea

Wailea condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$373

Price per night from

$373

(13) Excellent 

0

Wailea Sunset Bungalow

Maui / Wailea

Wailea house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Paradise at Wailea Sunset Bungalow” Our trip to Maui was fantastic, mostly due to the spectacular Wailea Sunset Bungalow. This home was stocked with absolutely everything a person or group could ever need for a week, even a month. We enjoyed the fam
…see more

Price per night from

$995

Price per night from

$995

(1) Excellent 

33

Spectacular 3rd Row at Ho'olei with Ocean Views

Maui / Wailea

Wailea villa

3 8 6 nights min

  • 3 bedrooms
  • sleeps 8
  • 6 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$745

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$745

(7) Excellent 

40

10th Night FREE all 2019

Maui / Wailea

Wailea condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$224

Price per night from

$224

(8) Very Good 

30

Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. It can sleep 6.

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Loved it” Loved the area the condo was located. Very clean, and spacious. Kids loved the pool =)
…see more

Price per night from

$199

Responds fast!
avg. 5 minutes

Price per night from

$199

14

Ekahi Village 46e - Double Lanai with an Ocean View

Maui / Wailea

Wailea condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool

Price per night from

$240

Price per night from

$240

(17) Very Good 

39

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

Maui / Wailea

Wailea apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“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
…see more

Price per night from

$169

Responds fast!
avg. 5 minutes

Price per night from

$169

23

Maui Kamaole #A209 2BR/2BA - Spectacular Panoramic Ocean View in best location

Maui / Wailea

Wailea condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$373

Price per night from

$373

(2) Excellent 

50

Castaway Cove C201 at Wailea Beach Villas

Maui / Wailea

Wailea house

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,195

Price per night from

$1,195

(7) Excellent 

8

Remodeled Elegance & Luxury - Daily Housekeeping Elua Village # 2107

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary
“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 b
…see more

Price per night from

$425

Price per night from

$425

(1) Very Good 

45

New Listing Budget Vacation! Kihei Akahi C-616

Maui / Wailea

Wailea apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$171

Price per night from

$171

(1) Excellent 

24

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

Maui / Wailea

Wailea apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$175

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$175

(7) Very Good 

16

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

Maui / Wailea

Wailea apartment

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary
“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, a
…see more

Price per night from

$612

Price per night from

$612

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.