Updating...

Enter dates for more accurate prices

Wailea Rentals with Pools

Filter

Wailea Rentals with Pools

1,408 vacation rentals

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, ri

Responds fast! avg. 3 hours 8 minutes

Price per night from

$284

1 / 22

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

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 2

“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

Responds fast! avg. 26 minutes

Price per night from

$189

1 / 49

One-of-a-Kind Maui Getaway!

Wailea house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 43 minutes

Price per night from

$1,335

1 / 28

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. Mah

Responds fast! avg. 26 minutes

Price per night from

$159

1 / 47

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) we

Responds fast! avg. 26 minutes

Price per night from

$294

1 / 38

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. 26 minutes

Price per night from

$249

1 / 34

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$254

1 / 47

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 beac

Responds fast! avg. 26 minutes

Price per night from

$210

1 / 30

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

Responds fast! avg. 26 minutes

Price per night from

$215

1 / 46

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

Price per night from

$1,196

1 / 21

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

Price per night from

$264

1 / 46

Price per night from

$548

1 / 23

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

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 wer

Responds fast! avg. 26 minutes

Price per night from

$220

1 / 34

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. 26 minutes

Price per night from

$298

1 / 32

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 cond

Price per night from

$294

1 / 21

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

“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

Price per night from

$762

1 / 16

Oceanview Condo just Moments from the Beach

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$324

1 / 31

Wailea Ekahi Ocean View 50A

Wailea condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$220

1 / 17

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

Price per night from

$288

1 / 26

Price per night from

$149

1 / 26

Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$745

1 / 33

Just Renovated 3bd 3ba in South Kihei, Hawaii

Wailea condo

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$493

1 / 26

Book Early Save Big - 2019 10th Night FREE

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$195

1 / 40

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

Responds fast! avg. 26 minutes

Price per night from

$234

1 / 27

Responds fast! avg. 2 hours 54 minutes

Price per night from

$130

1 / 24

Wailea Sunset Bungalow

Wailea house

2 bedrooms / 1 bathroom / sleeps 4

“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

Price per night from

$1,091

1 / 0

Castaway Cove C201 at Wailea Beach Villas

Wailea house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$1,191

1 / 50

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 pho

Responds fast! avg. 34 minutes

Price per night from

$169

1 / 31

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, a

Price per night from

$612

1 / 16

Wailea Elua Village # 202

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$440

1 / 16

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$359

1 / 41

Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. It can sleep 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. 26 minutes

Price per night from

$199

1 / 30

Price per night from

$324

1 / 23

IS214 2 Bed, 2 Bath Large Ocean View Condo

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

1 / 10

Wailea Elua Village #4C

Wailea apartment

1 bedroom / 1 bathroom / sleeps 4

“Pleasant” Though I was told that this was going to be on the beach. Not quite - but not a far walk either. Very good for couples but not so good for families. Some of the older folk looked at the kids and were not smiling :-( Very nice unit that

Price per night from

$235

1 / 16

Wailea Ekahi #22D

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$299

1 / 16

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$599

1 / 16

New Listing Budget Vacation! Kihei Akahi C-616

Wailea apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$129

1 / 45
Viewing 38 of 1,408
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more