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Start your Wailea, HI search

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Apartments With Pool

Apartments for Rent in Wailea, HI with Pools

8 rentals available

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Kihei Apartments
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Haliimaile Apartments

City Guide for Wailea, HI

Wailea Beach earned the moniker of "America's Best Beach" in 1999. Take that, Florida!

Located on Maui's southern coast, the community of Wailea is known primarily as a vacation destination for those seeking sun, sand and surf

View Wailea City Guide (opens in a new tab)

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Apartments With Pool

Last updated September 16, 2026 at 3:49 AM PDT

Top 8 Apartments for Rent with Pools for Rent in Wailea, HI (with pics!)

Listings

Upgraded Wailea Home in Prestigious Gated Residence in Kai Malu Available October 17, 2026 – Mid June 2027 Gallery 1

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Upgraded Wailea Home in Prestigious Gated Residence in Kai Malu Available October 17, 2026 – Mid June 2027 (opens in new tab)

100 Kai la Place, Wailea, HI 96753

$8,900/moFees may apply12-mo lease

1 unit available

2 bed

2747 South Kihei Road - 1#E305 Gallery 1

Amenities

In unit laundry, Patio / balcony, Granite counters, Dishwasher, Garage, Recently renovated + more

Wailea Fairway Villas 2 bed, 2 bathroom Condo! Gallery 1

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Wailea Fairway Villas 2 bed, 2 bathroom Condo! (opens in new tab)

3950 Kalai Waa Street, Wailea, HI 96753

$4,300/moFees may apply12-mo lease

1 unit available

2 bed

Amenities

Gym, Pool, Bbq/grill, and Furnished

31 Ahekolo St Gallery 1

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31 Ahekolo St (opens in new tab)

31 Ahekolo Street, Wailea, HI 96753

$8,300/moFees may apply12-mo lease

1 unit available

3 bed

Amenities

In unit laundry, Garage, Recently renovated, Walk in closets, Pool, and Air conditioning

3161 Mapu Drive Gallery 1

1 of 30

3161 Mapu Drive (opens in new tab)

3161 Mapu Drive, Wailea, HI 96753

$5,700/moFees may apply12-mo lease

1 unit available

2 bed

Amenities

Patio / balcony, Dishwasher, Parking, Pool, Air conditioning, Hot tub + more

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2747 South Kihei Road - 1#E305 (opens in new tab)

2747 S Kihei Rd, Wailea, HI 96753

$3,400/moFees may apply12-mo lease

1 unit available

3 bed

Amenities

In unit laundry, Parking, Pool, and Furnished

3105 Noho Loihi Way North Gallery 1

3105 Noho Loihi Way North (opens in new tab)

3105 Noho Loihi Way North, Wailea, HI 96753

$14,000/moFees may apply12-mo lease

1 unit available

4 bed

Amenities

In unit laundry, Patio / balcony, Granite counters, Hardwood floors, Dishwasher, Garage + more

Luxury Living with Ocean Views in Wailea at Kai Malu Gallery 1

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Luxury Living with Ocean Views in Wailea at Kai Malu (opens in new tab)

83 Kainehe Place, Wailea, HI 96753

$7,300/moFees may apply12-mo lease

1 unit available

3 bed

Amenities

In unit laundry, Dishwasher, Pet friendly, Garage, Gym, Pool + more

Modern Elegancy at Makali'i in Wailea on the boarder of Makena - Finely Furnished 2 Bedrooms / 2 Bathrooms Gallery 1

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Modern Elegancy at Makali'i in Wailea on the boarder of Makena - Finely Furnished 2 Bedrooms / 2 Bathrooms (opens in new tab)

172 Holomoana Way, Wailea, HI 96753

$6,500/moFees may apply12-mo lease

1 unit available

2 bed

Amenities

In unit laundry, Dishwasher, Stainless steel, Gym, Pool, Air conditioning + more

Frequently Asked Questions (FAQs)

How much is rent for an apartment with a pool in Wailea, HI?
Rental prices for apartments with pools in Wailea, HI range from $3,400 to $14,000 per month.
How many apartments with pools are available for rent in Wailea, HI?
Currently, there are 8 apartments with pools available for rent in Wailea, HI.

Best market deals

These units are the best deal in town.

2747 South Kihei Road - 1#E305 3 Bed

3 Beds • 2 Baths • 1035 sqft

Base monthly rent

$3,400+

Available

Now

825 Kumulani Drive 2 Bed

2 Beds • 2 Baths • 1200 sqft

Base monthly rent

$3,950+

Available

Now

Island Living in a Renovated 2-Bed, 2-Bath Unfurnished Maui Meadows Retreat 2 Beds, 2 Baths, $4200

2 Beds • 2 Baths • 920 sqft

Base monthly rent

$4,200+

Available

Oct 1

Wailea Fairway Villas 2 bed, 2 bathroom Condo! 2 Beds, 2 Baths, $4300

2 Beds • 2 Baths • 949 sqft

Base monthly rent

$4,300+

Available

Oct 1

3161 Mapu Drive 2 Bed

2 Beds • 2 Baths • 1014 sqft

Base monthly rent

$5,700+

Available

Sep 18

More Rental Options

Amenities

Wailea Furnished Apartments (8)

Cities

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Counties

Maui County Apartments (112)

Colleges

University of Hawaii at Manoa (120)
Hawaii Pacific University (104)
Kapiolani Community College (77)
Honolulu Community College (65)