Vacation rentals with a pool in Wailea, Wailea-Makena
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wailea, Wailea-Makena
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Wailea, Wailea-Makena rentals with a pool
House rentals with a pool
Home in Kula
4.91 out of 5 average rating, 303 reviewsKula Jewel - Pool, Hot Tub & Awesome Views!
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
Home in Kula
5.0 out of 5 average rating, 50 reviewsHike on Scenic Trails at a Luxury Home on 7 Acres
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
Home in Kihei
4.95 out of 5 average rating, 20 reviewsSouth Kihei Condo - steps to ocean and pool!
Home in Kihei
4.92 out of 5 average rating, 86 reviewsMaui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
Home in Kihei
4.97 out of 5 average rating, 29 reviewsAloha AKU Bamboo Suite - Beachfront, 1 BR/Bath, LR
Home in Lahaina
5.0 out of 5 average rating, 14 reviewsMahalo Pono @ Ka'anapali Royal
Condo rentals with a pool
Condo in Kihei
5.0 out of 5 average rating, 166 reviewsCozy Beach Condo Ocean & Mountain View’s
Condo in Wailea-Makena
4.94 out of 5 average rating, 281 reviewsA.R.A Retreats: The Curved Slab
Condo in Kihei
4.96 out of 5 average rating, 168 reviewsGreat Stylish Condo By The Beach!
Condo in Kihei
4.99 out of 5 average rating, 133 reviewsMaui Dream Place at Maui Kamaole G-209, Ocean View
Condo in Kihei
4.9 out of 5 average rating, 300 reviewsEverything you need to enjoy true paradise!
Condo in Kihei
4.78 out of 5 average rating, 267 reviewsSteps To Kam 3 Beach
Condo in Kihei
4.86 out of 5 average rating, 313 reviews1 minute to Beach & Downtown! Remodeled XL Apt!
Condo in Kihei
4.92 out of 5 average rating, 190 reviewsBeautiful & clean condo w/ excellent location
Quick stats about vacation rentals with a pool in Wailea, Wailea-Makena
Total rentals
1.7K properties
Wifi availability
1.7K properties include access to wifi
Rentals with dedicated workspaces
900 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
1K properties are a good fit for families
Total number of reviews
39K reviews
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