Vacation rentals with a pool in Wailea-Makena
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in 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-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 Maui
4.98 out of 5 average rating, 183 reviewsPrivate Hot Tub + Pool Access + AC - Star Lookout
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, 20 reviewsSouth Kihei Condo - steps to ocean and pool!
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
Home in Maui County
4.83 out of 5 average rating, 52 reviewsCliff House with Ocean Views in Haiku, Maui jungle
Home in Kihei
5.0 out of 5 average rating, 13 reviews*PANO EPIC OCEAN VIEW*RENOVATED*Dual AC*Owner MGMT
Condo rentals with a pool
Condo in Kihei
4.99 out of 5 average rating, 207 reviews“Paradise Views” Menehune Shores, Kihei, Maui
Condo in Kihei
4.99 out of 5 average rating, 131 reviewsMaui Dream Place at Maui Kamaole G-209, Ocean View
Condo in Wailea
4.94 out of 5 average rating, 155 reviewsSpectacular Ocean View condo beautiful inside out.
Condo in Wailea-Makena
4.98 out of 5 average rating, 140 reviewsGrand Champions 169 Beautiful 3 BR on the Fairway!
Condo in Kihei
4.91 out of 5 average rating, 212 reviewsGorgeous Getaway on the Beach
Condo in Kihei
4.9 out of 5 average rating, 298 reviewsEverything you need to enjoy true paradise!
Condo in Kihei
4.82 out of 5 average rating, 194 reviewsMaui Tropical Retreat - Maui Banyan
Condo in Kihei
4.84 out of 5 average rating, 343 reviewsCheapest Cozy Studio
Quick stats about vacation rentals with a pool in 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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