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 out of 5 average rating, 52 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, 21 reviewsSouth Kihei Condo w/AC - steps to pool and ocean!
Home in Kihei
5 out of 5 average rating, 62 reviewsYour Own Private Resort with Breathtaking Ocean Views
Home in Kihei
4.92 out of 5 average rating, 88 reviewsMaui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
Home in Kihei
5 out of 5 average rating, 22 reviewsCentrally located and steps to the beach!
Condo rentals with a pool
Condo in Kihei
5 out of 5 average rating, 142 reviewsSugar Beach Resort Beach / Ocean Front Unit 426
Condo in Wailea-Makena
4.98 out of 5 average rating, 145 reviewsGrand Champions 169 Beautiful 3 BR on the Fairway!
Condo in Wailea-Makena
4.97 out of 5 average rating, 134 reviewsStay at a Prestigious Tropical Resort in Wailea
Condo in Kihei
4.97 out of 5 average rating, 114 reviewsModern Luxury Remodel - Maui Kamaole J114
Condo in Wailea
4.94 out of 5 average rating, 156 reviewsSpectacular Ocean View condo beautiful inside out.
Condo in Maui
4.95 out of 5 average rating, 200 reviewsSeaside Tropical Maui Condo - Vaxed Only
Condo in Kihei
4.87 out of 5 average rating, 112 reviewsHale Kamaole, King Bed, Ocean View, Kamaole Beach!
Condo in Kihei
5 out of 5 average rating, 168 reviewsCozy Beach Condo Ocean & Mountain View’s
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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