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 Maui
4.98 out of 5 average rating, 183 reviewsPrivate Hot Tub + Pool Access + AC - Star Lookout
Dec 25 – Jan 1
Home in Kula
4.91 out of 5 average rating, 303 reviewsKula Jewel - Pool, Hot Tub & Awesome Views!
Feb 18 – 25
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
Sep 20 – 27
Home in Kula
5.0 out of 5 average rating, 50 reviewsHike on Scenic Trails at a Luxury Home on 7 Acres
Dec 2 – 9
Home in Kihei
4.95 out of 5 average rating, 20 reviewsSouth Kihei Condo - steps to ocean and pool!
Jul 28 – Aug 4
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
Feb 2 – 9
Home in Maui County
4.83 out of 5 average rating, 52 reviewsCliff House with Ocean Views in Haiku, Maui jungle
Jul 11 – 18
Home in Kihei
5.0 out of 5 average rating, 13 reviews*PANO EPIC OCEAN VIEW*RENOVATED*Dual AC*Owner MGMT
Dec 3 – 10
Condo rentals with a pool
Condo in Wailea-Makena
4.98 out of 5 average rating, 139 reviewsGrand Champions 169 Beautiful 3 BR on the Fairway!
Jan 4 – 11
Condo in Kihei
4.86 out of 5 average rating, 124 reviewsIsland Surf #206 Your South Maui Gem is here
Jul 23 – 30
Condo in Kihei
4.95 out of 5 average rating, 108 reviewsMaui Kamaole Ocean View...Walk to the Beach
Dec 11 – 18
Condo in Maui
4.95 out of 5 average rating, 198 reviewsSeaside Tropical Maui Condo - Vaxed Only
Apr 3 – 10
Condo in Kihei
4.78 out of 5 average rating, 238 reviewsMaui Banyan, King Bed, AC, Across Kamaole Beach!
Aug 19 – 26
Condo in Kihei
4.96 out of 5 average rating, 226 reviewsBeautiful Modern Decor in a Light-Filled Condo
Apr 9 – 16
Condo in Kihei
4.84 out of 5 average rating, 342 reviewsCheapest Cozy Studio
Sep 16 – 23
Condo in Wailea
4.89 out of 5 average rating, 19 reviewsGorgeous Condo in Wailea Ekahi Village!
Jan 23 – 30
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
Destinations to explore
- Kailua-Kona Vacation rentals
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