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!
Apr 13 – 20
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
Sep 20 – 27
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
Oct 25 – Nov 1
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
4.92 out of 5 average rating, 86 reviewsMaui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
Aug 18 – 25
Home in Kihei
5.0 out of 5 average rating, 13 reviews*PANO EPIC OCEAN VIEW*RENOVATED*Dual AC*Owner MGMT
Sep 11 – 18
Home in Kihei
5.0 out of 5 average rating, 18 reviewsCentrally located and steps to the beach!
Oct 2 – 9
Home in Kihei
4.9 out of 5 average rating, 62 reviewsMaui Sunset Resort A102 - Aloha Mai, Remodel, Grou
Sep 12 – 19
Condo rentals with a pool
Condo in Kihei
4.91 out of 5 average rating, 211 reviewsGorgeous Getaway on the Beach
Nov 29 – Dec 6
Condo in Kihei
4.94 out of 5 average rating, 198 reviewsMana Kai Maui - Oceanfront Condo in Kihei
Mar 5 – 12
Condo in Wailea-Makena
4.97 out of 5 average rating, 129 reviewsStay at a Prestigious Tropical Resort in Wailea
Apr 18 – 25
Condo in Wailuku. Maui
4.88 out of 5 average rating, 233 reviewsOceanfront Condo. Pool & Spa, 1 Br.
Aug 21 – 28
Condo in Kihei
4.83 out of 5 average rating, 138 reviewsUpdated Air Conditioned Condo Steps from the Beach
Sep 2 – 9
Condo in Wailea
4.94 out of 5 average rating, 155 reviewsSpectacular Ocean View condo beautiful inside out.
Sep 8 – 15
Condo in Kihei
4.85 out of 5 average rating, 310 reviews1 minute to Beach & Downtown! Remodeled XL Apt!
Oct 6 – 13
Condo in Kihei
4.96 out of 5 average rating, 226 reviewsBeautiful Modern Decor in a Light-Filled Condo
Mar 17 – 24
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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