Holiday 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.
Holiday 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!
13 – 20 Apr
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
20 – 27 Sept
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
25 Oct – 1 Nov
Home in Kihei
4.95 out of 5 average rating, 20 reviewsSouth Kihei Condo - steps to ocean and pool!
28 July – 4 Aug
Home in Kihei
4.92 out of 5 average rating, 86 reviewsMaui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
18 – 25 Aug
Home in Kihei
5.0 out of 5 average rating, 13 reviews*PANO EPIC OCEAN VIEW*RENOVATED*Dual AC*Owner MGMT
11 – 18 Sept
Home in Kihei
5.0 out of 5 average rating, 18 reviewsCentrally located and steps to the beach!
2 – 9 Oct
Home in Kihei
4.9 out of 5 average rating, 62 reviewsMaui Sunset Resort A102 - Aloha Mai, Remodel, Grou
12 – 19 Sept
Condo rentals with a pool
Condo in Kihei
4.91 out of 5 average rating, 211 reviewsGorgeous Getaway on the Beach
29 Nov – 6 Dec
Condo in Kihei
4.94 out of 5 average rating, 198 reviewsMana Kai Maui - Oceanfront Condo in Kihei
5 – 12 Mar
Condo in Wailea-Makena
4.97 out of 5 average rating, 129 reviewsStay at a Prestigious Tropical Resort in Wailea
18 – 25 Apr
Condo in Wailuku. Maui
4.88 out of 5 average rating, 233 reviewsOceanfront Condo. Pool & Spa, 1 Br.
21 – 28 Aug
Condo in Kihei
4.83 out of 5 average rating, 138 reviewsUpdated Air Conditioned Condo Steps from the Beach
2 – 9 Sept
Condo in Wailea
4.94 out of 5 average rating, 155 reviewsSpectacular Ocean View condo beautiful inside out.
8 – 15 Sept
Condo in Kihei
4.85 out of 5 average rating, 310 reviews1 minute to Beach & Downtown! Remodeled XL Apt!
6 – 13 Oct
Condo in Kihei
4.96 out of 5 average rating, 226 reviewsBeautiful Modern Decor in a Light-Filled Condo
17 – 24 Mar
Quick stats about holiday rentals with a pool in Wailea, Wailea-Makena
Total rentals
1.7K properties
Wi-Fi availability
1.7K properties include access to Wi-Fi
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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