Holiday 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.
Holiday 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
8–15 Nov
Home in Kula
4.91 out of 5 average rating, 303 reviewsKula Jewel - Pool, Hot Tub & Awesome Views!
31 Mar – 7 Apr
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
20–27 Sep
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
29 Oct – 5 Nov
Home in Kihei
4.95 out of 5 average rating, 20 reviewsSouth Kihei Condo - steps to ocean and pool!
28 Jul – 4 Aug
Home in Maui County
4.83 out of 5 average rating, 52 reviewsCliff House with Ocean Views in Haiku, Maui jungle
9–16 Jul
Home in Kihei
4.93 out of 5 average rating, 58 reviewsHo'olei #93-2-Beautifully Appointed-Well Equipped
3–10 Sep
Home in Kihei
5.0 out of 5 average rating, 18 reviewsCentrally located and steps to the beach!
1–8 Aug
Apartment rentals with a pool
Apartment in Kihei
4.99 out of 5 average rating, 130 reviewsMaui Dream Place at Maui Kamaole G-209, Ocean View
13–20 Dec
Apartment in Wailea
4.94 out of 5 average rating, 155 reviewsSpectacular Ocean View condo beautiful inside out.
27 Jul – 3 Aug
Apartment in Wailea
4.95 out of 5 average rating, 137 reviews4/21-5/30 Fabulous Peaceful 2bd in Upscale Wailea
29 Sep – 6 Oct
Apartment in Kihei
4.91 out of 5 average rating, 211 reviewsGorgeous Getaway on the Beach
1–8 Sep
Apartment in Kihei
4.95 out of 5 average rating, 111 reviewsSpacious Unit in Aston Maui Hill w/ Netflix&more
1–8 Mar
Apartment in Wailea-Makena
4.98 out of 5 average rating, 138 reviewsGrand Champions 169 Beautiful 3 BR on the Fairway!
31 Mar – 7 Apr
Apartment in Kihei
5.0 out of 5 average rating, 163 reviewsCozy Beach Condo Ocean & Mountain View’s
1–8 Jan
Apartment in Kihei
4.95 out of 5 average rating, 129 reviewsModern Condo. Just 3 Min Walk to Toes in the Sand
13–20 Oct
Quick stats about holiday rentals with a pool in Wailea-Makena
Total rentals
1.7T properties
Wifi availability
1.7T 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
1T properties are a good fit for families
Total number of reviews
39T reviews
Destinations to explore
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