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
28 Aug – 4 Sep
Home in Kula
4.91 out of 5 average rating, 303 reviewsKula Jewel - Pool, Hot Tub & Awesome Views!
28 Feb – 7 Mar
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
20–27 Sep
Home in Kula
5.0 out of 5 average rating, 50 reviewsHike on Scenic Trails at a Luxury Home on 7 Acres
12–19 Apr
Home in Kihei
4.95 out of 5 average rating, 20 reviewsSouth Kihei Condo - steps to ocean and pool!
8–15 Aug
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
26 Jan – 2 Feb
Home in Maui County
4.83 out of 5 average rating, 52 reviewsCliff House with Ocean Views in Haiku, Maui jungle
11–18 Aug
Home in Kihei
4.93 out of 5 average rating, 58 reviewsHo'olei #93-2-Beautifully Appointed-Well Equipped
1–8 Nov
Apartment rentals with a pool
Apartment in Kihei
4.99 out of 5 average rating, 130 reviewsLuxury condo • 180° Ocean Views • Steps to Beach
2–9 Feb
Apartment in Kihei
4.91 out of 5 average rating, 211 reviewsGorgeous Getaway on the Beach
9–16 Apr
Apartment in Kihei
4.99 out of 5 average rating, 130 reviewsMaui Dream Place at Maui Kamaole G-209, Ocean View
23–30 Jan
Apartment in Wailea
4.94 out of 5 average rating, 155 reviewsSpectacular Ocean View condo beautiful inside out.
13–20 Aug
Apartment in Kihei
4.95 out of 5 average rating, 120 reviewsLuxury Vacationing Modern Condo May Specials $249
4–11 May
Apartment in Kihei
4.94 out of 5 average rating, 198 reviewsMana Kai Maui - Oceanfront Condo in Kihei
6–13 Mar
Apartment in Kihei
4.95 out of 5 average rating, 111 reviewsSpacious Unit in Aston Maui Hill w/ Netflix&more
5–12 Apr
Apartment in Wailea
4.95 out of 5 average rating, 137 reviews4/21-5/30 Fabulous Peaceful 2bd in Upscale Wailea
12–19 Oct
Quick stats about holiday 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
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