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. 26 – Jan. 2
Home in Kula
4.91 out of 5 average rating, 303 reviewsKula Jewel - Pool, Hot Tub & Awesome Views!
Apr. 8 – 15
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
Nov. 18 – 25
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
Apr. 12 – 19
Home in Maui County
4.83 out of 5 average rating, 52 reviewsCliff House with Ocean Views in Haiku, Maui jungle
Jul. 9 – 16
Home in Kihei
4.93 out of 5 average rating, 58 reviewsHo'olei #93-2-Beautifully Appointed-Well Equipped
Sep. 3 – 10
Condo rentals with a pool
Condo in Kihei
4.99 out of 5 average rating, 130 reviewsMaui Dream Place at Maui Kamaole G-209, Ocean View
Dec. 13 – 20
Condo in Kihei
4.83 out of 5 average rating, 138 reviewsUpdated Air Conditioned Condo Steps from the Beach
Jun. 13 – 20
Condo in Kihei
4.95 out of 5 average rating, 111 reviewsSpacious Unit in Aston Maui Hill w/ Netflix&more
Feb. 6 – 13
Condo in Kaunakakai
4.94 out of 5 average rating, 180 reviewsWelcome to Hotel Molokai, Unit 102...
Aug. 10 – 17
Condo in Kihei
4.94 out of 5 average rating, 198 reviewsMana Kai Maui - Oceanfront Condo in Kihei
Apr. 18 – 25
Condo in Wailea
4.95 out of 5 average rating, 137 reviews4/21-5/30 Fabulous Peaceful 2bd in Upscale Wailea
Sep. 30 – Oct. 7
Condo in Kihei
4.91 out of 5 average rating, 211 reviewsGorgeous Getaway on the Beach
Mar. 16 – 23
Condo in Kihei
5.0 out of 5 average rating, 164 reviewsCozy Beach Condo Ocean & Mountain View’s
Dec. 31 – Jan. 7
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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