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
Kula Jewel - Pool, Hot Tub & Awesome Views!
Home in Lahaina
Kaanapali Cottage ICC 29 Indoor/Outdoor Living
Home in Kihei
South Kihei Condo w/AC - steps to pool and ocean!
Home in Kihei
GORGEOUS PRIVATE HOME WITH POOL
Home in Kihei
Your Own Private Resort with Breathtaking Ocean Views
Home in Kihei
Maui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
Home in Kihei
Centrally located and steps to the beach!
Home in Kihei
Beachfront Condo—3 bedrooms—Fully Renovated
Condo rentals with a pool
Condo in Kihei
Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
Condo in Kihei
Newly Renovated Beach Condo
Condo in Kihei
Everything you need to enjoy true paradise!
Condo in Kihei
Maui Banyan, King Bed, AC, Across Kamaole Beach!
Condo in Kihei
“Paradise Views” Menehune Shores, Kihei, Maui
Condo in Wailea-Makena
Stay at a Prestigious Tropical Resort in Wailea
Condo in Kihei
Gorgeous Getaway on the Beach
Condo in Kihei
Maui Kamaole Ocean View...Walk to the Beach
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
Destinations to explore
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