
Vacation rentals with a pool in Wailea
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wailea
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 rentals with a pool
House rentals with a pool

Maui Ocean View Villa, Pool, Spa

Kihei 533- A/C, Free Parking, and WiFi

Gorgeous Views! - Kihei Surfside #109

Stunning One Bd Partial ocean, AC, wifi,Pool C209

Walk to the Beach, Balcony w/ View, Communal Pool

Oceanview Home with Private pool and hot tub

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront
Condo rentals with a pool

Grand Champions - King Bed - Close to Wailea Beach

Oceanfront Getaway, Brand New, Steps To Beach

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

Spectacular ocean views @IslandSurf Oct Spec $175

Sugar Beach Resort Beach / Ocean Front Unit 426

Modern Renovated Palms at Wailea Condo!

Luxe 2bed Wailea, 5-min walk to beach, ocean view,

Beachfront Maui Oasis- Fully Remodeled, Beautiful
Other vacation rentals with a pool

Stunning Wailea 2/2, AC, Upper Fl , walk to beach

Wailea Elua 1101 - Beachfront Section - Ocean View

Wailea Ocean View Escape

Maui Retreat Ekahi 50F -All YOU Need!

Wailea Elua Village | 2108

Aloha Moon - The Honeymoon Hideaway

Wailea Hidden Gem

Wailea Fall Special, AC, Walk 2 Beach, Lg Lanai
Quick stats about vacation rentals with a pool in Wailea
Total rentals
1.7K properties
Nightly prices starting at
$14Â CAD before taxes and fees
Total number of reviews
46K reviews
Family-friendly rentals
990 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
950 properties have a dedicated workspace
Destinations to explore
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- Rentals with pools Maui County
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- Maui
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