
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

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

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

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Serene and Peaceful with Heated Pool
Condo rentals with a pool

Live, Love, Loft in Beautiful Maui

Spectacular Ocean Front 1bd at Menehune Shores

Gorgeous Condo in Wailea Ekahi Village!

*Last Minute Deal*Oceanfront Maui's Sugar Beach!

☀Very Desirable South Kihei | Enlivening Getaway ☀

Grand Champions 169 Beautiful 3 BR on the Fairway!

Maui Kamaole Ocean View...Walk to the Beach

Romantic One BR Condo (Remodeled)
Other vacation rentals with a pool

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

Beautiful Ocean Views and Aloha at Wailea Ekolu!

Wailea Elua 1101 - Beachfront Section - Ocean View

Wailea Ocean View Escape

Maui Retreat Ekahi 50F -All YOU Need!

Modern Renovated Palms at Wailea Condo!

Go Golfing from a Peaceful Apartment in a Beach Community

Wailea Ekolu Village | 912
Quick stats about vacation rentals with a pool in Wailea
Total rentals
1.7K properties
Nightly prices starting at
€ 9 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
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- Rentals with pools Maui County
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- Maui
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- Kahului Beach
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- Sandy Beach
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