
Holiday 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.
Holiday 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

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu
Apartment rentals with a pool

Live, Love, Loft in Beautiful Maui

Turtle Cove Oceanfront Views Island Sands Resort

Spectacular Ocean Front 1bd at Menehune Shores

Gorgeous Condo in Wailea Ekahi Village!

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

☀Very Desirable South Kihei | Enlivening Getaway ☀

Grand Champions 169 Beautiful 3 BR on the Fairway!

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

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

Wailea Elua 1101 - Beachfront Section - Ocean View

Amazing Ocean Views at Wailea Ekolu Village!

Wailea Ocean View Escape

Modern Renovated Palms at Wailea Condo!

Go Golfing from a Peaceful Apartment in a Beach Community

Wailea Hidden Gem

Wailea Ekolu Village | 912
Quick stats about holiday rentals with a pool in Wailea
Total rentals
1.7K properties
Nightly prices starting at
€ 8 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 a washing machine and dryer Wailea
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- Rentals with pools Maui County
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- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Honolua Bay
- Kapalua Bay Beach
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- Olowalu Beach
- Pahoa Beach
- Manele Golf Course
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