
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

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

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
Condo rentals with a pool

Makani A Kai A9 romantic beachfront Maui, pool,a/c

Live, Love, Loft in Beautiful Maui

Oceanfront Getaway, Brand New, Steps To Beach

Renovated Penthouse Studio @ Maui Banyan (NICE!)

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

☀Very Desirable South Kihei | Enlivening Getaway ☀

Grand Champions 169 Beautiful 3 BR on the Fairway!

Oceanfront Condo with Pool and Jacuzzi
Other holiday rentals with a pool

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

Gorgeous Condo in Wailea Ekahi Village!

Wailea Ocean View Escape

Modern Renovated Palms at Wailea Condo!

Aloha Moon - The Honeymoon Hideaway

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

Wailea Hidden Gem

Luxurious Tropical Retreat with Oceanview
Quick stats about holiday rentals with a pool in Wailea
Total rentals
1.7K properties
Nightly prices starting at
$15 AUD 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
- Hotel rentals Wailea
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- Rentals with an EV charger Wailea
- Waterfront rentals Wailea
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- Rentals with a kayak Wailea
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- Serviced apartment rentals Wailea
- Rentals with pools Wailea
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Honolua Bay
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Pahoa Beach
- Manele Golf Course
- Hāmoa Beach
- Maui Ocean Center
- Kaipukaihina
- Wailea Beach
- Oneloa Beach
- Changs Beach
- Puu Olai Beach
- Palauea Beach
- Old Lahaina Luau
- Maui Golf & Sports Park
- Wailau Valley
- Wailea Golf Club
- Ka'anapali Golf Courses