
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

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

Gorgeous Views! - Kihei Surfside #109

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

Wailea Ike by AvantStay | Walk to the Beach, Views

Oceanview Home with Private pool and hot tub

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

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

Ohe'o || Wailea Ekahi Unit 28B || Lowered Rates

Beautiful Ocean Views and Aloha at Wailea Ekolu!

Spectacular ocean views @IslandSurf Aug Spec. $125

Modern Renovated Palms at Wailea Condo!

Tropical Wailea Retreat

*Fully Remodeled* Modern Island Style*

Beachfront Maui Oasis- Fully Remodeled, Beautiful

Ground Floor | Building 1 | Across the Best Beach
Other holiday rentals with a pool

Prime Location, in the HEART of it ALL!

Newly Remodeled-AC-Ocean Views-Modern Finishes

Wailea Elua 1101 - Beachfront Section - Ocean View

Wailea Ekahi 1BR | 2 Beds | Steps to Beach & Pools

Luxurious Wailea Ocean Vistas

Wailea Ocean View Escape

Maui Retreat Ekahi 50F -All YOU Need!

Wailea Elua Village 803, Ocean Views, Modern Reno
Quick stats about holiday rentals with a pool in Wailea
Total rentals
1.7K properties
Nightly prices starting at
$17 NZD 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
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Honolua Bay
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Manele Golf Course
- Wailea Beach
- Hāmoa Beach
- Maui Ocean Center
- Kaipukaihina
- Kapua
- Oneloa Beach
- Palauea Beach
- Changs Beach
- Old Lahaina Luau
- Puu Olai Beach
- Wailau Valley
- Wailea Golf Club
- Maui Golf & Sports Park
- Paukukalo Beach