
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

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

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

Oceanview Home with Private pool and hot tub

3BR/3BA Pualei Beach House

Maalaea Kai 307 - Maui Prime Oceanfront

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Beautifully Remodeled 3 Bedrooms/2Bathrooms

CLOUD 9 BEACH HOUSE, Maui Family Owned and Managed
Condo rentals with a pool

Beautiful Ocean Views and Aloha at Wailea Ekolu!

Gorgeous Condo in Wailea Ekahi Village!

Kihei Akahi C-211, GF, Quiet & Private

Makani A Kai A7 modern beachfront, pool, a/c, w/d

Luxurious Tropical Retreat with Oceanview

“Paradise Views” Menehune Shores, Kihei, Maui

Beachfront Top Floor I Hale Kai O Kihei 307

Steps to Beach, Shops & Dining w Views!
Other vacation rentals with a pool

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

Wailea Elua 1101 - Beachfront Section - Ocean View

Ma'alaea Surf Oceanfront 2 Bedroom Condo on 2nd Fr

Wailea Ocean View Escape

Ekahi 22C Toes in the Sand in Under 2 Minutes

Modern Renovated Palms at Wailea Condo!

Wailea Elua Village | 107

Luxe 2bed Wailea, 5-min walk to beach, ocean view,
Quick stats about vacation rentals with a pool in Wailea
Total rentals
1.7K properties
Nightly prices starting at
R176 ZAR 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 a patio Wailea
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- Rentals with pools Maui County
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- Maui
- Kaanapali Beach
- Kahului Beach
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- Sandy Beach
- Honolua Bay
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- Manele Golf Course
- Hāmoa Beach
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