
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

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

Kihei Gem: Walk to Kam I Beach!
Apartment rentals with a pool

Fully remodeled, Ocean View, 3 mins walk to beach

Live, Love, Loft in Beautiful Maui

Beautiful Ocean Views and Aloha at Wailea Ekolu!

Wailea Elua Village | 1202

Wailea Elua 1101 - Beachfront Section - Ocean View

Spacious S. Kihei Suite New A/C across from Kam 3

Tropical Wailea Retreat

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

Prime Location, in the HEART of it ALL!

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

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

21A Grand Champions 1 Bed - Ulua & Mokapu beaches

Wailea Ocean View Escape

Ekahi 22C Toes in the Sand in Under 2 Minutes

Maui Retreat Ekahi 50F -All YOU Need!

Modern Renovated Palms at Wailea Condo!
Quick stats about holiday rentals with a pool in Wailea
Total rentals
1.7K properties
Nightly prices starting at
$13 SGD 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
- Kaanapali Beach
- Kahului Beach
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- Sandy Beach
- Laie
- Honolua Bay
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- Manele Golf Course
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