
Holiday rentals with a pool in Kaanapali
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kaanapali
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 Kaanapali rentals with a pool
House rentals with a pool

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

Mahalo Pono @ Ka'anapali Royal

Cliff House with Ocean Views in Haiku, Maui jungle

Newly Remodeled Cottage

Kapalua Ridge 622 Luxe Ocean and Coastal Views

Stunning ocean view, heated pool at home by Wailea

Kula Jewel - Pool, Hot Tub & Awesome Views!

#1 Kaanapali Beach Modern Condo C101 Maui Eldorado
Condo rentals with a pool

Dream-like ocean views! Steps from the Ocean

Crazy Good Deal MKV Resort Ka'anapali - Ocean View

Absolute Beachfront with Million-Dollar Views!

Pohailani 113 - Vacation West Maui - Gorgeous w/AC

Sugar Beach Resort Beach / Ocean Front Unit 426

Luxury condo • 180° Ocean Views • Steps to Beach

Amazing Ocean Views and First Class Accommodations

Romantic, Luxury Condo with Spectacular Ocean View
Other holiday rentals with a pool

Beautiful Ground floor! Ocean and Beach Access

Oceanfront penthouse - stunning view!

Turtles & Tales: Luxe Beachfront w/AC & Ocean view

Westin Studio Kaanapali Villas 3

Cozy Studio Hotel Stay w/ Resort Amenities

Papakea #A106 Oceanfront Studio * No Resort Fees*

Ocean View Condo with Beachfront Cabana for Guests

Gorgeous Kapalua Home with Views
Quick stats about holiday rentals with a pool in Kaanapali
Total rentals
4K properties
Total number of reviews
40K reviews
Family-friendly rentals
1.9K properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
2.4K properties have a dedicated workspace
Wi-Fi availability
4K properties include access to Wi-Fi
Destinations to explore
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- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Maui
- Kaanapali Beach
- Kahului Beach
- Kepuhi Beach
- Lahaina Beach
- Sandy Beach
- Honolua Bay
- Kapalua Bay Beach
- Olowalu Beach
- Manele Golf Course
- Kalani Beach
- Kaupoa Beach
- Hāmoa Beach
- Maui Ocean Center
- Wailea Beach
- Kaipukaihina
- Kapua
- Oneloa Beach
- Puu Olai Beach
- Changs Beach
- Palauea Beach
- Old Lahaina Luau
- Wailau Valley
- Maui Golf & Sports Park