Vacation 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.
Vacation 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
Home in Lahaina
5 out of 5 average rating, 13 reviewsNewly Remodeled Cottage
Home in Kihei
4.95 out of 5 average rating, 22 reviewsLuana Kai C209
Home in Haiku-Pauwela
4.91 out of 5 average rating, 11 reviewsViews and pool - escape reality
Home in Kihei
4.92 out of 5 average rating, 25 reviewsOceanview Home with Private pool and hot tub
Home in Lahaina
5 out of 5 average rating, 6 reviewsLuxury Panoramic Ocean Views!
Home in Lahaina
5 out of 5 average rating, 3 reviewsPualei Beach House
Home in Lahaina
5 out of 5 average rating, 12 reviewsKapalua Ridge 622 Luxe Ocean Views- 5th Night Free
Home in Kaanapali
4.91 out of 5 average rating, 105 reviews#1 Kaanapali Beach Modern Condo C101 Maui Eldorado
Condo rentals with a pool
Condo in Lahaina
4.98 out of 5 average rating, 52 reviews2 Master Bedrooms, 2.5 Baths with Ocean Views
Condo in Lahaina
4.93 out of 5 average rating, 29 reviewsDiscounted Rates! 305 Beautiful 2 bed/2 bath
Condo in Wailea-Makena
4.9 out of 5 average rating, 50 reviewsGaze out at Panoramic Ocean Views from an Airy Coastal Oasis
Condo in Kihei
4.89 out of 5 average rating, 124 reviewsIncomparable Maui Sunset condo, includes all taxes
Condo in Kihei
4.79 out of 5 average rating, 157 reviewsLuxury 2bd2bth Kihei Maui Condo Across from Beach
Condo in Kihei
4.84 out of 5 average rating, 102 reviewsFamily Friendly 2BR Condo Across from Beach w/ A/C
Condo in Kihei
4.84 out of 5 average rating, 235 reviewsCozy Cute Condo | Maui Vista | Walk to The Beach
Condo in Kihei
4.79 out of 5 average rating, 141 reviewsLuxury 3bdrm 3bth w/7 Beds Bunk Beds FULL AC Kihei
Quick stats about vacation rentals with a pool in Kaanapali
Total rentals
3.5K properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
35K reviews
Family-friendly rentals
1.6K properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
1.9K properties have a dedicated workspace
Destinations to explore
- Rentals with pools Hawaii
- Rentals with pools Honolulu
- Rentals with pools Maui
- Kid-friendly rentals Kaanapali
- Waterfront rentals Kaanapali
- Rentals with a patio Kaanapali
- Rentals with a hot tub Kaanapali
- Rentals with an EV charger Kaanapali
- House rentals Kaanapali
- Monthly Rentals Kaanapali
- Serviced apartment rentals Kaanapali
- Beachfront rentals Kaanapali
- Beach house rentals Kaanapali
- Condo rentals Kaanapali
- Pet-friendly rentals Kaanapali
- Rentals with a sauna Kaanapali
- Rentals with a fire pit Kaanapali
- Rentals with breakfast Kaanapali
- Villa rentals Kaanapali
- Fitness-friendly rentals Kaanapali
- Cottage rentals Kaanapali
- Rentals with a washer and dryer Kaanapali
- Resort rentals Kaanapali
- Rentals with an accessible height bed Kaanapali
- Family-friendly rentals Kaanapali
- Beach condo rentals Kaanapali
- Apartment rentals Kaanapali
- Rentals with beach access Kaanapali
- Rentals with outdoor seating Kaanapali
- Rentals with a kayak Kaanapali
- Hotel rentals Kaanapali
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes