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

Gorgeous Views! - Kihei Surfside #109

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

Beautiful One bd Ocean AC,wifi,pool A102

The Palms 1202 - The most expansive ocean views
Condo rentals with a pool

Full Ocean- Full Sunsets- Beaches at Royal Mauiian

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

Maui Condo Steps From Beach & Ocean (Hotel Zoned)

Beautiful Ocean Views and Aloha at Wailea Ekolu!

Wailea Elua 1101 - Beachfront Section - Ocean View

Modern Renovated Palms at Wailea Condo!

Grand Champions 169 Beautiful 3 BR on the Fairway!

Luxe 2bed Wailea, 5-min walk to beach, ocean view,
Quick stats about holiday rentals with a pool in Wailea, Wailea-Makena
Total rentals
1.8K properties
Nightly prices starting at
$99 NZD before taxes and fees
Total number of reviews
45K reviews
Family-friendly rentals
1K properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
1K properties have a dedicated workspace
Destinations to explore
- Rentals with a patio Wailea
- Townhouse rentals Wailea
- Villa rentals Wailea
- Kid-friendly rentals Wailea
- Rentals with a sauna Wailea
- Serviced apartment rentals Wailea
- Luxury rentals Wailea
- Hotel rentals Wailea
- Waterfront rentals Wailea
- Family-friendly rentals Wailea
- Pet-friendly rentals Wailea
- Fitness-friendly rentals Wailea
- Condo rentals Wailea
- Beachfront rentals Wailea
- Rentals with a hot tub Wailea
- House rentals Wailea
- Cottage rentals Wailea
- Rentals with an EV charger Wailea
- Rentals with a washing machine and dryer Wailea
- Beach condo rentals Wailea
- Apartment rentals Wailea
- Rentals with beach access Wailea
- Rentals with outdoor seating Wailea
- Rentals with pools Wailea-Makena
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- 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
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Kaipukaihina
- Laie
- Honolua Bay
- Kapalua Bay Beach
- Olowalu Beach
- Manele Golf Course
- Wailea Beach
- Hāmoa Beach
- Kapua
- Oneloa Beach
- Maui Ocean Center
- Wailea Golf Club
- Palauea Beach
- Old Lahaina Luau
- Kaulahao Beach
- Wailau Valley
- Papaloa Beach
- Ka'anapali Golf Courses
- Maui Golf & Sports Park
- Kalepolepo