Vacation 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.
Vacation 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
Home in Kula
4.91 out of 5 average rating, 303 reviewsKula Jewel - Pool, Hot Tub & Awesome Views!
Apr 8 – 15
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
Sep 20 – 27
Home in Kula
5.0 out of 5 average rating, 50 reviewsHike on Scenic Trails at a Luxury Home on 7 Acres
Nov 18 – 25
Home in Kihei
4.95 out of 5 average rating, 20 reviewsSouth Kihei Condo - steps to ocean and pool!
Jul 28 – Aug 4
Home in Kihei
4.95 out of 5 average rating, 21 reviewsGORGEOUS PRIVATE HOME WITH POOL
Apr 12 – 19
Home in Kihei
4.92 out of 5 average rating, 86 reviewsMaui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
Aug 8 – 15
Home in Kihei
5.0 out of 5 average rating, 13 reviews*PANO EPIC OCEAN VIEW*RENOVATED*Dual AC*Owner MGMT
Sep 17 – 24
Home in Kihei
5.0 out of 5 average rating, 18 reviewsCentrally located and steps to the beach!
Oct 2 – 9
Condo rentals with a pool
Condo in Wailea
4.93 out of 5 average rating, 144 reviewsStunning ocean view! 2/2 in the heart of Wailea
Nov 10 – 17
Condo in Kihei
4.91 out of 5 average rating, 211 reviewsGorgeous Getaway on the Beach
Mar 16 – 23
Condo in Kihei
4.95 out of 5 average rating, 111 reviewsSpacious Unit in Aston Maui Hill w/ Netflix&more
Feb 6 – 13
Condo in Wailea
4.94 out of 5 average rating, 155 reviewsSpectacular Ocean View condo beautiful inside out.
Jul 27 – Aug 3
Condo in Kihei
4.85 out of 5 average rating, 310 reviews1 minute to Beach & Downtown! Remodeled XL Apt!
Oct 6 – 13
Condo in Kihei
4.94 out of 5 average rating, 198 reviewsMana Kai Maui - Oceanfront Condo in Kihei
Apr 18 – 25
Condo in Wailea-Makena
4.97 out of 5 average rating, 129 reviewsStay at a Prestigious Tropical Resort in Wailea
Apr 19 – 26
Condo in Kihei
4.98 out of 5 average rating, 127 reviewsThe Pi Life: Ocean Views · 99 Steps from the Beach
Sep 17 – 24
Quick stats about vacation rentals with a pool in Wailea, Wailea-Makena
Total rentals
1.7K properties
Wifi availability
1.7K properties include access to wifi
Rentals with dedicated workspaces
900 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
1K properties are a good fit for families
Total number of reviews
39K reviews
Destinations to explore
- Rentals with pools United States
- Rentals with pools Hawaii
- Rentals with pools Hawaii
- Rentals with pools Maui
- Rentals with pools Waikiki Beach
- Rentals with pools Maui County
- Rentals with pools Wailea-Makena
- Family-friendly rentals Wailea
- House rentals Wailea
- Rentals with a washer and dryer Wailea
- Pet-friendly rentals Wailea
- Rentals with beach access Wailea
- Rentals with an EV charger Wailea
- Rentals with outdoor seating Wailea
- Beach house rentals Wailea
- Rentals with a hot tub Wailea
- Kid-friendly rentals Wailea
- Apartment rentals Wailea
- Cottage rentals Wailea
- Beachfront rentals Wailea
- Fitness-friendly rentals Wailea
- Rentals with a patio Wailea
- Beach condo rentals Wailea
- Serviced apartment rentals Wailea
- Waterfront rentals Wailea
- Townhouse rentals Wailea
- Monthly Rentals Wailea
- Villa rentals Wailea
- Hotel rentals Wailea
- Wheelchair accessible rentals Wailea
- Condo rentals Wailea
- 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