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Vacation rentals with a pool in Wailea-Makena
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in 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-Makena rentals with a pool
House rentals with a pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-749883/original/de79de34-443d-42cf-8453-1f7afaa454c3.jpeg?im_w=720)
Home in Maui
4.97 out of 5 average rating, 194 reviewsPrivate Hot Tub + Pool Access + AC - Star Lookout
![](https://a0.muscache.com/im/pictures/79998a63-10ba-4e54-a37d-1a856950b673.jpg?im_w=720)
Home in Kula
4.91 out of 5 average rating, 303 reviewsKula Jewel - Pool, Hot Tub & Awesome Views!
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-25751896/original/ee8cd7a9-c3b5-4c4c-b379-29b44352e146.jpeg?im_w=720)
Home in Kaanapali
4.91 out of 5 average rating, 99 reviews#1 Kaanapali Beach Modern Condo C101 Maui Eldorado
![](https://a0.muscache.com/im/pictures/6517e3d6-c81c-46b0-9c59-16df4a85caf5.jpg?im_w=720)
Home in Kihei
4.91 out of 5 average rating, 22 reviewsGORGEOUS PRIVATE HOME WITH POOL
![](https://a0.muscache.com/im/pictures/miso/Hosting-41481769/original/c5f5fd89-16b0-48e2-a1c6-e4ab0aa31f0d.jpeg?im_w=720)
Home in Maui County
4.74 out of 5 average rating, 31 reviewsWaterfall House with Ocean Views in Haiku, Maui
![](https://a0.muscache.com/im/pictures/9bb2f23b-dcfb-4d3f-808f-3b1e1d3c36b5.jpg?im_w=720)
Home in Kihei
4.92 out of 5 average rating, 88 reviewsMaui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6NTczNDc0MjE3OTE2NjAxMDAy/original/f36a4855-ec48-41da-a8b3-44b5d789188a.jpeg?im_w=720)
Home in Kihei
4.96 out of 5 average rating, 23 reviewsSunny South Kihei Condo: A/C, Pool & Ocean Access!
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-28813861/original/80e23305-1db9-4b98-8b5a-e3d746ebdc9b.jpeg?im_w=720)
Home in Lahaina
4.88 out of 5 average rating, 24 reviewsSerene and Peaceful with Heated Pool
Condo rentals with a pool
![](https://a0.muscache.com/im/pictures/203e76b7-ce46-47e0-b94c-afc6d7ae7cfa.jpg?im_w=720)
Condo in Kihei
4.89 out of 5 average rating, 128 reviewsKihei Akahi C-211, GF, Quiet & Private
![](https://a0.muscache.com/im/pictures/9148ffb8-190c-4b65-94b6-6d78bc58fa61.jpg?im_w=720)
Condo in Kihei
4.9 out of 5 average rating, 119 reviewsFall Sale! 3BR/2BA Villa with Ocean & Sunset views
![](https://a0.muscache.com/im/pictures/miso/Hosting-600885580372307973/original/d0e8ee6c-427a-41f0-99fb-d25bf7c25e33.jpeg?im_w=720)
Condo in Kihei
4.99 out of 5 average rating, 149 reviewsLuxury condo • 180° Ocean Views • Steps to Beach
![](https://a0.muscache.com/im/pictures/e2e4a158-7302-49cf-8a88-013c107eebb4.jpg?im_w=720)
Condo in Kihei
4.97 out of 5 average rating, 119 reviewsModern Luxury Remodel - Maui Kamaole J114
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MTA0OTQyNDk4NzE3NDAyNjkyOQ%3D%3D/original/edfe6be4-bdb3-4550-a255-411747244630.jpeg?im_w=720)
Condo in Kihei
5 out of 5 average rating, 7 reviewsMakena Surf: Maui on the Beach
![](https://a0.muscache.com/im/pictures/miso/Hosting-30347542/original/ab7c6acf-f148-4ef0-98d4-efae5ebcdc1c.jpeg?im_w=720)
Condo in Kihei
4.98 out of 5 average rating, 54 reviewsPURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA
![](https://a0.muscache.com/im/pictures/miso/Hosting-779864444004192126/original/5cf96100-3cbc-4219-8acc-c18b8b7a9eab.jpeg?im_w=720)
Condo in Wailea-Makena
5 out of 5 average rating, 8 reviewsOceanfront Elua Condo -Family Managed- Beachfront!
![](https://a0.muscache.com/im/pictures/miso/Hosting-29826817/original/9b20b6aa-26b2-4a05-a324-a2eb1c6c5683.jpeg?im_w=720)
Condo in Kihei
4.86 out of 5 average rating, 14 reviews•Luxurious • Ocean Views • 2 Lanais• Pickleball
Quick stats about vacation rentals with a pool in Wailea-Makena
Total rentals
1.7K properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
40K reviews
Family-friendly rentals
960 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
860 properties have a dedicated workspace
Destinations to explore
- Kailua-Kona Vacation rentals
- Island of Hawai'i Vacation rentals
- Kihei Vacation rentals
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- Lahaina Vacation rentals
- Kaanapali Vacation rentals
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