
Vacation rentals in Wailea
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Top-rated vacation rentals in Wailea
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Popular amenities for Wailea-Makena vacation rentals
Wailea-Makena condo rentals

Luxury Condo w/wide Ocean View (Palms at Wailea)!

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

Maui Retreat Ekahi 50F -All YOU Need!

Modern Renovated Palms at Wailea Condo!

Grand Champions 169 Beautiful 3 BR on the Fairway!

Wailea Ekolu Village | 912

Summer Sale Wailea, AC, Walk 2 Beach, Lg Lanai

Enjoy this Beachfront Unit w/Peaceful Ocean Sounds
Other great vacation rentals in Wailea

Gem near Keawakapu Beach - Privacy and Ocean Views

Prime Location, in the HEART of it ALL!

Stunning Wailea 2/2, AC, Upper Fl , walk to beach

Ocean Front Cottage, 30 steps to the beach!

Beautiful Beachfront Townhouse !

Oceanview Home with Private pool and hot tub

Ekahi 22C Toes in the Sand in Under 2 Minutes

Wailea Ekolu 1106 Remodel Peaceful Island Getaway
Quick stats about vacation rentals in Wailea
Total rentals
1.8K properties
Nightly prices starting at
G$2,089 GYD before taxes and fees
Total number of reviews
50K reviews
Family-friendly rentals
1K properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
1.7K properties have a pool
Your guide to Wailea
All About Wailea-Mākena
Located on the southern shore of the Hawaiian island of Maui, Wailea is a resort area famous for its white-sand beaches, sprawling golf courses, and relaxing spas. Wailea-Mākena provides a great base for visiting southern Maui’s sandy shores, such as the nearby Wailea Beach, which is just a short walk from town, or Mākena Beach, where you can go for a refreshing swim or explore the pristine coastline by paddleboard or kayak.
You can also find many interesting natural attractions nearby, such as La Perouse Bay or Ahihi-Kinau Natural Area Reserve, which is teeming with marine life. Take a break from the sun and water by visiting the Shops at Wailea, a complex that features 70 retail stores — art galleries, boutiques selling Hawaiian shirts and water-sports gear —and restaurants serving creative takes on local mahi mahi and deep-water ahi tuna.
The best time to stay in a vacation rental in Wailea
Thanks to Maui’s consistent heat all year round, this is a great place to visit at any time. During the summer, the days are long, hot, and sometimes muggy, which is why many travelers cool off in the crystal-clear water found on Maui’s beaches.
During the spring and fall, the crowds thin out, making this a great time to visit if you want to have the beaches and hiking trails all to yourself. While the clouds gather overhead more frequently in the winter and the region sees a higher amount of rain, the warm weather remains, and showers are generally quick to come and go. Winter is also the best time to visit if you’re interested in whale watching or driving along Maui’s Road to Hana, a winding road famous for its waterfall hikes and lush greenery.
Top things to do in Wailea
Mākena State Park
Mākena Beach State Park, on the south side of town, is home to one of the largest undeveloped beaches on Maui. This stretch of shoreline, commonly referred to as “Big Beach,” features glistening white sand and cerulean waters surrounded by native kiawe forests and mango groves. Wander inland and you can hike up the 360-foot-tall Pu’u Olai, a dormant volcanic cinder cone, where you can survey the coastline from on high.
Ahihi-Kinau Natural Area Reserve
Located less than a 10-minute drive from Mākena State Park, this marine reserve offers one of the area’s best snorkeling spots. The ocean floor is covered by a coastal lava field intermixed with coral, making it a popular home for many different species of tropical fish, including butterfly fish, parrotfish, surgeonfish, and turtles. At the reserve, you can snorkel directly from the shoreline.
La Perouse Bay
Just 20 minutes south of Wailea-Mākena, La Perouse Bay is outlined by lush green vegetation and jagged lava rock formations, created when the now-dormant Haleakalā Volcano last erupted in 1790. Now the blackened lava rocks shelter numerous tide pools. If you’d like to peer in at the marine creatures living there, bring shoes with thick soles, as lava rock has many sharp edges.
Frequently Asked Questions
Are there pet-friendly vacation rentals in Wailea-Makena?
Four-legged friends are welcome in Wailea-Makena. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Wailea-Makena?
Yes! Work meets play with ease at over 990 vacation rentals in Wailea-Makena featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do condo rentals in Wailea-Makena have a gym?
Absolutely! We offer over 530 condo rentals with a gym in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in condo rentals in Wailea-Makena?
Experience the best of Wailea-Makena with our condo rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly condo rentals in Wailea-Makena?
Wailea-Makena has more than 780 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in Wailea-Makena have wifi?
Absolutely! We offer over 1,340 condo rentals with wifi in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Are there Wailea-Makena condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 1,310 condo rentals with pools in Wailea-Makena, available on Airbnb. Make a splash and soak up the sun in style!
Do condo rentals in Wailea-Makena have a bbq area?
Absolutely! We offer over 670 condo rentals with a bbq area in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Wailea-Makena have air conditioning?
Absolutely! We offer over 1,290 condo rentals with air conditioning in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Condo Rentals in Wailea-Makena?
Enhance your stay in our Condo Rentals with the most popular amenities: over 670 homes with a bbq area, over 1,340 homes with wifi, over 1,290 homes with air conditioning, over 530 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Maui
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