
Vacation rentals in Wailea
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Wailea
Guests agree: these stays 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 vacation rentals
Wailea-Makena condo rentals

Stunning Ocean Views · Steps to Beach · Comfort

Oceanfront Getaway, Brand New, Steps To Beach

Wailea Elua 1101 - Beachfront Section - Ocean View

160KReno-Stunning Palms in Wailea Condo-Beach/Golf

Sugar Beach Resort Beach / Ocean Front Unit 426

Modern Renovated Palms at Wailea Condo!

Stylish Kihei Condo in Oceanfront Resort Complex

Luxurious Tropical Retreat with Oceanview
Wailea-Makena home rentals

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01

South Maui Guesthouse

12 Minute Walk Kamaole Beach II-Quiet Private Easy

Beautiful Beachfront Townhouse !

Oceanview Home with Private pool and hot tub

PAIA HALE Walk to beach and town

Modern Family Kihei Home by the Beach

Two Bedroom Paia North Shore Beach House
Other great vacation rentals in Wailea

Coastal Dream Oceanfront Condo!

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

Amazing Ocean Views at Wailea Ekolu Village!

Ekahi 22C Toes in the Sand in Under 2 Minutes

Maui Retreat Ekahi 50F -All YOU Need!

Mana Kai Palms: Beachfront Resort ~Keawakapu Beach

Wailea Elua: Huge Ocean Views, Pool, AC & Hot Tub

Tropical Wailea Retreat
Quick stats about vacation rentals in Wailea
Total rentals
1.8K properties
Nightly prices starting at
€ 9 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
What types of vacation rentals are available in Wailea-Makena?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Wailea-Makena. From over 1,340 condo rentals to over 60 house rentals, we've got you covered.
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.
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.
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 410 homes with self check-in, over 690 homes with a bbq area, over 1,340 homes with wifi, over 530 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 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 self check-in?
Absolutely! We offer over 410 condo rentals with self check-in in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
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.
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.
Do condo rentals in Wailea-Makena have a bbq area?
Absolutely! We offer over 690 condo rentals with a bbq area in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Destinations to explore
- Honolulu Vacation rentals
- O‘ahu Vacation rentals
- Kauaʻi County Vacation rentals
- Island of Hawai'i Vacation rentals
- Waikiki Beach Vacation rentals
- Kailua-Kona Vacation rentals
- Kihei Vacation rentals
- Kona Vacation rentals
- Kaanapali Vacation rentals
- Hilo Vacation rentals
- Princeville Vacation rentals
- North Kona Vacation rentals
- Hotel rentals Wailea
- Rentals with pools Wailea
- Beach condo rentals Wailea
- Rentals with an EV charger Wailea
- Rentals with a hot tub Wailea
- House rentals Wailea
- Rentals with outdoor seating Wailea
- Pet-friendly rentals Wailea
- Villa rentals Wailea
- Luxury rentals Wailea
- Serviced apartment rentals Wailea
- Family-friendly rentals Wailea
- Beachfront rentals Wailea
- Rentals with a sauna Wailea
- Fitness-friendly rentals Wailea
- Rentals with beach access Wailea
- Rentals with a washer and dryer Wailea
- Rentals with a kayak Wailea
- Waterfront rentals Wailea
- Rentals with a patio Wailea
- Apartment rentals Wailea
- Condo rentals Wailea
- Townhouse rentals Wailea
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Honolua Bay
- Sandy Beach
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Pahoa Beach
- Manele Golf Course
- Maui Ocean Center
- Wailea Beach
- Hāmoa Beach
- Oneloa Beach
- Kaipukaihina
- Puu Olai Beach
- Changs Beach
- Palauea Beach
- Old Lahaina Luau
- Wailau Valley
- Polo Beach
- Wailea Golf Club
- Maui Golf & Sports Park
- Things to do Wailea
- Sports activities Wailea
- Food and drink Wailea
- Art and culture Wailea
- Nature and outdoors Wailea
- Things to do Maui County
- Sports activities Maui County
- Nature and outdoors Maui County
- Art and culture Maui County
- Food and drink Maui County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Art and culture Hawaii
- Wellness Hawaii
- Tours Hawaii
- Entertainment Hawaii
- Food and drink Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Things to do United States
- Entertainment United States
- Art and culture United States
- Sightseeing United States
- Sports activities United States
- Tours United States
- Wellness United States
- Nature and outdoors United States
- Food and drink United States