
Vacation rentals in Wailea
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Top-rated vacation rentals in Wailea
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Mana Kai 608: Oct/Nov Now OPEN! Modern Surf Vibe
Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, right on the border of Wailea and Kihei! Our condo is designed with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5-star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!

Maui's Best - Wailea Ekahi 47A
Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

Oceanfront Mana Kai Penthouse..Heaven meets Earth!
Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and bi-coastal oceanfront views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (806) and includes two-bedroom suites on the world-famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent snorkeling, body surfing, whale watching, scuba diving, paddle boarding, and kayaking literally at your doorstep

A.R.A Retreats: The Molokini
FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

Sweeping Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

Luxury condo • 180° Ocean Views • Steps to Beach
Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Upscale and Elegant Vistas
Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled in September of 2021, no expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!
This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

Stunning ocean view, heated pool at home by Wailea
Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

*Fully Remodeled* Modern Island Style*
I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini

Ocean/Golf Course Views, Tropical Resort in Wailea
Breathe in and exhale slowly while gazing at serene greenery and misty mountaintops. Make the most of a country-club setting by lounging on sun decks and swimming in heated pools. Retreat to an updated condo to unwind and fall asleep in a comfy bed. (This unit is suitable for a maximum of four (4) guests. Infants of any age are counted as guests.)
Popular amenities for Wailea-Makena vacation rentals
Wailea-Makena condo rentals

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

Oceanfront Getaway, Brand New, Steps To Beach

Wailea Elua 1101 - Beachfront Section - Ocean View

Modern and Luxurious Property at Polo Beach

Modern Renovated Palms at Wailea Condo!

Luxe 2bed Wailea, 5-min walk to beach, ocean view,

Gorgeous 2 Story Townhouse in Wailea w/ Ocean View

Luxurious Tropical Retreat with Oceanview
Other great vacation rentals in Wailea

Beautiful Beachfront Townhouse !

Oceanview Home with Private pool and hot tub

Honalua || Wailea Ekahi Unit 2D || Lowered Rates

Amazing Ocean Views at Wailea Ekolu Village!

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
1.7K properties
Nightly prices starting at
€ 34 before taxes and fees
Total number of reviews
51K reviews
Family-friendly rentals
960 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
1.6K 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.
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- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Honolua Bay
- Sandy Beach
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Pahoa Beach
- Manele Golf Course
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- 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
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