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Wailea-Makena vacation rentals

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Top-rated vacation rentals in Wailea-Makena

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  1. Entire condo
  2. Kihei
Luxury condo • 180° Ocean Views • Steps to Beach

NEW LISTING! Enjoy panoramic ocean & 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 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.

$179 per night
  1. Entire condo
  2. Kihei
🌈🌴NEW Maui Schooner-2 bedroom condo-AC-pool-beach

Let this Polynesian splendor encapsulate you in its varied outdoor activities and nearby entertainment. Whether you are looking to play golf on the emerald greens of Maui, relax to the setting sun of this South Pacific paradise or search for wildlife in the crystal clear warm waters—the Maui Schooner Resort offers these luxuries and more. The heart of Maui awaits you, so come explore. Entire TWO bedroom condominium with full kitchen.

$125 per night
SUPERHOST
  1. Entire condo
  2. Kihei
Romantic, Luxury Maui Getaway with Ocean View

This is a luxury 1 bedroom 2 bathroom 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 and a Weber grill on one of the 2 lanais. . Sunset views from the lanai are stunning. If our Wailea Palms condo is not available during the days of your travel, please inquire about availability at our other Wailea Palms condo.

$232 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Stay near Wailea-Makena's top sights

Photo of Mākena State Park
Mākena State Park14 locals recommend
Photo of Kamaole Beach Park III
Kamaole Beach Park III28 locals recommend
Photo of Four Seasons Resort Maui at Wailea
Four Seasons Resort Maui at Wailea7 locals recommend
Photo of Makena Beach
Makena Beach84 locals recommend
Photo of Little Beach
Little Beach7 locals recommend
Photo of Redline Rafting
Redline Rafting7 locals recommend

Wailea-Makena condo rentals

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  1. Entire condo
  2. Kihei
Romantic One BR Condo (Remodeled)
$165 per night
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  1. Entire condo
  2. Kihei
Super Studio in Wailea, Maui.
$185 per night
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  1. Entire condo
  2. Kihei
Fully remodeled studio/Kingsize bed
$140 per night
  1. Entire condo
  2. Kihei
Cheapest Cozy Studio at Wailea Grand Champtions
$189 per night
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  1. Entire condo
  2. Kihei
Renovated Getaway on the Beach
$240 per night
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  1. Entire condo
  2. Kihei
Everything you need to enjoy true paradise!
$257 per night
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  1. Entire condo
  2. Kihei
Comfy Apartment near great beaches in Kihei Maui
$326 per night
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  1. Entire condo
  2. Kihei
Almost Wailea at a Kihei Price!
$164 per night
  1. Entire condo
  2. Kihei
4-309 Kamaole Sands**Newly Remodeled** Steps to Kamaole 3 Beach!
$235 per night
  1. Entire condo
  2. Kihei
Kamaole Sands #2-303 OV 1BR/2BA Condo w/Lg Lanai
$159 per night
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  1. Entire condo
  2. Kihei
Ground Floor Kihei Akahi C-211, Quiet & Private
$176 per night
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  1. Entire condo
  2. Kihei
3 Bdrm Oceanview Loft Condo in Maui
$189 per night

Wailea-Makena beach vacation rentals

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  2. Kihei
204 Punahoa Studio - Oceanfront with A/C
$166 per night
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  1. Entire rental unit
  2. Kihei
BEAUTIFUL*Partial Ocean View by TOP Swimming Beach
$159 per night
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  1. Entire rental unit
  2. Kihei
210A Studio/Hotel Room Across from Ocean
$125 per night
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  1. Entire condo
  2. Kihei
Location! Kalama Terrace, Garden Views, L-108
$160 per night
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  1. Entire condo
  2. Kihei
Maui Vista Ground Floor Across Street From Beach
$150 per night
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  1. Entire condo
  2. Kihei
Cozy Apartment near Charley Young Beach in Kihei
$299 per night
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  1. Entire condo
  2. Kihei
Stylish Ocean View Condo at Maui Vista Resort
$308 per night
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  1. Entire condo
  2. Kihei
*Charming OCEANVIEW*Fully Renovated*Ideal Location
$222 per night
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  1. Entire condo
  2. Kihei
WAILEA TREE TOP PARADISE
$195 per night
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  1. Entire condo
  2. Kihei
Ocean View Condo at the Island Surf bldg in Kihei
$335 per night
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  1. Entire condo
  2. Kihei
Beautiful Air Conditioned Condo Steps fm the Beach
$139 per night
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  1. Entire condo
  2. Kihei
Renovated Studio Directly Across from Ocean
$125 per night

Wailea-Makena house rentals

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  1. Entire home
  2. Kihei
Hawaiian-style 1 BR Condo - steps from the beach!
$195 per night
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  1. Private room
  2. Kihei
GARDEN ROOM, private bathroom, separate entrance
$175 per night
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  1. Entire home
  2. Kihei
Exclusive Beachfront Cottage, Ocean Views, WiFi/AC
$315 per night
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  1. Entire home
  2. Kihei
Spacious one bedroom, King bed, AC/WiFi,
$237 per night
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  1. Entire home
  2. Kihei
Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01
$310 per night
  1. Entire home
  2. Kihei
Beach Condo Ocean Views & Walk everywhere!
$336 per night
  1. Entire home
  2. Kihei
PrivateHome 3b/3b Spectacular Bi-Coastal Views/pool/AC/
$790 per night
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  1. Entire home
  2. Kihei
OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM
$999 per night
  1. Entire home
  2. Kihei
Maui Kamaole Condo w/ Shared Pool, Private W/D, and Free WiFi - Waves Await!
$323 per night
SUPERHOST
  1. Entire home
  2. Kihei
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, AC, Wifi, Pool!
$278 per night
  1. Entire home
  2. Kihei
Kihei Akahi Condo w/ Shared Grill, Private W/D-Snorkel, Surf, Swim!
$184 per night
  1. Entire home
  2. Kihei
Kihei Akahi Condo w/ Shared Pool, A/C-Beach Lovers Dream!
$184 per night

Your guide to Wailea-Makena

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.


How do I get around Wailea-Makena?

The closest airport to Wailea-Mākena is the Kahului Airport (OGG), which is around 35 minutes away. From the airport, it is possible to take a 20-minute bus ride to Queen Ka’ahumanu Center, where you can switch to another bus heading to Wailea. The total journey time should take just under two hours. You can also take a taxi from the airport, which should take around 40 minutes. Or you can rent a car and drive, which is your most convenient option if you plan on traveling around other parts of Maui, as public transportation can be limited in Wailea-Makena. Once you’ve settled in at your Wailea-Mākena vacation rental, several local outfits rent out bicycles for you to pedal around town, and you’ll find numerous charter boat companies offering guided snorkeling excursions.


When is the best time to stay in a vacation rental in Wailea-Makena?

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.


What are the top things to do in Wailea-Makena?

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.