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Wailea-Makena vacation rentals

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Top-rated vacation rentals in Wailea-Makena

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Home in Kihei
Stunning ocean view, heated pool at home by Wailea
Last minute bookings 5 days before arrival, and week long stays are 10% off. 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
Aug 8 – 15
$473 per night
Guest favorite
Condo in Kihei
Mana Kai 608- Oceanfront Remod- Modern Surf Vibe!
Mana Kai 608 is a remodeled oceanfront (2b/2b/sleeps 6) condo DIRECTLY on Keawakapu beach! This location is ideal, on the border of Wailea and Kihei. We have designed our remodel with a modern surf vibe 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 come stay with us! We have hired the best Property Manager in Maui, Tracy O'Reilly to take care of our guests.
Apr 19 – 26
$695 per night
Guest favorite
Apartment in Kihei
Wailea Couples Retreat, 300 FT To Keawakapu Beach
Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.
Jun 3 – 10
$440 per night

Popular amenities for Wailea-Makena vacation rentals

Stay near Wailea-Makena's top sights

Kamaole Beach Park II201 locals recommend
The Shops at Wailea222 locals recommend
Makena Beach149 locals recommend
Kamaole Sands3 locals recommend
Fairmont Kea Lani - Maui5 locals recommend
Andaz Maui At Wailea Resort - A Concept By Hyatt17 locals recommend

Other great vacation rentals in Wailea-Makena

Guest favorite
Condo in Kihei
160KReno-Stunning Palms in Wailea Condo-Beach/Golf
Feb 16 – 23
$325 per night
Superhost
Condo in Kihei
★Couples Paradise w/ Lanai★ 3 min. walk to beach!
Sep 27 – Oct 4
$133 per night
Guest favorite
Condo in Wailea-Makena
A.R.A Retreats: The Townhouse
Jul 16 – 23
$725 per night
Guest favorite
Condo in Kihei
Luxury condo • 180° Ocean Views • Steps to Beach
Jun 22 – 29
$611 per night
Superhost
Condo in Kihei
Mana Kai Maui - Beachfront Condo in Kihei
Oct 11 – 18
$500 per night
Guest favorite
Condo in Kihei
Everything you need to enjoy true paradise!
Feb 2 – 9
$278 per night
Guest favorite
Condo in Wailea-Makena
Romantic One BR Condo (Remodeled)
Aug 4 – 11
$225 per night
Guest favorite
Condo in Wailea-Makena
Stay at a Prestigious Tropical Resort in Wailea
Sep 27 – Oct 4
$308 per night
Superhost
Condo in Kihei
Gorgeous Getaway on the Beach
Sep 28 – Oct 5
$263 per night
Guest favorite
Condo in Kihei
Sugar Beach Resort Beach / Ocean Front Unit 426
Jan 11 – 18
$425 per night
Guest favorite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
Oct 9 – 16
$550 per night
Guest favorite
Condo in Wailea
Gorgeous Condo in Wailea Ekahi Village!
Dec 8 – 15
$428 per night

Other great vacation rentals in Wailea-Makena

Superhost
Condo in Wailea
Gorgeous Palms at Wailea 207 Central Maui Location
Aug 27 – Sep 3
$357 per night
Guest favorite
Condo in Kihei
Mana Kai Palms: Oceanfront Resort ~Keawakapu Beach
Oct 22 – 29
$618 per night
Guest favorite
Condo in Kihei
Luxe 2bed Wailea, beach, ocean view, spa, golf
Nov 6 – 13
$650 per night
Guest favorite
Condo in Kihei
Oceanfront Mana Kai Penthouse..Heaven meets Earth!
Jul 7 – 14
$550 per night
Superhost
Home in Kihei
Whales and sunsets, front row seats every day!
Oct 2 – 9
$800 per night
Guest favorite
Condo in Wailea-Makena
Aloha Moon - The Honeymoon Hideaway
Oct 19 – 26
$695 per night
Superhost
Condo in Kihei
Wailea Getaway (2BD/2BTH) in Best Location!!!!!
Jun 7 – 14
$611 per night
Guest favorite
Condo in Wailea
Amazing Ocean Views at Wailea Ekolu. 2023 Remodel!
Jun 23 – 30
$325 per night
Superhost
Condo in Kihei
Steps to the Beach-Sparkling Modern Condo sleeps 4
Jun 9 – 16
$350 per night
Guest favorite
Condo in Kihei
Modern Renovated Palms at Wailea Condo!
Sep 18 – 25
$359 per night
Guest favorite
Condo in Kihei
Ekahi 22C Toes in the Sand in Under 2 Minutes
Oct 27 – Nov 3
$625 per night
Guest favorite
Condo in Kihei
Wailea Ekahi Oceanview, Beachfront King Bed Studio
Jun 2 – 9
$295 per night

Quick stats about vacation rentals in Wailea-Makena

Total rentals

1.9K properties

Rentals with dedicated workspaces

960 properties have a dedicated workspace

Rentals with a pool

1.7K properties have a pool

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

41K reviews

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.


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.


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.

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