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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.

Condo · Kihei
Luxury Remodel - Wailea - Short Walk to Beach
Wailea Ekahi 45C received a total, high-end, remodel completed in the summer of 2022 and is set amidst lush tropical gardens - a perfect retreat for a couple. This spacious condo, with 795 sq ft of interior and 225 sq ft main patio, boasts high quality, top branded, Italian furniture, 2 split ACs, 3 ceiling fans, 2 wall-mounted smart TVs (65 inch & 55 inch ), remote controlled Hunter-Douglas shades, convenient closet system, and adjustable lighting throughout, to set the mood for relaxation.
Jul 19 – 26
$405 per night
Superhost
Condo · Kihei
100KContemporaryHawaiian Reno in Wailea-Beach/Golf
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with private wrap around lanai. King Master Bed with a contemporary private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel or take long tropical beach walks.
Sep 17 – 24
$280 per night
Superhost
Guest suite · Kihei
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.
Aug 31 – Sep 7
$485 per night
Superhost

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 The Shops at Wailea
The Shops at Wailea107 locals recommend
Photo of Mākena State Park
Mākena State Park14 locals recommend
Photo of Kamaole Beach Park III
Kamaole Beach Park III31 locals recommend
Photo of Four Seasons Resort Maui at Wailea
Four Seasons Resort Maui at Wailea7 locals recommend
Photo of Makena Beach
Makena Beach89 locals recommend
Photo of Makena Landing Park
Makena Landing Park17 locals recommend

Wailea-Makena condo rentals

Condo · Wailea-Makena
Enchanting Modern Wailea Vistas
Nov 3 – 10
$599 per night
Superhost
Condo · Kihei
Hale Wahi Nana
Sep 8 – 15
$375 per night
Superhost
Condo · Wailea
Luxury Wailea Condo Remodel! Gorgeous Ocean Views!
Apr 18 – 25
$475 per night
Superhost
Condo · Kihei
Newly Remodeled-AC-Ocean Views-Modern Finishes
Jul 14 – 21
$427 per night
Superhost
Condo · Wailea
Wailea Elua 1101 - Beachfront Section - Ocean View
Aug 19 – 26
$622 per night
Superhost
Condo · Wailea-Makena
Gorgeous Luxury Wailea Condo! BEST Ocean Views!!
Jun 3 – 10
$499 per night
Superhost
Condo · Wailea
Wailea ocean views! Large 2/2 near shops, beaches!
Aug 27 – Sep 3
$364 per night
Superhost
Condo · Kihei
Ekahi 22C Toes in the Sand in Under 2 Minutes
Sep 7 – 14
$625 per night
Superhost
Condo · Kihei
Cheapest Cozy Studio at Wailea Grand Champtions
Jun 7 – 14
$189 per night
Condo · Kihei
*UPDATED* Wailea Condo in Oceanfront Complex!!
Jul 17 – 24
$339 per night
Superhost
Condo · Kihei
Steps to the Beach-Sparkling Modern Condo sleeps 4
Mar 20 – 27
$470 per night
Superhost
Condo · Kihei
!!! Deluxe relaxing retreat. !!!
Jul 29 – Aug 5
$145 per night
Superhost

Wailea-Makena house rentals

Home · Kihei
Mana Hale Vacation Rental
Aug 24 – 31
$550 per night
Superhost
Home · Kihei
Spacious one bedroom, King bed, AC/WiFi,
Mar 14 – 21
$240 per night
Superhost
Home · Kihei
GORGEOUS PRIVATE HOME WITH POOL
Sep 11 – 18
$929 per night
Superhost
Private room · Kihei
GARDEN ROOM, private bathroom, separate entrance
Jul 7 – 14
$228 per night
Superhost
Home · Kihei
Hawaiian-style 1 BR Condo - steps from the beach!
Sep 18 – 25
$182 per night
Superhost
Home · Kihei
180' ocean views, heated pool at a villa by Wailea
Mar 25 – Apr 1
$725 per night
Superhost
Home · Kihei
PRIVATE POOL*Beautifully landscaped exclusive HOME
Apr 22 – 29
$942 per night
Superhost
Home · Kihei
Whales and sunsets, front row seats every day!
Aug 11 – 18
$750 per night
Superhost
Home · Kihei
401 Nani Kai Hale**Beachfront**Newly Remodeled!
May 2 – 9
$320 per night
Superhost
Private room · Makawao
Comfy/Quiet Room Maui - Sunrise Room
Feb 28 – Mar 7
$120 per night
Superhost
Home · Kihei
Exclusive Beachfront Cottage, Ocean Views, WiFi/AC
Aug 14 – 21
$386 per night
Superhost
Private room · Paia
Mike's House- Uilani Room
May 9 – 16
$98 per night
Superhost

Wailea-Makena cottage rentals

Cottage · Kihei
Luxury Cottage, Saltwater Spa, Walk to Beach/Dining/Shops
Jul 10 – 17
$765 per night
Plus
Cottage · Kihei
Entire Palm Cottage
Aug 8 – 15
$473 per night
Superhost
Cottage · Kihei
Private 2 bedroom cottage with pool
Sep 4 – 11
$499 per night
Cottage · Makawao
Luxury Upcountry retreat with breathtaking views!
Aug 15 – 22
$426 per night
Superhost
Cottage · Kihei
Charming Beach Front Cottage in Kihei!
Aug 21 – 28
$536 per night
Superhost
Cottage · Kihei
Chez Maui Beach Cottage Kihei 1 Block to the Beach
Mar 10 – 17
$325 per night
Superhost
Cottage · Makawao
Adorable Garden Gingerbread House
Sep 3 – 10
$250 per night
Superhost
Cottage · Wailuku
Newly Renovated Modern Cottage; Walk into Town!
Jul 29 – Aug 5
$149 per night
Cottage · Kihei
Remodeled Maui Meadows Cottage: AC & Ocean Views - Near Beach, Golf & Dining
Jul 2 – 9
$608 per night
Cottage · Kula
Oceanview Cottage away from heat! w/ County Permit
Jun 20 – 27
$385 per night
Superhost
Cottage · Kula
HALEKALANI - Paradise in Upcountry
Sep 30 – Oct 7
$276 per night
Superhost
Cottage · Haiku-Pauwela
Explore Waterfalls and Beaches from a Tropical Haiku Cottage
Aug 19 – 26
$369 per night
Plus

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.


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.

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