Vacation rentals in Wailea-Makena

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Top-rated vacation rentals in Wailea-Makena

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Guest favorite

Cottage in Kihei

4.98 out of 5 average rating, 219 reviews

Luxury Cottage, Saltwater Spa, Walk to Beach/Dining/Shops

Slip into a saltwater hot tub on a private deck with a cocktail and good company. The surrounding palm trees and stars above will surely add to the romantic moment. Rinse off under a warm outdoor shower, then retreat indoors to a stylish love nest. LOCATION, LOCATION, LOCATION Located in the heart of sunny South Kihei near the famous Kamaole sandy beaches. 10-minute walk to just about everything: - Kalama Beach Park (playground, tennis, volleyball, basketball, and more) - Over 23 restaurants, coffee shops, and bars - Shops, boutiques, open air markets - Farmers market and grocery store - The Cove Beach Park (paddle boarding and beginner surfing) - Kamaole Beach Park 1, 2, 3 (Kam 1 is a 20-min walk. All beaches within a 5-minute drive) Quick Drive (15-20 minutes): - Famous Makena Beach, Wailea and world class golf courses - Airport Stroll in cute little shops while trying some local shave ice. You will love Maui's most unique shopping and dining experience at Kihei Kalama Village with great places to eat and over 40 vendors and boutiques. At the south side of Kalama Beach, you will find Cove Park where you can take surfing lessons or try stand up paddle boarding. Walk beyond Cove Park and you find Charley Young beach which is part of the famous Kamaole beaches. In the morning, walk to the end of the street for coffee at Belle Surf Cafe or 5 minutes farther to the Lava Java Coffee Roasters and enjoy your coffee at the beach. During the early evening, you can relish sushi during Happy Hour at Sansei within a few minutes of the house or enjoy the gorgeous sunsets at the beach. PRIVATE OUTDOOR LIVING IN A TROPICAL SETTING - Lounging space in either deck or in a covered lanai - Weber Gas Grill - Salt water hot tub - Fully fenced tropical garden and lawn (yoga, croquet on the grass) Tropical outdoor living area for sunning, reading a book in the shade, connecting with someone close, grilling, or relaxing in the hot tub. AMENITIES - All-Clad gourmet cookware and kitchen tools - Induction range - 65-inch 4k OLED TV for the living room and 40-inch TV in the bedroom - WI-FI (high speed and easy to work from here, download 200 mb/sec, upload 20 mb/sec) - Books, games - many toiletry items provided The house includes island style furniture with a full kitchen that will delight a chef. High end cookware and kitchen tools like Henckel knives, French press, coffee grinder, a comprehensive spice rack, and a Vitamix blender. Make delicious Hawaiian smoothies from farmers market at the end of our street. 5-star luxury resort Queen mattress (Sealy Optimistic Plush Foam) with 400+ thread count pima cotton sheets and down comfortable assures a good night’s sleep. FOR THE BEACH Beach chairs, umbrellas, towels, boogie boards, coolers, ice packs, and snorkel gear provided. Lots of extras as well. We also have tennis rackets and balls for the park. Room rate includes: Hawaii Taxes (General Excise 4.166%, Accommodation: 10.25%) Private, keyless entrance to your free-standing cottage surrounded by a fenced garden paradise. Free off-street parking. Guests can call, text, or email us with any needs or questions they may have. Our housekeeper and our maintenance person live just down the street and can be at the house within 5 minutes for any urgent items. The house is right where the action is—the park, beach, restaurants, shops, and fresh market are all close by. Walk down the street to a friendly cafe for breakfast. Stroll along the shore watching carefree turtles and determined surfers. Walking around is great, but we still recommend a car. Car rental available at airport or locally in Kihei. A public bus stop is located about 5-7 minute walk from the house. Maui County approved vacation rental: Short Term Rental Permit STKM 2014 / 0001, Tax ID 085 / 245 / 5424 / 01

Sep 11 – 18

€ 830 per night

Guest favorite

Home in Kihei

4.96 out of 5 average rating, 387 reviews

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

Sep 9 – 16

€ 632 per night

Guest favorite

Condo in Kihei

4.98 out of 5 average rating, 59 reviews

Maui Retreat Ekahi 50F - All YOU Need!

May weekday special! Just bring yourself, everything else is HERE! Towels, beach chairs, umbrella, boogie board, whatever you need!!!Beautiful 2nd floor unit has an open, garden/ mountain view. The vaulted ceilings give that open air feeling. Tastefully decorated not overdone, 50F makes you feel at home from the moment you walk in. The NEW (3/23) sofa pulls out to a queen size sleeper in the living room. Zoom call if you are “flexcationing”. The BRAND NEW Fitness Room opened up February 2024!

Nov 17 – 24

€ 508 per night

Guest favorite

Condo in Wailea-Makena

4.95 out of 5 average rating, 169 reviews

A.R.A Retreats: The Waterfall

Nicknamed “The Waterfall” for its massive 105 inch by 65 inch peninsula with it large waterfall countertop, perfect for cooking and entertaining. This was the first time we had done this Waterfall feature in our unit. Located in Grand Champions Villas in Wailea. Guests can enjoy the spacious NEW condo that has everything you should need for your trip! Guests can enjoy the spacious and comfortable condo that has everything you should need for your trip--including smart TV's in each room :)

Mar 4 – 11

€ 802 per night

Guest favorite

Guest suite in Kihei

5.0 out of 5 average rating, 77 reviews

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.

Feb 1 – 8

€ 787 per night

Guest favorite

Apartment in Kula

4.91 out of 5 average rating, 943 reviews

Kula Treat - Upcountry Maui with Hot Tub!

Private, gracious apartment in desirable Upcountry Maui. Great home base for exploring, and a quiet country retreat for relaxing. Restaurants, food trucks and farmers’ markets nearby. Beaches, hiking and zipline within an easy drive. Perfectly located for Haleakalā Natʻl Park and day trips to Hana. A wonderful personal chef lives very close by. Dedicated to reducing single use plastics, we provide reusable water bottles for our guests! Fully permitted: BBMP 2015/0003 E komo mai! (Welcome)

Feb 28 – Mar 7

€ 180 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 142 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront 2b/2b 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.

Guest favorite

Apartment in Kihei

4.94 out of 5 average rating, 106 reviews

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.

Oct 24 – 31

€ 580 per night

Guest favorite

Condo in Wailea

4.93 out of 5 average rating, 142 reviews

Stunning ocean view! 2/2 in the heart of Wailea

ATTENTION: RARE cancellation for the holidays! Dec 22 - Jan 9, 2024 now available! Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this condo is in the visitor-friendly Wailea Resort area, and does not infringe upon any of the local neighborhoods of Maui.

Nov 2 – 9

€ 608 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 113 reviews

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.

Mar 24 – 31

€ 560 per night

Guest favorite

Condo in Wailea-Makena

4.95 out of 5 average rating, 57 reviews

Luxury Condo w/wide Ocean View (Palms at Wailea)!

There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

Aug 21 – 28

€ 634 per night

Guest favorite

Condo in Wailea

4.97 out of 5 average rating, 137 reviews

Wailea Gem-Remodeled Ocean View

Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.

Sep 3 – 10

€ 429 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Wailea-Makena vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Wailea-Makena's top sights

Kamaole Beach Park II201 locals recommend

Makena Beach149 locals recommend

The Shops at Wailea222 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

Apartment in Kihei

4.97 out of 5 average rating, 60 reviews

Wonderful Wailea Condo with Lanai Water Views

Aug 21 – 28

€ 481 per night

Guest favorite

Condo in Kihei

5.0 out of 5 average rating, 46 reviews

Luxe 2bed Wailea, beach, ocean view, spa, golf

May 11 – 18

€ 916 per night

Guest favorite

Condo in Wailea-Makena

5.0 out of 5 average rating, 28 reviews

Aloha Moon - The Honeymoon Hideaway

Oct 22 – 29

€ 900 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 93 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aug 13 – 20

€ 702 per night

Guest favorite

Condo in Kihei

5.0 out of 5 average rating, 21 reviews

Mana Kai Palms: Oceanfront Resort ~Keawakapu Beach

Aug 15 – 22

€ 794 per night

Guest favorite

Condo in Kihei

4.97 out of 5 average rating, 92 reviews

Barefoot Luxury at its Finest! WBV PHJ206

Mar 27 – Apr 3

€ 1,267 per night

Guest favorite

Apartment in Kihei

5.0 out of 5 average rating, 11 reviews

Wailea Luxury Resort Vista

Jun 27 – Jul 4

€ 909 per night

Superhost

Condo in Kihei

5.0 out of 5 average rating, 3 reviews

Makena Surf: Maui on the Beach

Jan 4 – 11

€ 1,126 per night

Show all

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	20 properties allow pets
Family-friendly rentals	1.1K properties are a good fit for families
Total number of reviews	43K 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.

Frequently Asked Questions

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.
Are there vacation rentals with a dedicated workspace in Wailea-Makena?
Yes! Work meets play with ease at over 960 vacation rentals in Wailea-Makena featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Wailea-Makena vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 1,740 vacation homes with pools in Wailea-Makena, available on Airbnb. Make a splash and soak up the sun in style!
Do hotel rentals in Wailea-Makena have a gym?
Absolutely! We offer over 20 hotel rentals with a gym in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in hotel rentals in Wailea-Makena?
Experience the best of Wailea-Makena with our hotel rentals, starting at about $800 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do townhouse rentals in Wailea-Makena have wireless internet?
Absolutely! We offer over 20 townhouse rentals with wireless internet in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly serviced apartment rentals in Wailea-Makena?
Wailea-Makena has more than 50 family-friendly serviced apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in Wailea-Makena have a bbq area?
Absolutely! We offer over 790 condo rentals with a bbq area in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Wailea-Makena have air conditioning?
Absolutely! We offer over 130 apartment rentals with air conditioning in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Villa Rentals in Wailea-Makena?
Enhance your stay in our Villa Rentals with the most popular amenities: over 50 homes with wireless internet, over 20 homes with a bbq area, over 50 homes with a gym, over 50 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Wailea-Makena

Top-rated vacation rentals in Wailea-Makena

Vacation rentals for every style

Apartments

Villas

Houses

Popular amenities for Wailea-Makena vacation rentals

Stay near Wailea-Makena's top sights

Other great vacation rentals in Wailea-Makena

Apartment in Kihei

Condo in Kihei

Condo in Wailea-Makena

Condo in Kihei

Condo in Kihei

Condo in Kihei

Apartment in Kihei

Condo in Kihei

Quick stats about vacation rentals in Wailea-Makena

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Your guide to Wailea-Makena

All About Wailea-Mākena

The best time to stay in a vacation rental in Wailea-Makena

Top things to do in Wailea-Makena

Mākena State Park

Ahihi-Kinau Natural Area Reserve

La Perouse Bay

Frequently Asked Questions

Are there pet-friendly vacation rentals in Wailea-Makena?

Are there vacation rentals with a dedicated workspace in Wailea-Makena?

Are there Wailea-Makena vacation rentals on Airbnb with pools?

Do hotel rentals in Wailea-Makena have a gym?

How much does it cost to stay in hotel rentals in Wailea-Makena?

Do townhouse rentals in Wailea-Makena have wireless internet?

Are there family-friendly serviced apartment rentals in Wailea-Makena?

Do condo rentals in Wailea-Makena have a bbq area?

Do apartment rentals in Wailea-Makena have air conditioning?

What are the most popular amenities for Villa Rentals in Wailea-Makena?

Destinations to explore