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Vacation rentals in Wailea

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Wailea

  • Total vacation rentals

    Explore 1,930 vacation rentals in Wailea

  • Nightly prices starting at

    Wailea vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 55,470 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,150 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    1,840 properties feature pools

  • Rentals with dedicated workspaces

    1,130 properties have a dedicated workspace

  • Wi-Fi availability

    1,930 of Wailea vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Wailea rentals

  • 4.8 Average rating

    Wailea stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Wailea

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

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Top guest favorite
A stunning beach scene captures vibrant sunset colors reflecting off wet sand. Rocky outcrops frame the tranquil waters, while palm trees sway gently in the foreground. Wispy clouds stretch across the sky, adding depth to the evening landscape.
Condo in Wailea
4.99 out of 5 average rating, 193 reviews

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury accommodations in the heart of Wailea, Maui. Our condo has lovely ocean views, views of the lush tropical gardens and the pool. Sunset views from the lanai are stunning. Gourmet kitchen. 2 HD TVs, Bose sound system, AC, washer/dryer in unit, complimentary assigned parking. 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 Our condo is not suitable for children or infants.

Top guest favorite
An expansive covered lanai features comfortable seating with plush cushions, accented by a decorative table. String lights adorn the ceiling, and panoramic ocean views showcase a vibrant sunset over palm trees and neighboring properties.
Guest suite in Wailea
4.99 out of 5 average rating, 142 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.

Top guest favorite
The kitchen area features warm wood cabinetry, a stainless steel refrigerator, and a modern microwave. A spacious countertop provides ample room for meal preparation. Sunflowers are arranged in a vase on the counter. Two wooden stools are positioned at the breakfast bar, adjacent to a round dining table.
Condo in Wailea
4.95 out of 5 average rating, 128 reviews

Luxurious Condo in South Kihei

Beautiful fully renovated condo. Located in Maui Kamaole, the best resort complex in South Kihei. Walking distance to the beach, shops, restaurants and bars. This condo has everything a renter needs during vacation. Full kitchen, washer and dryer, beach gear, towels, bedding and more. The complex has two swimming pools, barbecues, tennis courts and outdoor picnic areas. This location is next to fun activities such as swimming, snorkeling, diving, surfing, kayaking, fishing, and more.

Top guest favorite
Condo in Wailea
4.97 out of 5 average rating, 109 reviews

Modern Renovated Palms at Wailea Condo!

MODERN CONDO WITH ATTENTION TO DETAIL! Our bright, modern island condo awaits you! Breathe easy knowing that you have everything at your fingertips. Enjoy your morning coffee on the large lanai. Pack a beach bag and head to one of the best beaches just a 10 minute walk away. Explore the Shops at Wailea. You will feel right at home cooking in our fully equipped kitchen. Close out your day by watching the sunset from the pool area and then stargazing on the lanai. Then repeat!

Top guest favorite
A spacious living area featuring high vaulted ceilings and large windows offering ocean views. Comfortable seating arrangements include an oversized sofa and stylish armchairs. A dining table accommodates four, complemented by a decorative feature wall. Natural light enhances the airy atmosphere throughout the room.
Apartment in Wailea
5 out of 5 average rating, 103 reviews

Luxurious Wailea Ocean Vistas

Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful lushness while enjoying a charming well-designed hideaway. We have considered every detail to provide the most effortlessly luxurious stay possible. With beaches nearby and two pools onsite, this island paradise has everything and more.

Superhost
A view from the second floor displays lush tropical landscaping with palm trees and vibrant greenery. The ocean is visible in the background, framed by a clear blue sky. The scene offers a serene outdoor ambiance typical of Wailea.
Condo in Wailea
4.88 out of 5 average rating, 129 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.

Guest favorite
The living area is arranged with comfortable seating over a textured carpet. A low coffee table holds decorative elements, while art adorns the wall and a modern kitchen with stainless steel appliances is visible in the background, enhancing the open layout.
Condo in Wailea
4.97 out of 5 average rating, 160 reviews

130K Hawaiian Reno on Wailea Blue Golf *Ocean View

BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

Guest favorite
A modern kitchen features sleek white cabinets and a spacious granite countertop, with stainless steel appliances. A decorative arrangement of tropical flowers is positioned on the counter. A sliding glass door leads to a private lanai with ocean views, furnished with a dining table and chairs.
Condo in Wailea
4.95 out of 5 average rating, 197 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.

Top guest favorite
Condo in Wailea
4.98 out of 5 average rating, 203 reviews

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.)

Guest favorite
Home in Kihei
4.91 out of 5 average rating, 138 reviews

OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

Indulge in the ultimate coastal retreat at our exquisite ocean-front, ocean-view private home. Nestled in the serene and secure gated neighborhood of Kihei in South Maui, this remarkable 2 bedroom, 2 bath sanctuary offers an unparalleled experience with a private hot tub, and direct beach access.

Top guest favorite
A vibrant sunset casts warm orange and yellow hues over the ocean, with waves gently lapping at the shore. Silhouetted palm trees and lush greenery frame the scene, while rocky outcrops jut into the water, creating a picturesque coastal landscape.
Condo in Wailea
4.99 out of 5 average rating, 181 reviews

Romantic, Luxury Condo with Spectacular Ocean View

Our luxury condo in the heart of Wailea is close to the beach and world class golf. You’ll love our condo because of the beautiful upgrades, the high ceilings, the kitchen, the comfy bed, the wonderful sea breezes and the spectacular ocean views. Our condo is romantic and great for couples.

Top guest favorite
Condo in Wailea
4.96 out of 5 average rating, 673 reviews

Wailea Resort studio suite

Fully equipped studio suite at Grand Champions Villas in Wailea Resort. Free numbered parking stall, free Wifi in unit and both pool areas. Split A/C for quiet cool comfort. Very comfortable Tempur-Pedic bed. Walking distance to Shops of Wailea and beaches.

Popular amenities for Wailea-Makena vacation rentals

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,374ﺩ.ﺇ 1,451ﺩ.ﺇ 1,300ﺩ.ﺇ 1,138ﺩ.ﺇ 1,025ﺩ.ﺇ 1,058ﺩ.ﺇ 1,010ﺩ.ﺇ 973ﺩ.ﺇ 933ﺩ.ﺇ 995ﺩ.ﺇ 1,135ﺩ.ﺇ 1,340
Avg. temp16°C16°C16°C17°C18°C18°C19°C20°C19°C19°C18°C17°C

Frequently Asked Questions

  • What are the best places to stay in Wailea-Makena?

    Wailea-Makena has a variety of vacation rentals, including oceanfront homes, condos, and properties near golf courses and beaches. Many neighborhoods provide easy access to local shops, restaurants, and outdoor activities.

  • What are the best things to do in Wailea-Makena with kids?

    Children often enjoy swimming at sandy beaches, exploring tide pools, or joining marine life tours. Interactive cultural sites and family-friendly parks around Wailea-Makena are frequently suggested for a relaxed day out.

  • What are some of the best things to do in Wailea-Makena?

    Wailea-Makena has sandy beaches, snorkeling opportunities, and scenic coastal walks. Visitors often explore local parks, enjoy golf courses, or join guided tours highlighting marine life and Hawaiian heritage.

  • How is the weather in Wailea-Makena?

    Wailea-Makena has mild weather throughout the year, with winter temperatures averaging 53–68°F (12–20°C) and summer months reaching 59–76°F (15–24°C). Rain is more common in winter, while summers tend to be sunny and dry.

  • When is the best time to visit Wailea-Makena?

    Late spring and summer are frequently suggested for warmer days near 75°F (24°C) and lower rainfall, making beach and outdoor activities popular. Winter, around 68°F (20°C), is also lively with more visitors, and brings occasional rain alongside mild temperatures.

  • What are the best places to visit in Wailea-Makena?

    Visitors often explore sandy beaches, local parks, and scenic coastal paths in Wailea-Makena. Marine reserves and cultural centers highlight Hawaiian heritage, nature, and community events.

  • What are some hiking trails in Wailea-Makena?

    Visitors can explore coastal trails, gentle walking paths through local parks, or routes winding near lava fields and scenic overlooks. Some areas have accessible hikes suitable for diverse abilities and interests.

  • What are some family activities we can do in Wailea-Makena?

    Families can explore sandy beaches, try snorkeling in clear waters, or visit local parks with picnic spots. Cultural sites, marine life tours, and gentle hiking paths around the area are frequently suggested for visitors of all ages.

  • What are some of the best day trip ideas from Wailea-Makena?

    Day trips can include exploring coastal hikes, visiting traditional markets, or discovering historic towns around the region. Nature reserves, scenic viewpoints, and cultural attractions frequently appeal to visitors seeking local experiences.

  • Are there any pet friendly accommodations available in Wailea-Makena?

    Many vacation rentals in Wailea-Makena welcome pets, especially in neighborhoods near outdoor spaces or parks. Hosts often provide guidance on pet-friendly beaches and walking areas around town.

  • What are some local tips for visiting Wailea-Makena?

    Respect beach etiquette, bring reef-safe sunscreen, and consider reusable shopping bags for local markets. Early mornings offer quieter outdoor experiences, and chatting with local hosts or vendors can reveal community traditions.

  • What is Wailea-Makena known for?

    Wailea-Makena is known for its sandy beaches, distinct golf courses, and locally rooted hospitality. The area blends natural beauty, marine activities, and celebrated Hawaiian traditions throughout its neighborhoods.

  • What are the best hidden gems to explore in Wailea-Makena?

    Wailea-Makena has secluded beaches, lesser-known lava rock pools, and small local markets. Off-the-beaten-path walking trails and traditional workshops offer quieter, locally rooted experiences.

  • What are the best foods to try in Wailea-Makena?

    Local cuisine often features fresh seafood, poke bowls, and tropical fruits like papaya or mango. Try dishes rooted in Hawaiian traditions, including laulau, Loco Moco, or regional desserts made with coconut and taro.

  • What should I bring for a trip to Wailea-Makena?

    Pack lightweight clothing, swimsuits, sun protection, and sturdy sandals for outdoor activities. Reusable water bottles, hats, and light rain jackets are useful for changing weather and exploring coastal or park areas.

  • What is the nightlife in Wailea-Makena like?

    Wailea-Makena has a laid-back nightlife scene, with open-air lounges, live music at local venues, and casual beachside bars. Evening entertainment often blends local musicians, sunset views, and relaxed dining.

  • What are the most popular events or festivals in Wailea-Makena?

    Annual events often include cultural celebrations, Hawaiian music festivals, and food gatherings during summer or late spring. Community events, arts fairs, and outrigger canoe races are frequently suggested for visitors seeking local traditions.

  • Are there family friendly vacation rentals in Wailea-Makena?

    Wailea-Makena has a wide selection of family-friendly rentals, including spacious homes, condos with pools, and properties close to parks and beaches. Many hosts provide amenities like cribs, high chairs, and beach gear.

All about Wailea

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.

What are the 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.

Destinations to explore

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