Holiday rentals in Wailea

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Wailea

  • Total holiday rentals

    Explore 1,930 holiday rentals in Wailea

  • Nightly prices starting at

    Wailea holiday rentals start at $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 55,470 verified reviews to help you choose

  • Family-friendly holiday rentals

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

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    1,840 properties feature pools

  • Rentals with dedicated workspaces

    1,130 properties have a dedicated workspace

  • Wifi availability

    1,930 of Wailea holiday rentals include wifi 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 holiday rentals in Wailea

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

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Top guest favourite
This image showcases a balcony view overlooking a vibrant scene filled with palm trees and lush greenery. A sparkling pool can be seen in the distance, and the ocean glimmers under a clear blue sky. Sunlight filters through the palm fronds, enhancing the serene atmosphere.
Apartment in Kihei
4.97 out of 5 average rating, 172 reviews

The Pi Life: Ocean Views · 99 Steps from the Beach

We're Airbnb Superhosts w/ 100+ 5 Star Reviews. Welcome to The Pi Life! A cute and cozy condo, with gorgeous oceans views, that's 99 steps from the beach. We have everything you need for a perfect Maui vacation, including: ★ Ocean Views ★ Resort Amenities ★ Beach & Restaurant Access And, perhaps most importantly, we're deeply caring and responsive hosts ❤️ Our goal is to make your experience as fun, relaxing, and comfortable as possible. So please let us know how we can be helpful :)

Top guest favourite
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.
Apartment 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 favourite
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 favourite
Apartment in Wailea
4.97 out of 5 average rating, 111 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!

Guest favourite
The spacious living area features vaulted ceilings with exposed beams and large glass doors that open to stunning ocean views. Comfortable seating includes two patterned armchairs and a cozy sofa. A coffee table is centered in the room, and the dining area is illuminated by pendant lights.
Apartment in Wailea
4.95 out of 5 average rating, 128 reviews

Upscale and Elegant Vistas

Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled and freshly outfitted. No expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

Top guest favourite
The open living area showcases vaulted ceilings and warm wood beams. A modern kitchen island with a marble finish is complemented by stylish pendant lights. A cozy seating area invites relaxation, while large windows offer views of the surrounding landscape, enhancing the bright and airy atmosphere.
Townhouse in Wailea
4.97 out of 5 average rating, 143 reviews

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Welcome to Happy Everything! Wailea Ekolu Complex A fun, fully re-modeled, well appointed and comfortable townhome situated on hole 10 of the famous Wailea Blue Golf Course at beautiful Wailea, Maui. Comfortably sleeps 6. Spectacular views of the Ocean and Neighbor Islands. Close to beaches, shopping, restaurants, Wailea Resorts and just a chip shot away from the golf course and brand new Wailea Village shops.

Top guest favourite
An open-concept living area showcases a modern kitchen island with a fruit bowl. A sectional sofa is positioned beside a Samsung Smart TV, with beach-themed artwork adorning the walls. Natural light floods the space, highlighting the neutral tones and inviting layout.
Apartment in Wailea
4.99 out of 5 average rating, 149 reviews

*Fully Remodeled* Modern Island Style*

I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini

Guest favourite
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.
Apartment 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 favourite
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.
Apartment in Wailea
4.95 out of 5 average rating, 198 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.

Guest favourite
A modern living area features a large television set on a dark wooden console. Bright natural light illuminates the space through expansive sliding glass doors, leading to a small outdoor seating area. A decorative rug enhances the floor, complemented by a cozy sofa adorned with various cushions.
Apartment in Wailea
4.92 out of 5 average rating, 115 reviews

Maui Wailea Brand New Modern Spacious Condo

Beautifully designed, modern, and brand new vacation condo is situated on the Wailea Blue golf course and the Wailea tennis club. Walk to Shops at Wailea and 3 min drive to Keawakapu Beach. Brand new kitchen, spa like bathroom with walk in shower, in-unit laundry. Relax with friends and families at this peaceful place to stay. Book your vacation today : )

Top guest favourite
Apartment 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.)

Top guest favourite
A light-filled living room features a large gray sectional sofa and a 70-inch Smart TV mounted on the wall. Above the TV, a colorful 'ALOHA' sign is displayed. Sliding glass doors offer views of a spacious lanai overlooking lush green fairways.
Apartment in Wailea
5 out of 5 average rating, 138 reviews

Wailea Surf Shack: Beaches, Shops & Golf!

Welcome to Wailea Surf Shack, a beautifully renovated Maui retreat in the heart of Wailea. Book with confidence knowing that we live on the island, personally manage and care for the condo, and truly treat our guests like family. We go above and beyond to make sure your stay is comfortable, relaxing, and filled with wonderful Maui memories.

Popular amenities for Wailea holiday rentals

When is the best time to visit Wailea?

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Avg. price$483 SGD$510 SGD$457 SGD$400 SGD$360 SGD$372 SGD$355 SGD$342 SGD$328 SGD$350 SGD$399 SGD$471 SGD
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.

Destinations to explore

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