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Holiday rentals with outdoor seating in Wailea

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Quick stats about holiday rentals with outdoor seating in Wailea

  • Total holiday rentals

    Explore 840 holiday rentals in Wailea

  • Nightly prices starting at

    Wailea holiday rentals start at $191 NZD per night before taxes and fees

  • Verified guest reviews

    Over 34,170 verified reviews to help you choose

  • Family-friendly holiday rentals

    480 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    810 properties feature pools

  • Rentals with dedicated workspaces

    540 properties have a dedicated workspace

  • Wi-Fi availability

    840 of Wailea holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wailea rentals

  • 4.9 Average rating

    Wailea stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated Holiday Houses with Outdoor Seating in Wailea

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite
A modern living area features a light-colored sectional sofa and a coffee table adorned with decorative pinecones. An open design connects to the dining area, showcasing a table set for six and a kitchen visible in the background. Natural light floods the space through large sliding glass doors.
Condo in Wailea
4.88 out of 5 average rating, 162 reviews

ContemporaryHawaiianReno in Wailea*Pool*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.BOOK UP TO 365 DAYS

Top Guest favourite
A well-appointed kitchen area features a spacious granite countertop with rich wooden cabinetry. Hanging red pendant lights provide soft illumination. Large windows offer views of lush greenery and the ocean, enhancing the inviting atmosphere of the space.
Condo in Wailea
4.94 out of 5 average rating, 181 reviews

Gorgeous 2 Story Townhouse in Wailea w/ Ocean View

Perfect location for vacationers. Condo is located on the first row right on the the Blue Golf Course, next door to the new Wailea Village Shopping Center. It's in the heart of the resort community of Wailea, across the street from the Shops at Wailea and the Grand Wailea. The unit has been completely renovated with spacious and open floor plan with 20 ft. cathedral ceiling. Just a few minute walk from coffee shops, great restaurants, grocery stores, shops, and some of the world's BEST beaches!

Top Guest favourite
An open dining area features a round table made of natural wood, surrounded by woven chairs. A well-equipped kitchen with stainless steel appliances and quartz countertops is visible in the background. Large sliding glass doors provide unobstructed views of the ocean and nearby palm trees.
Condo in Wailea
4.94 out of 5 average rating, 329 reviews

A.R.A Retreats: The Molokini

FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

Top Guest favourite
A modern living area showcases a spacious L-shaped sofa adorned with blue accent pillows. A circular coffee table sits at the center, complemented by two stylish armchairs. Natural light floods the room through large windows, highlighting the green artwork mounted on the wall.
Condo in Wailea
4.95 out of 5 average rating, 167 reviews

Wailea Beauty - walk to the beach & shops

Our locally-owned, newly redesigned 2BD/2BA modern Maui condo is located on the award-winning Wailea Blue Golf Course at The Grand Champions Villas. The Villas are nestled in the heart of tropical Wailea; minutes from shopping, tennis, restaurants and pristine beaches. Stroll to upscale boutiques and restaurants, or take a short walk to some of the most beautiful beaches in the world. Our condo features local Hawaii art and is your perfect home away from home on the beautiful island of Maui.

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
A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.
Condo in Kihei
4.99 out of 5 average rating, 272 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Top Guest favourite
Condo in Wailea
4.97 out of 5 average rating, 112 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.
Condo 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.
Condo in Wailea
4.99 out of 5 average rating, 150 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
A spacious living area is featured with comfortable seating, a large television, and natural light streaming through generous glass doors. A private lanai is highlighted with a dining table for four, surrounded by lush greenery. The bedroom showcases a king bed with calming decor, while a tranquil pool and palm trees are visible outside.
Condo in Wailea
4.83 out of 5 average rating, 185 reviews

Last Minute Deal! Wailea Condo Oceanfront Complex

Step into your own private tropical oasis in this fabulous Wailea condo! This adorable 792 square foot, ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This lavish condo boasts an open and airy living space you will love with AC throughout. Relax on the remarkable lanais with a table with seating for four.

Top Guest favourite
Condo in Wailea
4.96 out of 5 average rating, 180 reviews

Luxury Vacationing Modern Condo Aug Specials $325

JUST RENOVATED THIS BEAUTIFUL CONDO IS BORDERING KIHEI AND WAILEA. THE CONDO BOASTS 17 FT CEILINGS, 1025 sq ft, 4 FRENCH DOORS THAT OPEN OUT TO A DOUBLE BALCONY WITH INCREDIBLE VIEWS OF THE OCEAN AND VOLCANO. TENNIS COURTS, SWIMMING POOL, BOCCE BALL, SHUFFLE BOARD,PUTTING GREEN AND ACROSS THE STREET FROM KEAWAKAPU BEACH. PERFECT FOR A FAMILY VACATION.

Popular amenities for Wailea outdoor seating rentals

When is the best time to visit Wailea?

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Avg. price$656 NZD$686 NZD$608 NZD$533 NZD$476 NZD$492 NZD$475 NZD$450 NZD$435 NZD$469 NZD$528 NZD$644 NZD
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