Vacation rentals in Poʻolenalena Beach

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Top-rated vacation rentals in Poʻolenalena Beach

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Top guest favorite
A picturesque view captures a beach at sunset with vibrant orange and purple hues in the sky. Swaying palm trees line the shoreline, where beachgoers can be seen enjoying the golden sand and gently lapping waves. The grassy area near the beach is dotted with lounge chairs.
Condo in Wailea
4.97 out of 5 average rating, 105 reviews

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

Welcome to Mana Kai Palms Our luxurious, newly renovated condominium is located on Keawakapu Beach, named Maui's best for its pristine sand, clear waters, and abundant marine life. The Mana Kai Resort offers a wide range of amenities and with only 100 units, provides a warm, family feel. We are conveniently located minutes from all South Maui has to offer. Hosted by Tracy O'Reilly, a Superhost and #1 rated rental agent on Maui. Do as much as you want or as little as you desire at Mana Kai Palms

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Top guest favorite
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, 333 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

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Guest favorite
Condo in Wailea
4.96 out of 5 average rating, 55 reviews

Beach Front Luxury in Makena

Only steps away from the beach, our newly remodeled 1600 sq/ft condo is tucked away in the coveted South Maui oceanfront resort of Makena Surf. Enjoy the exceptional view of islands Lanai, Molokini & Kahoolawe from our comfortable lanai. Dining, shopping & golfing are just minutes away. The condo is loaded with premium & luxury features. Two bedrooms, two bathrooms, and a gourmet kitchen. The resort has two pool, tennis courts and private beach access. Perfect for a family of 4 or 5 persons.

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Top guest favorite
A vintage toy van is positioned on a sandy beach, facing a vibrant sunset over the ocean. Warm golden light reflects off the waves, creating a serene scene. The gentle surf adds a sense of calm to the atmosphere, with small ripples lapping at the shore.
Condo in Wailea
4.93 out of 5 average rating, 205 reviews

Groovy bright condo 2 bed / 2 bath South Kihei

Enjoy our home away from home! Bright Groovy Beach Condo offers you a naturally lit and engaging space to relax with two bedrooms each with their own en suite bathrooms (4th bed is the pull out sofa bed in the living room). Enjoy your morning coffee on the lanai and listen to the birds. Haleakala Shores is located 300 meters from world famous Kamaole Beach III. You are also located within a casual stroll (or snorkel or paddle board) north to Kamaole Beach II, I and finally Charley Young Beach.

LocationFamilyOutdoor spaces

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, 197 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.

LocationFamilyBeach

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, 143 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.

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Top guest favorite
A bright living area offers ocean views through expansive sliding glass doors. Comfortable chairs are positioned towards the balcony, where coastal scenery includes palm trees swaying in the breeze. Neutral decor is accented with beach-themed cushions, and a TV set is present on a stylish console.
Condo in Wailea
4.99 out of 5 average rating, 232 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY ON Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, on the border of Wailea and Kihei. Our condo is designed with a modern surf feel in mind, welcome to the beach! If you enjoy Wailea's 5 star resorts right down the beach, but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best PM in Maui, Tracy O'Reilly to take amazing care of you!

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Guest favorite
Condo in Wailea
4.89 out of 5 average rating, 148 reviews

*Last Minute Deal*Luxurious*2b/2b OceanView Wailea

This ground floor 1071 square foot unit is situated just above the 11th fairway of the Wailea Blue Course. The living room and master bedroom have private lanais that step out to a relaxing open lawn with sweeping ocean views. Features include AC throughout the property, bamboo floors throughout, brand new tile in the master bathroom, granite counter tops, and cherry cabinets. Tastefully decorated this spacious condo truly has everything you will need!

LocationFamilyPool

Guest favorite
A clear view of a swimming pool is presented, surrounded by lounge chairs and tropical greenery. Palm trees frame the scene, with the ocean visible in the background under a bright blue sky dotted with clouds.
Condo in Kihei
4.92 out of 5 average rating, 195 reviews

3BR spacious Condo with Ocean View in top location

Enjoy ocean views and island living from this spacious 1,400 sq ft 3-bed/2-bath condo in the heart of Kihei. Located directly across the street from the beach, you can watch whales from the lanai or relax by the pool and BBQ area. Shores of Maui offers easy access to Kihei’s best beaches, shops, and restaurants, all within minutes. A perfect home base for families and groups looking for comfort, convenience, and the South Maui lifestyle.

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Top guest favorite
A modern dining area features a polished wooden table surrounded by six chairs. Natural light floods the space, highlighting the contemporary kitchen with granite countertops in the background. Large sliding glass doors open to a scenic view of the ocean and lush surroundings.
Condo in Wailea
4.94 out of 5 average rating, 198 reviews

Wailea Ekolu Village 2/2 with stunning ocean view!

Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

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Luxe
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, 152 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

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Guest favorite
A vibrant sunset is captured over the Pacific Ocean, with clouds in shades of orange and purple. Silhouettes of palm trees frame the foreground, while lush greenery and homes are visible at the edge of the golf course, enhancing the tropical setting.
Condo in Wailea
4.91 out of 5 average rating, 161 reviews

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

Experience the best of Wailea from this rare 3BR/2BA luxury villa, featuring breathtaking views of the Pacific Ocean, Wailea Blue Golf Course and majestic Haleakalā. Spacious enough for families or groups, this exceptional retreat offers all the comforts of home—just a short walk from world-famous beaches, luxury resorts, fine dining and premier shopping.

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Popular amenities for Poʻolenalena Beach vacation rentals