Vacation rentals with a pool in Wailea

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.

4.97 out of 5 average rating, 102 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

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.

4.97 out of 5 average rating, 165 reviews

Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

Stunning Full Renovation and Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the lanai.We are perfectly located just down from Money Pod+across from The Wailea Village popular with all the best restaurants. The Shops of Wailea with all of the exclusive brands is a short walk down the hill. Resort style amenities with 2 pools. Everything provided from Beach towels, Boogie Board, Yeti cooler and more.

4.88 out of 5 average rating, 171 reviews

A spacious living area features a large sectional sofa adorned with various throw pillows. A wooden coffee table sits in front of the sofa, while built-in shelves display decorative items and a flat-screen TV is positioned for easy viewing.

Apartment in Wailea

Go Golfing from a Peaceful Apartment in a Beach Community

Unit #903 – Key Features Garden views, ground floor A/C (3 zones) Lanai seating Quiet Updated appliances; washer/dryer Primary: king bed Second: twins (convert to king) Sleeper sofa Kitchen TV, Wi-Fi Free U.S./Canada calls Amenities Beach chairs, umbrella, boards, cooler, towels Baby gear: Pack ’n Play Pool, hot tubs Location Wailea—near beaches, golf, shops, dining. Keawakapu Beach is a short walk. Guest Support On-island contact after booking. Parking Dedicated space + guest parking.

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.

4.94 out of 5 average rating, 331 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

4.99 out of 5 average rating, 133 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

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.

4.99 out of 5 average rating, 196 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.

A spacious outdoor lanai features a dark dining table surrounded by several chairs, offering breathtaking views of palm trees and the sandy beach. The ocean stretches out in the distance under a clear blue sky, creating an inviting atmosphere for relaxation.

4.88 out of 5 average rating, 101 reviews

Beach Dream Suite-Mana Kai Maui Resort

Unforgettable ocean views are yours at the amazing Mana Kai Resort! One of One, directly on one of Maui’s best beaches! Our popular suite boasts serene decor, quality linens, fine finishes, tasteful furnishings, equipped kitchen w/island, AC, WiFi, Smart TV, lanai, free parking! Features combined with all there is to do equals vacation success! A state-of-the-art fitness center and business office on lower floor. Heated pool, lounges+tables. Note: The BEDROOM SPACE is OPEN TO LIVING AREA.

4.99 out of 5 average rating, 276 reviews

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

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.

4.97 out of 5 average rating, 113 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!

A spacious living area is characterized by wood-paneled walls and natural light from large sliding glass doors. A comfortable queen-sized sleeper sofa and two accent chairs are arranged around a coffee table. A flat-screen smart television is mounted on the wall, adorned with complementary artwork.

4.91 out of 5 average rating, 117 reviews

Luxury Condo in Wailea Ekahi w/Direct Beach Access

Do you want direct and private access to probably the best beach (i.e. Keawakapu) on Maui? Then look no further than our unit in the Wailea Ekahi complex! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. You are also in walking distance to the stores and restaurants at the Shops at Wailea and also the Wailea Beach Path. This condo has everything you need to make your Maui experience memorable, luxurious, and convenient.

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.

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.

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.