Holiday rentals with outdoor seating in Wailea-Makena

4.91 out of 5 average rating, 104 reviews

Ocean view in South Kihei

Newer AC units in bedroom and living room! Perfectly located in South Kihei, directly across from Kamaole 2 beach and 1/2 mile to over 30 restaurants, bars and small shops. Three sandy beaches are a 5 to 10 min walk offering great snorkeling, surfing, SUP’n & kayaking.Well equipped kitchen with cherry cabinets, granite counter-tops & newer appliances, LED lighting, both rooms have ceiling fans too.Very well equipped kitchen, highspeed internet, 2 beach chairs, umbrella, ice chests, room safe.

4.99 out of 5 average rating, 152 reviews

Ocean view and beach by Wailea

Infants and children welcome! Ocean views, beach across the street. Large lanai. Indoor and outdoor dining. Large bedroom, king bed, ensuite, east facing second lanai off bedroom. Guest bathroom living room. Double height single air mattress, pac n play, high chair. Comfortable and quiet split system A/C. Toys, beach wagon, umbrellas, beach chairs, boogie boards, beach towels provided. Close to shops and restaurants. Tennis courts and two pools in complex. Reserved parking by front door.

4.94 out of 5 average rating, 286 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

4.98 out of 5 average rating, 100 reviews

Spacious tropical oasis near gorgeous beaches!

Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located across Kamaole 3 Beach and minutes to Wailea. Our condo is perfect for couples and small families wanting space with stylish comfort in a prime location. Relax on a luxurious king-sized bed, custom sectional sofa w/ memory foam sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, and two large bathrooms. Unwind in paradise on two lush garden patios!

4.99 out of 5 average rating, 113 reviews

Guest suite in Kihei

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.

5 out of 5 average rating, 210 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.

4.95 out of 5 average rating, 119 reviews

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

4.93 out of 5 average rating, 275 reviews

Apartment in Kihei

Spring Special - One Bedroom, Closest to beach!

We're happy to assure you that our condo in South Maui is fully compliant and properly zoned for short-term rentals. Book with confidence! As Maui residents, my wife and I can truly say there is no better place to live or vacation than Maui Banyan.. We bought our condo with a long-term goal in mind.. retirement later but fun now. We ask that if you choose to stay with us that the rental agreement that will be sent to you is respected and followed. Welcome to paradise!

4.92 out of 5 average rating, 101 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.

4.93 out of 5 average rating, 167 reviews

Condo in Wailea

Upscale Wailea - 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 condo is in the Wailea Resort area, and does not infringe upon nor remove housing from the local neighborhoods of Maui.

4.99 out of 5 average rating, 114 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