Holiday houses in Wailea Beach

4.94 out of 5 average rating, 286 reviews

Condo in Wailea-Makena

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

4.97 out of 5 average rating, 120 reviews

Romantic Beach Retreat, New King Bed & A+ Wi-fi

Hale Kamaole: Remodel to be completed Nov 2025. Romantic Bright & Airy Beach Condo Across Street from Kamaole III Beach in South Kihei! Tasteful heritage decor, fast internet, King bed, walk-in shower, 1st floor unit. Perfect for honeymooners. Washer/Dryer. Spacious lawns & tropical gardens w/ 2 pools, Tennis court & BBQ grills. Popular snorkeling area. Eddie Pu walking trail w/ plenty of wildlife just steps away. Walk to shops & restaurants. Free Parking Pass NB:17.712% Hawaiian Transient Tax

4.99 out of 5 average rating, 163 reviews

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. 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 Not suitable for children or infants.

4.92 out of 5 average rating, 118 reviews

40% off ! Oceanfront Views in the heart of Kihei

40% off nightly rates during construction. Are you the kind of travelers who get up early and get going? This can be a great opportunity for you. Construction hours 8am-4pm. No construction on weekends or holidays. Noise ranges from spotty to very loud. Pano ocean views from this beautifully updated, fully air-conditioned condo. A guest favorite, it's a 2-minute walk to Kalama Beach Park and Cove Beach. Easy self-checkin, then a 2-3 minute walk to food trucks, bars, restaurants and shopping.

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, 211 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, 154 reviews

Newly Renovated Corner Unit w/ View at Maui Vista

Aloha - welcome to your Maui escape! Just steps from the iconic Charley Young and Kamaole I beaches, our newly remodeled condo offers comfort and convenience, with amazing dining and drink options a short walk away. Enjoy fresh seafood, tropical cocktails, and all the island vibes. Thoughtfully designed and continuously updated, our space has everything you need for a relaxing, unforgettable stay. Book your tropical getaway today—we’d love to host you! Mahalo, Dave & Neldie

4.93 out of 5 average rating, 275 reviews

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!

4.98 out of 5 average rating, 165 reviews

Prime Location! Walk to Beach, Shops & Dining!

Stay in a fully remodeled top-floor oasis at Maui Banyan—one of Kihei’s most beloved resort-style complexes. Enjoy peaceful privacy on your lanai surrounded by tropical trees, stroll to the beach in 3 minutes, and relax by two lush pools with hot tubs. Perfectly located near shops, restaurants, and sunsets that leave you speechless. Whether you're here to explore or unwind, this is the Hawaiian base you've been looking for.

4.99 out of 5 average rating, 270 reviews

Modern studio by the beach - Taxes included

Peaceful corner unit studio in North Kihei at the beginning of a 6 mile coastline into Kihei’s beach town. Kihei Bay Surf has a large pool, hot tub, BBQ, tennis court, coin/app operated laundry in the complex, and parking stalls up to your front door. Located right across the street from the beach. **Nightly Rates and Cleaning Fee are inclusive of Hawaii GE and TAT Taxes **Please message us for stays longer than 14 days

4.96 out of 5 average rating, 432 reviews

Home in Kihei

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

5 out of 5 average rating, 256 reviews

Guest suite in Kula

Kula Jacaranda Studio on the Slopes of Haleakala

Kula Jacaranda studio is reached by a treehouse walkway. Your private covered deck offers a place to dine and watch the sunset . The shared barbecue area offers a place to prep your own meals. We provide coffee, tea, oil, vinegar and salt. The luxurious walk-in shower offers double shower heads and benches. With years as AirBnb super hosts, we've got everything you need.

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Other great holiday rentals in Wailea Beach

4.95 out of 5 average rating, 65 reviews

Gem near Keawakapu Beach - Privacy and Ocean Views

DrewRating, 5 stars1 month ago

Amazing spot and stay

4.95 out of 5 average rating, 65 reviews

Maui Banyan, King Bed, Ocean View, Kamaole Beach!

JillRating, 5 stars2 weeks ago

We needed a place to stay in Kihei and found the perfect one. I had stayed in a couple of other places on other trips, but this was the best ever! It was extremely clean, with amenities such as dishwasher, air conditioning and washer and dryer. It also had everything available for when we went to the beach, which was a very short walk across the street. It was also a short walking distance to Freds Mexican Restaurant and Moose McGillycuddy's, both great restaurants to eat at. The only difficult thing was taking luggage up the stairs since it was on the second floor. I will be sure to stay there again on my next trip to Maui!!

5 out of 5 average rating, 59 reviews

Ma'alaea Surf Oceanfront 2 Bedroom Condo on 2nd Fr

MariiaRating, 5 stars2 weeks ago

Super clean and comfy condo! Was enjoying the view every time. Great location . The Host was super nice and helpful!

4.92 out of 5 average rating, 63 reviews

Ocean View Condo w/ King Bed & Steps to the Beach!

AmyRating, 5 stars2 months ago

Our place was very comfortable, clean, and nicely decorated. Had everything we needed to enjoy our stay. Location was terrific as well, with beautiful beaches close by. A short drive to many restaurants. Christopher reached out to help us if we needed anything. This was our first experience with Airbnb, and definitely a positive one!

5 out of 5 average rating, 71 reviews

Luxurious Wailea Ocean Vistas

CristianRating, 5 stars2 weeks ago

The place is amazing. We were sorry to leave.

Superhost

4.82 out of 5 average rating, 99 reviews

Luxury Wailea Remodel - Beachfront Community

DanielRating, 5 stars5 days ago

The place was exactly as described; comfortable and well-equipped. The kitchen had everything we needed, which made cooking easy and enjoyable. The beach is within walking distance, and the walk itself is very pleasant. The home was spotless, cleaning was truly top-notch. The host was very responsive and helpful throughout our stay. While the property is near a street, it’s not an overly busy one, so noise was never an issue. Overall, a great stay that we would gladly recommend.

4.96 out of 5 average rating, 76 reviews

Modern Renovated Palms at Wailea Condo!

FranziskaRating, 5 stars1 month ago

The condo featured everything we could hope for to enjoy the beaches and our vacation with a baby including full kitchen equipment, various baby chairs, toys, a bathtub and beach equipment (umbrellas, beach chairs, boogie boards, beachwaggon...). We really liked the interior design, it made us feel more at home.