Vacation rentals in Wailea Beach

A sandy path leads down to a serene beach, framed by lush greenery on either side. Gentle waves can be seen lapping at the shore, with a distant view of the islands on the horizon under a clear blue sky.

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

A spacious living area is presented with comfortable seating and decorative accents. Large glass doors provide natural light and offer views of the lush surroundings. The room features a ceiling fan, an entertainment unit with a TV, and a modern coffee table adorned with a vase of flowers.

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.

A serene outdoor dining space with a glass-top table surrounded by wicker chairs overlooks the ocean. Lush palms frame the stunning water view, while tropical flowers add a vibrant touch to the setting. The sky is clear with hints of blue.

4.99 out of 5 average rating, 187 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on incredible Keawakapu beach! This location is ideal, right on the border of Wailea and Kihei. We have designed our remodel with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5-star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach come stay with us! We have hired the best Property Manager in Maui, Tracy O'Reilly to take care of our guests

An outdoor dining area is surrounded by lush palm trees and tropical plants. Soft lighting provided by string lights creates a relaxed atmosphere. A large umbrella shades a table where guests are seated, enjoying their meals together. A pathway leads toward the gathering spot.

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

The spacious Ocean Blue Ohana is showcased against a vibrant sunset, surrounded by lush tropical landscaping. Multiple covered balconies provide comfortable seating, illuminated by soft outdoor lighting, inviting guests to enjoy the serene atmosphere and ocean views from a stunning elevation.

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.

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.

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.

A scenic view reveals lush greenery with various trees framing the background, showcasing glimpses of the ocean and coastline. A mix of tropical foliage adds depth to the landscape, creating a serene setting under a bright blue sky dotted with clouds.

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

Frosted glass doors create a stylish entry to the bedroom, revealing a cozy sleeping area with two framed art pieces on the wall. A neutral colored bed with decorative pillows is visible, along with a television and a side table in the foreground.

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!

4.93 out of 5 average rating, 167 reviews

A modern living area features a spacious dining table surrounded by six wooden chairs. Large glass doors provide access to a balcony with lush outdoor views. A comfortable sectional sofa is positioned nearby, and a stylish ceiling fan is visible above.

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.

4.96 out of 5 average rating, 432 reviews

A comfortable seating area is visible, featuring two wicker chairs under a large umbrella on a deck. The open door frames views of a tranquil ocean and lush tropical gardens, complemented by bright blue skies and palm trees.

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

Aerial view of the Kula Jacaranda property, showcasing lush greenery and rolling hills. The main house and nearby structures are surrounded by vibrant trees and open spaces, with winding pathways visible throughout the landscape, inviting exploration of the natural beauty.

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.

A dining table is set on the lanai, featuring a bottle of champagne in a cooler and two glasses filled with a sparkling drink. Lush tropical flowers are arranged in a vase, with a backdrop of a golden sunset over the ocean and silhouetted palm trees.

5 out of 5 average rating, 143 reviews

Romantic, Luxury Condo with Spectacular Ocean View

Our luxury condo in the heart of Wailea is close to the beach and world class golf. You’ll love our condo because of the beautiful upgrades, the high ceilings, the kitchen, the comfy bed, the wonderful sea breezes and the spectacular ocean views. Our condo is romantic and great for couples.

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Other great vacation rentals in Wailea Beach

4.96 out of 5 average rating, 51 reviews

Newly Remodeled-AC-Ocean Views-Modern Finishes

MichaelRating, 5 stars4 months ago

We had a fantastic experience staying here. The check in and check out was easy and the grounds of the condos are really well kept and beautiful.

4.92 out of 5 average rating, 77 reviews

A serene view is offered through the open window, showcasing lush tropical gardens, palm trees, and the ocean in the distance. Natural light floods the space, enhancing the vibrant greenery and inviting outdoor setting of the property.

Condo in Wailea

Wailea Elua 1101 - Beachfront Section - Ocean View

LisaRating, 5 stars2 months ago

Beautiful location and setting. Very well organized and equipped. Especially nice bathroom and kitchen. She was also very thoughtful on the smaller details too, such as hooks to hang towels, clothes line in tub, non scented cleaning products . Also Very nice setup on the lanai

The spacious kitchen features a large island with light countertops and ample cabinetry. A spiral staircase leads to the upper level, while a seating area with a wooden table and chairs overlooks a large window showcasing ocean views. Soft lighting is provided by a woven pendant lamp.

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!

Superhost

The image captures a spacious pavilion area overlooking the inviting swimming pool and ocean. Comfortable seating arrangements are visible, surrounded by palm trees. Umbrellas provide shade, and guests are seen enjoying the pool area against a backdrop of bright blue skies and ocean views.

4.82 out of 5 average rating, 99 reviews

Luxury Wailea Remodel - Beachfront Community

DanielRating, 5 stars4 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.

4.86 out of 5 average rating, 14 reviews

Apartment in Kihei

Remodeled ground floor Kihei condo, walk to beach

JahairaRating, 5 stars1 month ago

We went to Hawaii for the first time and found the best place to spend our 5 wonderful nights. The condo was very clean and cozy, it had everything we needed. Without a doubt, I would stay with them again. Thank you very much for such wonderful hospitality. God bless you.

4.96 out of 5 average rating, 76 reviews

Modern Renovated Palms at Wailea Condo!

FranziskaRating, 5 stars4 weeks 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.

4.98 out of 5 average rating, 46 reviews

Stunning Remodel I Kamaole Sands 5-207

KayleighRating, 5 stars2 weeks ago

This condo was well maintained and in a nice, convenient location! Had everything we needed. Things I really liked included two bathrooms/showers, gated property, family-oriented, elevator access to the unit, everything for the beach available within the unit, and the communicative and friendly host, Robert. I also greatly appreciated the ease of the checkout process. I highly recommend this condo and hope to stay here again!

An aerial view captures the lush landscape of Wailea Ekolu Village, featuring neatly arranged condominiums surrounded by tropical greenery. A swimming pool is situated in the center, with sunny blue water reflecting the sky. The ocean and distant mountains create a scenic backdrop.