Condo holiday rentals in Wailea

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, 199 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.

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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.

4.99 out of 5 average rating, 233 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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4.97 out of 5 average rating, 116 reviews

Large 1BR, Palms at Wailea, Pool, Walk to Beach

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!

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A modern kitchen and dining area are visible, featuring a round table set for four with woven placemats and plates. Stainless steel appliances are arranged in the sleek kitchen design, while large sliding glass doors open to reveal views of lush gardens and the ocean beyond.

4.96 out of 5 average rating, 185 reviews

A.R.A Retreats: Big Blue Pacific

Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing 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 and when the sun goes down, watch your favorite shows on on our smart tvs!

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4.96 out of 5 average rating, 149 reviews

Ekahi Ocean Studio: Wailea Paradise by the Beach

Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

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An open-concept living area features a spacious dining table with blue upholstered chairs, complemented by a calming color palette. The kitchen, equipped with modern appliances, is visible in the background, while natural light fills the space through large windows.

4.95 out of 5 average rating, 155 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!

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A private lanai features a round table with two high-backed chairs, offering panoramic views of the ocean and surrounding coastline. Lush palm trees and sandy beach are visible below, under a bright blue sky with scattered clouds.

4.96 out of 5 average rating, 143 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Wake up to breathtaking, panoramic north-to-south ocean views from the Mana Kai’s top-floor penthouse level, just steps from Keawakapu Beach—2.75 miles of Wailea’s longest sandy shoreline at your door. Snorkel, swim, paddleboard, body surf, or watch whales from your private 200 sq. ft. lanai. This spacious 2-bedroom, 2-bath oceanfront suite sleeps four, with two king beds and a beautifully updated private bathroom for each bedroom.

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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.

4.95 out of 5 average rating, 200 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.

4.99 out of 5 average rating, 154 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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4.83 out of 5 average rating, 191 reviews

Last Minute Deal! Wailea Condo Oceanfront Complex

Step into your own private tropical oasis in this fabulous Wailea condo! This adorable 792 square foot, ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This lavish condo boasts an open and airy living space you will love with AC throughout. Relax on the remarkable lanais with a table with seating for four.

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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.

4.96 out of 5 average rating, 202 reviews

Wailea Gem-Remodeled Ocean View

Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.

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4.98 out of 5 average rating, 208 reviews

Ocean/Golf Course Views, Tropical Resort in Wailea

Breathe in and exhale slowly while gazing at the beautiful ocean, serene greenery and misty mountaintops. Make the most of a country-club setting by lounging on sun decks and swimming in heated pools. Retreat to an updated condo to unwind and fall asleep in a comfy bed. (This unit is suitable for a maximum of four (4) guests. Infants of any age are counted as guests.)

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Popular amenities for Wailea condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.93 out of 5 average rating, 127 reviews

Spacious 3bd on Golf Course I Grand Champions 105

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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, 106 reviews

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

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A view from the second floor displays lush tropical landscaping with palm trees and vibrant greenery. The ocean is visible in the background, framed by a clear blue sky. The scene offers a serene outdoor ambiance typical of Wailea.

4.88 out of 5 average rating, 133 reviews

Luxury Condo w/wide Ocean View (Palms at Wailea)!

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A modern open-concept living area features a round wooden dining table in the foreground, surrounded by white chairs. In the background, a well-equipped kitchen displays sleek appliances. A cozy seating area with light-colored couches is visible, complemented by natural lighting from large sliding glass doors.

4.93 out of 5 average rating, 214 reviews

StunningReno*Palms in Wailea Condo-Beach*Golf*Pool

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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, 131 reviews

Upscale and Elegant Vistas

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4.98 out of 5 average rating, 126 reviews

A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.

Condo in Maalaea

Coastal Dream Oceanfront Condo!

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4.99 out of 5 average rating, 135 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

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4.98 out of 5 average rating, 195 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

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Pet-friendly condo rentals

A private lanai features a round glass-top table surrounded by colorful cushioned chairs. Lush tropical plants and palm trees create a serene garden view, while a clear blue sky adds brightness to the scene.

4.95 out of 5 average rating, 115 reviews

Walk to Kam Beach! King Bed, Pools, Pet Friendly.

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A serene beach scene at sunset showcases soft hues of orange, pink, and purple in the sky. Silhouetted figures walk along the shoreline, while a tall palm tree stands nearby, framing the tranquil landscape and creating a sense of calm.

4.84 out of 5 average rating, 432 reviews

Ocean View Superior Deluxe - 200

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Superhost

4.86 out of 5 average rating, 108 reviews

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

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4.95 out of 5 average rating, 40 reviews

Lava Shack | 1BR • 2ACs • 250 Steps to Kam 2 Beach

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A sandy path leads from lush greenery to a serene beach. Palm trees sway gently in the foreground, framing views of calm blue waters and distant islands under a clear sky with scattered clouds.

4.98 out of 5 average rating, 54 reviews

*Rare Find* Quiet Ocean View Condo in Sunny Kihei

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A living area is depicted with large sliding glass doors that open to a balcony view of the ocean and palm trees. A ceiling fan rotates gently above a comfortable seating arrangement that includes a light-colored sofa and two armchairs. A wooden coffee table is positioned in front.

4.95 out of 5 average rating, 42 reviews

High-Floor Island Surf | AC | Walk to Beach

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4.95 out of 5 average rating, 20 reviews

Condo in Maalaea

Steps to Beach Sand & Surf

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A modern living area features a comfortable sofa and a chair, with a flat-screen TV situated on a wooden media console. Large sliding glass doors provide access to a private lanai, with views of palm trees and the ocean in the background.

4.94 out of 5 average rating, 81 reviews

Oceanfront renovated luxury-best location! SBR 404

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Condo rentals with a pool

5.0 out of 5 average rating, 6 reviews

Wailea Ekolu 1204 - Modern, Ocean View, Split AC !

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A modern kitchen area is highlighted by a long island countertop with bar seating for four, featuring natural wicker stools. Pendant lighting with a straw-like design hangs above. Large windows provide views of lush greenery, enhancing the space's openness and connection to nature.

4.94 out of 5 average rating, 67 reviews

Aloha Moon - The Honeymoon Hideaway

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A spacious bedroom features a wooden bed with plush bedding in soothing colors. Artwork is displayed above the bed, and large sliding glass doors open to a private lanai, showcasing tropical greenery. Natural light brightens the room, enhancing the tranquil atmosphere.

4.98 out of 5 average rating, 50 reviews

Tropical Escape to Wailea with Stunning Oceanview

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5.0 out of 5 average rating, 24 reviews

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

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4.94 out of 5 average rating, 67 reviews

Stunning Wailea 2/2, AC, Upper Fl, walk to beach

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A spacious living room is presented with comfortable seating options, including a sofa and decorative chairs. Natural light floods the area through large windows, highlighting the neutral color palette. A wooden coffee table is centered on a textured rug, offering a cozy gathering space.

4.94 out of 5 average rating, 86 reviews

Wailea Hidden Gem

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An expansive view of the ocean is captured from the second-floor lanai, featuring lush greenery and palm trees in the foreground. The horizon meets the clear blue sky, framing gentle waves lapping at the shore. Nearby resort buildings are visible, complementing the serene landscape.

5.0 out of 5 average rating, 9 reviews

Beach Front Wailea, Full Ocean View A/C, ELUA102

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A scenic view of the beachfront property showcases lush green lawns and swaying palm trees near the ocean. The sandy beach lies just beyond the rocky shore, inviting guests to enjoy the coastal beauty and tranquility of the Wailea Elua Village.