Condo vacation rentals 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, 105 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

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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, 333 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

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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, 167 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.

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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, 197 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, 232 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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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, 154 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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4.89 out of 5 average rating, 148 reviews

*Last Minute Deal*Luxurious*2b/2b OceanView Wailea

This ground floor 1071 square foot unit is situated just above the 11th fairway of the Wailea Blue Course. The living room and master bedroom have private lanais that step out to a relaxing open lawn with sweeping ocean views. Features include AC throughout the property, bamboo floors throughout, brand new tile in the master bathroom, granite counter tops, and cherry cabinets. Tastefully decorated this spacious condo truly has everything you will need!

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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.

4.94 out of 5 average rating, 198 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

4.99 out of 5 average rating, 152 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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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, 209 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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A vibrant sunset is captured over the Pacific Ocean, with clouds in shades of orange and purple. Silhouettes of palm trees frame the foreground, while lush greenery and homes are visible at the edge of the golf course, enhancing the tropical setting.

4.91 out of 5 average rating, 161 reviews

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

Experience the best of Wailea from this rare 3BR/2BA luxury villa, featuring breathtaking views of the Pacific Ocean, Wailea Blue Golf Course and majestic Haleakalā. Spacious enough for families or groups, this exceptional retreat offers all the comforts of home—just a short walk from world-famous beaches, luxury resorts, fine dining and premier shopping.

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Popular amenities for Wailea condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Condo rentals with a pool

4.99 out of 5 average rating, 134 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

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The image captures a vibrant sunset over the ocean, with hues of orange, pink, and purple reflected across the water. Silhouetted palm trees line the foreground, adding a tropical feel. The landscape features rocky shorelines and gentle waves under the colorful sky.

4.96 out of 5 average rating, 142 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

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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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4.96 out of 5 average rating, 149 reviews

Ekahi Ocean Studio: Wailea Paradise by the 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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An aerial view highlights the expansive grounds of Ekahi Village, featuring lush greenery and walking paths. The ocean glistens in the background, creating a coastal ambiance. The unit's location is marked, showcasing proximity to amenities and nearby beach access.

4.95 out of 5 average rating, 103 reviews

Ekahi 22C Toes in the Sand in Under 2 Minutes

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A vibrant sunset casts warm orange and yellow hues over the ocean, with waves gently lapping at the shore. Silhouetted palm trees and lush greenery frame the scene, while rocky outcrops jut into the water, creating a picturesque coastal landscape.

4.99 out of 5 average rating, 187 reviews

Romantic, Luxury Condo with Spectacular Ocean View

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4.97 out of 5 average rating, 114 reviews

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

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Weekly condo rentals

4.96 out of 5 average rating, 237 reviews

King Bed + Pools | Steps to Kamaole Beach

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The spacious living area features a comfortable blue sofa, two accent chairs, and a wooden coffee table. A large window offers views of the balcony and surrounding palm trees, while a vibrant ocean-themed artwork enhances the room's bright interior.

4.95 out of 5 average rating, 102 reviews

Epic View! Lovely 2BR Beach Condo in Kihei/Wailea

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The kitchen area features warm wood cabinetry, a stainless steel refrigerator, and a modern microwave. A spacious countertop provides ample room for meal preparation. Sunflowers are arranged in a vase on the counter. Two wooden stools are positioned at the breakfast bar, adjacent to a round dining table.

4.95 out of 5 average rating, 128 reviews

Luxurious Condo in South Kihei

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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.

4.99 out of 5 average rating, 279 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

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A well-appointed kitchen area features a spacious granite countertop with rich wooden cabinetry. Hanging red pendant lights provide soft illumination. Large windows offer views of lush greenery and the ocean, enhancing the inviting atmosphere of the space.

4.94 out of 5 average rating, 181 reviews

Gorgeous 2 Story Townhouse in Wailea w/ Ocean View

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Superhost

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, 49 reviews

Tropical Escape to Wailea with Stunning Oceanview

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5.0 out of 5 average rating, 23 reviews

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

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4.94 out of 5 average rating, 66 reviews

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

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Pet-friendly condo rentals

A bright living area is showcased with large glass doors offering access to an outdoor space. Comfortable seating is provided by a gray sofa and wicker chairs, accented with blue and patterned cushions. A glass coffee table is placed centrally, complemented by a mounted flat-screen TV.

4.86 out of 5 average rating, 107 reviews

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

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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, 431 reviews

Ocean View Superior Deluxe - 200

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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, 114 reviews

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

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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, 53 reviews

*Rare Find* Quiet Ocean View Condo in Sunny Kihei

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Superhost

A panoramic ocean view captures the vibrant blue waters and lush greenery. Palm trees line the foreground, and the horizon is framed by distant land and clouds, providing a serene backdrop for the surrounding nature.

4.74 out of 5 average rating, 113 reviews

Ocean View! Modern, Walk to Beach, Shops, & Pool!

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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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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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A private lanai offers an inviting outdoor seating arrangement, consisting of a glass-top table surrounded by four chairs. Lush palm trees sway gently in the breeze, framing panoramic ocean views that extend towards the horizon, showcasing tranquil sea tones under a vibrant sky.