Condo vacation rentals in Wailea

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, 205 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, right on the border of Wailea and Kihei! Our condo is designed 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, stay with us! We have the best Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!

A clear blue pool is surrounded by palm trees, creating a relaxing atmosphere. Lounge chairs are positioned along the deck, offering spots for sunbathing. Umbrellas provide shade for outdoor dining tables nearby, all with a scenic view of the ocean in the background.

4.95 out of 5 average rating, 213 reviews

Maui's Best - Wailea Ekahi 47A

Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

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.

4.99 out of 5 average rating, 127 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and bi-coastal oceanfront views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (806) and includes two-bedroom suites on the world-famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent snorkeling, body surfing, whale watching, scuba diving, paddle boarding, and kayaking literally at your doorstep

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, 301 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

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, 177 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 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, 235 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.

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.

4.96 out of 5 average rating, 112 reviews

Upscale and Elegant Vistas

Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled in September of 2021, no expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

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, 131 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!

A dining table set for four is positioned on the private lanai, surrounded by lush greenery. A bottle of wine sits center stage, accompanied by a plate of fresh fruit and pastries. Bright blue skies provide a serene backdrop.

4.96 out of 5 average rating, 207 reviews

Top 5% Home with King Bed + Steps to Beach & Shops

Exquisitely remodeled top floor condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches, shops & restaurants and lounge in the multiple pools & hot tubs on property with this perfect Hawaiian oasis! Everything (and we mean everything) is fully remodeled. From a peaceful island getaway to your next Hawaiian adventure, Makana Condo is ready for your enjoyment!

Superhost

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.

4.89 out of 5 average rating, 114 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.

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.

4.98 out of 5 average rating, 127 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

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, 178 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.

Popular amenities for Wailea condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

A spacious living area features large windows offering views of the surrounding greenery. The open floor plan includes a dining table set for six, with a central decorative piece. A modern kitchen with stainless steel appliances is visible, complemented by stylish light fixtures and ceiling fan.

4.92 out of 5 average rating, 50 reviews

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

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, 144 reviews

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

A dining area features a circular bar with four woven stools and multi-colored pendant lights overhead. The textured orange walls and bamboo ceiling create a warm ambiance. A small desk with a chair is visible against the wall, along with decorative artwork and shelving.

4.95 out of 5 average rating, 60 reviews

Gorgeous Condo in Wailea Ekahi Village!

A bright and airy living space features vaulted wooden ceilings and large sliding glass doors, opening to a balcony with a garden view. A comfortable seating area is adorned with blue and white accents, while a dining table surrounded by six chairs is visible in the foreground.

4.95 out of 5 average rating, 109 reviews

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

A private lanai offers a breathtaking view of the ocean and sandy beach. Two light-colored chairs with striped cushions are positioned around a small round table, accompanied by two glasses of water. Lush greenery and palm trees frame the serene setting.

5 out of 5 average rating, 177 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

4.97 out of 5 average rating, 92 reviews

Modern Renovated Palms at Wailea Condo!

An outdoor lanai is equipped with a decorative table and six chairs, providing a comfortable area for dining. Lush greenery is visible in the surrounding landscape, alongside sweeping views of the fairway and the ocean in the distance, under a clear blue sky.

4.98 out of 5 average rating, 174 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

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.

5 out of 5 average rating, 75 reviews

Luxe 2bed Wailea, 5-min walk to beach, ocean view,

Pet-friendly condo rentals

A clear view of the ocean is presented from the lanai, framed by swaying palm trees. The expansive sky reflects vibrant shades of blue, while green grounds stretch toward the shoreline, creating a serene coastal atmosphere.

4.79 out of 5 average rating, 273 reviews

Amazing Oceanfront Apartment

A clear swimming pool is surrounded by spacious stone decking, offering lounge chairs arranged neatly under shaded umbrellas. Lush landscaping and palm trees are visible in the background, with a peaceful view of the surrounding hills.

4.6 out of 5 average rating, 30 reviews

Hale Kamaole 106: 1BR Oceanview | Pool

An aerial view of the Island Surf Building in Kihei, highlighting its convenient location near the ocean and Kalama Park. Lush greenery surrounds the building, and various vehicles are parked nearby, indicating a bustling environment. The coastline and blue waters stretch into the distance.

4.93 out of 5 average rating, 30 reviews

High-Floor Island Surf | AC | Walk to Beach

A private balcony is depicted overlooking a lush garden landscape. Two outdoor chairs with striped cushions surround a circular table, while vibrant green foliage and flowering plants add to the tropical setting. Soft sunlight filters through the foliage, creating a serene atmosphere.

4.85 out of 5 average rating, 130 reviews

Resort 2-Bed Studio- Steps to Beach/Shops/Dining

Superhost

A private lanai is showcased with woven seating and a wooden table, offering a view of vibrant green grass that leads to the ocean. Palm trees frame the scene against a clear blue sky, enhancing the relaxing beachside atmosphere.

5 out of 5 average rating, 5 reviews

Breathtaking Location-Sugar Beach #129

An open living area features high ceilings and natural light from large windows. Two upholstered armchairs with floral patterns are positioned near a wooden coffee table. A dining table for four is set next to a well-equipped kitchen, while a spiral staircase leads to an upper level.

4.86 out of 5 average rating, 14 reviews

2BR dog friendly condo with furnished lanai, W/D

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.

4.99 out of 5 average rating, 67 reviews

Oceanfront renovated luxury-best location! SBR 404

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.

4.97 out of 5 average rating, 33 reviews

*Rare Find* Quiet Ocean View Condo in Sunny Kihei

Condo rentals with a pool

A bright living area features sliding glass doors that open to a private lanai with ocean views. Comfortable seating options include a cozy sofa and armchair, complemented by a round coffee table and decorative pillows. Natural light fills the space, creating a welcoming ambiance.

4.98 out of 5 average rating, 142 reviews

Stunning Ocean Views

A modern kitchen is visible, featuring light cabinetry, stainless steel appliances, and a tile backsplash. A round dining table is surrounded by cushioned chairs, while bar stools are positioned at the countertop. The open layout reveals sliding glass doors leading to a covered lanai with tropical views.

4.96 out of 5 average rating, 75 reviews

Gem near Keawakapu Beach - Privacy and Ocean Views

Two comfortable chairs are positioned on a tiled patio, facing a stunning sunset over the ocean. A small glass table is placed between them, holding two red cups. Lush palm trees frame the view, enhancing the tranquil outdoor space.

5 out of 5 average rating, 64 reviews

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

A spacious bedroom features a comfortable bed with a light-colored, art-inspired bedspread. A wooden dresser stands opposite a corner television. Large windows provide views of the surrounding tropical landscape, while soft lighting enhances the serene atmosphere.

4.92 out of 5 average rating, 79 reviews

Wailea Elua 1101 - Beachfront Section - Ocean View

The living area features a comfortable seating arrangement with a rattan sofa and armchair, complemented by a glass-topped dining table surrounded by four chairs. Natural light flows through sliding doors leading to the garden-facing lanai, enhancing the spacious atmosphere.

4.92 out of 5 average rating, 71 reviews

21A Grand Champions 1 Bed - Ulua & Mokapu beaches

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.

4.93 out of 5 average rating, 45 reviews

Aloha Moon - The Honeymoon Hideaway

Superhost

A vibrant tropical landscape features lush greenery and flowering plants, with palm trees swaying gently. The expansive view reveals the azure Pacific Ocean in the distance, framed by the serene backdrop of neighboring low-rise condominiums under a partly cloudy sky.

5 out of 5 average rating, 4 reviews

Gorgeous Elua 1 Bd+2Ba Executive Vacation Condomin

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.