Waterfront holiday rentals in Wailea

4.96 out of 5 average rating, 135 reviews

Spacious S. Kihei Suite New A/C across from Kam 3

This spacious suite is perfect a relaxing stay for two. Brand new split system A/C in bedroom & living room to keep you cool. Peak-a-boo ocean views from the suite with glimpses of Kahoolawe. Located in S. Kihei across from one of the BEST beaches on Maui, Kamaole Beach III and steps from the Kihei Boat Ramp. Walk to shops and restaurants in South Kihei. Keawakapu Beach and Wailea is just minutes away. Choose from 2 pools or play a round of tennis or pickle ball. Large lawns and BBQ areas.

4.99 out of 5 average rating, 130 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

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.

4.98 out of 5 average rating, 115 reviews

Coastal Dream Oceanfront Condo!

Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

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, 221 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, 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 Manager in Maui, Tracy O'Reilly to take amazing care of you!

An outdoor dining area features a glass table and white chairs, situated on a balcony with a view of the ocean. Palm trees frame the scene, and distant mountains can be seen across the water, creating a serene coastal atmosphere.

4.91 out of 5 average rating, 140 reviews

Full Ocean- Full Sunsets- Beaches at Royal Mauiian

Hawaii License: T-174-283-2640 Full ocean & beach front - all year sunsets. Royal Mauiian - Highly sought location in S. Kihei. Nicely done 1 BR - 1 BTH Nicely furnished, very streamlined open feel. Walk to restaurants, steps to Kam 1 beach, close to shops & activities. Rent a paddleboard, buy Hawaiian memorabilia, or shop at Harvest Moons - close by. Split Air in Bedroom & Living Area. Fully equipped kitchen. In Unit Laundry GET & TAT tax total of 18.5% included in final price.

A modern kitchen features sleek white cabinetry and a spacious island, with a view of the ocean visible through large glass sliding doors. Natural light fills the room, and tropical décor adds a welcoming touch, enhancing the seamless transition to the outdoor space.

4.95 out of 5 average rating, 108 reviews

Ocean Front Paradise! Quiet Romantic!

THERES NO PLACE LIKE MAUI! OCEANFRONT condo greets you with endless ocean views, open floor plan and the feeling you have just arrived in Heaven! Step out onto the private lanai and you are captivated by the soothing sound of the waves, warm sunny breezes and turtles everywhere! You deserve the BEST and this home offers it! Located in a perfect location far from the maddening crowd yet walking distance to restaurants, shopping, nightlife, and sightseeing tours. APN2380140110057000

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.

4.96 out of 5 average rating, 166 reviews

Stunning Ocean Views

Welcome to our slice of paradise in Maui and enjoy breathtaking 180° ocean views . Located just steps from the sandy Kamaole 1 Beach and a short stroll from vibrant restaurants and bars, our chic coastal-modern condo is the perfect spot for a beach getaway. Condo features all the amenities you need for a comfortable stay, including A/C in all rooms, a luxurious king bed, high-speed internet, fully equipped kitchen and a private lanai to watch sunsets. Your Maui adventure starts here

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, 263 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 balcony table is set with a bottle of wine and two glasses, overlooking lush palm trees and an ocean view. The space is bright and airy, creating a welcoming atmosphere complemented by a calm beach landscape in the background.

4.96 out of 5 average rating, 165 reviews

Top Floor Ocean Views | Beach & Restaurant Access

As Maui heals, the community welcomes visitors to enjoy this beautiful island. Your presence will be a great way to give back and support local businesses. We are happy to host you :) Views From the Six is a gorgeous sixth-floor, penthouse condo in the perfect location. Enjoy unobstructed oceanfront views, a 2 min walk to the beach, and delicious food options nearby. ★ Panoramic oceanfront views ★ Walk to beach, food trucks, surf school ★ Resort amenities (beach gear, toiletries)

A serene landscape view features tropical greenery and palm trees leading to the ocean. Sun umbrellas are visible along the shore, providing shade, while calm blue waters stretch into the distance. Lush foliage surrounds the area, enhancing the tranquil outdoor environment.

4.96 out of 5 average rating, 145 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.

A scenic outdoor space features a table set for dining, overlooking a vibrant green lawn and an expansive ocean view. Nearby, comfortable seating invites relaxation. The kitchen area is equipped with modern appliances, while a stylish clock adorns the wall.

4.93 out of 5 average rating, 153 reviews

Oceanfront Getaway, Brand New, Steps To Beach

Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.

A bright living area is featured, showcasing a red sofa adorned with cream-colored pillows. A colorful artwork is displayed above the couch. A light wooden coffee table sits in front, with a magazine resting on top, next to a lamp and a small side table.

4.96 out of 5 average rating, 138 reviews

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

Hale Kamaole: 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:18.71% Hawaiian Transient Tax

Popular amenities for Wailea waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.85 out of 5 average rating, 139 reviews

Beautiful Studio Oasis Maui Banyan

A welcoming living area features a brown leather sofa adorned with colorful pillows. A wooden coffee table sits in the center, accompanied by a remote and decorative items. Natural light enters through sliding glass doors, enhancing the cozy atmosphere.

4.92 out of 5 average rating, 212 reviews

100 steps from the beach! Tranquil Seaside Oasis

A balcony setup features a solid wood dining table accompanied by two wooden chairs with cushions. Panoramic ocean views are framed by swaying palm trees, and a vase with tropical flowers is positioned on the table, enhancing the outdoor dining experience.

4.9 out of 5 average rating, 140 reviews

Sugar Beach Resort #532 - Maui HI

The modern kitchen features white cabinetry and a central island with a stove. Light wood flooring extends into the open living area, which includes a comfortable couch and a coffee table. Large windows allow natural light and offer views of greenery outside.

4.93 out of 5 average rating, 109 reviews

Steps to Charley Young Beach • Remodeled• Pool •AC

4.88 out of 5 average rating, 207 reviews

2BR Oceanview | Sleeps 5 | Beach, Pool, Hot Tub

Tall palm trees frame a view of a serene coastline at dusk, where gentle waves meet the shore. The scene includes a hammock suspended between two trees, and soft pastel hues illuminate the sky, transitioning from light blue to warm pink. A green lawn completes the tranquil atmosphere.

4.91 out of 5 average rating, 132 reviews

Charley's Hideaway (Oceanfront)

A cozy living area features a sofa and coffee table, illuminated by natural light through large sliding glass doors. An outdoor seating area overlooks a tropical garden, with BBQ grills available nearby. A view of the community pool and palm trees adds to the relaxing atmosphere.

4.96 out of 5 average rating, 111 reviews

Walk to Everything- Beach, Eat, Shop, Relax!

An outdoor dining area is presented with a glass table surrounded by four chairs. Lush greenery is visible in the background, complemented by tropical plants. A small barbecue grill is located off to the side, enhancing the inviting atmosphere of the private patio.

4.8 out of 5 average rating, 125 reviews

Remodeled, 40% off, steps from the beach, private

Waterfront house rentals

The kitchen and dining area feature modern appliances and a large wooden table surrounded by a built-in bench. Natural light enters through the window, illuminating the granite countertops and stylish cabinetry, while a beach-themed artwork complements the tropical surroundings.

4.89 out of 5 average rating, 118 reviews

Chic Villa 2 | Modern Vibes by the Ocean

A spacious living area showcases natural wooden elements, with a light-colored bamboo sofa and matching chairs. Large glass doors frame a stunning seaside view, allowing soft light to illuminate the room. A ceiling fan provides ventilation, complementing the relaxed ambiance of the space.

5 out of 5 average rating, 23 reviews

Beautiful Beachfront Townhouse !

A refreshing swimming pool is surrounded by lounge chairs, set among tropical palm trees. The water's surface reflects the nearby buildings and sky, creating a serene atmosphere. The pool area is designed for relaxation and enjoyment.

4.97 out of 5 average rating, 72 reviews

Centrally located and steps to the beach!

4.98 out of 5 average rating, 53 reviews

A relaxed living area features a blue sectional sofa with red and white decorative pillows. A coffee table sits in front, and a work desk is positioned near a glass sliding door that provides views of the ocean and surrounding palm trees.

Home in Maalaea

Maalaea Kai 307 - Maui Prime Oceanfront

4.66 out of 5 average rating, 264 reviews

Aerial view of the oceanfront beach house positioned near a rocky shoreline. Waves break across the water, and surfers can be seen in the distance. Solar panels are installed on the roof, indicating a focus on sustainability.

Home in Wailuku

Charming Direct Oceanfront North Shore Beach House

An outdoor lanai features a wooden table with two matching chairs, offering a view of manicured lawns and tennis courts. Lush greenery and palm trees frame the scene, while the ocean can be seen in the distance under a clear blue sky.

4.8 out of 5 average rating, 10 reviews

Remodeled One BD Ocean, AC,wifi, pool D202

A patio area features a round table with two chairs, decorated with a small potted orchid and a box of treats. Beyond the table, a lush green lawn stretches toward the ocean, with a striking weathered tree adding character to the peaceful view.

4.93 out of 5 average rating, 27 reviews

Aloha Aku Hula Suite – Find Peace by the Shore

A dining area features a round wooden table surrounded by four wicker chairs. Large sliding glass doors provide access to an outdoor space with ocean views and natural light. The kitchen area is partially visible, showcasing wooden cabinetry and coastal décor.

4.97 out of 5 average rating, 68 reviews

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC

Waterfront condo accommodation

4.89 out of 5 average rating, 9 reviews

Private Lanai · Steps to Beach · Resort Pools · Bo

A scenic ocean view from the private lanai showcases swaying palm trees against a bright blue sky. The manicured lawn below invites relaxation, while the tranquil water glistens in the sunlight, creating a serene atmosphere.

4.92 out of 5 average rating, 99 reviews

Oceanfront Maui Ohana: Best Beach & Wow Sunsets

An oceanfront view is captured from the lanai, showcasing gentle waves and a serene coastline. Lush greenery and vibrant landscaping can be seen below, accompanied by swaying palm trees under a clear blue sky. The horizon features distant islands and a calm sea.

4.96 out of 5 average rating, 137 reviews

Endless Waves, Spectacular Oceanfront views!

Silhouetted palm trees frame a golden sunset over the ocean, with the sun partially obscured by clouds. Gentle waves reflect the warm light, and grassy areas are visible in the foreground, contributing to a serene coastal scene.

4.94 out of 5 average rating, 225 reviews

Stunning Ocean Views - June Specials $199

5 out of 5 average rating, 4 reviews

Beautifully Updated Oceanview Condo in Wailea

A scenic view reveals the ocean with soft waves meeting sandy shores, framed by palm trees. In the foreground, tennis courts are visible against a backdrop of rolling hills, showcasing lush greenery under a clear blue sky.

4.97 out of 5 average rating, 113 reviews

Maui is Open - Come Support the Locals

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, 92 reviews

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

A private lanai features a table set for two with chairs, overlooking landscaped grounds and palm trees. The Pacific Ocean is visible in the distance, along with a glimpse of the resort building.