Waterfront holiday rentals in Wailea

A lifeguard tower stands elevated with a warm light glowing from within, framed by the silhouettes of palm trees. The sky is painted in deep purples and oranges, hinting at a picturesque sunset over the ocean.

4.98 out of 5 average rating, 166 reviews

*25% Off-Steps to Beach-AC in Every Room-Remodeled

☆ Are You Confused About Which Airbnb To Choose? We’ve Lowered Our Rates 25% Below Our Closest Competition. Located 160 Steps Away From The 2023 Travelers Choice Award Kamaole Beach Parks. Perfectly Positioned To Enjoy 1.5 Miles Of Beautiful Sandy Beaches With Captivating Views Of Molokini, Kaho'olawe, And Lana'i Islands. Great Restaurants And, Shopping Are All Within Close Walking Distance. You'll Have Quick Access To The Airport, Popular Beaches, Haleakala, The Road To Hana And, More Below...☆

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.

4.96 out of 5 average rating, 194 reviews

Stunning Ocean Views -November Specials $169

*PLEASE NOTE A 14.8% HAWAII STATE TA/GE TAX WILL BE ADDED AND COLLECTED BY THE END OF YOUR STAY** COMPLETELY REMODELED THIS SUMMER IN A COMFORTABLE MODERN-TROPICAL STYLE. THE HIGHEST THREAD- COUNT LINENS AND TEAK THROUGHOUT THIS HIGH STYLED CONDO. HUGE VIEWS FROM THE MODERN KITCHEN, LIVING ROOM AND LANAI All SET IN THE HEART OF KIHEI. FABULOUS LOADS OF BEACH GEAR SURFING LESSONS DOWNSTAIRS BIKE RENTALS DOWNSTAIRS PARKS AND BEACHES ACROSS THE STREET 2 BLOCKS FROM SOME OF KIHEI'S FINEST RESTAURANT

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!

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

4.99 out of 5 average rating, 124 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.

4.87 out of 5 average rating, 124 reviews

The oceanfront pool area is surrounded by swaying palm trees, providing a serene setting. Lounge chairs are arranged around the pool, which features a curved shape, complemented by a tiled deck. The expansive ocean view is framed by a cloudy sky.

Townhouse in Wailea

Wailea Getaway - 2BD - steps to great pool & beach

Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Our Wailea Ekahi Villa is a spacious and private home away from home that makes you feel far from it all yet is still close to everything! Situated above what is widely considered one of the most beautiful beaches in all of Maui Wailea Ekahi is like your own private oasis w/ 35 acres of open grassy spaces, private walk paths and the most AMAZING oceanfront pool to relax in and melt all your worries away!

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.

4.92 out of 5 average rating, 120 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 17.75% included in final price.

A vibrant rainbow arcs over a tranquil ocean, with gentle waves lapping at a sandy beach. The water reflects shades of blue and turquoise, while soft white foam from the waves meets the shore, creating a serene coastline scene.

4.96 out of 5 average rating, 283 reviews

Beauty & the Beach: Remodel+Ocean Vws! A+ Location

Welcome to Beauty & the Beach ~ Now Open 11/27 - 12/26! Beauty & the Beach is hosted by Tracy O’Reilly, a licensed realtor with Airbnb since 2009, earning SUPERHOST status 40+ consecutive times with a proven track record of 1000s of 5-star reviews. OCEAN VIEW, Remodeled, A+ Location, Steps2Beach, Cold AC, directly next door to food truck oasis, Heated Pool w/BBQ Grills!! ~ If your dates aren't available or if you’re traveling with a group, contact Tracy on Airbnb as she manages 16 units.

A modern kitchen is shown with sleek gray cabinetry and stainless steel appliances. An island seating area with two wooden stools is present, topped with a decorative tray and two cups. Pendant lights with blue shades illuminate the space, enhancing the open and functional layout.

4.96 out of 5 average rating, 183 reviews

Renovated Condo | 3 Min Walk to Toes in the Sand!

Welcome to Pacific Pearl — your serene Maui escape just steps from golden-sand Kamaole Beach Park II. Set in the lush, resort-style Maui Banyan complex, this fully remodeled ground-floor condo offers peaceful garden views, a walkable location near dining and shops, and all the comforts of home. Spend your mornings snorkeling, your afternoons lounging by the pool, and your evenings with sunset walks on the shore. Perfect for couples, families, or friends seeking the effortless Maui getaway.

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

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, 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.

4.96 out of 5 average rating, 139 reviews

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.

Flat in Wailea

Wailea Couples Retreat, 300 FT To Keawakapu 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.

Popular amenities for waterfront rentals in Wailea

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

The image captures a serene evening view of the complex, featuring lush greenery and palm trees. Soft lighting from tiki torches illuminates the pathway leading to the pool area, with the ocean visible in the distance against a colorful sunset.

4.91 out of 5 average rating, 177 reviews

Stunning Luxury Oceanview Condo

A brightly lit studio unit showcases a comfortable bed with decorative pillows. The kitchenette area features a compact fridge, microwave, and coffee maker, complemented by wooden cabinets. Large windows with sheer curtains offer a view of the outdoor space, allowing natural light to fill the room.

4.85 out of 5 average rating, 136 reviews

Beautiful Studio Oasis Maui Banyan

A welcome mat featuring the word 'aloha' is positioned at the entrance, overlooking a lush green lawn and the ocean. The sun sets on the horizon, casting warm hues across the sky as it reflects on the water, creating a serene and inviting atmosphere.

4.96 out of 5 average rating, 52 reviews

Oceanfront Ground Floor w/Stunning Sunset Views

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, 180 reviews

100 steps from the beach! Tranquil Seaside Oasis

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.

4.96 out of 5 average rating, 91 reviews

Renovated 1BD/1BA | 3 min Walk to Beach | A/C

4.88 out of 5 average rating, 198 reviews

Oceanview Family Favorite! Whale Season Views!

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, 134 reviews

Sugar Beach Resort #532 - Maui HI

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.

4.9 out of 5 average rating, 118 reviews

Charley's Hideaway (Oceanfront)

Waterfront house rentals

5 out of 5 average rating, 6 reviews

Home in Lahaina

Island-Inspired 2BD Oceanfront ~ Quam Properties

Superhost

A cozy outdoor patio is shown, featuring a round table surrounded by two modern chairs. The view includes well-maintained grassy fields and tall palm trees swaying gently in the breeze, with the ocean in the background under a clear blue sky.

Home in Wailea

Gorgeous Views! - Kihei Surfside #109

5 out of 5 average rating, 17 reviews

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.

Home in Kihei

Beautiful Beachfront Townhouse !

4.94 out of 5 average rating, 17 reviews

The living area features light-colored furniture arranged around a wooden coffee table, with a large wall-mounted artwork depicting a beach scene. A kitchen can be seen in the background, and decorative elements include a ceiling fan and tropical details on the walls.

Home in Lahaina

Oceanfront Napili Shores ~AC

4.97 out of 5 average rating, 62 reviews

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.

Home in Kihei

Centrally located and steps to the beach!

4.97 out of 5 average rating, 39 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 Wailuku

Maalaea Kai 307 - Maui Prime Oceanfront

Superhost

The resort's lush grounds extend toward the ocean, featuring multiple pools nestled among palm trees, highlighted by a vibrant sunset over the water. The building's architecture complements the tropical landscape, while a gentle breeze can be seen rustling the leaves.

Home in Lahaina

Westin Ka'anapali Ocean Resort Villas North- 2bd

4.93 out of 5 average rating, 27 reviews

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.

Home in Kihei

Aloha Aku Hula Suite – Find Peace by the Shore

Waterfront apartment rentals

A contemporary kitchen is presented, featuring sleek white cabinetry and modern stainless steel appliances. A large marbled countertop provides ample space for meal preparation. Two wooden bar stools are positioned at the counter, inviting casual dining. Soft lighting enhances the bright, airy atmosphere.

4.96 out of 5 average rating, 216 reviews

Fully remodeled, Ocean View, 3 mins walk to beach

4.97 out of 5 average rating, 101 reviews

A spacious living area features a large flat-screen TV and a dark brown couch. Open sliding doors reveal a beautiful lanai with a dining table and umbrella, overlooking the ocean and providing panoramic views of the water and distant islands.

Apartment in Wailuku

Dolphin Penthouse at Milowai

A bright living area is shown, featuring a dark leather sofa and decorative cushions. Large windows provide natural light, with views of palm trees visible outside. Blue curtains frame the windows, and a light wooden TV stand holds a flat-screen television.

4.97 out of 5 average rating, 178 reviews

Wailea/Kihei 2Bed 2bath, Beach Shops steps away

A table with two glasses is centrally placed on a private lanai, overlooking the ocean. Palm trees sway gently in the breeze, and the setting sun casts a warm glow across the water, creating a peaceful ambiance.

4.93 out of 5 average rating, 105 reviews

Oceanfront! Sugar Beach Resort Penthouse with a/c

A person stands in the ocean water, silhouetted against a vibrant sunset with shades of orange and gold. Gentle waves lap at the shore, reflecting the warm colors of the sky, while clouds drift above, adding texture to the scene.

4.9 out of 5 average rating, 137 reviews

Incomparable Maui Sunset condo, includes all taxes

A spacious covered lanai is depicted, featuring several white wicker seating options arranged to take in stunning island views. Large windows invite natural light, with tropical palm trees swaying outside and the ocean visible in the distance.

4.83 out of 5 average rating, 102 reviews

Stunning Ocean View Penthouse - Steps to Beach

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, 122 reviews

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

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.