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Waterfront vacation rentals in Wailea

Find and book unique waterfront accommodations on Airbnb

Quick stats about waterfront rentals in Wailea

  • Total vacation rentals

    Explore 340 vacation rentals in Wailea

  • Nightly prices starting at

    Wailea vacation rentals start at $171 CAD per night before taxes and fees

  • Verified guest reviews

    Over 6,470 verified reviews to help you choose

  • Family-friendly vacation rentals

    230 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    330 properties feature pools

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

  • Wifi availability

    340 of Wailea vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wailea rentals

  • 4.8 Average rating

    Wailea stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated waterfront accommodations in Wailea

Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.

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Top guest favourite
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.
Condo in Wailea

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

BeachViewAccess

4.97 out of 5 average rating, 108 reviews
Top guest favourite
Condo in Wailea

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.

BeachViewBackyard

4.99 out of 5 average rating, 137 reviews
Top guest favourite
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!

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.

BeachViewWalkability

4.98 out of 5 average rating, 128 reviews
Top guest favourite
This image showcases a balcony view overlooking a vibrant scene filled with palm trees and lush greenery. A sparkling pool can be seen in the distance, and the ocean glimmers under a clear blue sky. Sunlight filters through the palm fronds, enhancing the serene atmosphere.
Condo in Kihei

The Pi Life: Ocean Views · 99 Steps from the Beach

We're Airbnb Superhosts w/ 100+ 5 Star Reviews. Welcome to The Pi Life! A cute and cozy condo, with gorgeous oceans views, that's 99 steps from the beach. We have everything you need for a perfect Maui vacation, including: ★ Ocean Views ★ Resort Amenities ★ Beach & Restaurant Access And, perhaps most importantly, we're deeply caring and responsive hosts ❤️ Our goal is to make your experience as fun, relaxing, and comfortable as possible. So please let us know how we can be helpful :)

BeachViewIndoor spaces

4.97 out of 5 average rating, 174 reviews
Top guest favourite
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.
Condo in Wailea

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, come stay with us! We have the best PM in Maui, Tracy O'Reilly, to take amazing care of you!

ViewBeachLaundry

4.99 out of 5 average rating, 234 reviews
Top guest favourite
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.
Condo in Kihei

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.

BeachViewAir conditioning

4.91 out of 5 average rating, 151 reviews
Superhost
A spacious outdoor lanai features a dark dining table surrounded by several chairs, offering breathtaking views of palm trees and the sandy beach. The ocean stretches out in the distance under a clear blue sky, creating an inviting atmosphere for relaxation.
Condo in Wailea

Beach Dream Suite-Mana Kai Maui Resort

Unforgettable ocean views are yours at the amazing Mana Kai Resort! One of One, directly on one of Maui’s best beaches! Our popular suite boasts serene decor, quality linens, fine finishes, tasteful furnishings, equipped kitchen w/island, AC, WiFi, Smart TV, lanai, free parking! Features combined with all there is to do equals vacation success! A state-of-the-art fitness center and business office on lower floor. Heated pool, lounges+tables. Note: The BEDROOM SPACE is OPEN TO LIVING AREA.

BeachViewAccuracy

4.85 out of 5 average rating, 107 reviews
Guest favourite
Condo in Wailea

Oceanfront Maui Ohana: Best Beach & Wow Sunsets

Aloha and Welcome to Oceanfront Maui Ohana! Relax at this tropical retreat, perfectly situated within a short walk to Wailea in the Kihei Surfside Resort. Boasting stunning ocean views, direct access to Maui’s best beach, Keawakapu, and a sprawling lawn with a heated oceanside pool, perfect for sunsets and whale watching, this condo offers the ultimate Hawaiian getaway. With modern comforts, thoughtful family-friendly amenities, and a location second to none, your dream vacation awaits!

ViewBeachCleanliness

4.92 out of 5 average rating, 100 reviews
Top guest favourite
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.
Condo in Kihei

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.

ViewBeachDecor

4.99 out of 5 average rating, 284 reviews
Top guest favourite
Condo in Wailea

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.

ViewBeachKitchen

4.96 out of 5 average rating, 149 reviews
Guest favourite
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.
Condo in Maalaea

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.

ViewBeachComfort

4.93 out of 5 average rating, 168 reviews
Guest favourite
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.
Condo in Kihei

Maui is Open - Come Support the Locals

This beautifully upgraded penthouse condo, with stunning ocean and majestic mountain views, is centrally located in Kihei, which is widely considered to have the best beaches and weather on Maui. World-class restaurants, trendy food truck parks, and favorite local haunts are just a stone's throw away. Do you take advantage of the unlimited number of close-by activities, or just relax on the lanai and enjoy the view? It's your call!

ViewBeachHot tub

4.97 out of 5 average rating, 121 reviews

Popular amenities for Wailea waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Guest favourite
An oceanfront view is captured from the lanai, showcasing gentle waves lapping at a sandy beach below. Lush palm trees line the shore, swaying in the breeze under a bright blue sky with scattered clouds.
Apartment in Kihei

Ocean Front With Ocean View! AC, King Bed, 2 Bath!

ViewBeachPool

4.93 out of 5 average rating, 164 reviews
Guest favourite
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.
Apartment in Kihei

Charley's Hideaway (Oceanfront)

BeachViewAmenities

4.91 out of 5 average rating, 136 reviews
Superhost
An inviting private balcony features comfortable seating, including a round, woven chair and rattan seats with cushions. A telescope is positioned for views of the ocean and adjacent landscaped garden, showcasing palm trees swaying in the breeze and a glimpse of the heated pool.
Apartment in Kihei

The Whale Watch 208-Oceanfront Kihei

BeachViewQuiet

4.88 out of 5 average rating, 142 reviews
Guest favourite
A modern living area features a comfortable sofa and armchairs arranged around a wicker coffee table. A large wall-mounted television displays a scenic beach image. Floor-to-ceiling glass doors provide views of the ocean and tropical landscape, allowing natural light to fill the space.
Apartment in Kihei

Upscale Oceanfront Penthouse Vistas

ViewBeachValue

4.94 out of 5 average rating, 107 reviews
Top guest favourite
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.
Apartment in Kihei

Steps to Charley Young Beach • Remodeled• Pool •AC

BeachViewCondition

4.93 out of 5 average rating, 123 reviews
Top guest favourite
Apartment in Kihei

Family Oceanview | North Kihei Beach Access + Pool

ViewBeachParking

4.89 out of 5 average rating, 216 reviews
Guest favourite
The kitchen area is designed with light cabinetry and countertops, showcasing modern appliances. A dining table with dark chairs occupies the center, adorned with a fruit basket. Natural light fills the space, highlighting the open layout that connects to adjoining areas.
Apartment in Kihei

Premier Poolside Villa at Kihei Bay Vista (D202)

BeachViewAir conditioning

4.91 out of 5 average rating, 131 reviews
Guest favourite
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.
Apartment in Kihei

Stunning Luxury Oceanview Condo

ViewBeachSleep quality

4.9 out of 5 average rating, 193 reviews

Waterfront house rentals

Guest favourite
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.
Home in Kihei

Chic Villa 2 | Modern Vibes by the Ocean

ViewBeachLaundry

4.88 out of 5 average rating, 121 reviews
Guest favourite
A balcony table is adorned with a glass vase filled with colorful flowers, offering a vibrant contrast to the wooden surface. In the background, sweeping views of the ocean and lush palm trees are visible against a backdrop of distant mountains.
Home in Kihei

Stunning Ocean Two Bd Corner Condo,AC,Pool D301

ViewBeachGetting around

4.89 out of 5 average rating, 27 reviews
Superhost
Home in Kihei

Oceanfront Stunner with Pickleball Gear!

BeachViewAccuracy

4.74 out of 5 average rating, 128 reviews
Superhost
Home in Kihei

Bare Feet Retreat 515B:Walk everywhere + Strong AC

ViewBeachValue

4.64 out of 5 average rating, 287 reviews
Top guest favourite
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!

BeachViewQuiet

4.97 out of 5 average rating, 73 reviews
Top guest favourite
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

BeachViewLong stay

4.98 out of 5 average rating, 57 reviews
Guest favourite
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

ViewBeachCleanliness

4.93 out of 5 average rating, 29 reviewsA 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.
Home in Kihei

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC

ViewBeachLaundry

4.97 out of 5 average rating, 70 reviews

Waterfront condo rentals

Guest favourite
A clear view of a swimming pool is presented, surrounded by lounge chairs and tropical greenery. Palm trees frame the scene, with the ocean visible in the background under a bright blue sky dotted with clouds.
Condo in Kihei

3BR spacious Condo with Ocean View in top location

BeachViewHot tub

4.93 out of 5 average rating, 200 reviews
Guest favourite
A comfortable living area features a plush sofa adorned with decorative pillows, complemented by a wooden coffee table. Natural light filters in through large sliding glass doors, revealing a view of the outdoor balcony and surrounding landscape, while a television is positioned for easy viewing.
Condo in Wailea

Ocean Views Walking distance to Kam III Beach Park

ViewBeachHospitality

4.84 out of 5 average rating, 108 reviews
Guest favourite
A spacious living area features large windows showcasing ocean views and allowing natural light to fill the room. Comfortable seating is arranged around a central coffee table, with a dining table and chairs visible in the background. Modern ceiling fans are present, and a decorative rug adds warmth to the tiled floor.
Condo in Kihei

Beachfront Top Floor Views - Hale Kai O Kihei 307

BeachViewBathroom

4.92 out of 5 average rating, 301 reviews
Top guest favourite
The living area features a light-toned sofa adorned with decorative pillows, accompanied by a round coffee table. A view of the ocean is visible through floor-to-ceiling sliding glass doors, with tropical greenery framing the scene. A ceiling fan enhances the airy feel of the space.
Condo in Kihei

Stunning Ocean Views

ViewBeachTV

4.97 out of 5 average rating, 181 reviews
Guest favourite
A serene outdoor seating area features a small round table and two chairs, overlooking the ocean with distant mountains under a clear blue sky. Nearby, a cozy indoor space showcases a soft couch adorned with decorative throws, complemented by a light wooden accent table with greenery.
Condo in Maalaea

Oceanfront Spectacular Condo

ViewBeachComfort

4.95 out of 5 average rating, 129 reviews
Guest favourite
A spacious kitchen area features rich cherry wood cabinets and elegant granite countertops. The kitchen island offers ample workspace, while modern appliances are included. To the side, a bright living area with comfortable seating overlooks the ocean, enhanced by sliding glass doors that connect to the outdoor space.
Condo in Kihei

Beachfront Maui Oasis- Fully Remodeled, Beautiful

BeachViewGetting around

4.98 out of 5 average rating, 130 reviews
Top guest favourite
A private beachfront lawn is shown, featuring several lounge chairs arranged on lush green grass. Umbrellas stand nearby, providing shade. A backdrop of palm trees frames the view of the ocean, with gentle waves lapping against the shore under a partly cloudy sky.
Condo in Kihei

Oceanfront Condo on magic Sugar Beach - Ocean View

BeachViewOutdoor spaces

4.93 out of 5 average rating, 225 reviews
Top guest favourite
The modern kitchen features dark cabinetry and a large marble island with seating. Stainless steel appliances, including a refrigerator and microwave, are visible. A bowl of fresh fruit sits on the island, while natural light illuminates the space through ample windows and overhead pendant lighting.
Condo in Maalaea

Makani A Kai A5 beachfront, pool, a/c, w/d

ViewBeachKitchen

4.98 out of 5 average rating, 195 reviews

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$663 CAD$681 CAD$647 CAD$553 CAD$526 CAD$508 CAD$427 CAD$404 CAD$407 CAD$468 CAD$542 CAD$657 CAD
Avg. temp16 °C16 °C16 °C17 °C18 °C18 °C19 °C20 °C19 °C19 °C18 °C17 °C

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