Beachfront holiday rentals in Wailea

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, 191 reviews

Stunning Ocean Views -November Specials $175

*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, 204 reviews

Mana Kai 608: Oceanfront Remod! Summer now OPEN!

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!

Two lounge chairs are positioned on a sun-drenched patio, overlooking a vibrant garden. In the background, a majestic tree provides shade, while distant mountains and the ocean create a serene backdrop under a clear blue sky.

4.98 out of 5 average rating, 162 reviews

Ocean view and beach by Wailea

Infants and children welcome! Ocean views, beach across the street. Large lanai. Indoor and outdoor dining. Large bedroom, king bed, ensuite, east facing second lanai off bedroom. Guest bathroom living room. Double height single air mattress, pac n play, high chair. Comfortable and quiet split system A/C. Toys, beach wagon, umbrellas, beach chairs, boogie boards, beach towels provided. Close to shops and restaurants. Tennis courts and two pools in complex. Reserved parking by front door.

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, 126 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.

Superhost

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

4.87 out of 5 average rating, 123 reviews

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 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, 140 reviews

Stunning Ocean Views · Steps to Beach · Comfort

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, 234 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 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, 176 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

SPECTACULAR OCEAN AND SUNSET VIEWS, including outer islands from the living room and lanai. You'll enjoy drinks in the evening watching the incredible sunsets. The condo has been totally redecorated and upgraded. The kitchen and bathroom have maple cabinets and elegant granite counter tops. There is a comfortable king size bed, a well-stocked kitchen, central AC, with all new bamboo floors throughout, and a new washer / dryer. The Condo is owned and maintained by Maui residents.

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, 108 reviews

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

Aloha and welcome to your Maui escape! 🌺 This newly remodeled coastal-modern condo in Kihei is just a short walk to world-class beaches. Enjoy upgraded interiors with marble counters, walk-in showers, LED mirrors, SMART TVs, and A/C in every room. Step onto the lanai to take in lush garden views—perfect for morning coffee or sunset cocktails. The resort features two pools, hot tubs, tennis courts, and BBQ grills. Whether you're relaxing or exploring, your Maui getaway starts here!

4.96 out of 5 average rating, 138 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 beachfront rentals in Wailea

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Hotel room in Kahului

4.64 out of 5 average rating, 14 reviews

Kahului Bay Dream - Perfect for Families | Pool

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 wooden deck is furnished with a table and several patterned chairs, facing a lush garden with palm trees. The ocean is visible in the background, highlighting a sunset that casts warm colors across the sky.

Townhouse in Kihei

4.92 out of 5 average rating, 87 reviews

Maui Beach House

A private lanai features a round dining table with woven chairs, overlooking the ocean at sunset. Palm trees frame the view, while soft colors of the sky transition from blue to orange. The tranquil scene is enhanced by the calm water reflecting the fading light.

Beautiful Top Floor Oceanfront Condo with A/C!

4.86 out of 5 average rating, 7 reviews

A cozy sleeping area features a stylish mural of blossoming branches against a deep blue wall. A spacious bed is adorned with light-colored pillows and a textured blanket. A bedside table holds a lamp, accompanied by a small fridge nearby.

Flat in Kihei

Adorable Romantic Studio

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, 4 reviews

Breathtaking Location-Sugar Beach #129

Superhost

A modern kitchen is presented with dark wood cabinetry and granite countertops. Stainless steel appliances, including an oven and microwave, complement the space. A view of the adjacent dining area is visible through an open layout, with natural light filtering in from the windows.

Home in Lahaina

4.56 out of 5 average rating, 88 reviews

Walk to Front St., ALOHA CABANA, "PEOPLES CHOICE"

Hotel room in Kahului

New place to stay

4 Garden View Rooms, Enjoy Walk to the Beach

Beachfront home rentals with a pool

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

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 welcoming living area features modern furnishings and a colorful area rug. Large glass doors provide a view of palm trees and the outdoors, while a 65" Smart TV is positioned on a sleek media console. Natural light fills the space, enhanced by a ceiling fan.

4.96 out of 5 average rating, 234 reviews

OCEAN VIEW/FRONT A/C Modern 2Bed/2Bath Penthouse

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, 104 reviews

Oceanfront! Sugar Beach Resort Penthouse with a/c

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, 58 reviews

Gorgeous Condo in Wailea Ekahi Village!

A spacious lawn area features several lounge chairs and tables, surrounded by palm trees. Red umbrellas provide shade over some seating, while the ocean is visible in the background. The shoreline is framed by gentle waves under a bright blue sky.

4.87 out of 5 average rating, 425 reviews

Can be 2 Units! Modern On Beach Ocean View Balcony

An expansive garden view is presented, featuring lush greenery and vibrant flowering plants. Palm and tropical trees are visible, framed by a clear blue sky. The peaceful landscape invites a sense of tranquility and connection with nature.

4.96 out of 5 average rating, 91 reviews

Maui Retreat Ekahi 50F -All YOU Need!

A private patio features a round dining table and two chairs, offering views of palm trees and nearby streets. The ocean is visible in the distance, with vehicles passing along the road. The light-colored flooring complements the outdoor setting.

4.89 out of 5 average rating, 193 reviews

Island Surf #206 Your South Maui Gem is here

Private beachfront home rentals

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, 86 reviews

Oceanfront Maui Ohana: Best Beach & Wow Sunsets

A modern kitchen features white cabinetry and stainless steel appliances, including a microwave and refrigerator. A large window provides views of palm trees and the ocean. Four bar stools are positioned along the countertop, creating an inviting space for casual meals.

4.96 out of 5 average rating, 55 reviews

Newly Remodeled-AC-Ocean Views-Modern Finishes

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, 82 reviews

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

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, 78 reviews

Wailea Elua 1101 - Beachfront Section - Ocean View

The expansive pool area is surrounded by swaying palm trees, showcasing a vibrant sunset sky. The pool features a unique shape, with lounge chairs and umbrellas arranged nearby, inviting relaxation. The oceanfront pavilion offers covered seating and dining options, enhancing the outdoor experience.

5 out of 5 average rating, 15 reviews

Wailea Ekahi Gem! | 2 Beds | Steps to Beach & Pool

A bright living area features large glass doors showcasing ocean views and palm trees swaying in the breeze. The room includes a cozy couch, wooden coffee table, and a modern TV stand, with elegant dining furniture positioned nearby. Tropical decor elements add a touch of island charm.

5 out of 5 average rating, 5 reviews

Maui Resort Rentals: Polo Beach Club 608

4.95 out of 5 average rating, 76 reviews

Gorgeous Ocean View Condo steps to the beach

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.