Beachfront vacation rentals in Wailea, Wailea-Makena

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Top-rated beachfront rentals in Wailea, Wailea-Makena

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Top guest favorite

The living area features a cozy sectional sofa with textured pillows and a vibrant throw. A green coffee table sits atop a patterned rug, with a large mirror reflecting light. Sliding glass doors lead to an outdoor space surrounded by tropical greenery.

Condo in Kihei

4.99 out of 5 average rating, 152 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.

Top guest favorite

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.

Condo in Kihei

4.99 out of 5 average rating, 119 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

Top guest favorite

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.

Condo in Kihei

4.97 out of 5 average rating, 120 reviews

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

Hale Kamaole: Remodel to be completed Nov 2025. 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:17.712% Hawaiian Transient Tax

Top guest favorite

The spacious studio unit features a king-sized bed adorned with tropical-themed bedding. Soft lighting is provided by bedside lamps. Glass doors open to a shaded lanai with a dining table, revealing a lush garden view and tropical landscaping.

Condo in Kihei

4.99 out of 5 average rating, 115 reviews

Wailea Ekahi Oceanview, Beachfront King Bed Studio

Wailea Ekahi is a luxurious beach front resort offering the best of Maui and sunny Wailea. Unit 16B is a renovated ocean view studio unit with a King sized bed and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens. The resort fronts directly onto Keawakapu beach with miles of golden sand; perfect for walking, swimming and snorkeling. 16B is mid property and a short walk to the beach and one of the 4 pools.

Top guest favorite

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 Kihei

4.99 out of 5 average rating, 187 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on incredible Keawakapu beach! This location is ideal, right on the border of Wailea and Kihei. We have designed our remodel 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 come stay with us! We have hired the best Property Manager in Maui, Tracy O'Reilly to take care of our guests

Top guest favorite

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.

Condo in Kihei

5 out of 5 average rating, 171 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 are newly remodeled with maple cabinets and elegant granite counter tops. There is a very comfortable king size bed, a well-stocked kitchen, central AC, bamboo floors throughout, and a washer / dryer. The Condo is owned and maintained by Maui residents.

Guest favorite

A light-filled living area showcases a beige couch and two patterned chairs, positioned around a wooden coffee table. Floor-to-ceiling windows reveal expansive ocean views, allowing natural light to enhance the space. A ceiling fan adds to the comfort, while a mounted TV is visible on the sideboard.

Condo in Lahaina

4.97 out of 5 average rating, 125 reviews

Beachfront Designer Remodel/AC, 180⁰ Ocean Views

Your Romantic, Island Oasis awaits! Beachfront, luxuriously remodeled hideaway featuring Bali wedding headboard in the dreamy oceanfront bedroom, adding a touch of vintage charm and understated glamor. Watch the Whales breach during their migration while sitting up in bed with a cup of coffee. If you love the sound of the ocean, then this is the place for you. Whales Watch, a secluded corner unit with wrap around 180 ocean views, is located on the 5th floor of Valley Isle Resort in Kahana.

Top guest favorite

An updated kitchen features wooden cabinets and a polished granite countertop. Stainless steel appliances, including a refrigerator, microwave, and oven, blend seamlessly. A double sink and coffee maker are visible, with a backsplash of small, iridescent tiles adding texture.

Condo in Kihei

4.97 out of 5 average rating, 151 reviews

'E Komo Mai' ! 1 Bed/1 Bath in Tropical Gardens

Across the street from Kalepolepo Beach this 621 sqf. condo is nestled in the tropical Zen gardens of Kihei Resort and features a spacious lanai. The one-bedroom unit was completely renovated and has all amenities including a Queen bed in the bedroom and a futon sleeper in the living room, fully equipped kitchen, WiFi, Samsung Smart TV, keyless entry, indoor laundry, designated parking, beach equipment (chairs, towels, toys, Snorkel gear) Pool and Hot Tub. 10% DISCOUNT for stays 7+ days.

Top guest favorite

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

5 out of 5 average rating, 210 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.

Top guest favorite

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.

Apartment in Kihei

4.95 out of 5 average rating, 130 reviews

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.

Guest favorite

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 Wailuku

4.96 out of 5 average rating, 109 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.

Guest favorite

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

4.92 out of 5 average rating, 125 reviews

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

E Komo Mai to our remodeled oceanfront unit with stunning ocean view at the Nani Kai Hale. Feel the ocean breeze, listen to the waves, and watch the whales and sunsets from our tranquil, oceanfront condo. From our comfortable lanai seating you have view of the Islands of Molokini, Kahoolawe and Haleakala while enjoying your morning coffee, evening cocktail, or anytime meal. Walk along the beach and experience beautiful sunsets framed by swaying coconut palms.