Beachfront vacation 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, 187 reviews

Stunning Ocean Views -October Specials $174

*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

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, 160 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, 124 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

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, 202 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 an 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!

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

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

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!

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.

4.99 out of 5 average rating, 122 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.

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, 138 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, 231 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, 175 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.

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, 118 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. Recently replaced bed. Walk to restaurants, steps to Kam 1 beach, close to many shops & activities. Rent a paddleboard, buy Hawaiian memorabilia, or shop at Harvest Moons - just across the street. Split Air in Bedroom & Living Area. Fully equipped kitchen. In Unit Laundry

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.