Family-friendly vacation rentals in Wailea-Makena

A clear blue pool is surrounded by palm trees, creating a relaxing atmosphere. Lounge chairs are positioned along the deck, offering spots for sunbathing. Umbrellas provide shade for outdoor dining tables nearby, all with a scenic view of the ocean in the background.

4.95 out of 5 average rating, 209 reviews

Maui's Best - Wailea Ekahi 47A

Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

4.94 out of 5 average rating, 286 reviews

An open dining area features a round table made of natural wood, surrounded by woven chairs. A well-equipped kitchen with stainless steel appliances and quartz countertops is visible in the background. Large sliding glass doors provide unobstructed views of the ocean and nearby palm trees.

Condo in Wailea-Makena

A.R.A Retreats: The Molokini

FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

Superhost

A vibrant sunset is captured over the Pacific Ocean, with clouds in shades of orange and purple. Silhouettes of palm trees frame the foreground, while lush greenery and homes are visible at the edge of the golf course, enhancing the tropical setting.

4.91 out of 5 average rating, 141 reviews

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

Location and views are everything when it comes to this home. Nestled in the heart of Wailea, most consider the beautiful area of Maui. This RARE 3br/2ba villa has enough space for a large family or a group of good friends. Just a short walk to some of the most beautiful beaches in the world, World class shopping mall and 5 star resorts. Enjoy all the comforts of home while taking in breath taking Grand views of the Deep Blue Pacific, Hole 2 of the Blue Wailea Golf Course and Mount Haleakala.

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, 189 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 condo 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

4.94 out of 5 average rating, 172 reviews

A well-appointed kitchen area features a spacious granite countertop with rich wooden cabinetry. Hanging red pendant lights provide soft illumination. Large windows offer views of lush greenery and the ocean, enhancing the inviting atmosphere of the space.

Condo in Wailea

Spectacular Ocean View condo beautiful inside out.

Beautiful Inside Out w/ Spectacular Ocean Views from upstairs and downstairs, 2 bedroom 3 bathrooms 2-story townhouse on the Blue Golf Course with over 1500 Sq. ft. of living space + 2 large lanais. It’s located at the 1st row of condo across from the Grand Wailea and Shops At Wailea and only 3 minutes walk to the main shopping center of Wailea. There are retail shops and restaurants right next door. More beaches, restaurants, spas, and hotels are all within walking distance.

Superhost

A spacious living area is furnished with two light-colored sofas adorned with patterned cushions. A glass coffee table sits at the center, complemented by a potted plant in the corner. Natural light enters through large windows with sheer curtains, enhancing the inviting atmosphere.

Condo in Wailea

4.83 out of 5 average rating, 146 reviews

Beautiful Palms At Wailea #608-June/July Discount

Beautiful Palms At Wailea ,2BR/2BA,Condo, located in the heart of Wailea. 5* location. Vinyl wood flooring & Split Air-Cond. system in hallway & in master-B/R. Fans through-out. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., wide open floor plan ,2nd. fl.unit. Low rise complex. Very private. Large lanai . Barbecue grills located near entryway of complex. Views from the Club House & Pool.The best place to stay!

4.96 out of 5 average rating, 433 reviews

A welcoming living area features a comfortable sectional sofa beside a modern coffee table, with natural light filtering through large windows. An outdoor patio is visible, with an umbrella-shaded table and chairs overlooking lush tropical gardens and ocean views.

Home in Kihei

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

4.98 out of 5 average rating, 123 reviews

The open living area showcases vaulted ceilings and warm wood beams. A modern kitchen island with a marble finish is complemented by stylish pendant lights. A cozy seating area invites relaxation, while large windows offer views of the surrounding landscape, enhancing the bright and airy atmosphere.

Townhouse in Wailea

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Welcome to Happy Everything! Wailea Ekolu Complex A fun, fully re-modeled, well appointed and comfortable townhome situated on hole 10 of the famous Wailea Blue Golf Course at beautiful Wailea, Maui. Comfortably sleeps 6. Spectacular views of the Ocean and Neighbor Islands. Close to beaches, shopping, restaurants, Wailea Resorts and just a chip shot away from the golf course and brand new Wailea Village shops.

A cozy living area is highlighted by a large piece of local artwork depicting a green leaf garland. A gray sofa is adorned with soft, pastel-colored pillows, flanked by two blue chairs with light cushions. Adjacent side tables support glass lamps, enhancing the natural light.

4.95 out of 5 average rating, 169 reviews

Locally Owned & Managed - Walk to Keawakapu Beach!

This serene 2BD/1BA condo is located across the street from the world class Keawakapu Beach. Our quiet, first floor unit has a partial ocean view. Guests can enjoy the vibrant colors of a Maui sunset on the outdoor patio, or take a short walk to the beach. Our locally-owned and newly redesigned condo features local Hawai'i art and is your perfect home away from home on the beautiful south shore on island of Maui.

4.98 out of 5 average rating, 126 reviews

The living area is arranged with comfortable seating over a textured carpet. A low coffee table holds decorative elements, while art adorns the wall and a modern kitchen with stainless steel appliances is visible in the background, enhancing the open layout.

Condo in Wailea-Makena

130K Hawaiian Reno on Wailea Blue Golf *Ocean View

BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

4.97 out of 5 average rating, 258 reviews

A charming guest house is presented with a wraparound deck, framed by palm trees and lush greenery. The exterior features light-colored siding and a sloped roof, with windows allowing natural light. A clear blue sky enhances the inviting setting of this private retreat.

Home in Kihei

South Maui Guesthouse

This air conditioned very exclusive, private 2-bedroom Guest House is surrounded with lush gardens on a ½ acre property, off the street located in an upscale very private neighborhood (Maui Meadows, above Wailea), yet minutes from the best beaches Maui has to offer. A real Hawaiiian retreat, where you wake up to the sound of birds, not traffic. Permit Number BBKM2018/xxx3 GETxxxxxxxx2801