Family-friendly vacation rentals in Wailea-Makena

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Top-rated family-friendly rentals in Wailea-Makena

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Guest favorite

Home in Kihei

4.96 out of 5 average rating, 409 reviews

Stunning ocean view, heated pool at home by Wailea

Last minute bookings 5 days before arrival, and week long stays are 10% off. 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

Guest favorite

Condo in Wailea-Makena

4.94 out of 5 average rating, 261 reviews

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

Condo in Kihei

4.9 out of 5 average rating, 124 reviews

WinterSale 3BR/2BA Villa 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.

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 169 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.

Guest favorite

Condo in Wailea-Makena

4.98 out of 5 average rating, 156 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

LOCATION LOCATION LOCATION! Beautiful Ocean and Fairway Views! Rare 3 bedroom, Split System AC in all rooms!! Luxury awaits you in this beautiful ground floor unit with total of 1,698 square ft of living and a wrap around lanai! You will enjoy everything needed for your comfort stay! This central Wailea resort location makes it favorable as you can walk to Wailea Tennis Club, Wailea Blue Course, 5 star hotels, Shops at Wailea & Restaurants. Beautiful Beaches are approximately ¼ mile away!

Guest favorite

Cabin in Maui

4.97 out of 5 average rating, 190 reviews

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

Guest favorite

Condo in Wailea

4.95 out of 5 average rating, 148 reviews

Locally Owned & Managed - Grand Champions Villa

Our locally-owned, newly redesigned 2BD/2BA modern Maui condo is located on the award-winning Wailea Blue Golf Course at The Grand Champions Villas. The Villas are nestled in the heart of tropical Wailea; minutes from shopping, tennis, restaurants and pristine beaches. Stroll to upscale boutiques and restaurants, or take a short walk to some of the most beautiful beaches in the world. Our condo features local Hawaii art and is your perfect home away from home on the beautiful island of Maui.

Guest favorite

Condo in Kihei

4.94 out of 5 average rating, 214 reviews

Beachfront Condo in Kihei

Located on the shores of beautiful Keawakapu Beach lies your next island paradise vacation. The Mana Kai Maui resort straddles the communities of Kihei and Wailea offering the beauty and privacy of Wailea beaches with the value of Kihei. This Maui beachfront condo offers stunning ocean views from a private lanai and is just steps to the beach, with access to a swimming pool, restaurant, general store and beach equipment rental. With 2 bedrooms and 2 baths, it sleeps four people comfortably.

Guest favorite

Rental unit in Kula

4.91 out of 5 average rating, 1,019 reviews

Kula Treat - Upcountry Maui with Hot Tub!

Private, gracious apartment in desirable Upcountry Maui. Great home base for exploring, and a quiet country retreat for relaxing. Restaurants, food trucks and farmers’ markets nearby. Beaches, hiking and zipline within an easy drive. Perfectly located for Haleakalā Natʻl Park and day trips to Hana. A wonderful personal chef lives very close by. Dedicated to reducing single use plastics, we provide reusable water bottles for our guests! Fully permitted: BBMP 2015/0003 E komo mai! (Welcome)

Guest favorite

Condo in Wailea

4.94 out of 5 average rating, 163 reviews

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.

Guest favorite

Condo in Kihei

4.78 out of 5 average rating, 251 reviews

Affordable Accommodations in Maui

A welcoming 1st floor, one bedroom 723 sq ft condo at Kihei Kai Nani complex across from beautiful Kamaole II beach, in Kihei. It is updated, fully furnished and equipped with full kitchen, Queen size bed and a fold out Full sofa-bed. NOTE: The Kihei Kai Nani resort has been zoned as a Hotel / Business Resort since it was built in the 70's. It is not one of the resorts being targeted by current legislation to curb Short Term Rentals on Maui.

Guest favorite

Townhouse in Wailea

4.98 out of 5 average rating, 104 reviews

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.