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, 388 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

Nov 6 – 13

$473 per night

Guest favorite

Condo in Kihei

4.88 out of 5 average rating, 105 reviews

100KContemporaryHawaiian Reno in Wailea-Beach/Golf

Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with private wrap around lanai. King Master Bed with a contemporary private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel or take long tropical beach walks.BOOK UP TO 365 DAYS

Mar 15 – 22

$300 per night

Guest favorite

Condo in Wailea-Makena

4.94 out of 5 average rating, 235 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

Nov 22 – 29

$515 per night

Guest favorite

Condo in Wailea-Makena

4.98 out of 5 average rating, 138 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!

Mar 31 – Apr 7

$470 per night

Guest favorite

Cabin in Maui

4.98 out of 5 average rating, 171 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✔

Feb 20 – 27

$674 per night

Superhost

Condo in Wailea-Makena

4.88 out of 5 average rating, 169 reviews

Ocean View Wailea Ekolu Condo #804

Come enjoy the best of Wailea, and its beautiful beaches at this desirable, very spacious one bedroom two bath condo. The property is nestled on the Wailea Blue Golf-course, just walking distance from Wailea, Mokapu & Ulua beaches. The Wailea Shops & Tennis Club and five of the most prestigious hotels of Wailea. The Fairmont, Four Seasons, Grand Wailea, Wailea Resort & Spa, and The New Andaz Hotel. NO HIDDEN FEES- Resort Taxes, and Free Parking. 13.5% Hawaiian Tax are included in the price.

Aug 1 – 8

$329 per night

Guest favorite

Condo in Wailea

4.95 out of 5 average rating, 137 reviews

4/21-5/30 Fabulous Peaceful 2bd in Upscale Wailea

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.

Sep 29 – Oct 6

$265 per night

Guest favorite

Condo in Kihei

4.94 out of 5 average rating, 198 reviews

Mana Kai Maui - Oceanfront 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.

Apr 17 – 24

$500 per night

Guest favorite

Apartment in Kula

4.91 out of 5 average rating, 948 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)

Mar 14 – 21

$136 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 143 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront 2b/2b condo DIRECTLY on Keawakapu beach! This location is ideal, on the border of Wailea and Kihei. We have designed our remodel with a modern surf vibe 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.

Sep 2 – 9

$695 per night

Guest favorite

Condo in Wailea

4.94 out of 5 average rating, 155 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.

Jul 27 – Aug 3

$550 per night

Guest favorite

Guesthouse in Lanai City

4.88 out of 5 average rating, 339 reviews

de Brums Lanai/BBLA 2021/0001

Our one bedroom cottage rests on the hill above Lānaʻi. It offers a complete kitchen and a lovely view from the covered lanai. Shady and cool, we are a 12 minute walk into town. There is no need for either AC or heat. While we do have ceiling fans in every room, you will find Lānaʻi to have a lovely climate with tropical breezes during the day and cool, upcountry temperatures for great sleep in the evenings.

Mar 24 – 31

$178 per night