Family-friendly vacation rentals in Wailea, Wailea-Makena

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Top-rated family-friendly rentals in Wailea, Wailea-Makena

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Guest favorite

Condo in Kihei

4.91 out of 5 average rating, 135 reviews

160KReno-Stunning Palms in Wailea Condo-Beach/Golf

Brand New 160K Renovation+Redecoration 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 floor condo with private lanai that overlooks the grass.King Master Bed with a private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel/take long tropical beach walk.BOOKINGS UP TO 365 DAY

Apr 7 – 14

ﺩ.ﺇ1,271 per night

Guest favorite

Home in Kihei

4.96 out of 5 average rating, 389 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

Oct 24 – 31

ﺩ.ﺇ2,001 per night

Guest favorite

Condo in Wailea-Makena

4.98 out of 5 average rating, 139 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 25 – Apr 1

ﺩ.ﺇ1,912 per night

Guest favorite

Condo in Kihei

4.9 out of 5 average rating, 112 reviews

Spacious 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.

Apr 8 – 15

ﺩ.ﺇ2,348 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 8 – 15

ﺩ.ﺇ2,115 per night

Guest favorite

Apartment in Kula

4.91 out of 5 average rating, 950 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 21 – 28

ﺩ.ﺇ576 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.

Mar 26 – Apr 2

ﺩ.ﺇ4,150 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 146 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront 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 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.

Sep 2 – 9

ﺩ.ﺇ2,932 per night

Guest favorite

Condo in Kihei

4.96 out of 5 average rating, 165 reviews

Romantic and Modern Condo by the Beach!

Indulge in island luxury at our stunning condo in South Kihei. Recently remodeled to perfection, this oasis boasts a full kitchen, in-unit laundry, and a private outdoor lanai with breathtaking ocean views. Walk to fabulous shopping, dining, and pristine beaches just minutes from your front door. With 2 pools, 2 spas and lush tropical gardens, you'll enjoy one of the best condos in one of the best resorts in South Maui. BOOK NOW, endless summer awaits you!

Sep 8 – 15

ﺩ.ﺇ945 per night

Guest favorite

Condo in Wailea-Makena

4.94 out of 5 average rating, 279 reviews

A.R.A Retreats: The Curved Slab

Nicknamed “Curved Slab” for its massive peninsula in the kitchen which has a subtle but sleek curve. This Slab is 105 inches by 67. The peninsula is perfect for family cooking and eating, providing ample space for preparing and enjoying meals together. Located in Grand Champions Villas in the luxury, resort community of Wailea. Newly renovated and decorated. Guests can enjoy the spacious and comfortable condo that has everything you should need for your trip.

Apr 17 – 24

ﺩ.ﺇ1,894 per night

Guest favorite

Condo in Kihei

4.92 out of 5 average rating, 190 reviews

Beautiful & clean condo w/ excellent location

This condo is marked with special touches to accent the beauty of the location. The condo is beautifully decorated with local and tropical art and furniture. We value cleanliness, comfort, beauty and exceptional service and hospitality. Whenever we have the chance, we escape to our condo and feel the peace and tranquility the space and surrounding location has to offer. We return to our busy lives feeling refreshed and invite you to do the same.

Oct 24 – 31

ﺩ.ﺇ642 per night

Guest favorite

Condo in Kihei

4.93 out of 5 average rating, 219 reviews

Hale Kai O Kihei 307 | Direct Beachfront

Hawaii Life Vacations presents a new addition to "The Hotel Collection". This fully remodeled top-floor suite boasts sweeping ocean views. Enjoy watching the waves lapping the golden sandy beach from your balcony. Light, bright, and well appointed, 307 @ HKOK offers A/C in the living room, fully equipped kitchen w/amenities, and on-site pool and lounge area for your enjoyment. GE/TA# - W-13763254-01

Mar 31 – Apr 7

ﺩ.ﺇ1,621 per night