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

4.98 out of 5 average rating, 141 reviews

Spectacular ocean views Kihei @iconic IslandSurf

*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 RESTAURANTS

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

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

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

Condo in Kihei

4.96 out of 5 average rating, 182 reviews

Oceanview Condo - Pool+Spa, Beach Access, Parking

LOCATION, LOCATION, LOCATION! Discover ultimate comfort in our newly remodeled condo with a full kitchen, in-unit laundry, and a private lanai boasting breathtaking ocean views. Enjoy resort-style amenities, including 2 sparkling pools, 2 relaxing spas, and lush tropical gardens. Just a short walk to premier shopping, dining, and the beautiful Kamaole II Beach. Your endless summer adventure awaits—book your stay today!

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.

Guest favorite

Condo in Wailea-Makena

4.98 out of 5 average rating, 117 reviews

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.