Family-friendly vacation rentals in Wailuku

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Top-rated family-friendly rentals in Wailuku

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Guest favorite

Condo in Wailuku

4.85 out of 5 average rating, 281 reviews

Maui HI. 1br 1ba Oceanfront Condo

The Island Sands is a third floor oceanfront condo 30 feet from the water. It has a 180 degree view of the ocean. All remodeled with all new appliances. It has A/C, W/D, D/W. Free high speed internet. Free local phone and long distance calling to the US and Canada Centrally located to explore all of Maui. The condo is centrally located in Maalaea Village on the South Coast. It is directly east of Maalaea Harbor along the waterfront. The condo off the beaten path on a dead end street that ends up at the west end of Sugar Beach, a powdered sandy beach that extends 3 1/2 miles all the way to Kihei. We walk barefoot almost every day we are there. You can see Green Sea Turtles popping their heads up for air in front of the Island Sands unit where they live in their caves. Humpback Whales arrive every year in Maalaea Bay directly in front of the condo looking out from the lanai where mama whales give birth to baby calves that you can see breaching and fin slapping and growing up for their journey back to Alaska in April and May. Look across Maalaea Bay and up to the summit of Mt. Haleakala to see spectacular sunrises from the lanais. We are also steps from the Harbor and the Maui Ocean Center, (the number #1 attraction in all of Hawaii.) Free high speed internet. Heated swimming pool. Gas grills on the grounds. Fully furnished kitchen. Bed linens and towels. Designated parking space. Short walk to the harbor and the Maalaea Shopping Mall and aquarium and restaurants. Guests are available to call me, email me The neighborhood is very peaceful and scenic. It is right On the waterfront. Centrally located to explore all Maui has to offer. Walking distance to the harbor for whale watching tours, dinner cruises, fishing and snorkeling trips. There is the Maui Ocean Activity Center and restaurants, shops and a bar that serves great food just a few blocks away. At the end of our street is Sugar Beach, the best barefoot walking beach on Maui.

Jul 3 – 10

$225 per night

Superhost

Condo in Wailuku

4.79 out of 5 average rating, 379 reviews

Romantic Beachfront Getaway

Your beachfront escape awaits... This is the perfect spot for your romantic getaway! Right on the beach, you'll enjoy days in the sun, romantic meals dining on the private garden lanai with views of the azure Pacific and nights falling asleep in the luxurious canopy bed listening to the ocean waves lapping at the shore. Just 30 steps to the white sand beach and warm Pacific from both the private garden lania and front door! This truly is a magical spot. Newly remodeled and updated with all the amenities (everything is brand new). You'll enjoy luxury accommodations at a fraction of what you would pay elsewhere. Maalaea Bay is perfectly located and central to the entire island so it's easy to get out and explore... Watch the sunrise from high atop the clouds at the 10,000 ft. summit of Haleakala Volcano (about 45 minutes to the summit). Shop the luxury stores of Wailea (about 20 minutes away). If it is snorkeling, fishing or whale watching that interests you, just walk 5 minutes to Maalaea Harbor and jump on one the many different boat tours leaving throughout the day. Craving a little nightlife? Lahaina is only about a 20 minute drive away. I hope you can come and stay to enjoy what I believe to be one of the best spots in Maui. See you soon !

Mar 26 – Apr 2

$195 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

Sep 19 – 26

$446 per night

Guest favorite

Condo in Wailuku

4.99 out of 5 average rating, 156 reviews

Beautiful Oceanfront Condo- Great View, A/C,Wi-Fi

The convenient location in Maalaea leaves you minutes away from beautiful beaches, restaurants, and all Maui destinations. An open layout consisting of 1 bedroom and 1 bath gives an expansive feel to this exquisite unit. Central A/C. Luxury upgrades include: luxury plank flooring, custom kitchen and bathroom cabinetry, granite counter-tops, new stainless appliances, stone flooring and stone/glass shower. Meticulously maintained grounds along with a refreshing swimming pool and grilling area.

Apr 21 – 28

$275 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✔

Mar 28 – Apr 4

$674 per night

Guest favorite

Condo in Kihei

4.93 out of 5 average rating, 139 reviews

1-Bedroom Tropical Getaway, Kihei Bay Vista

You home away from home in Maui! Kihei Bay Vista is steps away from white sand beaches while still conveniently located near shops, restaurants, and transportation; 5 mins. in any direction. This 1-bdrm unit is a newly converted rental and shows pride of ownership. Kihei Bay Vista is known as the choice for many returning Maui vacationers due to its quiet low key ambiance yet resort-like amenities, with pool, jacuzzi, bbq area, and private lanai for hanging out and enjoying the breeze.

May 11 – 18

$173 per night

Guest favorite

Townhouse in Kihei

4.79 out of 5 average rating, 283 reviews

Kihei Bay Surf #149 / HI Taxes included in price

Kihei Bay Surf #149 is a first floor studio with patio and grass area. The unit is located across the street from the State Beach and the National Humpback Whale Sanctuary. Quiet split system A/C (no noisy window unit) 55 inch Samsung TV, DVD, Wireless and wired internet. Full Kitchen with all amenities. In addition, there is a large pool, hot tub, tennis court and gas grills in the pool area for your use. Free parking and no additional resort fees or taxes are added to your daily rate.

Oct 8 – 15

$160 per night

Guest favorite

Apartment in Kula

4.91 out of 5 average rating, 949 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)

Apr 16 – 23

$136 per night

Superhost

Guesthouse in Wailuku

4.88 out of 5 average rating, 217 reviews

2B/2Bcottage/central/private/ historic town/wi-fi

2B/2B cottage , attached to a plantation home, in the heart of Maui, in historic Wailuku town...home of the famous Iao theater and minutes from Iao valley & the famed "Needle mountain ". Private, fully furnished, and equipped with all amenities needed for a comfortable short-term stay. Well located to connect you to all parts of the island within a 10-30 minute drive. It's great for business travelers doing business in Wailuku , hikers ,bikers, and true hawaiiana seeking tourists .

Mar 30 – Apr 6

$247 per night

Guest favorite

Condo in Wailuku

4.91 out of 5 average rating, 198 reviews

Luxurious+Modern Maui Top Floor Beachfront Condo

Completely renovated with high-end RH furniture, quality white cotton sheets, Sonos audio, marble shower, gourmet kitchen, motorized shades, & A/C in every room-- just steps away from 3 miles of undeveloped beach! Bright spacious 2nd floor 2bed/2bath condo with vaulted ceilings, fully stocked kitchen, and views of the bay, Haleakala volcano, and Haycraft Park. Great spot for swimming, paddle boarding, snorkeling, and surfing-- amazing value for families or couples.

Mar 1 – 8

$710 per night

Superhost

Apartment in Kihei

4.83 out of 5 average rating, 212 reviews

Quiet Studio, Great location across from beach

My place is located in sunny Kihei and only 20 minutes from the airport. The studio is right across the street from Kalepolepo Beach and the Whale Sanctuary. The studio is centrally located in Maui near many beaches, restaurants, and shopping centers which is very convenient. The famous Ululani's shaved ice along with various fruit stands are only a few minutes away. You can whale watch, paddleboard, snorkel, sight see, and enjoy the most amazing sunsets in Maui!

Apr 15 – 22

$131 per night

Guest favorite

Condo in Wailuku

4.94 out of 5 average rating, 163 reviews

Rare Beachfront Ground floor Oceanview from Lanai!

Enjoy a Romantic yet affordable Direct BeachFront, Ground floor condo with a partial ocean view from the Lanai. NOT ACROSS THE STREET FROM THE OCEAN! Located on gorgeous Sugar Beach, Maalaea- the LONGEST WALKING BEACH on the entire island. Humpback Whales (Nov-April) and turtles are often seen in the waters. On a a quiet, non-through road, this is like your own little neighborhood paradise! GE-210-827-7760-01 TA-210-827-7760-01 General Excise/Transient Tax

Aug 30 – Sep 6

$189 per night