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Family-friendly vacation rentals in Wailuku

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Top-rated family-friendly rentals in Wailuku

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Condo in Wailuku

4.79 out of 5 average rating, 404 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 !

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

Condo in Wailuku

4.99 out of 5 average rating, 171 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.

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.

Condo in Wailuku

4.81 out of 5 average rating, 111 reviews

Maui is OPEN! Come and visit your Oceanfront condo

Maui is OPEN for tourists, after the devastating wildfires! Your condo is far away from Lahaina, and the people of Maui need you to visit their Island, to assist them recover financially from the fires! Enjoy the spectacular, treetop, panoramic, view of Maalaea Bay and Haleakala, from your private lanai. Watch turtles feeding along the shoreline and in the winter see humpback whales jumping in the Bay. Your condo is far away from Lahaina, yet close to everything fun to do in Eastern Maui!

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)

Condo in Wailuku

4.92 out of 5 average rating, 215 reviews

Modern Clean 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.

Rental unit in Kihei

4.82 out of 5 average rating, 234 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!

Condo in Wailuku

4.91 out of 5 average rating, 190 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

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.

Farm stay in Haiku-Pauwela

4.95 out of 5 average rating, 374 reviews

Kalani at Haiku Garden Cottages

Welcome to Haiku Garden Cottages, a permitted BnB (Permit#BBPH 2017/0002 SUP2 2016/0011) located in the lush countryside of Maui's North Shore. Surrounded by beautiful beaches, amazing waterfalls, great hikes, and starlit nights, you'll feel like you're staying in a private paradise, while still being able to enjoy the convenience of being close to everything.

Rental unit in Kihei

4.83 out of 5 average rating, 515 reviews

Hawaiian Paradise Escape Across Street from Beach

We are centrally located on the island and directly across the street from several lovely beaches. Our unit is on the first floor of a two story complex. This studio is in a very quiet and peaceful location over looking the central courtyard just steps from the beach. Price includes tax. ** Hawaii Tax I.D. TA and GE posted in unit**.

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Popular amenities for Wailuku family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Kihei

4.88 out of 5 average rating, 142 reviews

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01

Condo in Kihei

4.93 out of 5 average rating, 136 reviews

Expansive Ocean View!

Condo in Kihei

4.81 out of 5 average rating, 298 reviews

Ocean view studio. 1k ft from water!June $149 m-th

Condo in Maalaea

4.96 out of 5 average rating, 118 reviews

Spectacular Oceanfront views!

Condo in Kihei

4.89 out of 5 average rating, 124 reviews

Incomparable Maui Sunset condo, includes all taxes

Condo in Kihei

4.92 out of 5 average rating, 152 reviews

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

Rental unit in Kihei

4.91 out of 5 average rating, 352 reviews

Winter Special! King Bed, Closest to Ocean

Cottage in Haiku-Pauwela

4.81 out of 5 average rating, 188 reviews

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

Family- and pet-friendly home rentals

Condo in Lahaina

4.88 out of 5 average rating, 125 reviews

Beautiful Views~

Townhouse in Wailea

4.98 out of 5 average rating, 105 reviews

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Home in Makawao

4.84 out of 5 average rating, 44 reviews

Pookela Paradise-Newly Renovated, Fantastic Views!

Home in Wailea-Makena

4.99 out of 5 average rating, 82 reviews

WOW! Stunning Ocean Views, Large Deck &Luxury Beds

Rental unit in Lahaina

5 out of 5 average rating, 4 reviews

Maui Westin Kaanapali Ocean Resort Studio

Home in Kihei

4.92 out of 5 average rating, 25 reviews

Oceanview Home with Private pool and hot tub

Townhouse in Lahaina

4.2 out of 5 average rating, 5 reviews

Puamana 80-4 Superior Garden View

Home in Lahaina

4.56 out of 5 average rating, 88 reviews

Walk to Front St., ALOHA CABANA, "PEOPLES CHOICE"

Family-friendly home rentals with a pool

Condo in Kihei

4.94 out of 5 average rating, 214 reviews

Beachfront Condo in Kihei

Rental unit in Kihei

4.91 out of 5 average rating, 271 reviews

Ocean View, 1 minute walk to the beach 2BR/2BA

Condo in Lahaina

4.92 out of 5 average rating, 412 reviews

Napili Nani cottage for 2 w/AC ~ *Renovated*

Condo in Kaanapali

4.98 out of 5 average rating, 125 reviews

MAHANA 505 OCEAN FRONT W/ SPECTACULAR VIEWS

Condo in Lahaina

4.96 out of 5 average rating, 241 reviews

Soothing Waves with 180° View In Kahana, HI

Condo in Kihei

4.79 out of 5 average rating, 296 reviews

Hale Kamaole Steps To Kam 3

Condo in Kihei

4.82 out of 5 average rating, 264 reviews

Sea Views entire 1 Bedroom Apartment Poolside

Condo in Kihei

4.92 out of 5 average rating, 143 reviews

Ocean View Condo in Kihei

Quick stats about vacation rentals that are family-friendly in Wailuku

Total rentals
20 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
630 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Destinations to explore