House holiday rentals in Wailea

Enjoy paradise living at the THERE Maui House!

Permit #STKM 2018/0006 Located on the south side of Maui in a quiet neighborhood close to the beach & the best shave ice, this cozy, two bedroom house with newly added split AC system awaits! Whether you decide to dance to Don Ho on vinyl, try a new recipe, or play the ukulele, this space was thoughtfully designed to inspire you to be THERE & enjoy your time in paradise! For more pictures & tips, check out the THERE Maui House on our blog at there maui dot com and on IG at @livetravelbe.there

Value · Family · Wi-Fi

The Blue Door on Church Street | Spacious Two Bedr

Enjoy Haleakalā views from this spacious two-bedroom upstairs retreat at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Features include a king Helix bed, queen Helix bed, full-size memory foam sleeper sofa, full kitchen, rainfall shower, AC, fast WiFi, Smart TV, parking for two vehicles, and a large private deck with outdoor dining and lounge seating. Walk to local cafés and restaurants, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui attractions

Location · Family · Barbecue

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

True Hawaiiana charm, comfort, and convenience for your family vacation. Located in the heart of Maui, in historic Wailuku town, with easy access to all parts of the island for all your planned activities. Beaches within 10 minutes drive time in 3 directions and the beautiful West Maui mountains w/ Iao Valley National park behind. After a day of adventure come home to a restful time in the HOT TUB under the bright stars . Walk to boutiquey stores ,Coffee shops, First Friday party w/the locals

Value · Family · Check-in

40% off monthly stay! 4 Bed Family Home (Kihei)

4 BEDROOMS, 2 FULL BATHROOMS - FULLY REMODELED HOME Located in central Kihei just two blocks from the beach, Starbucks, golf courses, Kalama park, restaurants, movie theater, food trucks, entertainment, Foodland, etc. This property is secured and fully fenced. The common area consists of a driveway, garden and 2 outdoor showers. A/C in all rooms + private outdoor BBQ and laundry. You will be staying in the main house of the property and will have your private parking spot with EV charger.

Family · Location · Access

Beautiful Beachfront Townhouse !

OUR MAUI BEACH HOUSE... This is the perfect place for a family vacation and retreat!! And it is right on the beach! Many of our guests enjoy staying right on our property or on our beach -- no need to leave. A very large two bedroom, three bath - solar powered redwood townhouse we built in 1977 as a family retreat, with a fully-equipped kitchen and laundry. This is a comfortable beach house and we have done remodeling, refurnishing and updating. The master bedroom has huge ocean views.

Family · Location · Laundry

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

WONDERFUL! Three bedroom hale (home) in the Central Kihei area of Maui. Wood floors, lots of space, kitchen fully stocked, BBQ and so much more. Great for kids, elderly, and young at heart. This house is your home away from home. We have all of the necessary items for a home. If we do not have something please let us know and we will try our best to accommodated. Walking distance to the beach, shopping, park, public transportation, etc... You will not find a better place in Kihei.

Location · Value · Parking

12 Minute Walk Kamaole Beach II-Quiet Private Easy

This 1 bedroom/1 bath suite is a self contained, attached ohana (ADU) with private entry. Off street parking is 10 seconds from your door. Located a 12 minute walk straight down to Kamaole Beach II. Convenient Location, Quiet and Private. Not a condo with condo noise. I am a SUPERHOST, see the 4.97 reviews and comments. INSTANT BOOK for a great stay. All fees and taxes are listed & collected when you book. There are no surprise or additional costs. Permit #BBKM 2O19/OOO2

Value · Location · View

Modern Family Kihei Home by the Beach

Aloha! Welcome to one of the best located homes on the island! Located just under half a mile (or 5 minute walk) from the beach, surfing, park, restaurants, shops and stores. Our modern property offers complete relaxation for the perfect Maui vacation. Our home offers kid friendly amenities, A/C in ALL ROOMS, an espresso machine and Vitamix. Our calendar is always up to date. Please inquire with any questions, we will respond within 1 hour!

Value · Family · Nearby

Stunning ocean view Villa, Heated pool, Wailea

Legendary Maui sunsets from your private lanai. Whales splashing offshore in season. A heated pool all your own, tucked into over half an acre of tropical gardens. This artist-designed Victorian-style villa is 5 minutes from Keawakapu Beach and the Shops at Wailea, and made for families, with shallow-end pool steps, a gated lanai, and baby gear ready on arrival. Boutique hotel attention, complete privacy. Your view retreat awaits.

Location · Family · Amenities

4BR Kihei Retreat Walk to Beach A/C Family Ready

We are Experienced Hosts through other channels. See some of the GREAT 5 STAR reviews in the Property description. BOOK NOW AND ENJOY A 5 STAR HOME Our South Maui rental home accommodates up to eight guests, a comfortable space for your Tropical Hawaiian vacation. Four bedrooms and 2,400 square ft of living space and the beautiful outdoor living room to enjoy and relax after a day of sightseeing

Family · Location · Accuracy

South Maui Guesthouse

This air conditioned very exclusive, private 2-bedroom Guest House is surrounded with lush gardens on a ½ acre property, off the street located in an upscale very private neighborhood (Maui Meadows, above Wailea), yet minutes from the best beaches Maui has to offer. A real Hawaiiian retreat, where you wake up to the sound of birds, not traffic. Permit Number BBKM2018/xxx3 GETxxxxxxxx2801

Location · Value · Getting around

Mermaid Bungalow, cozy and ready for action.

Come as guests, live like locals. Your private Maui home away from crowded condos — where the real island life happens. 🏝️🏡 🚗💨Cruise with Edward our white handsome Jeep, 🏄‍♂️🏄‍♀️ two surf boards, 🚴🚴‍♀️ e-bikes 🐠🤿and just bring your sense of adventure. This is where you’ll discover Maui the way locals do — genuine, unhurried, and absolutely unforgettable. 🌈

Location · Value · Outdoor spaces