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

Family · Value · Hospitality

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Tranquil Beachfront Estate w/ 5 Luxurious Private Full Suites & Exotic Fruit Grove. Full amenities. Our luxury Beachfront estate has 4 beachfront one-bedroom suites and a garden view two-bedroom Ohana. Each suite has a private entrance, separate living room, full kitchen and is like having your own condo at the beach in Maui. This special place is hidden behind a private, double gated entrance, lined with 700 ft of lighted coconut palms that lure you into the feeling of leaving the world behind.

Location · Accuracy · Hot tub

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.

Value · Location · Cleanliness

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.

Value · Family · TV

Stunning Ocean Two Bd Corner Condo,AC,Pool D301

D301 is a two bedroom, two bath corner unit with AC. There is a king bed in the master, king and twin in the guest room & a sofa bed in living room. The lanai has a dining table and chairs for relaxing while enjoying dining or the spectacular view. There are ceiling fans and a/c units in each bedroom and living room. Lovely pool area with hot tub, saunas & 5 gas bbq grills. Tennis and pickleball courts. Located on the third floor, you will walk up 3 flights of stairs FREE parking

Family · Location · Decor

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 · Condition

South Maui • Pool • Hot Tubs• Beach • Ocean View

Remodeled 1BR/2BA condo in the heart of Kihei—an easy walk to the beach. Cool, quiet AC, fast Wi-Fi, and a full kitchen make relaxing easy. Sip coffee on the shaded lanai, then hit the resort pool, hot tubs, BBQs, and tennis/pickleball courts. King bedroom + comfy living space, two full baths, in-unit washer/dryer, beach gear, and free parking. Close to Wailea dining, shops, and great snorkeling. Perfect for couples or remote work—perfect for sunset looking out to the west.

Location · Beach · Comfort

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!

Location · Value · Hospitality

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 · Value · Walkability

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

**NEW OWNER, SAME GREAT CONDO AND EXPERIENCE** Welcome to your serene Kihei oasis. Perfectly located between Kihei and Wailea, this stylish condo is walkable to beaches, sunsets, local eats, and the pool—yet tucked away on a quiet cul-de-sac with no street noise. Enjoy a bright, coastal space, fully stocked kitchen, beach gear, Roku, Bose speaker, and brand-new bedroom AC plus AC in the main living area. Relax, explore, repeat.

Family · Value · Decor

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 · Nearby

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 · Wi-Fi